Jenn Oswald

Contact Jenn: jenn.oswald@orgshakers.com

Jenn is a Fractional Chief People Officer, Head of People, and Operating Partner, People & Culture, with 25 years of experience helping early-stage and high-growth companies build People functions that scale. She works closely with founders and CEOs as their first People leader, supporting organizations through critical growth stages where speed, clarity, and execution are essential.

She has a strong track record of building People infrastructure from zero. Jenn has served as the first Chief People Officer or Head of People for eight companies, partnering directly with leadership teams to design and implement scalable recruiting and hiring systems, People Operations, and leadership foundations while the business is actively growing. She is known for her ability to build the plane while flying it, combining strategic People design with hands-on execution in fast-moving, ambiguous environments.

A core focus of Jenn’s work is building recruiting and hiring systems that support hypergrowth. She designs practical, repeatable hiring processes that enable early-stage and scaling companies to attract, assess, and onboard talent quickly without sacrificing quality. Her experience includes building early recruiting functions, defining hiring criteria, creating interview frameworks, and implementing scalable hiring processes that founders and leaders can sustain as headcount accelerates.

Jenn began her Human Resources career in training and development, which continues to shape her work as a trusted partner and mentor to founders and executive teams. She brings deep expertise across People Operations, organizational design, leadership development, performance frameworks, and culture building. Her work is supported by certifications in DISC, MBTI, Predictive Index, Leadership Through People Skills, and the Dimensional Sales Program. Her approach is modern, pragmatic, and tailored to the realities of each company’s stage, growth velocity, and leadership maturity.

Her background spans early-stage startups, a technology unicorn, and Fortune 500 and Fortune 200 organizations, giving her a well-rounded perspective on how People systems evolve as companies scale. In addition to technology, Jenn has deep experience in hospitality, where she developed a strong bias toward efficient hiring, low-cost high-impact solutions, creative retention strategies, and employer branding that resonates with frontline teams. That experience continues to influence how she builds People programs that are both human-centered and operationally effective.

Jenn works with companies across the United States and globally, supporting leadership teams in building scalable hiring and People systems that enable sustainable, long-term growth.