HR’s Rising Stars: A hunger for building drives this leader’s success at InStride

Michelle Hamilton was in college when the Great Recession hit—and she knew she couldn’t afford to be choosy about her job options. Even though she wasn’t in school for HR, when she landed an HR internship, she jumped for it—and quickly found her footing, and her passion.

“I simply fell in love,” says Hamilton, one of HRE’s 2024 HR’s Rising Stars. Now the vice president of people at workforce education provider InStride, Hamilton spent the early part of her career in relatively traditional HR settings: SAGE Publications and CBS Corp., both of which she says were large-scale, heavily resourced and fairly tactical, which helped lay a strong HR foundation. When she found her way into the start-up world, however, her excitement for HR really sparked.

Michelle Hamilton, InStride, HR's Rising Stars
Michelle Hamilton, InStride

“It wasn’t until start-ups that I think I really understood I was made for this,” she says.

That’s because Hamilton describes herself as a builder—someone who likes to foster HR work as it grows from the ground up. She’s had that opportunity in spades at InStride, which she joined in 2019 as an HR business partner when the company was less than a year old. She says she was attracted to the mission-oriented nature of the business, as well as the company’s acknowledgment of the power of workforce education.

“What HR professional doesn’t want what InStride offers?” she says, noting she was “excited” by the chance to power the people processes that would make that work come to life. “It was very much in build mode, which is where I thrive.”

‘Drink your own champagne’

While InStride was helping organizations develop their workforces, InStriders were craving more clarity about their own opportunities for career growth within the company, Hamilton says. Faced with a turnover rate nearing 30% by 2022, Hamilton and her team turned to employee sentiment surveys, using the feedback to drive a new investment in learning and development.

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“You’ve got to drink your own champagne,” she says about InStride’s increased attention to internal workforce education. “We’re selling something to HR professionals and executives of very large organizations, so we have to be able to say that we did it, we tested it, we understand it and we believe in it. And we can show you the ROI.”

Hamilton built out her team with a new point person for L&D, who was tasked with, among other focus areas, driving forward InStride’s Step Forward program. Through the offering, employees can take free courses—for skills development or college and graduate degrees—from accredited providers.

Hamilton adds that the “wild” market of the last few years necessitated that InStride deepen its development efforts—for both employees and leadership—to stay competitive as it strives for rapid growth.

“We’re only five years old, so we’re still developing our leaders,” she says. “There are a couple ways to think about talent—build, buy, borrow—and we’d rather build where we can. That’s a big focus for us.”

Alongside the deepening investment in L&D, Hamilton also brought on another team member who focuses on employee engagement.

By the end of 2023, these moves were part of a successful effort that reduced turnover by 10%. Hamilton notes that the team effectively leveraged data to uncover and tell the story of L&D’s impact on retention—for instance, they found a correlation between enrollment in L&D programs and higher retention rates.

Bucking start-up trends

These transformations were also happening in the wake of the pandemic, which Hamilton says “flipped our ways of working upside-down.” The organization, whose workforce previously worked entirely in-person, had a limited tech stack at the time to drive remote collaboration and culture; having to change how it planned and managed projects was critical for driving success and reducing burnout risk.

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“We had to reinvest our morale and HR budget to adjust to our new world, which meant more time building leaders, focusing on goal and role alignment,” she says. “InStride was lucky it never had to reduce hiring or delay any big projects, but we had to refocus and slow down, which was not in our DNA at the time; start-up speed was our only option prior.”

Leadership ultimately decided to embrace a remote-first environment and lean on employee benefits to enhance employee wellness—and, ultimately, drive engagement and productivity.

Hamilton notes that InStride’s benefits offerings are unusual for a company of its size—fewer than 200 employees—and one still in its early stages. For instance, the organization offers a 401(k) contribution match, a supplemental caregiver benefit launched at the height of the pandemic and a parental leave program. Hamilton notes that 8% of the workforce has taken advantage of this latter program since the organization launched, an adoption rate that is above average for InStride’s size.

While Hamilton jokingly attributes that success to “something in the water,” she acknowledges the role of the company’s holistic focus on employee growth in employees’ willingness to take leave and return to continue their career at InStride.

“There’s a stereotype with start-ups: You burn and churn your junior folks, and just rinse and repeat until it works. That’s not us,” she says. “We’re very thoughtful about how we can help build our employees’ future and hope that they see that future with us. If you want to get a degree, get a certification, grow your family, take care of a family member—we want our people to be able to have a future with us while they do all that.”

To empower workers to be their best while they pursue such goals, InStride instituted companywide wellness days during the pandemic. These wellness days have become a highly attractive part of its benefits package, which also includes unlimited PTO.

However, Hamilton notes that unlimited PTO only has value if employees are actually taking time off—and her team, like many during the pandemic, noticed that employees weren’t using their time.

“[Companywide wellness days] are a way to force the organization to stop,” she says. “Especially in a sales organization, you’re always selling, you always need to be in contact. So, this was a way to say, ‘Hey, we’re all on the same page. Let’s take that breath and do it together.’ ”

Building InStride together

Under Hamilton’s leadership, the company has also come together around diversity, equity and inclusion. When Chief Legal and People Officer Stephen Chu joined the organization in 2022, he gave the HR team a license to pursue its goal of enhancing DEI work.

With People Operations Manager Jasmine Anderson helping to helm the project, Hamilton’s team brought on a consultancy firm and conducted extensive employee listening activities to inform its strategy.

“We didn’t want to use the Band-Aid solution that others use: ‘We’re going to do this’ but then they put nothing against it or just throw some money at an affinity group,” Hamilton says. “We were much more strategic about it. We knew this was a value-add for our business and our leaders.”

Ultimately, the organization rolled out Instride Together, which includes infrastructure to support employee resource groups, training on issues like unconscious bias and micro-aggressions and the tie-in of DEI into its leadership development work to build a more diversified leadership bench. Hamilton’s team is also launching a sponsorship program later this year.

Chasing the ‘North Star’

As InStride continues to grow in the coming years, Hamilton says, her HR team will stay focused on its “North Star”: bringing a customer-service mentality to its work.

“We are a service for our business and our people, first and foremost,” she says. That focus will take the form of an ongoing emphasis on internal mobility, transparency and efforts to empower leaders to become coaches for their teams.

As she leads that work, Hamilton says, she will lean into her tenacity, resilience and the growth mindset that makes her thrive in start-up settings.

“I’m just naturally very hungry,” she says. “I want to build, I want to create things, I want to try new things—and so, that makes me more open to doing things a little differently than what we might be used to in HR.”

HR’s Rising Stars judge Jennie Yang, senior vice president of people at 15Five and a 2022 HR’s Rising Star, says it was clear that Hamilton’s role at InStride aligns with her personal drive to advance workforce capabilities through education and development.

“Here, Michelle has not only expanded the team significantly but also introduced impactful programs like employee engagement management and comprehensive benefits, which have reduced turnover and fostered a robust corporate culture,” Yang says. “These efforts highlight her adaptability, foresight and a deep commitment to nurturing talent and organizational growth, positioning her as a strategic leader with the potential to shape the future of HR at the highest levels.”

In that vein, Hamilton adds, she is eager to continue bringing empathy into HR’s work. Years ago, a mentor once told her that HR professionals should “put something on their desk that makes people talk” to them.

“So, you’re not scary, right? Because HR can be so scary,” Hamilton says. “I think there are subtle touches of your human self that you need to bring into this role. I want to continue to embrace and refine that and make sure my team feels it too, so they can be themselves as we’re learning, growing and developing.”

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Jen Colletta
Jen Colletta is managing editor at HRE. She earned bachelor's and master's degrees in writing from La Salle University in Philadelphia and spent 10 years as a newspaper reporter and editor before joining HRE. She can be reached at [email protected].