How Big Companies Can Hire (and Retain) Startup Talent

A few of my recent conversations at tech mixers have drifted to the topic of building great teams. Some people I’ve chatted with are drawn to the idea of pulling in entrepreneurs to their corporate business units.

Start-up know-how and the scrappy ethos that goes along with it are assets to creating change and bringing a different sort of impact in large companies.

Having deep startup experience, myself, and but also having frequently worked with huge corporations, I absolutely agree that teams stocked with a true entrepreneurial roster are often the most effective and dynamic to work with.

However locating the truly skilled ones and keeping them around can be immensely tricky.

Startuppers, as the tech community calls them, are different humans, and big companies need to treat them as such to retain them long enough to reap the benefits of their expertise.

Here are a few tips to help people who work at large corporations understand, source, and retain talent from the startup community.

Why startuppers are sexy

  • They get it done. They measure success on results, not the picture-perfect strategy created for a dozen stakeholders to bestow their buy-in. The only lazy startupper you’ll find came from an over-funded idea with a high cash burn.
  • They are lightening fast. While you were looking for frameworks to adopt, they built a tool with software they’ve never before touched. Then they tested, launched, optimized and wrote up the framework that you just downloaded.
  • They embrace the uncomfortable. Startuppers don’t defer to office politics. They put themselves in the prickly conversations that corporate employees hide from.
  • They are scope-bending ninjas. There is no such thing as “working out of scope,” because their scope has ever-expanding boundaries. I’ve seen back-end engineers pitch to their prospects and have known CFOs who managed marketers and doubled as the HR department.

How to find the right startup candidates
This is not easy. They likely won’t come directly to your team, but here are some tips on finding them:

  • Make a shopping list. Even if your recruiters are already actively sourcing candidates, you can play a role. LinkedIn’s “advanced search” feature can be helpful here. If you have companies in mind where you think your ideal candidates might have worked, start by figuring out the title of the person you’d be interested in recruiting. Your job listing almost certainly has a different title than the ones used at a startup. Do a bit of research to identify what your ideal candidate’s titles might have been at that company, and then look for that title — not the one you’re hiring for — in the search function. If you don’t know what companies you should be looking to recruit from or don’t have the time for open-ended exploration, you can get some help from the same advanced search feature. Set the criteria to 200 employees or below, name your city and industry, and the results will help you narrow down your list.
  • Fish where the fish are. Figure out where those same target companies post their own job listings, and post yours there, too. Figure out they found their candidates and emulate what they’re doing. If you truly want small-company influence, you might scout on Just be sure to thoroughly vet them for a cultural fit with a big company. (See the next section.)
  • Join LinkedIn and Facebook groups. This is going to be *way* more helpful than most things, since group members are eagerly looking for and sharing referrals, and they usually come from a range of company sizes. The Bay Area has several of these. Some groups like Albert’s Job Listings or Bay Area Internships & Jobs require quick approval from the moderator. Others like Hire Club are invite only, so ask your network for a referral (or friend me and I can add you).
  • Go to networking events. A time-consuming yet popular way to meet people from early stage through Series A companies, people will often be more responsive in-person and can easily introduce you to others. Plus the face time helps you more quickly build rapport.
  • Work with the right recruiter. If all of the above sounds like too much work, then hire a recruiter. Make sure this person has experience hiring for startups. Your usual enterprise-level recruiter for your vertical might not have the right network. Not sure where to find a startup-focused recruiter? Use the same search tactics above.

What X-Startuppers need from big companies
Okay, now that I’ve explained who a startupper is and how to find them, if you want to keep them around, you absolutely have to create the right environment for them to succeed. This might mean side-stepping some of your normal processes.

  • Let them write their own job description. Let them live beyond their LinkedIn profile, and you will unlock their best. Personally, having had a long run in the startup space, my best experiences working in large companies have been when I could talk to the C-team enough to understand the company’s short- and long-term needs, and propose a role that would address them and get expanded upon over time. This approach also usually involves a large degree of innovation with systems, processes, or other people (sometimes dubbed “intrapreneurship”) and can feel very rewarding to the right candidate.
  • Be realistic about their motives and dangle the right carrots. Startuppers often have no idea when their next trip to the beach or holiday with the family will be. They may go months or years without teeth cleanings and doctor checkups. And they’ve long since forgotten about long-term savings. The steady income, benefits and predictable time-off that a more established company can offer can be great initial attractors and bargaining chips along the way, and might be your first step in earning their loyalty for the next few years.
  • Give them independence. Let them own their projects end-to-end. Forget about making them “go through the right doors” or work with a large, process-heavy team that comes from corporate. They’ll resent the system, despise their colleagues, and feel miserable without ownership and completion of their work. Where you can, offer them the ability to identify areas of improvement, seek out their own collaborators, and create low-friction workflow.

Startuppers can make healthy transitions into big organizations so long as big companies understand how to set them up to succeed.

Sounds good. Whats next?

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