Jennifer Wincey
Senior HR Consultant
Education & Credentials
- Certified in AI for HR
- Certified in leadership and team effectiveness methodologies (including Five Dysfunctions of a Team)
Recent Client List
CarbonRun
Golden Ventures
Digital Nova Scotia
Lillio
About Jennifer
Jennifer Wincey is a Senior HR Consultant with over 20 years of experience in business, operations, and organizational strategy, including more than a decade in executive human resources leadership roles.
Jennifer works with organizations to strengthen how they operate, helping leaders connect strategy to execution through their people, structure, and ways of working. Using her background in operations and organizational strategy, her approach goes beyond traditional HR, focusing on organizational effectiveness, leadership capability, and building scalable systems that support growth.
She partners with companies at key inflection points, whether they are scaling, navigating change, or working to improve alignment and execution. Jennifer is known for quickly identifying where organizations are experiencing friction, and for helping leaders put practical, sustainable solutions in place.
Areas of Expertise
Jennifer brings a strategic and hands-on approach across a range of people and organizational challenges, including:
- Organizational design and role clarity
- Leadership development, executive coaching and training
- Performance management and feedback systems
- Culture and employee experience
- Workforce planning and capability development
- HR strategy and program development
- Change management and organizational transformation
- Employee relations and complex workplace situations
She is particularly skilled at helping organizations move from reactive ways of working to more structured, scalable, and aligned operating models.
Approach
Jennifer takes a structured, diagnostic approach to understanding how an organization is operating and where opportunities exist to improve effectiveness.
She begins by working with founders and leadership teams to clarify business priorities and uncover where execution is breaking down, whether through misalignment, unclear roles, leadership challenges, or inefficient ways of working.
Her process typically includes:
- Leadership conversations to understand strategic priorities, decision-making, and areas of friction
- Targeted input from leaders and teams to surface how the organization is experienced in practice
- Assessment of key organizational dimensions, including alignment, structure, execution, leadership capability, and culture
Jennifer then synthesizes these insights to identify:
- Patterns and root causes
- Gaps between intent and reality
- Areas where the organization may struggle as it grows
From there, she works with leaders to define a focused, practical path forward, prioritizing the changes that will have the greatest impact on clarity, alignment, and execution.
Her approach is grounded in the belief that organizational challenges are rarely isolated, and that meaningful improvement comes from addressing how the system works as a whole, not just individual issues.
Experience
Prior to joining H2R, Jennifer held senior executive leadership roles in human resources and organizational strategy, including Vice President positions where she led people strategy across growing and evolving organizations.
She has worked with organizations across a variety of sectors, including climate tech, SaaS marketplaces, manufacturing and others and has extensive experience supporting small and mid-sized companies as they scale.
Jennifer is also the Founder of AdaptPath Consulting Services, where she works with startups and scaling companies to build the organizational systems and leadership capability needed to support growth.
Testimonials
A Bit More About Jennifer
Jennifer is passionate about helping leaders and teams work better together and believes that strong relationships, clear expectations, and open communication are at the heart of every successful organization.
Outside of work, she enjoys exploring new ideas, reading and learning, gardening and the outdoors, and finding ways to bring creativity and connection into both her professional and personal life.