Jill Hanson Rainford – Round Hill Capital

Jill Hanson Rainford has always been more than just a legal leader. Over a decade-long career at global real estate investment manager Round Hill Capital, she’s consistently blurred the lines between legal counsel, operations lead, and people strategist. With a sharp legal mind, a collaborative leadership style, and an innate commercial instinct, she’s helped transform Round Hill into what it is today: a vertically integrated, globally respected platform for innovative accommodation solutions.

Founded in 2002 by CEO Michael Bickford, Round Hill Capital has become a powerhouse in the real estate space, managing billions in assets while maintaining a commitment to affordability, sustainability, and community impact. Its unique structure—serving as the investment, asset, development, and property manager—demands both strategic agility and operational discipline. And Rainford has been at the center of that engine for the past decade.

“I’ve worn many hats here over the years,” she says, laughing. “General Counsel, co-Chief Operating Officer, Chief Compliance Officer, and Head of HR —some simultaneously. But really, I’ve always seen my role as helping to ensure the business runs well. That means aligning the legal, operational, compliance and HR, pieces so the people and the company can thrive.”

From firm to global operator

Before joining Round Hill in 2015, Rainford had already amassed significant experience in international law firms on both sides of the Atlantic. With a JD from Suffolk University Law School and an undergraduate degree in international relations from Boston University, she spent more than eight years at Edwards Wildman Palmer, focusing on cross-border M&A, venture capital, and private equity transactions. She even ran the start-up program for the business law department in London, supporting high-growth companies as they scaled.

But it was at Round Hill where her career would evolve into something more entrepreneurial.

“When I came on board, the business was just starting a significant growth phase, bringing on global investors and expanding into new markets. I set up the legal, compliance and HR functions, helped onboard over 15 new institutional investors and opened nine of our fourteen offices – both from a legal and operational perspective.  It’s been gratifying.”

That operations-centric mindset would eventually position her as more than a legal partner. Rainford became a trusted advisor across the business for all manner of commercial matters.

“Several people in the business have told me that I’m the most commercial GC they’ve ever worked with,” she says. “That’s probably because I’ve always treated legal as just one piece of the business puzzle.  The commercial considerations must always drive the legal solution and not the other way around.”

Leading through transformation

Perhaps no experience demonstrates Rainford’s leadership better than Round Hill’s recent strategic transaction. The nearly year-long transaction concluded in July 2024 with a significant capital infusion to support the platform’s continued growth and expansion under the new name of Round Hill Capital Ventures.

Rainford and her legal team were instrumental in guiding the due diligence and negotiation process, giving her team valuable experience and insight. It was, by all accounts, a textbook example of professionalism and selfless leadership.

“There were a lot of late nights and weekends spent getting us through the process, but I’m proud of how my team handled it.” she says.

Rainford’s career isn’t just defined by strategy and execution but also by empathy, mentorship, and authenticity. Her leadership style is rooted in open communication and empowerment.

“I’ve always tried to foster an environment where people feel comfortable and can take ownership of their work and grow. That’s when teams really shine.”

It’s no surprise that many of her team members have gone on to take leadership roles elsewhere. Someone who recently left her team to step into a Head of Legal role told her she was their favorite person to work for and thanked her for her mentorship over the years.

“That means more to me than almost anything,” Rainford says with a proud smile.

Rainford also played a crucial role in shaping Round Hill’s culture. After stepping away from the HR function during maternity leave, she resumed the role in 2023, leading with clarity and compassion as the company navigated complex staffing changes.

“The human side of the business matters just as much as the financials,” she says. “Whether hiring or restructuring, you need to look beyond CVs. Culture fit, personality, and potential—they’re everything.”

A break, then a new beginning

Despite Rainford contemplating an exit from the business to pursue a new challenge after her 10-year tenure at Round Hill, she offered to help facilitate both the transaction and the transition as she believed it was important to help navigate the business through this exciting time. Since the transaction closed in July 2024, Rainford has continued to lead the transition into the business’ next growth cycle. As she winds down her remaining responsibilities at the end of June, she’s looking forward to something rare in her high-powered world: a break.

After a meaningful chapter at Round Hill Capital, she is embracing this transition as an opportunity to thoughtfully shape the next phase of her career. While she has had early conversations with recruiters and explored several opportunities, she’s made a deliberate choice to pause before committing to her next role. This moment is less about leaving and more about aligning with a future that offers greater scope to influence business strategy, drive sustainable growth, and lead with purpose.

With a strong track record, deep operational and legal expertise, and a respected market reputation, she is confidently exploring roles that reflect her evolving ambitions—whether as a COO, in a hybrid legal-operational capacity, or in non-executive board positions. What’s clear is that she’s not seeking just another role, but the right challenge—one that values strategic leadership, cross-functional collaboration, and integrity at its core.

For her, the end of one chapter is simply the beginning of another—one defined by clarity of purpose, thoughtful leadership, and a commitment to making a lasting impact.