Tag: Milestone Inc

Jennifer Bouyoukos is the Chief People Officer at PureFacts, a global wealthtech company, where she is leading organizational transformation and growth. A multi-award-winning HR leader with over 25 years of international experience, she has worked with high-performing companies across media, technology, and financial services, including Entertainment One, SAP, RBC, Manulife, Kobo, and Workbrain.

Jennifer has been recognized as one of the Top 100 HR Leaders Globally by HRD, Top 25 Elite Women in HR and among the Top 50 Women Leaders in Toronto. Her career spans Canada, the U.S., the U.K., EMEA, and APAC, where she has led international expansions and over 20 M&A transactions—four among the largest tech and media exits in Canadian history.

She is proud to have led teams recognized with Canadian HR Team of the Year Excellence Awards (twice) and Corporate Social Responsibility Excellence Awards, and was nominated for Canada’s Most Admired CPCO in 2024. Her expertise includes organizational development, total rewards, executive development, talent strategy, and employee experience.

Jennifer is also a board advisor to HR tech startups, PE Firms, an angel investor, and an advocate for DEIB. She is dedicated to mentoring the next generation of HR leaders and creating inclusive, high-performing workplaces.

Jennifer (Jenn) Bouyoukos is an undeniable force in the HR industry and has been for over 25 years. An award-winning executive whose influence over the past 12 months alone has left a profound mark on Canadian business, the global HR community, and the next generation of leaders.

In the past year, Jenn has led two major cultural and structural transformations: first at Bench Accounting, where she served as Chief People Officer through a high-stakes acquisition by Employer.com, and now at PureFacts, a PE-backed fintech scaling globally. At both firms, she architected people strategies that enhanced ARR per employee, increased EBITDA, and rebuilt entire leadership teams, earning her recognition as one of HRD’s Global 100, a Top 50 Woman Leader in Toronto, and a Most Admired CPCO finalist.

Jenn is a pioneer in redefining how HR contributes to business. At Bench, she turned DEI from an abstract concept into a system-wide cultural competency, embedding inclusive practices into hiring, onboarding, performance, and pay. Her policies on reproductive loss, mental health, and parental leave set new industry standards for empathy-driven, evidence-based HR

At PureFacts, she is building leadership frameworks, internal communications platforms, and global talent infrastructure to support a data-driven scale-up.

Beyond corporate success, Jenn is a tireless advocate for women and underrepresented groups. She serves on advisory boards for multiple HR tech start-ups and private equity firms, mentors rising HR professionals, and invests in female-led ventures through Women’s Equity Lab. Her collaboration with the First Nations Technology Council is helping Indigenous talent access meaningful tech careers
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Jenn’s influence extends outside HR. She has coached first-time CEOs through leadership transitions, advised on multi-billion-dollar M&A deals, and is frequently sought out by VC and PE firms for her ability to lead through change with clarity and courage

She is known for combining data with humanity treating every challenge as both a business opportunity and a chance to build belonging.

Whether she’s designing scalable systems, fighting for pay equity, or helping a young professional find her voice, Jenn leads with purpose, boldness, and impact.

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Jenn Bouyoukos has had an outsized impact on the HR community and the broader people and culture profession through her consistent commitment to advancing the field, developing others, and challenging outdated thinking. Over nearly 28 years, she has actively contributed to elevating the role of HR from a functional discipline to a true strategic and value-creating partner. Jenn shares her experience openly, whether through formal mentorship, peer advising, industry forums, or one-to-one support, and she does so with a generosity that reflects a deep belief in strengthening the profession as a whole, not just individual organizations.

Jenn is a trusted mentor and sponsor to many HR leaders at different stages of their careers. She invests time in developing others by offering practical guidance, candid feedback, and real perspective shaped by experience across high-growth, global, and complex environments. Her support goes beyond theory. She helps HR professionals build confidence, sharpen judgment, and navigate real leadership challenges, including transformation, workforce decisions, executive dynamics, and personal resilience. Many leaders credit Jenn with helping them step into larger roles, think more strategically, and lead with both conviction and humanity.

Beyond mentorship, Jenn is an active contributor to the evolution of the HR industry itself. She is frequently sought out by venture capital and private equity firms, founders, boards, and executive teams for her insights on the future of work, organizational design, leadership effectiveness, and people strategy. Jenn is known for translating emerging trends into practical, scalable approaches that work in real businesses. She challenges conventional wisdom, encourages data-driven decision making, and pushes the profession to stay relevant in an environment defined by constant change, technology, and rising expectations.

What truly distinguishes Jenn is her commitment to continuous learning and innovation within the HR community. She consistently stays ahead of shifts in the profession, embracing new thinking, tools, and models while maintaining a strong ethical and human core. Jenn models the growth mindset she encourages in others, demonstrating that HR must continually adapt, evolve, and lead from the front. Through her leadership, mentorship, and thought partnership, Jenn has helped shape a stronger, more credible, and more future-ready HR profession, and her influence continues to ripple across the industry.