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 sustainable 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 in organizations where the playbook didn't exist yet.

Startups scaling faster than anyone predicted. Nonprofits building their first people function across multiple regions. Healthcare systems extracting workforce intelligence from decades-old infrastructure. Companies needing compliance overhauls while operations were already in motion. In every case, the ask was the same: build something that works now and still holds up when everything changes.

That pattern taught me what I'm actually good at. I see how organizations really work, not the org chart version, but the human version. Where decisions actually get made, where information gets stuck, where leaders are confident and where they're quietly drowning. I read the system underneath the system, and I build infrastructure around what I find there.

I'm a systems thinker who leads with empathy. I design performance frameworks that actually develop people, not just measure them. I coach leaders through the conversations they've been avoiding. I use workforce data to tell the story of what's really happening, not just what's easy to report. I do this across global employment landscapes, in unionized and non-unionized environments, in person and across distributed teams.

What makes me different from most People and Culture leaders: I'm as comfortable in Power BI and Power Automate as I am in a coaching conversation with a first-time manager. I don't just build people strategies, I build the tech-enabled systems that make them sustainable. I think in frameworks, I process by building, and I see patterns in organizational behaviour that others walk past.

I don't need perfect conditions. I thrive when the work matters and the people are at the centre of it.

What I Bring

Organizational Design & Workforce Planning
Building structures that flex when things change, not just when things are stable.
Change Management
The architecture behind change that actually lands, not just launches.
Leadership Coaching & Development
Helping leaders have the conversations they've been avoiding.
People Analytics & Workforce Data
Using data to tell the story of what's really happening, not just what's easy to report.
Tech-Enabled HR Systems
Power BI, Power Automate, HRIS, and the systems that make people strategy sustainable.
Workforce Innovation & Human-Centred Design
Designing with people, not for them. Solutions that start with the humans doing the work.

Work
Selected Deliverables
Sample deliverables from my consulting, change management 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
Change Leadership

From Launch to Landing: The Leadership Architecture Behind Sustainable Enterprise Change

A framework for how change actually works in complex organizations. Covers the difference between change management and change leadership, diagnostic partnerships, structural barrier removal, political intelligence, and why most transformations launch but never land.

Basecamp Innovation
Enterprise

Talks & Workshops
On Stage & In The Room
Keynotes, workshops, and learning programs I've designed and delivered.
AI Workforce Summit speaker announcement
ATS panel discussion
DisruptHR Windsor speakers
WEST Gala 2024
Women Supporting Women Charity Event 2024
EPICentre University of Windsor