Recaps of our weekly CEO Mastermind tracks

Summary of the challenges, big lessons learned and the key questions to reflect upon

Weekly Recaps from our CEO Mastermind

15 August 2022 – “Timing is our enemy.”

Last week’s live CEO Mastermind session was about this question: “Would your customers care if you’d cease to exist today?” We chose this question to answer a bigger one: What’s your ability to deliver something valuable and desirable?

Concerning this, one participant said: “𝘛𝘰𝘥𝘢𝘺, 𝘰𝘶𝘳 𝘷𝘢𝘭𝘶𝘦 𝘱𝘦𝘳𝘤𝘦𝘱𝘵𝘪𝘰𝘯 𝘪𝘴 𝘯𝘰𝘵 𝘵𝘩𝘦𝘳𝘦. 𝘉𝘶𝘵, 𝘢𝘴 𝘱𝘦𝘰𝘱𝘭𝘦 𝘴𝘵𝘢𝘺 𝘰𝘯 𝘰𝘶𝘳 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮, 𝘵𝘩𝘢𝘵 𝘷𝘢𝘭𝘶𝘦 𝘴𝘵𝘪𝘤𝘬𝘪𝘯𝘦𝘴𝘴 𝘨𝘳𝘰𝘸𝘴.” Another participant said, “𝘞𝘦 𝘩𝘢𝘷𝘦 𝘵𝘰𝘰 𝘮𝘢𝘯𝘺 𝘱𝘳𝘰𝘫𝘦𝘤𝘵𝘴 𝘸𝘦 𝘤𝘢𝘯 𝘤𝘰𝘯𝘴𝘶𝘮𝘦. 𝘛𝘩𝘦 𝘳𝘢𝘤𝘦 𝘸𝘦 𝘩𝘢𝘷𝘦 𝘪𝘴 𝘮𝘰𝘳𝘦 𝘢𝘣𝘰𝘶𝘵 𝘵𝘪𝘮𝘪𝘯𝘨. 𝘛𝘪𝘮𝘪𝘯𝘨 𝘪𝘴 𝘰𝘶𝘳 𝘦𝘯𝘦𝘮𝘺. 𝘐𝘵 𝘫𝘶𝘴𝘵 𝘵𝘢𝘬𝘦𝘴 𝘵𝘰𝘰 𝘭𝘰𝘯𝘨 𝘵𝘰 𝘥𝘰 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨.”

This brings the valuable distinction between Timing and Time. So, where do you put your bets?

𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘁𝗵𝗶𝗻𝗴:
Research has shown that the single biggest reason startups succeed is timing (link in 1st comment). But, unfortunately, that’s super hard – and tied to many critical decisions.

  • Where do you place your bets? How many eggs do you want to have in your basket? One to go fast or three to spread your options?
  • What’s the right moment to launch? With a minimum viable product to find your wedge in asap, or with a more mature solution?
  • Do you decide on a product-led growth approach and eliminate all the friction to make adopting fast and low touch?
  • Or do you bet on a Sales led approach with more vetting upfront (slowing down sales cycles) but less churn risk after decisions are made?

𝗧𝗵𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺? Offering something valuable and desirable isn’t about short-term wins. It’s about embedding yourself for the long term.

𝗪𝗵𝗮𝘁’𝘀 𝗮𝘁 𝘀𝘁𝗮𝗸𝗲? If the value & desirability isn’t there from the start, it hurts your ability to grow ‘enough’ traction. If it’s the value is too shallow, the desirability will fade out fast, resulting in churn.

𝗧𝗵𝗲 𝘂𝗿𝗴𝗲𝗻𝗰𝘆? Finding the balance – enough to find your wedge in at the right moment and enough bandwidth to keep building the value & desire momentum. And this is all about resourcefulness.

𝗦𝗼 𝗺𝘆 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻 𝘁𝗼 𝗿𝗲𝗳𝗹𝗲𝗰𝘁 𝘂𝗽𝗼𝗻 𝘁𝗼𝗱𝗮𝘆:
In your SaaS business – what’s your major enemy: Timing or time? What could you change to turn this around?

25 July 2022 – How can you grow 3x YOY selling compliance software?

This was the challenge we addressed in the CEO Mastermind just before my holiday. 

During the mastermind, we explored a case study of a B2B SaaS company from Seattle in the cybersecurity compliance business. 

The first thing you likely think about when you hear this is: “Tough sell – not a ‘sexy’ business at all, and heavily focused on endless details, checking off boxes, and mitigating risk.” Right? 

Fact is – nothing of that is true.

Here’s the thing:

This is a compelling example of getting clear what business you are really in. And as the founder & CEO shared: 

“What I realized when dealing with the problem is that this is a revenue issue. And if you want to build a business that has good growth and makes money, there’s nothing better than tying yourself to a company’s revenue in some way. Because when they look at all the Costs or Expenses, the thing that drives revenue is always worth more than any other expenditure at the organization.”

The impact: 

Their business started 2.5 years ago, and since then, it has grown 3x every single year, won over 150 enterprise customers, and employs well over 50 employees today.

Key take away: Too often, we’re too literal about the business we’re in, which holds us back.

  • The problem? It stops us from seeing and addressing the real opportunity.
  • What’s at stake? It leaves buckets of money on the table and slows everything down.
  • The urgency? It undermines creating solid traction and drains your runway.

Some ideas to avoid this.

Step away from the functionality you offer – and ask these two questions:

  1. What will go wrong when we take our solution away from our customers? Don’t stop – keep asking: What else?
  2. What in this list will make them scream you give your back to them?

The question I want to leave you with to reflect upon:

How can you tie your business’s value prop to your prospect’s revenue potential?

18 July 2022 – “Focus on BEP or go all-in on growth?”

This was the challenge we addressed in last week’s live CEO Mastermind session.

One of the members is at a cross-road on what to bet his business on for the next 12 months: The path to break-even-point or go All-in to reach/fund the next growth point.

The problem?

  • His business has been growing fast in the past years, and the outlook for 2022 is still strong (4x).
  • However, his investors are pushing towards a cost-conservative plan, anticipating a global downturn.

What’s at stake?

  • Choosing route A (BEP) – growth slowdown, impacting future valuation and ability to raise funding.
  • Choosing route B (bet on growth) – Burn cash fast, shorter runway, and potentially put the entire business at risk

The difficulty?

  • “The voices in my head: We have survived 4 crises in the past years, and our offering is mission critical to our customers – especially in turbulent times. That said, what’s different now is that we have grown so much – so every decision has a bigger impact on employees, customers, and investors.”

Here’s the thing:

No one has a crystal ball – and one crisis isn’t the other. From all my interviews with SaaS CEOs for my second book ‘Remarkable Resilience’, two themes are very strong: Avoid emotions to lead your decisions and Help your customers survive.

One perspective to take is: What would help your customers most? And it’s clear that the platform serves as the core Operating System for this scenario. If the company falls away, their business is at risk, so stability is what they want. 

Some questions that we explored that might help you in respect to this:

  • How sure are you that with more money (funding) you can scale so much more (given the circumstances)?
  • You don’t have to be the guy that raises the most to be the most successful – so what does success look like, and what are the routes to achieve this?

The question I want to leave you with to reflect upon:

What would you decide if you’d be in the hot seat with these parameters?

11 July 2022 – How to surprise our customers in a downturn?

This was the challenges we addressed in last week’s CEO Mastermind. The inspiration for this topic: A quote from Jonathan Stark: “Proactiveness in a time where a lot of people are going to be reactive is a huge differentiator”

Here’s the thing:
We tend to shift our focus internally when adversity happens. There’s fear building up and instead of being proactive, we get reactive. But so do our customers. And that’s where the opportunity lies to make a difference. Here’s why:

The problem?

  • Our key decision-makers will be under more pressure.
  • Budgets get cut, often in combo with layoffs while at the same time they have to step up
  • The things they manage can’t fail – no matter what happens

What’s at stake?

  • A big revenue/income dip (or worse: customer churn)
  • The reputation of the business is at risk if things fail
  • Their own job is down the line in

The urgency?

  • This was already mission-critical without any crisis – but now it’s even more
  • If there’s ever a moment for them to shine – it’s now

In respect to this, this quote expresses the instant value to you can add:

“I called a large industrial client today, asking “What are you worried about? He said: “My big problem is – I have five of my technicians leaving. We have to lay them off and this is affecting 10% of my ability to deliver the services to our customers. I said: “I can help you further optimize on top of what you already have from us by about 20%. That will cover the 10% drop that you are going to have from the layoffs. They loved it. We activated that for them today to try.”

One call – showing empathy and having a helpful conversation, can make a huge difference for your customer, and for yourself.

Some ideas

  • In a downturn, Government will get more aggressive with audits. What systems do your customers have that are mission-critical that need to pass?
  • Which customers operate in industries where customer loyalty is really low – where risk of churn is increasing in a downturn when service levels drop (due to layoffs)?
  • For which of your customers is employee retention even more important in the current market? Where is getting harder and harder to retain people due to everything happening?

The question I want to leave you with to reflect upon:
Which customers could you proactively reach out to and positively surprise with help that comes super timely for them.


4 July 2022 – Economic Downturn – How’s your target market changing?

This was a challenge we addressed in today’s live CEO Mastermind session.

With an economic downturn looming, the big question is: How are the priorities of your ideal customer profile changing? What are the macro-economic factors that are changing for your customers? And what does this mean to the perspectives of your business? 

The problem with uncertainty is:

  • Specific segments of your target market will do well; others not
  • Most organizations get conservative and switch to a wait-and-see approach.
  • Priorities shift towards securing cash flow and protecting costs.

What’s at stake?

  • What used to sell yesterday won’t necessarily sell well tomorrow
  • Demand could drop to 0. Sales cycles could double in size.

The urgency

  • Figuring out who you’re (still) for and who you’re not for (anymore)

Here’s the thing:

Your positioning doesn’t necessarily change in a downturn, but your USP likely will. As your customers’ priorities are shifting, so will their perspective about what problems are highly valuable AND critical to solving. That’s where your opportunity is. Reassess the longlist of what keeps your customers up at night, and rate each challenge around two angles:

  1. For whom has this challenge become MORE valuable to solve? 
  2. For whom has this challenge become MORE critical to solving?

Zoom in to those challenges where you know you can exceed expectations, i.e., the challenges that have become more valuable and critical. Refocus on those customers.

The question for you to reflect upon:

If you assess your target market – which niche will you be able to be ultra-relevant for when a recession becomes a reality? 


27 June 2022 – What’s slowing your SaaS business down?

What’s slowing your SaaS Business down. This was the big question we addressed in last week’s live CEO Mastermind session.

Why? Here’s the thing
Because too often we’re only looking at the opposite question: What can we do to go faster?

The problem with this:
More often than not that’s about doing more, spending more, and working harder

What’s at stake
We push and push and push and wear people out along the way
We still don’t meet our aspired growth because we don’t have an eye for the fundamental roadblocks that we should actually remove

The difficulty
Taking a 30000 ft view and seeing the big picture
Connecting the dots and being open to killing hobby horses

Here are some outcomes from our breakout session

  1. Slow down area #1: Educating the market
    What can you do differently to educate the market as you are building it?
  2. Slow down area #2: Funding the business
    What can you do differently to speed up the funding process or to eliminate it all together?
  3. Slow down area #3: Pipeline velocity
    What can you do differently to qualify out faster and grow urgency with the right leads
  4. Slow down area #4: Onboarding velocity
    What can you do differently to remove more manual steps – and in what order?
  5. Slow down area #5: Product adoption
    What can you do differently to help customers achieve ROI faster, to create pull
  6. Slow down area #6: Upsell potential
    What can you do differently development-wise to accelerate releasing monetizable features

The question I want to leave you with to reflect upon:
What’s slowing down the SaaS business you own, run or work for? What could you start today to make it 10% faster?


20 june 2022 – To fund or not to fund – that’s the question.

This was one of the challenges we addressed in last week’s CEO Mastermind session.

“I’ve got to be very conscious of the competitive situation at the moment. More competition is entering the market, kicking off what in the category creation world would be the two-year war to see who will win.”

The urgency

  • “The category leader takes 73% of the economics of the market. and if we’re not that one, some VC will mint a winner – and that’s the problem.”

What’s at stake /the fear 

  • “We’ve been generating cash for the last 18 months – so don’t need the raise.”
  • “But we cannot not be the minted winner.”

The problem

  • “Last year’s growth was 30%, this year it will be 130% – though VCs expect 300% YOY.”
  • “It’s public sector led – a capped (200 local authorities) and slow market.”

Here’s the thing:

It’s a real dilemma: Choosing between valuation and speed, or creating value and building a sustainable business around a meaningful mission. You can feel torn between sub-optimal decisions. It’s where true leaders rise to the table – and make the right decision – whatever that is.

  1. Staying true to the mission vs. prioritizing (valuation) money
  2. Prioritizing rapid growth over building a sustainable (profitable) business
  3. Fighting for dominance in a dense market vs. having a first-mover advantage in a new market
  4. Going all-in on one use case or placing your bets on multiple options.

The question for you to reflect upon:

Imagine the dynamics in your market would change overnight and create a category war: what would you double down on, and what would you be willing to give up?


13 june 2022 – “Which audience should we place our bets to achieve 20K subscribers by year-end?”

“We have traction (+7000 installs) for the free app (an app in the mental health/wellness space) – and now need to scale towards 20K paid subscribers. With a runway of 7 months, so my strategic challenge is – which channel do we bet our efforts on: B2C, partners (f.ex. professional coaches) or B2B?”

This was one of the challenges we addressed in last week’s CEO Mastermind session

The problem/struggle

  • “B2B obviously can accelerate traction, however, sales cycles are way longer (months) compared to a B2C motion (hours)”

What’s at stake /the fear 

  • “Running out of time if we bet on the wrong channel. Our runway is 7 months, and we don’t have any intentions to do fundraising”

The difficulty

  • “The B2B and/or influencer motion is new to us. Interest is absolutely there, just no signs of purchase”

Here’s the thing:

A discussion about ‘channel’ is meaningless if it’s not 100% crystal clear what ‘expensive’ problem is solved. And for each target audience in this case that’s different. 

The art is to get super specific on the ‘Why’, instead of sticking to the ‘What’.

How? By creating a list of the problems potential customers struggle with – and then quantify the size of the problem ( on a scale of 1-10: how valuable is it to solve and how critical/urgent is it on their agenda). Then lastly quantify (1-10) on per problem where can your app exceed expectations. 

That gives focus. This creates resourcefulness  – and most likely, the clarity which channel will be most obvious to focus on. 

With respect to this, these quotes might be of value to you:

  • ​​”Hyper-segment your target user group so you could focus all your efforts of marketing, product development, and sales on this.”
  • “Once you know this – create a series of landing pages (per problem) to test market desire. Maybe even ask willingness to pay (as in how much they would pay). This would identify size of market and demand.”
  • “It does seem that there’s not much reason why you couldn’t do B2C, B2B and professional coaches/psychotherapist at the same time – as long as you hone in on the most valuable/critical problem each of them faces” 

The question I want to leave you with to reflect upon:

If you’d ask your ideal customers to visit your website – would they be able to articulate in <7 seconds what’s the exact problem you could help them solve? If not – what if they could? 

6 june 2022 – “Should I go fundraising or continue bootstrapping?”

This is one of the challenges we addressed in last week’s live CEO Mastermind session.

“We’re still relatively small, just close a multi-year $1M a year deal, and have a healthy pipeline. However, I am not a ‘COO’ type person and have no background selling software. My question is: Should I try to raise as much as I can and bring in the team, or should I stay lean right now?”

The problem/struggle

  • “There’s a downturn kicking in – not an ideal period to fundraise”
  • “Fundraising eats a lot of your time and energy – can you afford that?

What’s at stake /the fear

  • “Dropping the ball on the delivery side to my new customers”
  • “Making the mistake of hiring the wrong people”
  • “Insecure about what challenges will come our way”

The urgency

  • “I have the $1M contract – but the money isn’t in yet”

Here’s the thing:
It’s such a common conversation. Fundraise ….bootstrap. The lessons I have learned from all the hundreds of SaaS CEOs that I’ve interviewed and worked with is: Traction before funding. Period. Find the product-market-fit.

Get some larger fires burning (discount your whale account – create genuine pull around your product) and do things that don’t scale yourself (even if it’s for 6 months) to deeply understand what works and what doesn’t. Then decide.

That way you have a much stronger negotiation position (IF you consider funding). And you can properly target where you invest your funding to make those fires big fires.

With respect to this, these quotes might be of value to you:

  • “What’s your objective for the next 12-24 months i.e. is this funding itch temporarily (to mitigate risk,…) or one that will genuinely help achieve your mission?”
  • “Be honest: Do you need to fundraise, … or want to fundraise?”
  • “If you got cash flow, you’re in a luxury position few companies (<10%) have today. Leverage that.”
  • “If you raise you’re going to have to set yourself in a mode of continuously raising (even if you think you don’t need it). VCs hate companies that have long gaps in their raising history.”

The question I want to leave you with to reflect upon:
The question about raising will come up sooner rather than later. If you could grow as fast (or even faster) by continuing to be bootstrapped – would you take that shot? What would have to be true to do so?


30 May 2022 – “Financial ROI can be counter-productive in a deal”

In relation to the blog I posted last week exploring the question “How can you turn a market downturn into your tailwind,” we focused our CEO Mastermind last week on the importance of ROI in B2B SaaS Sales. This revealed some interesting insights.

One participant summarized the challenge around ROI nicely
“I understand that sometimes ROI needs to have like $ value to it, but I think that shouldn’t be like a generalized rule of evaluation”

The problem?
It all depends on who you are selling to.

  • For a head of Field Service operations, ‘ROI’ is often “Are my people safe”.
  • For the CFO in a stock listed company ROI can be extremely important to drive EBITDA
  • For a CFO in a VC-backed scale-up focus will be on maximizing top-line growth, not cost reduction.

What’s at stake?

  • “Very often ROI comes up as an argument because you’re selling to the wrong audience.  The group in the middle that basically like the idea of your solution, but feel like they need to justify themselves to be able to get it signed off”

The urgency?

  • “How then can you take advantage of the companies where the pendulum has swung too far in the wrong direction. Where companies have over-corrected. That creates the opportunity.

Here’s the thing:
As they say: ‘Not everything that can be counted, counts. And not everything that counts can be counted.’ Having extremely fast ROI can be an accelerator – but it can also lead you in the completely wrong direction – and hence be counterproductive in a deal.
This goes back again to truly understanding your customers and how external factors influence their decision-making. Getting crystal clear what’s changing and what’s become most challenging?

Find the areas where your solution can exceed expectations around mission-critical situations. Only then – decide if there’s anything in the way that could delay a deal. That can be ROI – but it can very well also be the way you communicate about your value.

With respect to this, this one participant shared this:
“We’ve repositioned the entire business off the back of that. With first Brexit,  then COVID, and now the Ukraine war we shifted from being very advertising/marketing lead to being sales lead. Because budgets are just completely different.”

The question I want to leave you with to reflect upon:
What is currently shifting for your customers, and how is this affecting how you are positioned in their eyes?

23 May 2022 – “How to position yourself when you’re biggest ambassador hates you?”

One of the challenges we addressed in the live CEO Mastermind session last Thursday.

We focused on a tedious positioning use case from the Cyber Security space. All the ingredients were ideal. The product…

  • …solves a highly expensive problem: Avoiding ransomware attacks from happening
  • …has clear Product-market fit
  • …has incredible differentiation
  • and …nobody in the market disagrees Ransomware is a problem

Still – not enough traction.

The problem/struggle?

  • “Distrust – People generally cannot believe it’s possible what we do”
  • “Being the enemy – Our biggest ambassador (CISO/CIO) sees as us a threat to his/her job – hence they hate us”

What’s at stake /the fear? 

  • “Obviously runway drying up. Without enough traction, no single company survives”

The difficulty?

  • “Changing attitude: Companies rather pay the ransomware fees than goin through the process of setting up a proper infrastructure to protect themselves”
  • “Overcoming Fear: Companies rather refrain from telling their strategic partners that they are compromised with ransomware – in fear of harming the relationship”

Here’s the thing:
it’s a dream for any company to solve an extremely valuable problem in a way no one can. Still, it’s not always the best technology or product that wins. Often it’s positioning or packaging that sits in the way. And that’s the case here. 

The problem to overcome is a psychological one rather than a business issue. And that starts by finding a way that will make your biggest ambassador feel like a hero. Until that’s the case – the door will be smashed in your face.

Here are some ways to go about that

  • Turn negative into positive – f.ex. by helping turn a cost centre into a profit centre 
  • Reconsider the moment you do your magic – i.e. before the harm has been done.
  • Who can you leverage that recognize they lack something you have in abundance?

The question I want to leave you with to reflect upon:
Looking at this case, a dream case on paper – could it be you are leaving money on the table with your SaaS solution? If so, what positioning change could you consider to find the maze to that hidden tipping point? 


16 May 2022 – “Our next raise is 100% dependent on a compelling Ecosystem plan”

“How do I create a partner ecosystem that’s rewarding enough to enroll in, but also drives loyalty and doesn’t detract quality?”

This was one of the challenges we addressed in last week’s CEO Mastermind session..

The problem/struggle?

  • “Our aspiration is to start a movement. Right now, we have an onboarding team in our company. It isn’t scalable.”
  • Having a sizeable onboarding team is too much of a liability for my business at this point

What’s at stake /the fear?

  • “That onboarding fee that we’re offloading to our partner simply isn’t enough for them to make a dent in their business”
  • “That the quality of work will suffer if done by partners – which will instantly affect our aspired customer experience.”

The urgency?

  • We’re raising €1.5M round at this stage, and a partner strategy is a very important ingredient to secure that.

Here’s the thing:

Scaling a SaaS business has many facets, and leveraging the ecosystem can be a fundamental one. The big question is, how can you make it a flywheel that accelerates momentum. An often-made mistake is that the motivation for leveraging partners is an internal one. We forget to articulate what would make it irresistible for ‘the other side’. This doesn’t mean we have to give everything away. It means we offer something valuable and desirable. 

In respect to this here are some ideas to consider

  • What upside will a partner experience beyond the obvious service they provide to your customers? 
  • Who in your network recognizes they lack something valuable that you have in abundance?
  • Often certain things are not negotiable for us – like exclusivity. But what would have to be true for you to be perfectly comfortable offering this?
  • Which groups in your network are you discounting to be of value because you believe it would never work? What if you’d reframe how you position your offering? 

The question I want to leave you with to reflect upon:

What would have to be true to 10x the size of your SaaS business by going all-in on an Ecosystem strategy?


9 May 2022 – “The challenge we have is Top of the Funnel, not conversion”

“We’ve grown fantastically over the past two years and built a multi-million dollar business based on my network and connections in the industry. However, entering the next phase of scale, my ‘fabulous network’ can’t keep up with the demands of the funnel.”

The problem?

  • “Our decision-makers are not on social, and not heavy email users either. So leveraging the efficiencies of digital tools for outbound doesn’t work for us
  • “Leveraging networking and personal networks works, but it’s not scalable to the level we need it”

What’s at stake?

  • “Not meeting growth expectations from our investors”

The urgency?

  • “The middle of the funnel is drying up rapidly and we’ve exhausted the personal networks in our company”

Here’s the thing:

To grow enough traction, constantly fueling the top of the funnel every is critical for every B2B SaaS company. The question is: with how many leads? Answering that question depends on basically 3 components: your topline target, your average win rate, and the velocity of your sales cycle. This is where clarity around segmentation, positioning, and value proposition (i.e. your value foundation) becomes a critical lever.

The better you define who you’re for (and not for), the better you’ll be able to attract the right leads, speed up deal velocity and increase win rates. I’ve seen companies transform from winning 2 out of 10 to winning 8 out of 10. Suddenly you don’t need 100 leads per month (to win 20), but just 25. Suddenly the problem becomes much more manageable.

In respect to this, this quote might be of value to you:

“Having a clear value proposition really helped us in ways we couldn’t have anticipated. Everything that I expected to happen from investing in this, happened, which is a bit strange, cause that rarely happens. The best thing: Focus. Focus on the things that we’re actually good at. Focus on the things the market should know us for. But beyond that: the ability to standardize things, and the ease of explaining what we’re doing in a way that resonates both internally and externally. Lastly – it helps with capital fundraising. What was missing was a simple way to explain how we are going to catch the market. The value foundation gave is the three pillars.”

The question I want to leave you with to reflect upon:

What’s the quality of the leads at the top of your SaaS funnel? How much does really this cost your business in marketing, sales, and eventually services and development?

2 May 2022 – How to maintain multiple X growth?

This was one of the challenges we addressed in last week’s CEO Mastermind session.

The struggle

  • “Finding enough critical mass and creating repeatability”
  • “Growing traction, without giving up on the  long-term vision”
  • “How do we spark a movement around the ‘huge’ societal problem we’re solving tomorrow when there’s a disconnect with the ‘expensive’ problem our customers are dealing with today?”
  • “Scalability of the business – not being able to onboard new customers fast enough”

What’s at stake

  • “Being forced to look for additional investment money to solve the short-term runway challenge”
  • “Not living up to investor’s expectations to secure the next round”

The urgency

  • “Runway. We need to bring in money today to fuel the mission”

Here’s the thing:

The difficulty of achieving multiple X growth varies where you are on your journey in terms of ARR. That said, poor product-market fit, too broad segmentation, unclear positioning, or a generic value proposition complicates things in all stages. 

This leads to a vicious circle: Short-term runway challenges. A need to fund the business when it’s not ideal. Unfavorable funding conditions. Unwanted pressure from external investors to meet their expectations. And so on….. 

The odd thing is when we’re experiencing challenges to create traction or see growth stagnation, 9 out of 10 start/scaleups decide to shoot wider, instead of focusing on the essence.

Here are some gems from the call that might help you to overcome this:

  • The two-way punch: “Invest time in creating a narrative that addresses a use case customers are willing to pay a premium for while making your long-term promise the cherry on the cake”
  • Don’t only focus on product (technical) scalability, but also invest in business scalability – f.ex. through a monetization model that incentivizes adoption
  • Stickiness of your product or platform: Give people a reason to come back often and even better – drive vitality for your product amongst peers
  • Focus – Niche down (rather than broaden your scope). Get critical mass fast and then address an adjacent area

The question I want to leave you with to reflect upon:

What’s standing in the way of your startup to sustain multiple X growth? What’s the one thing you can start tomorrow to change that?

25 April 2022 – “Hiring the ‘big shots’ in my SaaS Business – when’s the right moment?”

“It’s tempting for me as a new entrepreneur to start thinking about hiring veterans. But when is the right moment – and why?”

This was one of the questions we addressed in last week’s CEO Mastermind case study.

“We bootstrapped up to about $3M ARR and about 30FTE (no veterans) and did our Series A. One year after… we crashed. In hindsight, we didn’t have a repeatable, go-to-market engine. If you cannot repeatedly close X amount of deals in a certain period with almost the same type of funnel metrics then I would never hire a senior exec team at that stage anymore.”

The problem?

  • Big shots come with a lot of experience, but also with a big price tag

What’s at stake?

  • Hiring too early (not having a repeatable go-to-market engine) you won’t be able to leverage their experience to scale your business multiple X.

Here’s the thing:

Too often we start scaling too early. There’s barely a product-market fit. Segmentation is off, positioning isn’t crystal clear, and the value proposition is not compelling enough. Still we make the bet, often through a VC funding round. And this is where problems exponentially grow. Expectations about growth trajectory are unrealistic and wrong choices are made about where and how to invest the money. This drives unnecessary stress (not even talking about the unnecessary dilution at this early stage)

There’s nothing wrong with VC funding as long as it can be spent on amplifying a fire that’s already burning strongly.

In respect to this, this quote might be of value to you:

“We were selling to 20 different industries. It wasn’t sustainable. Too many different sales motions, and product roadmap requests. We decided to double down on 1 industry where we could leverage a big market trend. In 2 years we grew that segment to half the revenue of the company (from just 4%). It’s the reason we got acquired. It accounted for 75% of our valuation. That’s the power of focus and positioning.” 

The question I want to leave you with to reflect upon:

Does your SaaS business has a strong repeatable go-to-market engine? If not –  What if you narrowed your focus and leverage positioning to become a vendor no one can ignore?

19 april 2022 – “How to avoid the hidden traps around exclusivity deals in SaaS”

This was one of the challenges we addressed in last week’s CEO Mastermind session

The problem/struggle

  • “How much should we charge for exclusivity?”
  • “What traps should I look for?”

What’s at stake /the fear 

  • “What if they don’t deliver upon their promises? We can only do this deal once – it’s exclusive?”
  • “What if we leave money on the table?”
  • “How do we prevent we don’t end up with no deal at all?”

The urgency / difficulty

  • “There’s momentum now. We have two parties chasing me for exclusivity, however, which one do we bet on? One is much larger (but can’t move fast), the other one can move fast (but has a much smaller reach).

Here’s the thing:

Exclusivity deals in SaaS can be a very effective way to gain rapid traction in specific niche markets that are dominated by aggregators, especially when you’re an “embedded play” with an API.  ​​Doing exclusive deals (as opposed to selling through a traditional OEM/Partner model) can dramatically reduce your variable costs and Opex, and help you gain momentum fast through specific verticals simply because of the rules and commitment around such a deal. 

The big question is: Given the ‘exclusivity’ aspect – how do you structure the commercial side of the deal? How do you prevent undercharging / giving away too much margin? Cause once the deal is a deal, that’s your only route to market in that niche – and success is in their hands. 

So, one tip: keep your options open by tying exclusivity to performance – and incorporating critical milestone review moments in your contract.

The question I want to leave you with to reflect upon:

In what areas of your SaaS business could you spark momentum through an exclusive deal? What would be the go/no go conditions for such a deal?


11 April 2022 – “How do you define best quality growth?”

“We all know that 10x a year is not necessarily the best or most sustainable, but how do you go about defining your optimal growth trajectory?”

This was the challenge we addressed during last week’s CEO Mastermind session.

The problem:

  • “advisors primarily want us to go after the biggest markets rather than where we have the highest value”

The fear:

  • “Being all over the place i.e. lack of focus, and not being able to live up to expectations”

The difficulty: Being stretched

  • “Internal: longer sales cycles, low win rates and compromised deal value with all consequences to the business” and 
  • “On the investor side: Lower valuation or no funding at all because they don’t believe the market is big enough”

Here’s the thing:

Just because the market is billions in size, and growing with +20% a year doesn’t mean you’re going to dominate, let alone win in it. Zooming into the niche within that massive market where you can gain rapid traction – winning 8 out of 10 and selling to people who are prepared to pay a premium just makes everything easier.

In respect to this, this comment might be of value to you:

“When we get into a new market we have a gated process to define if this market is great for us. We score three questions: 

  1. Market Size, and more importantly, how many customers can we realistically get in that market? How much ARR can it add to our tally? 
  2. Market Sense i.e. is there market maturity? Is there urgency / a compelling event?
  3. What’s the resource required from us to create critical mass in that market?

This becomes a formula. If the score is good we’ll make the plan – so it’s not purely based on the addressable market”

The question I want to leave you with to reflect upon:

Is your SaaS business optimized around the best quality growth for the stage you’re at? What if it was?


4 April 2022 – “How to become the dominant force in a market that requires continuous heavy R&D investment?”

This is the key question we addressed in last week’s CEO Mastermind session.

“The biggest challenge was that we operate in this space, which requires a lot of investment, especially on the r&d side. There is no place for number five or six in the market, you need to be in the top three if you want to be successful and profitable in the longer term.”

The problem/struggle

  • “we’re competing against competitors with much deeper pockets”
  • “Our original founders bootstrapped the company in a very strict way, and beyond that were very risk and change-averse”

What’s at stake /the fear

  • “My biggest fear back in 2019 was: being too late.”

The urgency / difficulty

  • “That we wouldn’t be able to take enough market share by the time our category would really explode”
  • “We were building a plane while we were flying while bringing in $30M funding to scale.

Some of the key lessons and Aha! moments:

  1. “Nail it before you scale it. Avoid attracting funding if you haven’t found Product- and Go-to-Market fit”
  2. “Constantly find the bottlenecks and weed out single points of failure that slow you down. And delegate responsibilities, not tasks”
  3. “You don’t need a lot of people – you need the right people – so deeply know your ideal buyer persona.”
  4. “Brand the problem and create a category – but don’t do it alone. Bring on like-minded players (instead of competing with them)”
  5. “Invest in being different (don’t try to be better) – Stand out in a way that’s pattern breaking and creates significant value for your ideal customers”

The question I want to leave you with to reflect upon:
How well are you positioned to become a dominant force in your market? What could you do differently to accelerate this process?

28 March 2022 – “How to 10x the number of advocates we have without wearing out our scarce resources?”

This was the topic we dug into in last week’s CEO Mastermind.

The problem

  • Without advocates creating traction is very hard, and very expensive.

The difficulty/doubt

  • The traditional thinking is that creating advocates is resource-consuming. That we have to be someone famous, or a big brand. That it has to be expensive. 

What’s at stake

  • Being unable to creating fans can (or losing them) can quickly make your brand bland – and this is felt in recruiting, in your marketing budget, sales conversion – everywhere.

Recently what we’ve done is try to break down the human. We broke it down into two phases, a utility and an emotion. As human beings, we have a purpose that is useful. That’s a utility. And then we have a purpose as an emotional, right, which is the connection, the love, and these things. So how do we put that into the product and into the marketing? And basically, that’s our r&d. Literally, our r&d is the marketing.

Here’s the thing:

We always look up to those companies that have their advocates spread the word for them. What we forget however is that all those companies all started at some point as well. This is much more a mindset issue, than a budget issue. 

  • It’s about being creative
  • It’s about finding leverage

In respect to this, these quotes might be of value to you:

  • “What really changed things for us is talking about my why and getting on more stages. People don’t need to be my customer to be my raving fan.”
  • “We’ve started focusing on the epiphany moment in the demo – the wow moment. One thing we did is making our data beautiful”
  • “The art is in surprising people. Step over the fact you’re offering ‘just a’ B2B solution.”
  • “There’s a fine balance between emotion, unexpectedness, and credibility.”
  • “What rituals can you create – ideally things that are Instagrammable?”

The question I want to leave you with to reflect upon:

“How can you 10x the number of advocates for your SaaS products without wearing out your scarce resources?


21 march 2022 – “They want an exclusive, and I don’t know what I am giving up”

This was a core challenge we addressed in last week’s CEO Mastermind session.

The dilemma

  • “Two market-leading companies in the same vertical have put focus on getting our software – but want an exclusive”
  • “One of them is commercially much more attractive to us, but there’s no way they can move fast” 

The urgency

  • “Our runway is short because we lost our largest customer 6 months ago”

The fear 

  • “I don’t know what I am giving up”
  • “What if I underprice this deal?”
  • “These guys are expert negotiators…. I am not”
  • “I can’t let any of them know what our actual situation is”

Here’s the thing:

It’s a fantastic situation to be in if two companies are fighting over exclusivity. In this scenario, this type of deal was never the setup. So how do you deal with it? Especially when the pressure is on. The way to approach this is by getting a solid understanding of: 

  1. What’s in it for them – what’s the value creation for them IF they get the exclusive. What gets them so excited about ‘wanting an exclusive?’ What’s the upside for them? Is it revenue-related? Is it profit-related? Is it speed to market? Is it differentiation?
  2. What’s at stake when this doesn’t happen? Is this about competitiveness? Is this about cutting the paths of other players? Is this about getting ahead? Is this about catching up? What will they lose when the deal goes to ‘the other side?’
  3. Lastly: With whom can you make the biggest difference? And how does this come to play? 

For Exclusives your normal pricelist don’t work. Throw them out of the window. This is value pricing. And the risk is you underplay what’s really behind this. 

The question I want to leave you with to reflect upon:

Extreme deal situations like this can be eye-openers. So if you look at the essence of your SaaS business – could it be that you’re undercutting the true value of your solution?


14 march 2022 – How to successfully merge a freshly acquired SaaS business? 

Acquiring a company is one, merging it is something different. So what are the mistakes to avoid? This was a topic we addressed in last week’s Mastermind session. 

The problem

Too often we get too excited about the process to close the deal and forget about the fact a lot of the potential is dependent on how successfully we merge the new entity

What’s at stake

Failing to successfully merge a newly acquired SaaS business can drag the entire business down

The difficulty

When you acquire another business, 9 out of 10 you end up with two entirely different businesses – with two entirely different cultures, products, and go-to-market approaches. 

Here’s the thing:

I’ve been involved in many acquisition processes when I worked at Unit4. Many succeeded because they were deliberately not merged: they were acquired for a different reason: Market access, profitability, a legacy installed base.

When we switched to acquiring for technology everything changed. We had to merge to obtain the value. A very painful process – and only after the third acquisition we’d learned some tough lessons. 

The biggest lesson: make sure you’ve got the full plan ready AT the moment of the acquisition: Technology Integration approach and GTM approach i.e. who’ll you’ll sell this to (and who not), joined-up positioning, joined-up value proposition, packaging, pricing, the narrative to the market (to counter competitive FUD), etcetera

It’s a very valuable exercise to do upfront. Not only because it will optimally prepare you for success – but you’ll also learn a lot about what it will be like to work together.

The question I want to leave you with to reflect upon:

Could making a strategic acquisition accelerate the momentum of your business? If so, what would need to be true?

7 march 2022 – “What would your customer miss most?”

Last week we focused the live CEO Mastermind session on this situation:

“Imagine your product would be replaced with another (similar) product. If we’d interview all your customers in 3 months and ask: What do you miss most? How would they respond?”

Some reactions from the reflections:

  • ‘It told me there’s a hell of a lot more work to do’
  • ‘It’s the knowledge of our people, we are experts, but that’s not scalable’
  • ‘A lot of it is hidden – And now I’d question whether people realize this enough’’
  • ‘It makes me uncomfortable – but we must be doing something right cause we’re winning customers and not losing them.

Here’s the thing:

Far too often this is an afterthought. We’re too busy getting our solution out, pushing to build traction, and then doing whatever we can to try to make and keep our customers happy. We end up with ‘so so’ answers to this question, realizing our customers won’t miss our solution as much as we think they would. 

So, what if we’d design with this in mind? Wouldn’t that make everything easier? It’s those things that create the equity around our solutions – giving it defensible differentiation. 

In respect to this, you’d possibly value this

An article from HBR on Bains’  40 elements of value in B2B model. The more boxes you ‘tick’ the more your customers would miss if it if you’d take it away from them.

The question I want to leave you with to reflect upon:

How would your ideal customers respond if you’d ask them the question: ‘What would you miss if we’d take it away from you?’

28 feb 2022 – “I was shocked…”

“We did a long and hard exercise recently about: What is the value we deliver to our customers? Part of the was inspired reading ‘The Remarkable Effect.’ And I’m the first to admit: I was shocked…. whatever we thought was the value we’re delivering wasn’t the reasons our customers were buying our product….”

This was one of the challenges we discussed during last week’s CEO Mastermind session

The problem?

“How do we make the sales cycle leaner, that will enable us to scale faster?”

The urgency

Continue to meet renewed expectations around traction (on the back of Series A)

Here’s the thing

We can think we’re growing ‘just fine’ – but the big question is: Can we sustain it? Growing 3x from $500K to $2million is solid. But with renewed funding the pressure is on – so the next 12 months you have to do it again (and possibly even more) i.e. +$6Million. And again… that’s super hard if there’s a mismatch around what you think is the value you deliver, and what your customers think it is.

In respect to this, this quote might inspire you:

“I have 35 people on my team, but this is something I wanted to do myself. As an entrepreneur you strive for two things: You strive to build something that’s solving a problem and making a valuable impact. The other thing is delivering that with that value with impact. So I interviewed our top 25 customers about what they thought was most valuable. It was a fantastic investment of my time. This changed everything. And it accelerated our growth immensely.”

The question I want to leave you with to reflect upon:

How confident are you that what you believe is the value of your SaaS business is delivering is what your customers think it is? If not – what damage is that causing?


21 feb 2022 – “Will our dual product focus be suicidal?”

This was the essence of the question we addressed in last week’s CEO Mastermind hotseat.

The situation is like this: There’s a platform (SDK) play (broad, not deep) that’s revenue- and profit-generating, and there’s a B2C product play (deep, not broad) that is still in MPV mode, still requires heavy investments and has a higher risk profile

The problem/struggle: “Should we go broad, or deep – or both? 

What’s at stake /the fear: “Continuing on both reduces focus – and could become suicidal”

The urgency / difficulty / doubt

  • “The current funding round, where VCs are asking the tough questions”
  • “The connection to our vision and mission is critical to us.”

Here’s the thing:

These decisions aren’t easy. They are loaded with emotion, to begin with. Obviously focus is key. Trying to do too many things at the same time, often leads to failure on either side. 

Going with the product that brings ‘the easy revenue’, can also be dangerous. Think about questions like this:

  • Which product addresses the most valuable and critical problems for your ideal customers
  • With which product will you be able to exceed expectations
  • Which product has (potentially) the biggest defensible differentiation?

And then there’s something else that’s important (and often overlooked): Passion

In respect to this, this quote from one of the participants might make you think:

“6 months ago I completely restructured my business. We could do three things with our platform and split it up in three companies. The third option was by far the most difficult route of the three of them,

What I learned was this:  I have overlooked the importance of passion and dedication. And I very much overlooked the uninteresting side of the direct financial results. If I would be waking up to a VC who’s pushing me into an area that I am not passionate about, I won’t say I’d kill myself, but it will quickly start doing something else.

The question I want to leave you with to reflect upon:

What in your SaaS business could you change to deliver the biggest possible value to your customers, create the strongest defensible differentiation, and gain the most energy? 

14 February 2022 – “Embrace stress removers and get rid of stress creators”

Last week’s live CEO Mastermind session we celebrated progress on top priorities and shared the key learnings. Here are a couple

  • “Frameworks take the emotion out of things” (one member successfully implemented the Radical Product Thinking framework from Radhika Dutt)
  • Fight to make sure the entire team is aligned with the vision. A sports team that has everybody doing a b-minus plan together is better than a sports team where everyone is doing their own A-Plus plan.
  • “Hire for skills instead of experience. We started to invite people from outside of B2B SaaS. They bring diversity in thinking about a problem that typical ‘b2b SaaS people’ would approach the same way that they’ve done in previous SaaS companies.”

A quote that caught my attention: 

“We let go of our CTO. Making the decision created a lot of anxiety in our management team and but actually, to me, it created a lot of opportunity. 

The key learning: the learning: It took me too long since I didn’t trust my gut. 

I’m normally a guy who rips the band-aid off. But we’re also in a human business, so there is also an element of empathy. But in the end, what you always need to realize is: It’s great that you work with very talented people and with people that are nice, but in the end, you have a business to run. And if the business is being pulled down by somebody, and you can’t coach them to go to that next level, then you need to let them go.

The question I want to leave you with to reflect upon:

Who or what are the stress creators in your SaaS business? Could it be you’re hiding from making the decision your business needs to move forward? 

7 February 2022 – “How to replicate the profitability and scalability model with our biggest partner without damaging our strong relationship?”

One was the essence of the hot seat track we had in last weeks’ CEO Mastermind session. 

The problem?

  • “70% of our revenue is coming from one big whale customer/partner (and growing). Common business thinking suggests putting our eggs in different baskets. This means however, we have to work with other partners – which often are their competitors”

What’s at stake?

  • “Losing the big whale – while not having any backup. It’s volatile. I’ve got so many single point of failure.”

The difficulty

  • “How to derisk the fact searching for partners will be perceived as a threat them”
  • “Compared to our partner, we’re very small. So how critical are we really for them?”
  • “We do have a champion within our partner’s organization – but not at the highest level.”
  • “Going with some of their competitors would be perceived crossing the red line”
  • “The market playfield is really ‘small’ – they control virtually every market that has some volume – so keeping things under the radar is hard”

In respect to this, this quote might be of value to you:

“There are kind of two pieces in play. One is obviously you guys are in different weight classes and they’re in a stronger position. And the other is you’re the one trying to solve all the puzzles and problems. And so is there a way that you can get them to make decisions? 

This means you come in with strength and respect and say ‘Here’s the situation I’m in, I am a builder, I want to ensure sustainable growth, and you guys can lock me out of entire regions and screw my business. So I have to do something about that. I have to diversify my opportunities, but I want to keep a good relationship with you. So help me solve this problem.”

So, change your mindset and remove the emotion from the conversation. Instead of turning you into a negotiation with them, figure out a way to pull them onto your side of the table, so that you guys are solving the same problem.”

The question I want to leave you with to reflect upon:

Are there areas in your business where you’re undermining your potential? What if you’d remove the emotion from the situation and have an objective conversation about it? 

31 january 2022 – Lessons from experiments in embracing Product Led Growth

Last week’s CEO Mastermind session we focused 100% on exploring the big lessons learned in an attempt to embrace Product-Led Growth (with a product that’s high touch)

The problem to solve:

  • How to improve the direct impact of Marketing can have on Sales
  • How to drive a more relevant dialog with potential customers
  • How to shift 6-9 month sales cycles to weeks

Some of the key takeaways worth sharing: 

  • No matter how good your onboarding process is – if there’s no urgency in the mind of your customer, you’ll end up with churn and frustration.
  • It’s not about offering a free version of the full product – it’s about meaningful offering value early in the process (even if that’s with a tiny slice of your product)
  • It’s about helping customers understand/educate them about the gap between where they are today vs. where they want to be. This drives urgency.

In respect to this, this quote might be of value to you:

Rather than targeting key decision-makers, have you thought about going bottom-up? 

We originally targeted CIOs or heads of IT. What we actually found was that by talking to architects who are battling with transformation challenges day in day out, and getting them to try the product, understanding the pains, we actually turned them into internal champions and advocates. That drove the engagement upwards.

The question I want to leave you with to reflect upon:

What component of Product Led Growth could you use to grow your SaaS pipeline with highly relevant leads?

24 January 2022 – Scoring Green on two VC Metrics, and one Red….

The core topic of last week’s live Hot Seat session as part of our CEO Mastermind was: Gross Margin. 

The problem/struggle?

  • Too low gross margin (44%)
  • This drops us to the lowest tier in SaaS performance.
    VCs look at three things: growth rates, gross margin, and Life Time Value. On two of those, we are in the green zone, on margin we’re in the red zone.

What’s at stake?

  • Not enough leverage to fund our next stage of growth
  • It pulls our VC valuation down and hence our ability to secure funding 

The difficulty

  • Changing industry practice: Pricing based on the volume of messages. It’s how it’s been done for years. It pulls us into a race to the bottom.
  • Getting our customers to start thinking about us as a value-add business, as opposed to message volume business

With respect to this, this quote might be of value to you:

“It seems to me that what’s missing is your customer’s return on ‘investment’ i.e. the value you bring. I’m sure your customers know what this is, but it sounds like you don’t know, or at least that you don’t know what their ROI is relative to your customers.

It seems obvious that it’s best to move away from price per message and towards price per result achieved. Assuming you can’t lower your direct cost, all you can do is increase price. To do so, you need to leverage the ROI you achieve. You can only do this if your ROI is higher than your competitors. 

So: Can you find out what the ROI is from your product, how this compares to your competitors, and then propose a new pricing model that is directly linked to ROI?”

The question I want to leave you with to reflect upon:

Does your SaaS pricing model have a direct relationship to the ROI your customers obtain? If not – what if it would? How can you change your pricing model in a way it drives higher Gross Margin, while at the same time your customers would say ‘Thank you’?

17 January 2022 – With a smaller team, we’re getting in more customers than we did with a bigger team”

Last week’s CEO Mastermind was about reflecting on the key takeaways from 2021. 

What I saw was this: Everyone grew – ranging from 30% to 3x. Obviously great, but what I pushed for was not the growth stories, but what was hard – and what did we learn from that. Here’s are just a few insights:

  1. “You can spend so much time pushing out marketing messages and content into the stratosphere. But that doesn’t equal a drip. So pause, don’t invest, make sure you got a drip before you invest”
  2. “Making an attempt to quantify what’s happening internally in our business has proven invaluable. When we now get the question ‘Which growth drivers should we place our bets with funding’ we can answer in detail, instead of just responding ‘more this, more that”
  3. “If you want to go really distributed first, you should seriously consider taking the office(s) away. You’ll avoid ending up with two (poorly aligned) speeds and the corporate politics”
  4. “Don’t compromise on the people that we get. We would have never achieved what we have achieved in 2021 with average-performing employees – never.”
  5. “Communication is key – open door. However, what’s really worked for us in 2021 is learning from each other cross-functionally.”
  6. “The strongest steel, it’s forged in fire,” – if you have a team that’s going through a really difficult time, they’re battle-hardened. And when they get to the upswing in your business they’re really ready to rock and roll”
  7. “An emotional learning experience for me: As soon as you feel that the combination is not fully right: Nip it in the bud. Act – don’t let it ebb…”
  8. “Your product can be a perfect fit. Your technology can be a perfect fit- but if the business model isn’t, things won’t scale. Pivot – fast.”
  9. “I betted on entering a new vertical in 2021. Everyone thought I was crazy. Learning: if you can provide a story that will resonate with just one customer in that segment – a story about change – then they will help you get over all of the bureaucratic safeguards and gates,”
  10. “Think twice before aiming for external funding. It can be a soul-crushing experience. We pulled out – and focus on solving the challenge of generating recurring revenue without putting ourselves into the shade and stressful situations of dealing with investor.”

In respect to this, this quote might be of value to you:

“What I’ve learned is to put in place retention schemes for your top talent. Because we’re all startups because we’re all small companies. So every employee makes a dent, and it makes a big impact. So if it’s a bad hire, it makes a big impact. And if it’s a great hire, it makes an even bigger impact if they leave.

​​​The knowledge they bring and develop while they’re with your company is, to some extent, almost irreplaceable. It becomes really difficult to replace and retrain somebody and get them into the vibe. A lot of business books will tell you startups should shuffle people around to keep on getting new blood, etc. I’m finding the opposite. You get the most out of your top talent by retaining them and getting them to go on and build this journey with you.

The question I want to leave you with to reflect upon:

What’s been the hardest nut to crack for you in 2021 – and how can you leverage that to your advantage in 2022?


3 January 2022 – “How to scale faster by embracing Scaling Deep?”

First of all: Happy New Year – I truly hope the next 12 months will be remarkable, both for you personally and for your SaaS business. 

And the topic in the headline could be one of value for you: Scaling Deep. It was the topic for the hot seat track I ran the last day before Christmas part of the CEO Mastermind program. Fascinating topic – here’s why:

Wikipedia: Although scaling is often associated only with “more, better, bigger” it is important to consider that it has three dimensions:

  • Scaling out involves expanding the geographical spread, or reach, of a technology or practice over time. It is associated with quantitative processes like replication, expansion, extension, adoption, dissemination, transfer of technology, mainstreaming, and multiplication.
  • Scaling up entails creating the necessary social and institutional preconditions for scaling out to happen efficiently. It is associated with qualitative processes like transition, institutionalizations, transformation, integration, evolution, and development.
  • Scaling deep deals with the notion that sustainable and transformative impact is achieved only “when people´s hearts and minds, their values and cultural practices and the quality of relationships they have are transformed”, to make the use of the innovation the new routine.

I agree, virtually every B2B SaaS business is always occupied with Scaling Out and Up – Scaling Deep is often forgotten. And it’s in this domain where we can fire up the flywheel. 

Scaling deep is about creating a movement behind our software business. This is about creating fans and ambassadors. This is about creating leverage by enabling the people that believe what we believe, that see what we see to spread the word for us

The question I want to leave you with to reflect upon:

What can you do differently in 2022 to leverage the power of Scaling Deep to accelerate your momentum?

20 December – “How to best govern a rapidly growing and 100% remote sales team across 3 global regions?”

This was the challenge we addressed during the Hot-seat session in last weeks’ CEO Mastermind session

The problem

  • “Centralizing sales and sell from HQ into different territories just won’t work.”
  • “Our software is very high touch – and establishing trust is key. So having our boots on the ground in all countries works best for us.”
  • “We target customers that are quite old-school who want to interact with people physically. Spanish people like to buy from Spanish people in Spain.

What’s the difficulty

  • “Making this scalable i.e. how to balance centralization and decentralization”
  • “Growing buzz and energy when even people within countries are not together”

What’s at stake?

  • “Losing business – because we’re (locally) too small
  • “Demotivation of our best salespeople – if energy lacks even the performance of our best salespeople drops. Eventually, they’ll leave”

In respect to this, this quote might be of value to you:

I know an amazing leader, David Novak, author of “Taking People with you”. He transformed Taco Bell, Kentucky Fried Chicken and Pizza hut. His secret: Sincere curiosity. When a leader shows curiosity, and sincerely cares about people, amazing things happen. I remember listening to a guy saying, ‘for that man, I would walk through fire, because he cares about me.’ And so as soon as you’re growing a company to the size, where salespeople feel disconnected from the leadership, theor ego makes it real easy for them to give you the finger and do things their way. But as soon as they believe you care, and you’re showing up with sincere questions about them and their life, that does a lot for pedaling the bike.”

The question I want to leave you with to reflect upon:

Beyond bringing disparate sales teams together digitally (via slack or platforms like SalesScreen), what can you do differently to make people walk through fire for you?

13 December – CEO Mastermind recap – “How to reduce waste in our pipeline?”

This was the topic of the hot-seat track in last week’s CEO Mastermind session.

The struggle

  • “We have a lot of inbound requests coming in, but a young, inexperienced team that needs to follow up”
  • “How are we going to filter out who we’re going to help, and who not?”
  • Adding people is no option. We’re fundraising, but haven’t closed the round yet”

What’s at stake?

  • Wasting valuable deals in our pipeline
  • Developing a bad name in the market

The urgency?

  • Our runway isn’t solid

Here are some of the routes explored:

  • What can you do on your website/communication to credibly qualify out the wrong people while growing energy with the right people?
  • What you’re optimizing for? Revenue, profit, volume of users, positive reviews….?
  • How could implementing a ‘waitlist’ concept become a win-win for your prospects and your business? 
  • How could you leverage the value in the waitlist to speed up fundraising?
  • How would having a buzzing waitlist give you an opportunity to raise prices?

In respect to this, this quote might be of value to you:

“All VCs care about is a monthly recurring revenue arbitrage. If you say, ‘our customer acquisition costs is this, we currently have a waiting list of this, and our lifetime value of a customer is that,’ they’ll plug that into an Excel spreadsheet, and they tell you how much money they’re going to give you.”

“And what if you’d use the fact you’re giving away equity in the company to get people onboarded faster? From a story perspective, it would make your company look incredible (not only to investors). It would make your service look valuable to the people on the waiting list, It would create a buzz in PR. And all of a sudden, more people would want to work for you.”

The question I want to leave you with to reflect upon:

What if you’d turn your sales pipeline into a buzzing waitlist? 

6 December – “What keeps me up at night: How to reach more people faster, in a more scalable way.”

In last week’s live CEO Mastermind session we launched the new monthly theme: Remarkable Software companies surprise and hit the right nerve. When I asked for some critical challenges in relation to this, this came to the table:

The struggle

  • “How to be capital efficient, without missing out on big opportunities”
  • “We have an opportunity to accelerate our funding with the VC that funded us in July. Our challenge: clearly illustrate how we’re going to accelerate our topline”
  • “This summer was a bit of a rocky summer for us. I wrote a plan how to survive. That plan should have been our plan, not my plan.”
  • “It’s quite a stressful time. Our partnership should have been launched a couple of weeks ago at their sales annual sales Summit. But it has delayed..”

What’s at stake?

For all the challenges above what’s at stake is: The fear of losing out on the right deals with customers, partners, venture capitalists, and even employees.

The urgency

“Time – We’re grinding our way forward, dodging enough bullets to stay alive, and running as fast as we can to get towards our goal”

With respect to this, this quote might be of value to you:

“In the last in this month we created a “cookbook” with an X amount of recipes, which we can use whenever we want and wherever we think it’s right to take. It’s a cookbook dedicated to us, to our teams, to our capabilities, to our products to our market.”

The question I want to leave you with to reflect upon:

What could you do differently in your organization to enable everyone to surprise, and hit the right nerve? 

25 November – “My biggest challenge is scaling 3x next year again”

One of the challenges we addressed in last weeks live CEO Mastermind session was this: “How do you triple the size of your business year-on-year without breaking it”

The struggles

  • “Internal growth: Christmas last year I had 45 staff, I’ve now got just under 100 team members globally”
  • “Growing responsibility: We’ve become an essential service – growing +40 customers a quarter”
  • “Ramping up the eco-system – the more business we outsource to partners, the bigger the risk we run customer success will drop’

The dilemmas 

  • “At the moment we’re experiencing 0.5% churn. And NRR is going at 115% YOY, but during the pandemic, it dropped to 104%
  • “If you don’t have that retention, if you don’t have the proof of a quality product, you don’t get your reviews
  • “90% of our inbound leads is coming through reviews – that’s our flywheel”

The fear

  • “That market valuation drops instantly since we’re publicly listed (ASX)”

In respect to this, this quote might be of value to you:

“At the end of day, how the product is actually implemented is where the customers get the value. So if you outsource that you actually outsource the success of your platform.

If you got a high churn business, no one’s paying attention to you. If you’ve got a low churn business you’ve got a quality product. But there’s always going to be that urge for quick win optimization, improving, or speeding up onboarding. Fact is: if you don’t have that retention, if you don’t have that proof of quality product, you don’t get your reviews. 

At the end of the day, it’s the reviews that are actually positioning us on the grids. The better our reviews, then the more organic we can actually get review site traffic versus having to pay for it.

The question I want to leave you with to reflect upon:

How do you ensure your SaaS business can rapidly scale – without breaking things? 


18 November – “We now just have four months runway left…”

This single line set the scene for the CEO Mastermind hot seat last week – and although Runway obviously ebbs and flows constantly, this was a special one:

The struggles:

  • “This was a sudden hit: A strategic partner decided not to pay a significant bill…”
  • “There’s a lot of vibe at the top of the funnel, nothing at the bottom…”
  • “All our deals in the pipeline require long procurement cycles and/or are part of a larger (embedded API) roadmap with our (ISV) customers.”

The dilemmas:

  • “We’re not aligned. My choice “Double down. Chase the dream.” vs. My COO’s: “Exit now”.
  • “Having to cut costs to survive (i.e. salary) with our developers that are critical getting out of this challenge i.e. support vendors successfully embed APIs into tech-stack.”
  • “Raising money is a full-time job – meaning I am not driving the sales…”

The fear:

Running out of money before we get even close to revenue”

The hot seat highlighted many solution directions – some obvious, some eye-opening.

Most value came from active reflection though – on responses like this:

“Survival as a strategic goal has never worked for me. Usually, when you just focus on that survival, your stress level goes through the roof, you barely make it. Sometimes you don’t.

There’s a number of different routes you can take.


But all of them depend on what you want.

Do you have lots of IP, and there’s one thing you’re really passionate about?

Are you’re willing to let other things go? Do you have a desire to be the person running it?

Are you more interested in seeing the product itself take off and grow than you are having yourself be the one at the head?”

As such, the reflective question I want to leave you with is:

Imagine a setback like this hits your desk: How do you take out emotions and get to clarity?

11 and 12 November – “We want to accelerate our Series A, but I am worried that for whatever reason they will not follow in..”

In last week’s live CEO Mastermind session, we addressed a bunch of strategic, but also emotionally drained topics:

  1. “How to avoid the stress of hitting the investor targets who never want to see you miss one”
  2. “We’re making decisions in a dysfunctional fashion – not teasing out the problem well enough, using gut feel and intuition too often. How can we scale it  – cause if we don’t do it now, we can’t retrofit it”
  3. “We started our Series A discussion this week – and the challenge is going to be to prove the scalability of our solution i.e. how it helps accelerate towards €15M ARR and bring our margin up from 45% to at least 60%”
  4. “We made the decision to go full virtual as an organization – but how do we maintain our culture advantage”

One key takeaway worth sharing on this key question: How do you deal with people who feel they only contribute a little bit to the vision by virtue of their role? 

“Well, there are basically two options: Either you or they are going to find some way to better contribute or they’re going to leave the company. I think it can it boils down to you’re either aligned, or you’re not aligned with the vision. And if you’re not aligned – and honestly  I had a lot of struggle with this – but one person in this call beginning of this summer said: ‘if you’re misaligned, nip it in the bud.’ That’s exactly what I did over the summer, and I think that’s been something super important.”

That leaves me to give you a question to reflect upon for yourself: 

How do you enable anyone in your business to live and breath the vision as your business doubles or triples year on year?


5 November – “My board meeting was tough this week. My first really, really lonely moment.”

This was one of the quotes that set the tone in our CEO Mastermind session on Thursday. Beyond this, we addressed a bunch of strategic topics like:

  1. “Being the CEO and an operational specialist is not sustainable any more – so how do I go about this?”
  2. “One of our biggest partners decided not to pay any of the bills from the last six months – this has significantly impacted our runway.”
  3. “How to go about finding funding when the heat is on The biggest challenge we have is not demonstrating weakness when we act with urgency. So how can we be urgent without looking needy?”
  4. “How do I take our existing vision and mission and make it ingrained in our company?”
  5. “What is the single most meaningful metric you’re using to measure traction and impact on customers?”

One key takeaway worth sharing:

“We have a good vision. And as long as we have a very clear mechanism in place that says: ‘As long as people use our product, we make money with good margins.’ Then the real thing that we need to measure is how many people are using it? It’s much more motivating for the team as well.”


30 October – “I realized again I should more often step away from the problem”

In yesterday’s and Thursday’s live CEO Masterminds, this quote came up three times. 

We addressed a bunch of strategic topics that I believe could be relevant to you as well:

  1. “How to optimize my investor pitch deck to secure the next round of funding to grow the momentum behind our purpose?”
  2. “How to avoid accruing technical depth in our platform?” 
  3. “How to remove the dependency on one strategic global partner – without putting our relationship at risk?”

One of the Aha-moments worth sharing (in relation to point 1):

“It’s critical to get crystal clear about the big picture (our vision) and connect the dots to how you translate this into a believable go-to-market approach. Being a purpose-driven business it’s too easy to stay at “the dream” level. Investors need to believe in the vision – but even more in how we’ll practically make it happen.”

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