This is the third in a three part series on the Operators Dilemma you can read the first post here The Operators Dilemma #1:Navigating your career through the Start, Build, and Scale journey and the second post The Operators Dilemma #2: Understanding Your Place in the VC-backed Business Lifecycle Through the Philosophy of Ikigai.

• The Serial Starter, Builder or Scaler: Gain invaluable repeat experience in a specific stage of the startup journey.
• The Tour of Duty: Embrace mission-driven assignments to expand skill sets and stay relevant within the company..
• The exception to the rule: While rare, some individuals transition from individual contributors to top executives within the same company, requiring self-awareness, humility, and continuous skill evolution.

In the first article we discussed the realities of startups and the discontinuous nature of growth, and in the second we explored the philosophy of Ikigai to better understand ourselves. The question of this article then is this: how can you use this better understanding of the stages, yourself, you and your founder to master the art of career development in VC backed startups? 

Here are three scenarios:

1. Nail the stage and I go somewhere else and do it again (and again, and again…);
2. Go on multiple tours of duty; or
3. Be the exception to the rule and go all the way..

All three can be great outcomes, but each has very different challenges.

The serial starter, builder, scaler…

There is huge value in being the person a company brings in to get them smoothly from one milestone to the next, from $10m to $30m for example.

My advice on this is three fold:

1. Build experience in a stage, but in multiple different models: sales led, product led, API platform, enterprise, open source…;
2. Signal your intention early to your founders, “if you hire me, this is what you should expect…” and be part of the discussion to hire your replacement to take the business to the next stage, be an excellent leaver; and 
3. Collect your options and move on. And repeat.

VCs will love you, no matter which stage you operate at.

For me, the single most important person in my network is “The Builder” - the person who creates order from chaos, creates repeatability, defines every stage of the customer life cycle, and optimises every aspect of the business. Whether in sales, marketing or customer success. So many companies fail unnecessarily post PMF, because they fail to find go to market fit, which is tragic.

There are numerous people at our portfolio who have been at other companies in our portfolio, learning from that success, taking what they have learned and applying it again. 

This approach gives you the opportunity to be world class at one particular stage, as Jacco van der Kooij, by applying yourself consistently to your craft “you should aim to not just be in the top 10%, but in the top 1% in your field.” 

Go on a tour of duty…

In "The Alliance," Reid Hoffman introduces "tours of duty" (a phrase which has its origins in military terminology) as a way to structure employment relationships based on mission-driven assignments, tailored to achieve the company's goals and advance the employee's career.  

I love the idea of the tour of duty, though I never pulled it off myself. The benefits are huge individually and institutionally. As a company grows they want to keep you as the person who got them to where they are, but you hopefully both appreciate you are not the person to take their current function to the next stage. 

One of the most obvious routes is related to international expansion: 

• “You’ve built a great function for us in our domestic market, now go and do that in the US?” 
• “You built a great team, can you do this again for a new channel or product.? 
• “Can you look into this emerging market and explore its viability?”

If you have attached yourself to a rocketship, then this is a very effective way to stay all the way.

Over the last year I’ve come to know a few people at Snowflake who have stayed with the business for over 10 years, while moving from one function to the next. For example, Ryan Lieber was Snowflake’s first SDR and has undertaken a series of tours of duty: the first SDR in San Mateo, an account exec in the UK, a Sales Director in Israel and now the EMEA Startup Program Manager in the UK.

“The only thing that is constant when you are part of a fast-growing startup is change. If you can’t adapt to these changes whether it is from a product or leadership perspective, then you will slowly become irrelevant within the business. However, it is not enough to just change within the business, it’s critical to ensure that as change occurs, you are still aligning your position and actions close to the drive-train of the core business.

‍From a personal perspective, I live by the motto that if you are not uncomfortable, you’re not growing. Within a startup, if you find yourself getting too comfortable, then you are not pushing the boundaries about what is possible from a creativity, innovation and impact standpoint.” - Ryan Lieber

It may sound easy, but it requires high levels of self awareness and humility to accept you are not the right person to continue leading your function, or to recognise that your long term interests lie in other areas, and to take on a new challenge in a different role with different levels of responsibility. But also requires a high degree of empathy and strategic thinking on behalf of the founder. But the benefits can be enormous. For the individual the life experience and for the company as a way to maintain a healthy culture.

Be the exception to the rule and go all the way.

We all know the saying the exception proves the rule, and there are without doubt people who have made the transition from an individual contributor to CXO of a post IPO business, but I haven’t found any.

When we looked at the top 20 IPOs of 2020 and 2021 we could see that in 75% of cases the founding CEO was still in place, which is extraordinary, even two years after the listing. But there was no one else on the SLT that had been in situ for more than three years.

Nevertheless, let's imagine the journey of a sales person from IC to post-IPO CRO.

The first step moving from IC to sales leader is letting go of your comp plan and becoming comfortable with the fact that your best people would earn more than you. Plenty of people pull this off. 

The second is to learn all the facets of sales management and what it takes to recruit, empower, lead, manage and develop a sales team. The core sales skills are laid out best in Mark Roberge’s book, The Sales Acceleration Formula, but even more important is learning the soft skills of leading, managing, setting goals, giving feedback, and communicating to inspire. All the skills that are too often lacking in startups.

The next step is from a manager to a manager of managers, an even steeper learning curve. 

And then alongside that evolving your skills and capabilities from focusing only on bookings, to revenue as a whole and ultimately to managing a P&L

It's not impossible to do this within one company but it is unlikely. Perhaps more likely is someone developing these skills incrementally over 3-4 roles in 2-3 different companies and then being actively pursued by the hottest startups, post Series A and then taking them all the way. But I’d like to be proven wrong.

‘Put yourself in the path of growth - growth equals opportunity’ This piece of advice has served me well over the years, and one that i’ve applied to each new emerging wave of tech as i’ve looked to secure my seat on the fastest rocketship. WIth growth the organisation will always be expanding and growing, hence new seats opening up. Your choice then is do you become a serial builder, complete a new tour of duty or stretch and grow yourself? I’ve always taken the latter route, using my layers of diverse experience to blueprint what success looks like in my next leadership challenge, because every single role, team and business will be unique. There is no single playbook for success, you need to be agile, nimble, smart and at times contrarian to carve a path to great outcomes - and each time you’ll earn more respect, empowerment, freedom and authority to do it again, Carry your reputation forward in stretching and challenging yourself in new ways each and every time. - Andy Leaver, Notion Capital Operating Partner.

Either the people change, or change the people.

This aphorism, as described by Andy Grove in Only the Paranoid Survive is the answer facing founders as they encounter existential inflection points.

For the operator the question is better positioned as balancing what is best for you and the company. Are you the best person to take the company to the next level or would the company be better to trust someone else. After all, what is best for the company is after all best for you as an equity holder. If I reflect on my journey, in the two years after I left the business it trebled in revenue and was acquired for $700m. So a win-win all round.

Understanding the inflection points of growth and making strategic career decisions is not straightforward and I certainly don’t have answers, but hopefully some useful ideas that can help founders and operators be more successful.

In the fast-paced world of VC backed startups, the key to long-term success is not just about riding the wave but knowing the kind of waves you like to ride.