Switchers, Growers, Heroes and Rocketships

Career Navigation in Start-up Land

Career advice is one of the most common motivations that people reach out to me. Given the impact that these decisions have on people’s lives, I take these conversations very seriously and try to help whenever possible. Over time, I’ve started to develop somewhat of a process for how one might think about exploring new roles.

The first step is to identify the type of candidate that you are. For simplicity’s sake, let’s call them switchers and growers.

A switcher is someone who is new to working in a start-up environment. They can be coming from college, a large operating company like CocaCola, a service provider like a law firm, or an academic setting. These people are often unfamiliar with the types of roles at start-ups that suit their skills and interests.

Making the transition into the start-up world is daunting. Saying ‘no’ to higher paying jobs in more understood industries can be tough to justify to a spouse, parent, or friend. It feels like there is a new start-up formed every minute. So, how does one separate the wheat from the chaff?

If you are a switcher, consider working for one of your professional start-up heroes. Think about the people that you look up to from afar occupationally. It could be someone as publicly visible as an Elon Musk, Jack Dorsey, Marc Benioff, Marissa Mayer, or Mark Zuckerberg. It could be someone lesser known (such as Paul from Kayak, Neil & Dave from Warby Parker, Brendan from Oculus VR, Hayley or Katia from Birchbox, Georg from FiftyThree, Andy at Bonobos, or Dharmesh from Hubspot), but no less inspiring in their craft, work ethic, leadership, vision, and execution. I suggest you think about your heroes as a starting point because your connection to them is emotional. With heroes, you often cannot put your finger on it, but let your heart be your guide. Few people will ever get to work directly for one of these notable people coming in cold, but I’d encourage you to explore roles on their teams. Working with them will help you understand yourself, and who you want to be. Working for start-ups requires adopting a religion. These are the spiritual leaders.

A grower is someone who has experience working in a fast-paced start-up environment. They are familiar with the types of roles available in the start-up ecosystem and have found the realm that most suits them. That said, they are are looking for a change to accelerate their learning curve in their domain, diversify their experiences, or accommodate a required geographic transition (while staying in same domain).

If you are a grower, “get on a rocketship.” These are the famous words uttered by Eric Schmidt (Google’s long-time CEO) to Cheryl Sandberg (Facebook’s COO) as she was contemplating whether or not to take the Facebook role. Why a rocketship? Some people say that it is better to have a small piece of something massive, than a big piece of nothing. But to me, the argument for joining a rocketship is once again spiritual. When you are on a rocketship, you are winning. You are on team with some of the smartest people in the world, tackling problems that only that team could possibly solve, with the resources to persevere. These are the people who will push you to be better. These are the people who will push you to grow.

So how do you identify “rocketships”?

To begin with, consider piggybacking off of the work of people who’s job it is to identify rocket ships: venture capitalists. There are a couple dozen world class venture firms who have built their multi-decade long track-records doing just this across numerous sectors, but to simplify your search, you can start by looking through the portfolios of the following notable 10 firms (links directly to portfolios): Accel, Andreessen Horowitz, Benchmark, Bessemer, First Round Capital, General Catalyst (my firm), Greylock, Kleiner Perkins, Sequoia, and Union Square Ventures [for a longer list of notable VCs, click here]. These portfolio companies not only captured the imaginations of those who have their eye on innovation, but they are also likely well-capitalized and therefore able to hire new people. One thing to keep in mind is to make sure to validate how well-funded the company is, as it may affect potential job security.

When looking at the logos on VC websites, a couple things will start to happen…you’ll start to recognize emerging categories of companies (i.e. cryptocurrency, crowdfunding, drones, vertically-integrated ecommerce, 3D printing, labor marketplaces…). That may help you identify industries riding on rising tides (mobile, ecommerce, freelancing, cloud, wearables…). Given how quickly the start-up landscape changes, there will undoubtedly be logos of companies that you do not recognize — which could also serve as inspiration.

Many of the companies that you stumble upon will have “Jobs” or “Hiring” pages. Some venture firms provide a consolidated view of what job openings are available across their portfolio. There’s even a new category of “common app” websites, such as Underdog, that help candidates simultaneously apply to many start-ups backed by notable venture funds, or start-up focused platforms like Angelist, which aggregate relevant opportunities. If you do not see a role that suits you, but are deeply passionate about the sector and believe this is your rocketship, do not stop there. Based on what your target company aims to do, what might they need that you can offer? Make up a role — in start-ups there’s more than enough work to go around, and people wear all kinds of hats.

Only after you’ve done your research, begin networking. Find your way to current and former employees of your companies of interest. Find your way to the VCs who have backed them. LinkedIn and Facebook are your friends here. Start with your warmest relationships, and don’t stray too far (asking weak ties can actually hurt you). You may be tempted to email senior people, but know that their time is precious. Focus on the people who have the right combination of insight, connective tissue, and ability to actually follow through.

Once you’ve done connected with folks close to your target company, your goals in speaking with them are four-fold. First, you are looking to understand how things are really going at the company. Often times, start-ups do a great job of portraying an image of things going well (make sure to prod here). Second, you’re trying to get a sense for the level of talent that the start-up is attracting. When I think about where a number of my smarter friends from college are now congregating, for example, there is a lot of talent headed to Oscar Health (a GC portfolio company). Third, you want to know what the culture is like. Is it fun to work there? Do people work the way you do? Is it a place you’ll thrive? You might even check out job boards sites like Glassdoor, which have online reviews of what it’s like to work at most companies (see their review of GC portfolio company, Stripe, here). Fourth, and only if you’ve checked the boxes on each of the prior three, you want a warm introduction to a relevant person at the business as a means to ensure that your interest is noticed.

When asking someone to reach out on your behalf, keep in mind it is asking them to do work for you — time that they could be spending on other things. If you are serious about finding a few opportunity, you should do your research up front to make sure that such outreach is efficient and effective. To this end, I‘d suggest composing an email with your resume (or LinkedIn profile) attached which can be forwarded to relevant company contacts expressing what your precise interests and qualifications are (a modern day cover letter). Such referrers will add editorial to their outreach emails as is appropriate to each situation.

Make sure to always think about how you can be provide reciprocal help to those who help you. If they are working on a start-up, perhaps you can introduce them to a new customer or two from your network. If they are a VC, perhaps you can tell them a couple companies or products that you think are interesting. Every situation is unique, but the thought goes a long way.

Lastly, know that the start-up employment ecosystem changes rapidly, and new roles emerge daily. If someone has clearly demonstrated an interest in helping you find your next job, do not be ashamed to follow-up with them on a polite basis (every couple weeks works with me). A simple reminder service you could consider using is FollowUpThen, an email-based CRM tool that will ping you whenever you want a nudge to follow-up. Venture folks are constantly seeing new things, and sometimes, those turn out to be rocketships.