This is the first in a three part series on the Operators Dilemma that explores how operators can shape their careers through a better understanding of the startup journey, themselves and the options available to them.

Highlights:

• Success in high-growth startups often leads to redundancy due to constant company evolution and changing needs.
• Transitioning through Start, Build, and Scale stages requires different skills and approaches; understanding where you fit is crucial.
• Average tenure for sales, marketing, and success leaders is less than three years, with even shorter durations in fast-growing companies.
• Company growth involves discontinuous changes, requiring adaptation at each stage to avoid failure.
• Operators must develop situational awareness, self-awareness, and a growth mindset to navigate career transitions effectively.

A few years ago I was chatting to one of our CROs, Jennifer Bers, about her role and what was in store for here over the next few years. And she said something that struck me as profound;: “I just landed my dream CRO position. I’ll probably be out of a job in two years.” 

I encouraged her to lean into this topic and write the article above, which we posted on the Notion Capital website, and is in the top three most read articles on our site every month. Two years later she had done great work and was indeed out of a job: self-prophesied obsolescence. The business was going in a different direction and she was no longer the right fit.

She was and is successful, a real operator, but the paradox is that often the more successful you are, the sooner you will be out of the job. 

Companies grow and change. Some of that change is internal. Some is external. Your challenge as an operator is to understand and anticipate that change and respond in a way that is good for you and the company.

“Mews, because of the pace that we're growing, is often outgrowing the rate of the ambitious people we have working for us. So we have to be thinking further ahead in terms of the scope and profile of the people we need.

Founders need to be thinking in every area, “is it now time to bring in a specialist?” Five years ago, person X, who's been here for three years, could maybe give that a go. But now we definitely need someone that's done it before. 

This is hard for people. We try to balance making sure that we develop talent internally as well as bringing in new people because that's critical and it helps us maintain the culture as well."

- Naomi Trickey, Chief People Officer, Mews

Getting into the Founder’s head

The reality is that in the high-stakes, high growth world of venture-backed startups, success means you're paving the way to your own redundancy. Often unwittingly.

This happened to me. And I didn’t see it coming. And it left me reeling for years, questioning and doubting myself. It took me far too long to come to terms with it.  And ultimately accept the company, MessageLabs, was right.

At the time, my father in law said something I’ll never forget: “It’s all well and good to blame your employers, but you need to think about what you could and should have done differently.” Harsh but true.

So while my father in law was right, I needed to learn more about myself - my strengths and my weaknesses and the work I really loved to do. But I also needed to understand better what was going on with the business to understand what was needed next and, just like a relay racer, pass the baton along.

Venture-backed startups operate at extreme levels of pressure and growth, with limited time and resources. They have a death clock ticking in their heads; countdown to burn out, goals to achieve, milestones to hit. They haveVCs breathing down their neck “triple, triple, double, double, double!” Which, by the way, is absurd and incredibly unhelpful, but there it is. 

Whatever the mantra and the VC BS, the founder needs to maintain momentum to sustain a healthy valuation for the next investment round and they need to do that within the constraints of the money they’ve raised. They are hiring great people, who are good for that moment but - assuming the company is being successful are soon way out of their comfort zone. Most really want to keep their best people. Of course they do. Especially in Europe, founders often want to find a way of complimenting the OGs with new blood. But they don’t know how.

Meanwhile, the operators, are head down and killing it. Numbers are up, up, up. But so too are the targets and the expectations. Suddenly the company hits an inflection point. What used to work no longer does. Fingers are pointed. The VCs are whispering in the founder’s ear; “everyone’s in the biggest job of their life!”  Sales, marketing and success leaders are fired. VPs leave. The shit hits the fan.

The more successful you are, the sooner you will be out of a job

The reality of the operators dilemma is born out by the tenures of sales, marketing and success leaders which averages less than three years across the board.  Clearly averages do not tell the whole story. Approximately ⅓ of CROs last more than 5 years. Whereas only ⅓ of the CMOs hired in 2020 were in situ for four years and less than 1/10 are still in the same role after 5 years (data from Thrive TRM). 

When we look at public companies it reinforces the turnover story with, on average, three CROs pre-IPO. 

Looking at the top 20 IPOs of 2020 and 2021, in every instance they had appointed new CROs and CMOs in the two years prior to the listing. Interestingly, In 75% of the companies, the Founding CEO was still the CEO in 2023, but nearly everyone on their leadership teams had changed multiple times.

Tenures can be even shorter in the fastest growing companies. Unsurprising when we understand why.  Without knowing it, the more successful those operators were the sooner they were out of the job. 

But here’s the rub. You can totally play this to your advantage, if you understand what and how companies change as they grow and take responsibility for the career you want.

Growth is a step function

Herein lies the problem. People think of the entrepreneurial startup journey - building a VC backed tech company - as a linear process. It isn’t. Things change dramatically as companies grow and what and who makes a company successful at one stage will not just not make them unsuccessful at the next stage, it will lead directly to their failure. 

The fact that the startup journey is tough, fraught with risk and chaotic is well understood. The fact that it is discontinuous, less so. 

As a VC, when we make an investment, the most important question we ask ourselves is “do we see a credible pathway from $1m to $100m plus in revenue, in less than ten years?” We know the reality is quite different; on aggregate only 1% hit $100m in revenue, but we believe in the possibility of that highly improbable outcome. 

Our research (and experience) tells us that companies stall at common revenue and organisational milestones:  40% stall at or before $3m in revenue; another 20% never pass $10m revenue; and another 20% will never reach $30m.  But a final group, approximately 20% of the companies, will hit $30m revenue, but failure is still endemic; less than 5% (of the 20%) reach $100m in revenue, giving us our 1% success rate.

Why are these failures so consistent? Because the requirements of each stage are profoundly different.

Imagine you are 20 people - all generalists, all “jacks of all trades,” you are doing what it takes to find and win customers, figuring out how to make them successful. Hacky and scrappy. Doing things that will not scale to find product market fit.

Now imagine you have $10m ARR and you have 100 employees, with 10 sales reps and are onboarding another 2-3 every quarter. Has the way you work changed? It better have. Is the sales leader different? Most probably.  Have you specialised roles across every stage of the customer lifecycle? Hopefully! Have you implemented new systems, processes, methodologies? Very probably.

What about when you hit $30m revenue, with 200 people? Or $100m revenue with 600 people. Are we running the business in the same way? Or are we managing the business based on robust data, allowing us to calibrate and optimise every aspect of the business? Do we have managers managing managers? Are we selling multiple products, through multiple channels, in multiple markets? 

You get my point. Everything changes. What and who made you successful at one stage will lead to your failure at the next. 

At Notion we call this Start, Build, Scale.  Each of these three stages requires a fundamentally different approach and of course different people.  Companies inability to anticipate and adapt to these inflection points or step changes is why so many fail.

You can read more about Start, Build, Scale here (overview) and here (full resources).

Armed with this understanding of the journey you can start to ‘Find Your Ikigai’ and shape the career you want, which is the subject of the next post The Operators Dilemma #2: Understanding Your Place in the VC-backed Business Lifecycle Through the Philosophy of Ikigai. You can also have a sneak peek at the third in the series: The Operators Dilemma # 3 - Mastering the Art of Career Development in VC backed startups.