People & Culture Strategy

I help organizations build people systems that hold up when things get messy.

Strategic people partner with deep expertise in organizational development, change management, and building HR infrastructure for scaling companies.

Jenna Bossaer

About
Bringing structure to ambiguity
without losing the human element.
I partner with leaders who are navigating growth, change, and the gray areas in between.

I've spent my career working in organizations where the playbook didn't exist yet. From a cannabis company growing from 250 to 1,250 employees with no precedent, to a national nonprofit building its first HR function across five provinces, to healthcare systems where legacy infrastructure meets modern workforce demands.

That experience taught me something: the organizations that scale well aren't the ones with the best policies. They're the ones where leaders know how to have honest conversations, where performance systems actually develop people, and where data tells the story of what's really happening, not just what's easy to measure.

I'm as comfortable in Power BI as I am in a coaching conversation. I design tech-enabled people solutions, not just processes. And I believe the best HR work happens at the intersection of strategy and empathy, not in a silo between them.

Credentials & Tools

People & Organizational Development
  • Organizational Development Practitioner AIHR
  • Learning & Development Specialist AIHR
  • EQ-i 2.0/360 Practitioner In Progress
  • Strategic Workforce Planning
  • Strategic Leadership & Culture Management Vokes
  • Disability Awareness & Confidence ODEN
Technical
  • Microsoft Power BI Data Analysis
  • Microsoft Power Automate
  • Workday Beyond Basics
  • AI in Healthcare NIHI
  • HRIS/ATS (BambooHR, legacy systems)
  • Microsoft 365 / Survey Platforms
Education
  • Post-Grad Certificate, HR Management (Conestoga College)
  • BA, English & Family Relations (University of Guelph)
Industries
Tech / SaaSHealthcareNonprofitCannabisConstructionRetail

Work
Selected deliverables
Sample deliverables from my consulting and leadership development work.
Leadership Development

Innovating at Altitude: A 6-session program for senior leaders driving innovation and culture change

Designed and built a leadership development experience for directors and senior leaders who need to unlock innovation from every level of their organization. Six half-day experiential sessions over six to eight months, covering psychological safety, change resistance, intrapreneurship, and scaling impact. Grounded in strategy, not theory.

Basecamp Innovation
50 to 2,500 employees

Thinking Out Loud
Thinking out loud
On organizational change, people systems, neurodivergence at work, and what AI means for how we build organizations.
01I Asked AI to Find Me. It Couldn't.Essay02Why Change Management Fails Before It StartsFramework03Neurodivergence as a Systems AdvantagePerspective04Connection Over Consumption: Rethinking Leadership DevelopmentThought Piece05AI as Infrastructure, Not ReplacementEssay

Contact
Let's talk.
Whether you're scaling a team, navigating a change, or rethinking how your organization develops people, I'd like to hear about it.
jenna.mae.frye@gmail.com226-344-0729