Partner Spotlight: Trey Guinn, Cloudflare Hiring Manager

Trey Guinn followed a nontraditional path to his current career, which motivated him to take part in the returnship program as a hiring manager. He talks about his experience with the returnship program, where his first cohort of returnees is now, and the special qualities that caregivers returning to work have that other candidates often lack.

Company: Cloudflare
Role: Head of Solutions Engineering

Tell us a little bit about yourself. How long have you been at your company? How long have you been managing a staff?
When I moved to San Francisco, Cloudflare was a company of about 42 people. I was inspired by their technology so I just called them up and pitched them on the need for solution engineering. I had never worked in sales before and had never been a solutions engineer, but I had a lot of experience working with customers in infrastructure architecture and Internet application delivery. I argued that if Cloudflare was going to keep expanding, they would have to work with bigger businesses and those customers would need someone to help them along the way—and hopefully that someone could be me. In the end I asked them to try me out for two weeks, and the gamble worked out better than I could have imagined.

That was seven years ago, and I’m now Head of Solutions Engineering at Cloudflare. There are now over 1,200 employees, and I lead a department of 90. It’s a global team with folks across the world, from San Francisco to London to Singapore.

How did you get involved in the returnship program at your company? What made you choose to participate?
As we built the SE team, I was more focused on soft skills and personality characteristics than just finding someone who had done the job before. Given my own background, I am open to diverse and non-traditional talent. We focus on candidates with an aptitude to learn and the right attitude to empathize with customers, this is much more important than “having done this job before.” Some of our most successful early hires for solutions engineers included developers, project managers, and some people who were only one job out of college—I was basically looking for people who could learn fast, and most importantly enjoyed helping customers solve technical challenges (while you can teach anyone technical skills, I’ve never figured out how to teach someone to enjoy something).

When the returnship program manager at Cloudflare first went around introducing hiring managers to the program, I thought it sounded like an awesome way to hire, and agreed to take part immediately. At that point, Cloudflare had started growing fast and my team was hiring like crazy—we were nearly doubling headcount every year. It’s always been important to Cloudflare to have a more diverse workforce, and that’s not just lip service. A team with different backgrounds is more creative, and can solve problems better and with more unique solutions. So building a team with diverse backgrounds was a huge motivating factor in deciding to take part in the Path Forward program. 

What was your mindset going into the returnship? Did you have any preconceived ideas about what your returnees would be like?
I was pretty much a believer in the program before my returnees got here. My mom is a badass executive, and my aunt was the CFO of a large public company before she turned 30. My aunt then took a decade off to raise her kids before pivoting into a consulting career. I couldn’t get better proof of the talent pool. Not to mention my own background—I recognized that my strange diversity of experience made me good at a job that I had never done before. I think of myself as being biased in the direction of nontraditional talent, and have never been focused on hiring candidates based on titles or direct job experience. I’d rather hire someone who has a foundation of technical experience who is curious, humble, and eager to learn.

How has this initiative changed the way you think about talent? (Has this program changed the way you think about/approach job candidates? Did this program help you think differently about talent?
I’ve found that the Path Forward returnees have both technical foundational knowledge and the valuable soft skills that do well in the general workforce. You can always build on an employee’s knowledge, but life experience can’t be taught. For instance, one of my returnees had been an engineer, then took an eight-year career break. She took the time to raise her kids and do some teaching. So in addition to having the baseline technical knowledge to do well in her role, her career break gave her the maturity, emotional intelligence, and conflict-resolution skills that other candidates often lack.

Did you put your returnee to work on mission-critical projects right away?
We take a more long-term perspective in evaluating and on-ramping our returnees. The framework our team established is to evaluate returnees on the strength of their trajectory. We look at someone’s ability to pick up new knowledge, and a general interest in the role. We set the expectation that an on-ramp could take four months or more, which might mean that it would take several months for the returnee to handle a customer on their own. The returnee might instead act as a force-multiplier, working alongside other solution engineers, which gives them a chance to ask questions, learn quickly, and figure out if they’re a good fit to this role. 

What’s your returnees’ onboarding like? Can you talk a little bit about the support you put in place for your returnees?
We treat the entire returnship as an extended onboarding. We have a really collaborative team and thrive on helping each other out. We match our returnees with more senior members of our team, and encourage them to ask questions constantly, take every opportunity to learn, and to take on as much as they can. So while I do not expect my returnees to be full-time solutions engineers during the returnship, there is an expectation that, by the end of the returnship, they will be at the same level as a candidate coming in with direct experience as a solution engineer. 

It’s now been several years since your first returnees. How are they doing now? Do you feel that they’re delivering?
Absolutely! One of the returnees I mentioned previously is on a path to becoming a director and knocking it out of the park. Other returnees are also on leadership paths, both as technical and people leaders. I’m a very strong advocate of the idea that once you match a person with the right environment success is inevitable. Also, if you only fish from the same talent pond as everyone else, then your chances of finding the best people are radically smaller.  

What would you say to those who are thinking about managing a returnee but aren’t sure yet?
For most positions, when you’re looking purely at hard technical skills, you can find 100 people who could check that box. But hard skills are also the most teachable, so when looking for candidates I suggest focusing on the candidates that have attributes that are very hard to teach: humility, curiosity, empathy, and grit.

The returnship program provides you with a source of employees who have these attributes, a diversity of experience, and an eagerness to learn. If you’re not getting candidates with these qualities from your traditional hiring sources, then you need to broaden your sources to places like returnship programs.

How has this initiative changed the way you look at your company?
It reinforces my trust in Cloudflare’s leadership. Not only is the returnship program the right thing to do, it’s also the smart thing to do. It’s one of those programs that only has upsides, which makes me realize Cloudflare is taking every opportunity to do things better to move our business forward, including being smart about the ways we bring in talent.