How We Hired: Jackpocket Founder and CEO Pete Sullivan

When you’re in the early days of growing your team, it can be tough to figure out where to start and how to get the best talent. Hearing from those who’ve been where you are and succeeded in bringing great people on board can be invaluable. Jackpocket, an app that lets users play U.S. state lottery games on their smartphones, grew from a two-person team that was part of the original iteration of WeWork Labs in 2012 to having a team of 60 on its payroll today. WeWork Labs spoke with founder and CEO Pete Sullivan about their early hiring strategies, the best hiring advice he's received and the one thing founders have to do to attract great talent.

WeWork Labs: Tell us about your first hires. How did you find them?

Pete Sullivan: It all started with me and Leo Shemesh, who is our CTO, meeting literally across the desk. And we found our original engineers through connections we knew at WeWork. In the early days at WeWork, there’d be a crew of people that were staying late working on their startups. You could quickly see who was really hustling and we were always trying to utilize the great people who were there and the networks they’d established.

WeWork Labs: What strategies were you using to attract talent in those early days?

PS: First was talking about the opportunity and how they were going to have a direct impact on that opportunity. We were hiring engineers more than marketing or business functions, so I think it was interesting for them to see the impact they were having every day. Another thing was showing momentum. Nobody wants to work in a stale environment. We also used WeWork Labs. We’d bring potential hires to the Lab and let them know that they were going to be part of this community. We showed them that they’d have an exciting atmosphere to work in every day and that they were going to be able to have fun. That helped get people.

WeWork Labs: What traits or qualities were you looking for in those first hires?

PS: One was low ego. A big ego is never a good trait. We also wanted people who could learn quickly and be agile, because we knew there’d be challenges. Persistence was another one. We were trying to disrupt the lottery industry, which is highly bureaucratic and regulated, so we needed people who understood we’d have to jump over hurdles to get there. So it was about not having an ego, willingness to learn and take ownership, and having the persistence to go the full length of the challenge.

WeWork Labs: Have those target qualities changed as you’ve grown to a team of 60?

PS: It’s mostly the same but we try to showcase our core values more. Scaling makes it difficult but I think we’ve done a really good job at recruiting people who fit those core values. That being said, we were also willing to take a risk on someone in the early days because they were willing to take a risk on us. So for example, prior experience wasn’t as much of a core requirement for us then as it is today. Now we’re in a position to really take our time with hiring, especially in crucial roles to make sure that they have the experience we need. That way, they aren’t learning on the job. And we can actually learn from them on day one. So we were more open to taking risks on people but now that we’re more established, pay market rates, and be competitive, it changes things.

WeWork Labs: What lessons have you learned about hiring as you’ve scaled?

PS: What I’ve learned is that the advice to follow your gut sounds cliche but it’s true. A lot of times you’ll know very quickly in your gut if a hiring decision is right or wrong. Another thing is that there could be a right time for the right hire, but as the company changes and challenges change, roles may have to be eliminated or edited. And that’s okay.

WeWork Labs: How has your interviewing process changed as your team has grown?

PS: One change we’ve made happened within the last few weeks. Before, when we were hiring for priority executive positions, the meeting with me would be one of the final meetings. We decided to stop that and have the initial meeting with me. That way we’re not wasting anyone’s time if I feel they’re not a good fit.

We’ve also become proactive rather than reactive. Instead of posting an open role online and shuffling through the resumes that come in, we’re looking in the marketplace for the best people. Then we figure out how we can get in front of them and use our network to talk to them.

Another thing that’s changed is how we score candidates during the hiring process. You can go through a list of characteristics but it’s more helpful to write a list of what you expect this person to achieve in 30, 60, 90 days, etc., and rate them on how confident you are that they can achieve the desired outcomes. You can lose insight when you’re just focused on characteristics like years of experience.

WeWork Labs: What about hiring challenges that didn’t exist when you were just starting out?

PS: We’re now in a position to compete for and get top talent. And it turns out the selection pool for some of these roles is small. We have the characteristics we want in a given role and there aren’t that many people who fit them. And we’re learning that we have to expand the pool for some of these positions beyond New York. A prime example of this is that we were able to get a general counsel from Kentucky. We knew we’d have to deal with a relocation package and it would be a slower hire, but we weren’t finding candidates in New York who met all of the criteria we wanted.

WeWork Labs: What’s the best advice you’ve ever received about hiring?

PS: Having patience with hires and taking your time. There are a million lawyers in New York but getting the right lawyer for our general counsel mattered. You want to fill the position because it could really help accelerate the company but at the same time, making the wrong hire could have the exact opposite effect.

WeWork Labs: What advice would you give to Labs members who are starting to hire for their startups?

PS: Get out there. You have to do that early on because you don’t have the other characteristics that’ll attract people, like capital or a strong brand. What you do have is hustle and the ability to create a culture and a feeling. So get out there, be personable, be social. Figure out how to network, talk to everyone. That’s a characteristic you have to have early on as a founder because it becomes more difficult as the company becomes more complex. Just get yourself out there.

Learn more about hiring as an early-stage startup.

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