Winter Washington’s path to leadership in Diversity, Equity, and Inclusion (DEI) at Gainwell Technologies is rooted in a career spent observing gaps, connecting people, and finding ways to create meaningful change. As the company’s head of DEI and Employee Experience, Washington has worked to transform abstract concepts of equity and inclusion into actionable strategies that deliver measurable results.
Finding Her Footing in DEI
“My time at Enterprise Holdings shaped a lot of my early thinking,” Washington explains. “I started out running offices and later moved into HR roles—everything from recruiting and training to generalist work and those less glamorous unemployment hearings.”
What stood out to her in those early years were the visible gaps in inclusivity. “I was often the youngest in the room, one of the few women, or the only person of color. Naturally, I ended up answering a lot of DEI-related questions or pushing the agenda because I was in a position to do so,” she recalls. These experiences laid the groundwork for her approach to DEI, which she began formalizing during her time at Enterprise, even if it was just called “diversity training” back then.
After transitioning to Chubb, a global insurance company, Washington’s role became more targeted. “I worked in a team called Culture, which was created to act as a bridge between HR and employees during a major merger,” she explains. “My focus was on workforce diversification, employee engagement, and ensuring employees felt connected during a time of significant change.”
Laying the Groundwork at Gainwell
Washington’s move to Gainwell Technologies in 2020 marked a pivotal moment—not just for her, but for the company. Gainwell was newly independent, and DEI was identified as a priority from the outset. “The role didn’t exist before,” Washington says. “When I came on, they handed me a blank slate and said, ‘What should we do?’”
Her first task was establishing a shared understanding of what DEI would look like at Gainwell. “We had to define it,” she says. “What does diversity mean for us? What’s the difference between equity and equality? What does inclusion look like in practice? These aren’t abstract questions—they’re foundational to how we operate.”
Washington’s strategy included framing DEI conversations in ways that avoided alienation. “If you label something as ‘diversity training,’ it can feel divisive or triggering for some people,” she explains. “Reframing it as general people training or culture training helps. It’s about creating shared norms for behavior, not singling anyone out.”
Progress Through Action
Since Washington took on the role, Gainwell has made significant strides in embedding DEI into its culture:
- Building and Growing ERGs: Gainwell started with five Employee Resource Groups (ERGs) and now has six, with membership growing by 30% in the past year. “We’ve got more than 600 employees involved,” Washington shares. “What’s exciting is seeing these groups evolve from places of shared interest to real agents of change for retention, talent development, and engagement.”
- Transparency Through DEI Reports: Gainwell published its first DEI report last year, followed by a second this year. “As a private company, we’re not required to share this information,” Washington says. “But doing so signals our commitment. The reports include everything from leadership insights to employee stories, making the work more tangible.”
- Diversifying Hiring and Promotions: Gainwell’s progress in recruitment and advancement has been noteworthy. “Sixty-five percent of our new hires are racially diverse, and 57% are women,” she highlights. “In tech, these are impressive numbers—and we’re not stopping there.”
- Veteran Support: Gainwell has partnered with organizations like Hiring Our Heroes to expand opportunities for veterans. “We already have nearly 8% of our workforce made up of veterans,” Washington says. “But it’s not about stopping at a good number; it’s about continuously asking, ‘What more can we do?’”
Breaking Down Barriers
Washington is clear that meaningful DEI work doesn’t happen overnight. “I often tell people, ‘This is a long game.’ The seeds we plant today won’t grow into shade trees tomorrow,” she reflects. “But that doesn’t mean the work isn’t worth it.”
She also emphasizes the importance of normalizing difficult conversations. “We’ve hosted training on topics like unconscious bias and microaggressions, but we’ve also tackled tougher subjects like racial fragility,” she says. “It’s about building the muscle to have these conversations and creating a culture where they’re not considered taboo.”
Washington believes DEI efforts must also be deeply integrated into organizational frameworks. “If DEI sits in a silo, it becomes an extra thing, rather than part of the company’s DNA,” she explains. “My HR background helps me tie DEI into broader strategies around recruitment, retention, and engagement.”
Looking Back and Moving Forward
When reflecting on the progress made at Gainwell, Washington points to the company’s annual engagement survey. “Seventy-nine percent of employees believe that Gainwell is a place where people with diverse backgrounds can succeed,” she notes. “That’s a big number, but it’s not the finish line. It’s a benchmark.”
The company’s DEI work has also extended beyond the workplace into community engagement. Through initiatives like Gainwell Cares, which supports both employees in need and broader philanthropic efforts, Washington is helping to create a holistic approach to inclusion.
Lessons for the Industry
For Washington, the ultimate takeaway for other HR and DEI leaders is patience and persistence. “This work is still in its infancy compared to other business functions,” she observes. “It’s evolving all the time, and that means we have to be flexible and open to change.”
Her advice? “Define what DEI means for your organization, build a strong foundation, and don’t rush the process. When it’s done right, the results will outlast us all.”
Lin Grensing-Pophal is a Contributing Editor at HR Daily Advisor.
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