Jobs where former founders have unique advantage

The rare assets that former founders have and the jobs that need those assets the most

Regardless of the outcome of the startup, building a startup forces founders to develop rare and valuable skills, mindsets, and experiences which make them uniquely qualified for certain jobs.

Last week, I asked a friend who is hiring for a lot of roles at a big comapny if he put a premium on candidates with backgrounds as builders. His response was “oh hell yeah.” He elaborated that for some of the highly ambiguous roles where candidates would need to be pseudo-GMs, he would prefer former founders. And even for some of the roles with less ambiguity, when it comes to candidates with similar backgrounds, he puts a premium on the candidates who have built something.

So why are former founders such strong candidates? Through their founder experience, they are more likely to have the skillset, mindset, and experiences that enable them to thrive in ambiguity. They also have some of the rare experiences that you can only get through starting a company which give them more deeper insight on the challenges of building things and credibility in the startup ecosystem.

Here are some of the valuable and rare assets that are fortified by experience building a startup:

• Resourcefulness as a skill

• Persuasiveness as a skill

• Resilience as a skill

• Intellectual Honesty

• Deeply understanding the challenges of building something from nothing

• Founder empathy

• Startup ecosystem fluency + network

• Startup street cred

These assets make former founders uniquely qualified for certain jobs, especially these six:

1. Startup ecosystem growth or GTM at a company serving startups

2. Community builder within startup ecosystem

3. Venture studio operator or EIR

4. Venture Capital

5. New Project teams at BigCos

6. PM or GM role where the founder has relevant experience

Startup ecosystem growth or GTM at a company serving startups

B2B companies are increasingly focusing on going to market in the startup ecosystem. For developer tools, like AWS (cloud services), Stripe (payments infrastructure), and Segment (customer data platform)), their biggest customers in 5 years are likely startups today. Additionally, there are other service providers where startups are part of their target market, like MainStreet (tax credit claiming), Brex and Ramp (corporate cards and banking), and Carta (cap table management software).

These companies build out BD, Growth, and GTM functions which require partnering with players in the startup ecosystem and engaging in founder communities.

These roles leverage a unique blend of a former founder’s startup ecosystem fluency + network, founder empathy, and startup street cred -- whether it be a BD role, a product marketing role (where you would need to speak the language of founders), or an evangelism role. Additionally, given how nascent and ambiguous the “Startup Ecosystem GTM” function is, these roles require ownership, humility, resourcefulness, and resilience to succeed.

To find these jobs, go to startups or companies which might be focusing on Startup GTM. Usually, if you search for something like, “startup” or “venture” you’ll find some roles. AWS has a whole landing page dedicated to its startup business development roles and you can also find roles by using “aws” “startup” in a search query. Searching “startup” on Stripe’s career page yields 26 roles. Using ‘ctrl+F’ and searching “startup” on Brex’s career page surfaces a job as a Marketing Lead for their Tech Startup GTM.

Startup ecosystem community builder

Online communities are exploding. Whether it’s VCs building communities within their startup ecosystem, community-focused startups like On Deck which provide community as their primary value-proposition, or companies trying to grow up their Startup GTM functions via community-building, there’s a growing need for people who can build these communities. 

Building a community is easier when the person kick-starting and managing the community is a member of the community themselves. They deeply understand the needs of others in the community, can speak their language, and can serve as astroturf in the community, seeding and answering questions to spark community engagement. Therefore anyone trying to build a community focused on founders or the startup ecosystem will look to someone who is a member of that community themselves -- which is perfect for former founders. 

Finding these roles usually starts with identifying the companies investing in startup ecosystem community-building. They don’t all use the “community” word for specific roles, but fellowship programs, alumni networks, or VC firms that are focused on community or platform services are likely to be investing heavily in ecosystem community-building right now.

Venture studio operator or EIR roles

Venture Studios are essentially startup-building factories. They have teams of operators and entrepreneurs-in-residence who work on internal projects with the goal of spinning them out into successful startups which receive external investment. Working at a Venture Studio -- either as an EIR or another internal role -- is a lower risk way of working on new early stage startups than starting your own. While some internal roles are pretty specialized (e.g. backend engineering, finance), others can be more generalist operational roles (e.g. Entrepreneur-in-residence roles, Business Lead roles, Platform roles).

These are some of the most interesting roles for former founders who want to keep applying their founder skills. These roles take full advantage of all of the skills that founders develop building a startup, but compressed into multiple ventures at the same time.

The best way to find Venture Studio jobs is to go to Venture Studio websites and look at their careers pages. Most of these Venture Studios also showcase jobs for their portfolio companies, so if you’re seeing jobs for their portfolio companies, a pro-tip is to filter the jobs by company and select the venture studio itself. Examples of job boards on Venture Studio websites that have active in-house roles include AI2, Alive Ventures, Atomic (filter company = Atomic), Coplex, Create, Diagram, Founders Factory, High Alpha (filter for company = High Alpha), Human Ventures, Madrona Venture Labs, Pioneer Square Labs, Redesign Health, Science, and Share VC (to name a few).

Venture capital

There are two things that former founders are unique qualified to do in VC: (1) build dealflow and (2) due diligence.

Through former founders’ startup ecosystem fluency, startup ecosystem network, founder empathy, and startup street cred, they have an inherent advantage in building deal flow compared to others trying to break into VC. Even if other candidates have stronger networks on day 1, founder empathy and startup street cred are assets that you can’t fake. New founders prefer to work with someone who can relate to their experience. As one former-founder-turned-VC once told me, “founders like to work with someone who’s gotten blood on their hands.” 

On the other hand, with their deep understanding of the challenges involved in building something, former founders can quickly and intuitively identify challenges that new founders are either underrating or obfuscating, making them invaluable for due diligence and even portfolio support.

However, jobs in VC generally don’t leverage most of the unique founder/operator skills and mindset that former founders have. 

One of the quickest places to start to peruse VC jobs (other than talking to VCs) is this Venture Capital job board.

New project teams

Both at scaling startups and big companies, there are often teams or individuals dedicated to special projects or new projects. These teams work on bold new bets, building new ventures within a company that already has strong resources. These teams value former founders because of their skills building things from zero to one and their ability to thrive in ambiguity. But they also value former founders for thee startup street cred and entrepreneurial DNA they bring to their teams. New project teams within bigger companies need to constantly fight the gravity of bureaucracy that comes with being a scaling startup or big company. Bringing in people who can fight that gravity and keep the company entrepreneurial is important.

Searching for roles and teams that say, “New Projects” or “Special Projects” is a good place to start for these roles. Searching for “New Projects” on Amazon’s job surfaces roles on teams like Amazon Music where hiring managers value entrepreneurial backgrounds. A ctrl+F on On Deck’s career page for “projects” surfaces a role for Head of Special Projects. Searching linkedin Jobs for “Special Projects” yields jobs like the Manager of Strategy and Special Projects at Codeacademy and the Special Projects Manager (New Bets) at Revolut.

PM or GM role where you have relevant experience

While founders - especially former CEOs – have a lot of the assets that would make them successful product owners (AKA product managers) business line owners (AKA General Managers), they also are often risky hires for those roles given lack of deep experience as a focused PM or GM. The way I’ve seen former founders overcome these risks is by finding PM or GM roles where their experience gives them relevant domain expertise for the PM/GM roles. For example, when I moved on from my startup which was in the freelancer space, I was a strong candidate for PM roles at bigger companies that were building products in the gig economy or freelancer space.

Former founders who are looking for these PM or GM roles should first reflect on what deep domain expertise they have from their founding experience and find companies building in similar or adjacent spaces, then explore product roles at those companies that would value that domain experience.