When he first shared this statistic with other engineering leaders, they were blown away. “Three years in, I started going around town saying, ‘I’ve had zero regrettable turnover,’” says Boufford. (In fact, it was at a First Round CTO salon where we first heard about this remarkable retention.) “As I realized that it was uncommon, it started to feel like a badge of honor,” he says.
But as the years ticked by and the team remained intact, a feeling of unease started to set in. “Around the four- and five-year marks, it started to feel different, like I was jinxing myself.” says Boufford. “When I saw that our recruiting team had modeled zero attrition for engineering during headcount planning, I had a pit in my stomach.”
It was a conversation with Greenhouse’s CEO that prompted Boufford to inspect this feeling more carefully. “He challenged me to examine why I was laser-focused on maintaining a 100% retention rate. And I was taken aback,” says Boufford. “Prior to that conversation, I’d never entertained the idea that there could be anything wrong with how I’d been thinking about retention. I had viewed it as an unmitigated good.”
Now, a few years later, and with a team that’s since crossed the 100-person mark, Boufford has seen a handful of engineers leave to take on new challenges, bringing an end to the engineering leader’s version of pitching a perfect game.
In this exclusive interview, Boufford reveals why he’s no longer hung up on attrition numbers. In sharing his take on what the industry’s conversation on regrettable attrition gets wrong, he makes the case for why we should all be talking about healthy and unhealthy turnover — instead of aiming for zero.
First, Boufford takes us back to the beginning by sharing how Greenhouse crafted a culture that made engineers want to stay, detailing the recruiting tactics and retention strategies that counteracted common impulses for leaving. Then, he flips the script by sharing why he opened a dialogue with his team about moving on, unveiling the leadership tools he used to jump start the conversation. Let’s dive in.
To better understand how he pulled off the feat of zero regrettable attrition, Boufford takes us back in time, recalling how he built Greenhouse’s engineering team from the ground up. “If I had to put my finger on why people stayed, I think it’s because from our very first hire, we spent so much time thinking through how the culture was going to be established,” he says.
That intentional approach to team building had an unexpected source of inspiration: contemporary philosopher John Rawls. “When I took on the opportunity to build Greenhouse’s engineering team, I took the responsibility of creating a new community really seriously. I started thinking back to a college course that I had taken where I learned about Rawls’ ‘original position,’” says Boufford.
For those who haven’t cracked open a philosophy tome recently, Rawls’ thought exercise works like this: You imagine a blank-slate society and are asked to develop a system of rules, values, and norms behind a “veil of ignorance” that shields you from any foreknowledge as to what advantages or disadvantages you might inherit. Because you could find yourself in any position in society, the exercise forces you to think about creating fair rules from an impartial perspective.
“In starting a new team, I had the chance to create a new ‘society,’ and I wanted to be really intentional about building the team that I’d want to be a part of. I thought about all of the things that had made me frustrated enough to move on from prior roles, and tried to build my team in such a way that those same feelings wouldn’t be conjured up in the engineers who joined Greenhouse,” says Boufford.
From the original position, you’re incentivized to do good and be just. When you create a new team or company, it’s a chance to design the group you always wished to be a part of.
With that philosopher's mindset lighting his way forward, Boufford set to work to assemble his team and gear up for hypergrowth. “Between the summer of 2014 and the summer of 2015, we closed our Series A, B and C, all in the span of about 14 months — which was insane,” he says. “We were growing incredibly quickly and we needed to win the talent war. We ultimately did — I hired 30 engineers in 2015 alone — but it wasn’t easy.”
During that period, Boufford took on much of the recruiting load for his team. “Early in the year, I handled cold outreach to hundreds of engineers, so I had to get creative with my hiring tactics. Just about every day, I had breakfast, lunch, dinner and drinks with engineers. I asked for referrals, then I asked my referrals for referrals. I started an engineering meetup in New York and got on the public speaking circuit,” he says.
“But at seed and Series A, the reality is that recruiting can be unbelievably hard,” he says. “You can meet with engineering candidates for every meal, every single day, but it’s still going to be tough to sell them on working for a company that they've never heard of. The hard truth was we had no brand equity and many of the candidates I wanted to hire had a ton of other options.”
Boufford turned his attention toward carving out a differentiated recruiting message — and drew inspiration from another function. “When I read SPIN Selling, everything clicked into place. It’s a sales book, but I found so much overlap with recruiting engineers. It unpacks solution selling as a principle,” he says. “Solution selling is about discovering pain points and demonstrating how your solution — or in this case, job — scratches their specific itch. You shouldn’t waste time talking about the perks if what they really care about is professional growth or programming in Go.”
A common mistake early-stage startups make is trying to hire every engineer that passes the technical bar. Instead, work to figure out whether your vision matches what the candidate is looking for. Misalignment between what you’re selling and what they think they’re buying inevitably leads to turnover down the road.
To suss out that motivation, Boufford relied on these two questions:
What do you hope will be different about your next role?
When you’ve left jobs in the past, what drove you away?
These questions unlocked emotional stories. “Most people have dealt with deeply frustrating moments at work — I certainly have. One year, while at another company, I had worked hard to achieve a lot of important goals, but during our annual performance conversation, my manager seemed to have no idea what I’d accomplished,” says Boufford. “It left me feeling that my work wasn’t valued, and I found myself frustrated enough to start a job search two months later. It was such an impactful moment — that conversation was about fifteen minutes out of my manager's life, but it changed the course of my career.”
After hearing hundreds of stories similar to these in his conversations with candidates, Boufford noticed a few emerging themes. When engineers were dissatisfied at other companies, they often:
Felt unfairly treated or assessed, whether it was about pay, performance, or other forms of recognition.
Felt they weren’t growing. They started feeling inertia in their careers, had stopped learning, or didn’t see a path to the job they really wanted.
Felt disrespected. It was tough to go into work every day feeling disrespected, whether it’s because their ideas got shot down, they had to deal with an overbearing manager or work closely with an unkind colleague.
The final nail in the coffin for many, Boufford found, was a feeling of powerlessness to make their pain point go away — that’s when people head for the exits. Armed with these insights, he set out to solve for these challenges, hoping to find their antidotes and use them as cornerstones to anchor Greenhouse’s cultural foundation.
“By unpacking why people left other companies, I thought I could reverse-engineer reasons Greenhouse would be a place they would stay. In the early days, if I could lay out a vision of how we’d be different on those very targeted, specific fronts — and in the later years that vision rang true — then we could actually do less recruiting over time, because people would stick around,” he says.
People view candidate conversations as a recruiting tool. And while each is an opportunity to add someone to your team, it’s also a chance to figure out how to nail retention. Uncover what other companies are getting wrong — and make sure you don’t repeat those mistakes.
Determined to avoid these missteps, Boufford laid the groundwork for Greenhouse’s culture from the start. Here’s a closer look at the tactics that helped him attract top talent and drive down turnover:
To address common complaints around a lack of fairness, Boufford set out to intentionally build transparency. “People don’t trust that managers or companies are going to treat them fairly by default, so you have to prove it — and too many leaders forget that,” he says.
Here, he gets granular on how fairness can be woven into every part of the hiring, compensation, and performance review process, sharing examples of how Greenhouse pulled it off:
Paint the picture during the hiring process — but don’t overpromise. The bread and butter of early-stage recruiting is pitching a yet-to-be-realized vision. “Your early hires will participate in making your vision real — or not. When you barely exist as a company, the main message you have to lean on is all conjecture: ‘Next year when we're three times as big, this is what it's going to look like,’” he says. “But make sure to underline to candidates that it’s not a promise, it's more like a North Star — it’s on all of us together to make it a reality.”
Open up on how you think about comp. Comp can be a source of frustration and feelings of inequity, particularly in early-stage startups. Boufford recalls how he approached a thorny salary issue at Greenhouse: “Many hires came in at lower seed or Series A wages, and new hires were coming in quite a bit higher after taking our Series B and C. So when it came time for comp reviews, we had a real challenge,” he says. “I had to figure out my comp philosophy. From my recruiting conversations, and my personal experience, I knew it was critical to get this right.” To open up the conversation, Boufford took this question to his team: Is it more important to reward top performers this year, or to level up the people around you who are underpaid because they were hired at an earlier stage? “I asked around among engineers, team leaders, and the top performers to get their take. Without exception, every single one said it was more important to ensure fairness among their peers. So we set aside about 85% to level people up and only spent about 15% to reward top performers that year,” he says. “I talked about this decision publicly — and repeatedly — to make sure everyone knew how we’d allocated funds that year, and why we thought that was the right approach. And it went a long way toward signalling fairness and cementing trust throughout the team.”
Proactively consider emotional reactions. “Too often we don’t stop to consider ‘How do you think our engineers will feel about this comp change? Will it seem reasonable? Fair?’” Boufford bakes this consideration into his team’s comp review process — and recommends other leaders do the same. “I have a template for managers to fill out, with details on their team members’ current comp and a number for the next year along with a simple question: ‘How do you think they’ll feel about this comp change?’ I don’t actually need to review the answers, it’s just a prompt to get my team leads to proactively think about it before they have such a meaningful conversation.”
When you’re hiring engineers, make sure they know what they’re getting themselves into, and then work overtime to ensure you meet those expectations. That’s the recipe for getting people to stick around.
In Boufford’s own experience and in hearing from hundreds of engineering candidates, growth was a lightning rod, an area where complaints — and turnover — spiked. “When I was developing as an engineer, I desperately wanted my managers to take my growth seriously. I’m a big believer in continuous improvement, and I wanted my manager to be a partner, mentor and advocate who would help me to get better, every day. I had high expectations. So, when I had a chance to build a management culture, I made growth a top priority,” he says.
In rapidly scaling startups, personal growth is often put on the back-burner in favor of moving fast and shipping. But even during crunch time, you have to carve out space for your engineers to learn something new — otherwise they’ll look to scratch that itch elsewhere.
Here are the tactics Boufford used to keep growth front and center at Greenhouse:
Evangelize the gospel of servant leadership. “At every All Hands and team meeting, I’d tell the engineers: ‘Your managers work for you. If they’re not serving your needs, shout about it. The leadership team is all overhead — our main job to ensure that all of you can work effectively.’ As the CTO, it’s your duty to reinforce the mindset that the engineers can and should have high expectations for the managers that work for them,” Boufford says.
Act early — and quickly. “I had biweekly 1:1s with every single person on the team and helped to manage their workload until we were up to 20 engineers. I would find out what each person wanted to learn and the types of issues they wanted to tackle, and then I would act,” says Boufford. “I’d reassign them to projects they were interested in as quickly as possible to make sure that they felt heard. If they found themselves stalled in learning new things, I’d help figure out a curriculum or work through a problem together in a whiteboard or pairing session.”
Add programming as you scale. “After our Series B, we had to adapt those personal growth tactics for scale,” says Boufford. “As a management team, we tried to offer lots of support as various team members started lunch and learns, formal mentoring programs, peer groups that took courses together, a computer science book club, all sorts of content programming that communicated that their growth was sacred, necessary and supported.”
Hunt for spots of sagging personal growth during skip-levels. “I spend a lot of my skip-level 1:1 time on whether or not my managers are meeting their direct reports’ needs,” says Boufford. Here are two questions he relies on in skip-levels: What’s on the growth plan you’ve worked on with your manager for this quarter? Do you feel like you’re improving in the dimensions you care about?? “If an engineer can’t articulate how their manager is helping them to level up, that’s probably a good indicator that the manager's not doing everything in their power to support their direct reports,” says Boufford.
Startup cultures typically emerge organically. “When people walk into a new community, they observe the social norms and, for the most part, act accordingly,” says Boufford. “If there's a healthy, respectful environment, most new employees will pick up on that and automatically adapt. That’s why it’s so important that the dominant tone be one that’s rooted in respect.”
Here are two tactics he used to intentionally shape the tone of Greenhouse’s culture as they scaled:
Proactively intervene. “I was always clear that there was no room for intentional disrespect. I remember in the early days of Greenhouse, two engineers were having a ‘voices-raised argument.’ I discreetly let them know that I did not want that to be part of our culture,” says Boufford. “As leaders, it’s easy to avoid the confrontation and just let it slide. But I felt I had to intervene so we didn’t slide down the slippery slope of more problematic behaviors.”
Give your team the toolkit for building respect. For Boufford, this ran deeper than just setting the tone — he also wanted to ensure the team had the tools they needed to exercise respect. “We wanted to bring this to all aspects of our organization. For example, we brought in a communication and negotiation consultant to teach the entire team how to conduct code reviews with empathy and deliver criticisms in a way that would be well-received,” he says.
With a cultural foundation that addressed common causes of turnover, Boufford’s recruiting message resonated — the team continued growing and the engineers kept sticking around. But as he previewed earlier, while that zero regrettable attrition metric had become a badge of honor, it eventually morphed into a source of anxiety. After pouring so much energy into designing an environment with built-in defenses against common causes of attrition, Boufford was now grappling with whether he had been approaching retention with an incomplete perspective.
“As a manager, when someone on your team leaves, it can feel awfully personal, as though it’s a reflection on you, like you failed in some way,” he says. “But our job is to think about the needs of the people on our team. And sometimes what they need is support in taking the next step on their path. I’d go so far as to say that serving the true interests of the people on your team is always serving the best interests of the company as well. If people leave to do other things, and the story of their time at Greenhouse is one of fairness, respect, growth, and empowerment, then they will recruit the next generation of engineers for us by simply recounting their experience.”
Boufford decided to retrain his focus. “I realized I’d been too concerned with the number of people who may leave when what really mattered was why they want to leave,” he says. “When we talk about ‘regrettable attrition,’ we really mean ‘regrettable-to-the-company attrition’ – we’re putting the focus on the manager’s feelings about an employee leaving, versus the employee’s motivations for walking out the door. Maybe that person was treated poorly by the team and you’ve got a real cultural problem that needs to be addressed. Or maybe she got an incredible opportunity that perfectly aligned with her career path and she’s now going to be an ambassador for how far someone can go after working at your company,” he says. “There are healthy and unhealthy reasons for turnover — that’s where our focus should be, not simply on deciding whether or not the company mourns their departure.”
Aiming for zero regrettable attrition is problematic, because it obfuscates the reasons that people leave — and the reasons they stay. Optimize for healthy behavior, not retention at any cost.
This new framing crystallized the path forward. “The right approach is to focus on doing what’s in the long-term best interests of the people on our teams. We realized that we needed to do more to normalize and spur conversation around healthy next steps. As counterintuitive as it seemed and after all the work we had put into making people want to stay, we had to open up the conversation about their whole career — not just the part of the story being written today,” says Boufford.
To kick off that conversation, Boufford started giving what he called the “gold watch talk.” Harkening back to the days when retiring employees were traditionally given a timepiece as a parting gift, Boufford gave variations of these talking points at All Hands:
It’s okay if you don’t plan to get your gold watch here at Greenhouse. A lot of you are early in your career. You can — and should — have other experiences under your belt. Of course, your experience here will be important and formative, but it won’t be your only one. So, to the degree that we are meeting all of your long-term needs, you should stay. This is a great work environment. It's a place to learn a bunch of things, and if there are short-term issues that we can address, we’ll do our best to fix them. But you should still challenge yourself to grow in as many ways as you can — and challenge yourself to stay open to other options throughout your entire career when the timing is right for you.
“Given our lack of turnover, I wanted to create a feeling of safety for those who might be thinking about other opportunities. I wanted to remove the fear as much as possible. My main goal was just to communicate that I didn't expect that everyone would stay at Greenhouse forever, and we didn’t have to pretend otherwise or tiptoe around it,” he says.
On the heels of these talks, here are the additional tactics Boufford leaned on to continue the conversation around healthy turnover.
Create safety. “Not only did I want people to know it was okay to consider other opportunities, I also wanted them to feel comfortable talking to me (or their managers) about possible next steps,'’’ says Boufford. “People have this fear that if they talk to their employer about thinking about leaving, they're going to get fired on the spot — and that fear can be well founded at companies with poor people practices. But as a leader, you have to do as much as you can to create a safe space for open dialogue.”
Be a resource. “I wanted people on my team to leverage me as a resource when they were ready to move on. So I started telling people in All Hands and in 1:1 conversations about the role that I would play if people came to talk to me,” says Boufford. “It was as simple as, ‘I'm well-networked in the New York tech world, so if you decide it’s time to move on, I will help you get a really cool next job, not just a next job.’ I’ve also offered help in how to think through opportunities, talking through the business models of new companies that folks were considering, and helping to examine whether that job would really help them grow in the ways they’re after.”
Open up about your own ambitions. “I’d also frequently tell folks that while I don’t see myself leaving Greenhouse any time in the foreseeable future, I also don’t plan to collect my gold watch here at retirement. I want to be a founder and start my own company one day, and I think sharing that lets people know it's okay to talk about the dreams they have that go beyond Greenhouse,” says Boufford.
Handle departures well. “As CTO, you set the tone,” says Boufford. “Be respectful and grateful. You want to both make it feel positive for the person who is leaving and send the message that departures will be met with respect. There are two mistakes leaders tend to make here: They either complain publicly after someone’s left or they pretend that the person never existed. There’s value in building out an alumni community — I encourage folks to come by the office or to social events after they’ve left.”
After adopting these tactics, Boufford noticed a marked change on his team. “We went from ignoring the elephant in the room to having career conversations in a much more open way,” he says. “Since then, a few folks have left, almost uniformly for healthy and exciting reasons.”
Now that he’s reframed his perspective on attrition — and has a few departure data points to lean on — Boufford has a more fine-tuned understanding of how he’d like to assess turnover.
“The conversation I have with a person that is thinking about leaving mirrors the conversation that I had when I was first trying to recruit them: I want to know what they want to be different from the experience they’re having today," he says. “I want to see whether I have something I can offer to fulfill their needs, and if not, I want to get to clarity around how I can help them land in the best place possible.”
When someone is considering moving on, it’s either due to excitement about a new possibility or it’s a symptom of stress. If it’s the latter, I want to better understand the underlying forces driving them away. If it’s the former, I want to do all that I can to support them in their growth.
Here, he shares a few healthy and unhealthy causes of turnover, peppering in real-life examples from his experience at Greenhouse in the hopes that other leaders can use these examples to start thinking about turnover through this lens:
Healthy: “If every departure fell in this bucket, I’d be pumped,” Boufford says.
Pursuing a new passion: “One person on my team made the decision to leave to study theology. Pursuit of that passion required devotion to something beyond what can be offered by traditional startup life. I deeply respect and admire the decision to take a risk to pursue something meaningful — whatever that may be,” Boufford says. “We only live once, sometimes you just have to go for it.”
Moving on up: “Another was an engineering director, and he eventually realized that for his next challenge, he needed to be at the top of the org chart. He wanted to have all of the pressure, responsibility, and everything else that comes with being the head of engineering, so he joined a Series B startup as the VP of Engineering,” says Boufford. “In this case, I couldn't offer him that advancement at Greenhouse — unless he wanted to plan a coup or try to wait me out.”
Striking out on their own. “Another employee left to become an entrepreneur. If someone wants to be a founder, then at some point they actually have to leave to start a company. If they leave, it doesn’t reflect poorly on the company,” he says. “Greenhouse itself wouldn't exist if not for a couple of folks taking the leap to start a company.”
Unhealthy: In contrast, here are a few causes of turnover that would leave Boufford feeling that Greenhouse needs to do better.
Leaving to a parallel universe: “If we're a Series D SaaS startup running on Ruby on Rails and we pay a certain amount, and then an engineer leaves to go to another startup that has all the same superficial characteristics, I think that's probably an indicator that something unhealthy drove them to that decision,” says Boufford. “I’d worry that there’s something lingering beneath the surface.”
Team dynamics: “If I were to see subtle hints in 1:1s, exit interviews, or pulse surveys about issues with a manager, feeling treated unfairly, or a problem with a colleague, that would worry me. It’s important to follow those breadcrumbs if they appear, as the first person to leave for those reasons probably won’t be the last,” says Boufford.
Stalled learning: “There is perhaps no part of our jobs more important to the long-term health of our teams than the development of our people. If people were to cite ‘learning opportunities’ as a motivation for moving on, that would send up a big red flag for me that their manager had shirked a core responsibility of their role.”
“As we continue to refine this framework, I can see it becoming a key part of how we report on attrition at our next stage of growth,” says Boufford. “Regrettable attrition metrics may not be going anywhere for now, they’re still a helpful lens that helps us to understand what’s happening with people inside an organization. But, I’d argue that ‘healthy’ vs. ‘unhealthy’ attrition offers a sharper snapshot of what’s really going on in a team — and I hope it’s the direction we all start to move in as we rethink our approach to retention.”
As a leader, I want to make sure my departing employees are running toward something, not away from a problem here.
While it might be natural to fear that having more open conversations about what comes next will unleash an exodus of talent, Boufford has found that it doesn’t necessarily open up the floodgates. “One of the engineers on my team confided in me that his goal is to be ‘employee number two’ at a startup. Well I definitely don't have that to offer — we’re a 300-person company now. But I told him, ‘I'm going to go find that for you. Send me your resume and I'll mine my network to make sure that you get that experience,’” says Boufford. “But as soon as I offered that up he said, ‘You know what, I actually want to give it another few months.’ He opted to pump the brakes. I think knowing that option is available, and being able to talk about it sincerely and openly, made a world of difference.”
Boufford’s own perspective on leadership has changed dramatically as well. “I want this to be a place where people can contribute, learn and, if and when it makes sense for them, leave to go do other great things in the world,” he says. “My goal has shifted from holding onto people for as long as possible, to creating the next generation of leaders that's going to fan out and make New York an even better tech scene. If this place is a great springboard for talent, we’ll never have a shortage of people who want to come work here.”
Photography by Michael George.