Startups are an environment full of both opportunities and challenges for career advancement. The opportunities usually come in two distinct stages: founding and scaling. During the founding stage anybody can take any title and that’s often precisely what founders do. I have previously written about how this is generally a bad idea, but even when it works out well, it doesn’t really extend to more than the first few contributors.
The scaling phase lasts for as long as the company experiences significant growth, and generally offers opportunities for everyone in an organization, rather than just the top layer. As a company expands, new roles will emerge at a very fast rate creating opportunities for those who exhibit leadership and ownership. The emergence of new roles will always be preceded by the need to get something done. Depending on the skills of the leadership team, it will often take some time before the organization formally recognizes the need, codifies it as a position, and starts a formal hiring process. That’s the window of opportunity for career advancement: Recognize the need, take it over without a formal mandate, and just get it done. If you do that there will often be no hiring process because the job will be yours.
Almost all companies prefer to promote from the inside, they are usually just too scared to do so. Once senior leadership recognizes that there is a functional gap, they will generally assume that internal candidates aren’t a good option. After all, the existence of the gap is almost by definition evidence of a lack of internal capability, right? Good coaching might still bring internal contributors into the new role, but time is often working against internal candidates at this point. That leaves the pre-formal period as the best time for people to advance their career as your company scales. Take ownership, execute, and rise into the role. Opportunities for this will pop up all the time as a company scales.
But what happens when the opportunity isn’t directly above your current role? A rising tide will lift up a lot of bodies but it will also scatter them all over the ocean. Your choices at that point depend mostly on the differential between your company’s expansion rate and your personal expansion rate.
The company expansion rate is an obvious concept. New roles will emerge faster during periods of product introduction, business pivots, and other major functional shifts. Of course, some ventures also just grow faster than others.
Your personal expansion rate is a bit more complex, and depends on how fast you can embrace and successfully execute new roles. Unless you have some kind of historical advantage (i.e. having done the job in the past or having been hired below your capability), you will have to learn the new role from scratch – and do so quickly. That requires a blend of critical thinking, extra work, and interpersonal leadership. You need critical thinking to figure out the new role, extra work hours to compensate for the fact that you initially won’t know how to do the new job efficiently; and interpersonal leadership to gracefully obtain support from others when you inevitably stumble (or fall).
How you approach career growth will depend on your personal expansion rate compared to your company’s expansion rate. If the company’s expansion rate is below your personal expansion rate, then go for the brass ring and put in the effort to ride the wave. If the inverse is true, things will be a bit more difficult as you will eventually slide off the top of the wave. That’s unavoidable. Fighting it will only make you unhappy, and even hurt your company if you have sufficient power to actually slow down the venture to your pace. Instead, carefully decide the direction of your slide and ensure that the new role you are headed towards is good for you. This needs to be a deliberate decision and part of your ongoing career dialog with your boss. Otherwise, the decision will just be made for you when your lack of performance becomes actionable. At that point you won’t be obviously qualified for any of the individual subordinate positions either (e.g. doing a bad job in several areas doesn’t make you an appealing candidate for any one of them). End of the line.
I have been in both situations in my career. At Sunnybrook, our company was expanding quickly on both the product engineering and licensing strategy front. My history as the founding technical executive made me the nominal leader for both directions. At the time I was a full time undergraduate student and this was my first job in life. I very quickly realized, in part through some immensely valuable mentoring, that I simply wouldn’t be able to scale fast enough to do both directions justice. Our fledging company would grind to a halt waiting for me to catch up. Instead, we hired a VP of Engineering to take over all product engineering activities.
I had the opposite experience after we sold BrightSide to Dolby Labs. The BrightSide team became a research function at Dolby and my role thus confined to research management. A leadership vacuum quickly became apparent when the video program expanded into other functional areas (engineering, product, tech strategy, etc.). As an audio company, Dolby just didn’t have the existing resources or external recruiting speed to adequately drive the new functions. The pace of the company was a lot slower so I rode the wave  – ultimately rising to take cross-functional responsibility for all the functions as they emerged.
Both cases were extremely positive for my career. That’s obvious for the second example but also true for the first. At Sunnybrook my focus shifted to intellectual property strategy and technology architecture. Doing so not only enabled us to build a successful company, it also allowed me to truly own my now “down-graded” CTO role, become a domain expert in video technology strategy and be much more deeply involved in the business side of the venture when we shifted strategic direction to a pure technology licensing play (thus laying not only the foundation for my later cross-functional role at Dolby but even for my current one at TandemLaunch).
Career progress requires both planning and opportunistic action. As a contributor, I encourage you to develop your career in close dialog with the leadership of your company. As a founder or CEO, it is part of your job to ensure that your team understands the organizational roadmap, the pace of scaling and the opportunities that open and close. Combining that knowledge with close coaching of your people will make the difference between the success and failure of your team (and thus your venture).
 That short sentence hides an inordinate amount of effort and interpersonal engagement. I flew over 150 times per year in order to be on the ground in my different departments and at HQ, built bonds with teams forming in record time, and consistently stayed a few steps ahead of deeply experienced domain veterans despite figuring out the new roles on the fly. My role, which in this form didn’t exist at Dolby before or after, wouldn’t have been possible without that effort or the incredible support of my teams and some key leaders above.