Wyatt Jenkins’s path to product management was unconventional, to say the very least. After traveling the world as a professional DJ for nearly ten years, Wyatt enrolled in an information technology master’s program because he wanted to learn computer science so he could, as he puts it, “make better techno music.”
Armed with his new degree, Wyatt started seeing more areas for improvement at the intersections of technology and music. In 2003, he joined forces with similarly technically-minded musicians and worked as an early employee of Beatport.com, an online music store and community that allows DJs to distribute their music as MP3s.
For Beatport to survive, Wyatt had to become a jack-of-all-trades. Outreach, contract negotiation, market research, staffing, content management, prototyping, product strategy, and data science only scratch the surface of the laundry list of responsibilities Wyatt owned as Head of Operations.
That versatility and penchant for task management are perhaps why Wyatt never had to take a junior product manager role. He went straight for VP – first, at Shutterstock, where he led twenty cross-functional product teams for five years in their New York headquarters.
Pivoting from professional DJ to start-up partner to an executive at a midsize company might give anyone else, if not culture shock, then at least motion sickness. But, for Wyatt, most of the transitions went smoothly – that is, until he moved to the Bay Area.
Nearly a decade spent performing for people from all walks of life and the five years leading product at Shutterstock had primed Wyatt – a self-described ‘white guy in tech’ – to take diversity for granted.
“When I started out in tech in New York, I knew that people of color and women and LGBTQ people and older folks were underrepresented in the industry, but I still worked on relatively diverse teams. I thought that I understood the extent of the problem, but I moved to the West Coast and realized I hadn’t seen the half of it.”
Wanting to get a handle on the forces behind the stark inequity that he had witnessed since his move, Wyatt spent his first few month in San Francisco doing some initial research. “I started to see managers and recruiters using school and employer brand as a proxy for skill and competence – a shortcut which amplified all the biases of past admissions and hiring committees.”
His newfound understanding inspired him to seek out out a role at one of the few companies he thought could bring him to the source of the problem and set him up to address it on a broad scale. A few months later, he landed yet another gig as SVP of Product, this time, leading the team at one of the Bay Area’s most beloved sourcing platforms, Hired.
Since then, Wyatt has become VP of product at Patreon, where he has continued participating in the larger, ongoing conversation about tech’s diversity problem and what product leaders can do about it.
In the second installment of our series on diversity in product, Wyatt shares what he has learned so far, including: what inclusion has to do with innovation; the similarities between the reproduction of bias in machine-learning and the reproduction of bias in hiring practices; the increasing overlap between diverse teams and data-driven teams; and the growing threat of tech’s elitism to the future of ethical innovation and long-term progress.
To develop an inclusive leadership strategy, make diversity the new normal
As Wyatt readily admits, he has only started to confront tech’s diversity problem in the past two years. Before that, he had come to expect the many identities and backgrounds represented by the ravers in his audiences and, later on, the PMs on his Shutterstock team. If moving to the Bay Area was Wyatt’s fish-out-of-water moment, then diversity was his water.
“My music career set the stage for how I think about difference and identity. It started when I was seventeen. Eventually, I signed with a record label, When I started writing music that got signed by record labels, I had the opportunity to DJ internationally – from Chicago to Rio De Janeiro to Russia to Japan – where I played music for thousands of people, many of whom were very different from me.
“At the time, the rave community accepted people regardless of their race or gender or sexuality. It was a little utopia, a place where people gathered for their chance to be their wild, authentic selves for a night. I saw that openness and celebration of difference, of what makes us unique, on a daily basis. And I was young and impressionable, so I thought other places were, at least mostly, that way, too.”
Wyatt managed to keep this worldview during his time at Beatport, where he regularly worked with musicians, music-lovers, and music labels – the people who made up Beatport’s champions, clients, and users. From there, Wyatt went to Shutterstock, where he led a team of PMs that, as Wyatt puts it, reflected New York’s “melting pot of national origin and educational, socioeconomic, and professional backgrounds.”
Very soon after taking the role at Shutterstock, Wyatt realized that he would need each of his PMs to fully participate in product ideation and roadmap planning for the team to see success. “I wanted the team to feel like they could take risks because that’s what building great products is all about.” In order to encourage risk-taking behavior on a diverse team, though, he had to adopt new habits – habits which eventually became Wyatt’s tenets for inclusion.
Over the years, Wyatt noticed that PMs had varying levels of comfort with sharing what was top of mind. Those differences often corresponded with the person’s identity and their past experiences receiving feedback from a group. “Some of the best ideas can sound incredibly off-base at first. That’s why I wanted everyone on my team to feel psychologically safe in our team meetings. That way, they would put out their ideas, regardless of how silly or impractical they sounded at first.”
During his time at Shutterstock, and now, with his teams at Hired, Wyatt sets aside time at the end of his meetings to directly solicit the opinions of people who haven’t spoken up. “I try not to ask in a way that puts them on the spot, but in a way that encourages them to engage and test the waters with their idea.”
Once someone is punished – whether socially or professionally – for offering up a “bad idea,” however, it becomes harder to get them to participate in a brainstorm. This ends up starving product teams of potentially innovative ideas that certain PMs keep to themselves. To make sure PMs keep taking risks, product leaders have to tread carefully when addressing failure.
“When an idea doesn’t pan out, there are two ways that I, as a manager, can talk to my PMs about it. But there is usually only a split second between when I find out about a problem and when I have to respond to it. That’s why product leaders have to master a calm, thoughtful approach to these conversations. It has to be second nature, otherwise, most of us will react poorly.”
Though executives in tech often talk a good game when it comes to embracing failure, Wyatt still sees a majority expressing disappointment, frustration, and even anger when things don’t go as expected. In product, things often don’t go as expected, so leaders have to be especially careful. A negative reaction – “I can’t believe this happened! What did you do that made it go wrong?” – can have potentially devastating consequences for a team’s dynamic.
“There are two ways to approach addressing a project’s failure. In one scenario, leadership points to the merit of the idea behind the project, acknowledges that they signed off on it too, and then helps generates some new ways to solve the problem. That typically encourages the PM who had the failed idea to keep trying. In the other scenario, leadership laments about the failure, and then inadvertently – or sometimes intentionally – makes everyone feel like they suck. I think it goes without saying that PMs won’t leave that meeting with a bunch of exciting new ideas.”
After witnessing many examples of what not to do, Wyatt focused developed an inclusive leadership strategy that made more room for failure. As a result, Wyatt saw more participation from underrepresented groups in tech, who sometimes feel less comfortable speaking out about what is top of mind. In the long-term, his patient, thoughtful leadership style has generated enormous rewards – allowing Wyatt to lean on the unique expertise of each PM to build incredible user experiences.
Product teams lean on diverse perspectives when they take action on data
The success of Wyatt’s team at Shutterstock hinged on the willingness of every PM to speak up when they felt the product was going in the wrong direction. Full participation was especially important when it came to taking action on data.
“I try to make data-driven decisions whenever possible, but, many times, an anomaly or trend in the data doesn’t contain the contextual clues I need to point me to a next step. Sure, data can tell us valuable information, but it can’t tell the entire story that product teams need to decide on the best path forward.”
Wyatt recalled when his team found huge disparities between the popularity of certain images by location. “For example, when our users search for buildings, our algorithm mostly surfaces photos taken from the base looking upwards, which makes the building the centerpiece of the photo and makes it appear larger than its actual size. Though these images perform very well with our users located in the United States, our users in Japan ranked them very low.”
Most people on the team, including Wyatt, were stumped. They didn’t think about the composition as a stylistic choice, so they didn’t understand why the photos of buildings ranked highest in one country wouldn’t be popular in another.
“Luckily, we had someone on the team from Japan who provided the context we needed to understand the trend. He explained that most people in Japan don’t worship individuality and exceptionalism the way the United States often does. When it comes to composition, a Japanese photographer would be more likely to shoot a photo of a building straight on, so that it looks proportional to the buildings around it. And that was likely why the photos of buildings taken by US photographer performed poorly among a majority Japanese users.”
Once the team situated the trend in their data within a cultural context, they could make the necessary changes to their search algorithm for users based in Japan and bring users the photos they will likely prefer, more quickly. “If our team hadn’t been diverse, and, as a result, not representative of our user base, we wouldn’t have been able to understand and fix the problem.”
Pattern-matching in the recruiting process amplifies existing bias
Though stories like Wyatt’s (and an increasing number of studies) have demonstrated the competitive advantage of diversity in business, many tech companies, particularly in the Bay Area, have failed to increase diversity on their teams or even in their applicant pools. There are many factors – both systemic and interpersonal – that contribute to the lack of diversity in tech, but Wyatt has focuses on a specific trend in the recruiting process that he has seen up close since joining Hired.
“Often, recruiters are overworked. They have to look through hundreds of resumes a day and identify candidates that they think the hiring managers at their company will deem ‘qualified.’ Perhaps unconsciously – and for some, consciously – they will start looking for shortcuts that help them move through the process more quickly.
“Similar to an algorithm, the brain starts to pattern match for certain attributes that they assume make a candidate more successful, or, at least, that the recruiter can point to as evidence that the candidate is ‘qualified.’ Unfortunately, an overwhelming majority of recruiters pattern match on school and employer brand. And then suddenly, having a position at Facebook on a resume or a computer science degree from Stanford becomes a proxy for talent.”
This kind of pattern matching not only makes individual hiring processes biased towards certain candidates, but it also reproduces the race and gender biases of past recruiters and admissions officers. In order to build diverse teams, then, recruiters and hiring managers have to actively fight the instinct to prioritize speed over research.
“To move towards equality, we have to stop valuing certain kinds of degrees, universities and employer brands over others. To move towards equity, we have to seek people outside our existing networks and considering candidates from different backgrounds, who might not immediately seem ‘qualified.’”
Wyatt sees too many hiring committees over-indexing on computer science as the end-all-be-all component of a successful product team. “Some people just need to learn one language and be proficient at it to accomplish certain tasks, and then they have to do other tasks related to product – like management or planning – that don’t require coding. There is a place for all kinds of skills when it comes to a product team. Not everyone needs a master’s in the science of how computers work. Often, that’s not even relevant on the day-to-day.”
Another factor that contributes to the lack of diversity on product teams is widespread belief in the ‘pipeline problem’ – the idea that tech isn’t diverse because the available talent pool isn’t diverse. From Wyatt’s perspective,“That kind of thinking is a bad excuse for laziness.” Moreover, the argument behind it has been disproven. “I just came from the Grace Hopper conference and saw 18,000 female engineers. Companies need to start thinking more creatively about sourcing candidates. And they need to understand that people can come to programming by a less “traditional” path like a boot camp or Coursera and still excel. Or they can be technical in some other way and pick up the necessary skills quickly on the job. If companies just put up a job posting and then hire the inbound candidates, they’ll never fix the problems they have. They have to invest in sourcing tools. They have to invest in outbound.”
To that end, Wyatt encourages companies to adopt programs, partnerships, and incentives that can help recruiters grow a more diverse candidate pool and avoid ones that bring in more from the same cookie-cutter. Referrals, for example, just speed up the process of hiring the same kind of people that currently work at the company.
“If the company has a referral program specifically for a Latinx or LGBTQ employee resource group, for example, that will likely help increase company diversity. A company-wide program, on the other hand, will probably just exacerbate any gaps in diversity that already exist in the organization. In that sense, a referral program is like an algorithm – it just automates the process of reproducing the existing makeup of the company.”
Does tech’s culture of disruption threaten its burgeoning a code of ethics?
If traditional recruiting methods like company-wide referral programs won’t work, then what will? As VP of Product at Hired, Wyatt is always trying to find new ways his product can help recruiters find fantastic talent outside of their existing employee network. Along the way, he and his team have bumped into some of the ethical debates that have cropped up around diversity in tech.
“Like many technology platforms, we have an instinctual desire not to make judgment calls for our users. We want to do our best to serve all the candidates that use Hired in a way that is fair and just. But some of our users on the recruiting side say they want to actively diversify their candidate pool, so we have to balance those two interests. We’re still working towards an agreement about the best way to handle that.”
In the past few years, there has been a push for hiring platforms to start adding filters for different identity groups. Wyatt sees pros and cons on both sides. “On the one hand, it might help remedy historical and present inequities in the hiring process if we gave marginalized groups a boost. On the other hand, we don’t know how people would use it – maybe they would search for overrepresented groups or maybe they would start selecting candidates exclusively to ‘fill quotas.’
Wyatt is more in favor of adding a filter for people’s group affinities – the groups or organizations they belong to or support – which he feels represents values, identity, and culture, rather than the box a person checks on census data. “Not only would it help recruiters source candidates that they otherwise might not have found, but it could also help with inclusion – making sure that diverse candidates actually have the resources and the support they need to thrive at their company. For example, I went to Grace Hopper, a gathering of women technologists, because I care about gender inequality in engineering. I’m not a woman or underrepresented on technical teams, but I recognize the problem and want to help solve it. In that sense, having an interest in Grace Hopper is a proxy for a value: you’ll either hire someone who is a woman or someone who wants to hire more women.”
In terms of addressing tech’s culture problem on a broader scale, Wyatt thinks companies need to practice transparency when it comes to their product. “I think our candidates and customers should know exactly how Hired functions. We should explain why a list of search results is ordered the way it’s ordered because then the end user can ultimately make that judgment call about how they will use the product.
The kind of deep thinking the product team at Hired does about their responsibilities to their users shouldn’t be restricted to companies who focus solely on a recruiting. All midsize companies – and especially ones rapidly moving towards IPO – should start thinking about what they want their code of ethics to look like once they grow into an enterprise company. That way, they don’t make promises to shareholders that they can’t keep.
Of course, it doesn’t help enterprise companies that bureaucracy and process have long been the villain in Silicon Valley’s narrative. “Ultimately, teams can’t adequately address these problems on an ad-hoc basis – it just doesn’t work. They need to build out a process, and everyone else needs to get out of their way.”
Unfortunately, many startups don’t. “Tech’s ethical problems are exacerbated by this culture of disruption.” When well-worn, established companies do spend the time and resources nailing down a clear set of ethical dos and don’ts, they have to reckon with the threat posed by their potential competition – the agile startups who can move quickly, unburdened by the process because they don’t necessarily have ethics to uphold.
Tech can’t solve its opportunity crisis by hiring more white guys
A scalable solution to tech’s deeply intertwined ethics and diversity problem is not a nice-to-have, but a must-have if the industry wants to continue innovating at its current pace. “The number of open positions in technology roles is out of control. I think there will be something like 1.3 million software development jobs in the next ten years and only 400,000 domestic graduates to fill them. So that means not just investing in more diverse teams at the hiring stage, but also making sure underrepresented groups have the same access and support when it comes to getting an education and a technical degree.”
Already, companies and organizations are taking initiative to make sure a diverse pipeline of technical talent remains full in the years to come. “One of my friends actually founded a company called Andela that is trying to address that latter problem. It helps match technical talent from different countries in Africa with engineering companies in the United States. Those are the kinds of programs that need to be built, the kind of talent that we need to source, in order address the opportunity crisis and the lack of diversity in tech.”
Leaders in tech won’t be able to solve one of those problems without solving the other. Wyatt knows that, which is why he isn’t taking any shortcuts. As a DJ turned VP of Product at some of the most successful startups in the tech, Wyatt understands that some lessons take time to learn. And what he learned about the value of difference in the formative stages of his life have followed him throughout his career.
That’s why Wyatt doesn’t kid himself into believing there’s any quick fix for tech’s diversity and inclusion problem. “It’s a long-standing issue that requires an ongoing commitment from leadership. We can’t just make one intervention and expect it to make a meaningful difference – diversity has to be an everyday priority.”