Jason Stypula
Jason Stypula is a seasoned sales and partnerships leader with over two decades of experience helping companies grow, modernize, and build strong commercial relationships.
He has worked across SaaS, technology, and service-based industries, taking on roles where he has opened new markets, built partner ecosystems, and led teams to significant year-over-year growth.
Most recently, Jason led strategic partnerships at Medidas Technology, where he developed joint ventures, scalable partner programs, and collaborations with government, education, and commercial stakeholders to advance public-safety initiatives. Prior to that, he held enterprise sales and leadership roles focused on helping organizations modernize legacy systems and accelerate digital transformation through high-performance technology solutions.
What Does a Sales Executive Do?
At City Wide, Jason works directly with property managers, facility managers, and business owners to understand their buildings and identify opportunities to simplify and improve facility maintenance.
He takes a consultative approach by:
- Conducting detailed facility walkthroughs (building surveys)
- Identifying gaps or inefficiencies in current service delivery
- Recommending solutions across multiple facility services
- Coordinating the onboarding of services through the City Wide team
Jason’s background in strategic partnerships and complex solution selling allows him to bring a structured, results-driven approach to every client engagement.
Representing the Client
A key part of Jason’s role is helping clients understand how City Wide is different.
Rather than selling a single service, Jason works on your behalf to represent your interests. City Wide will:
- Evaluate and vet multiple contractors
- Select the provider that is best suited for your facility
- Coordinate services through one point of contact
- Continue to manage performance and accountability over time
This approach allows clients to benefit from specialized service providers while avoiding the time and complexity of managing multiple vendors.
A Strategic Partner for Your Facility
Jason is known for his straightforward approach, strong relationship-building abilities, and bias toward action. He thrives in fast-moving environments where strategy and hands-on execution come together.
His goal is to help clients:
- Reduce the time spent managing vendors
- Improve service quality and consistency
- Gain better visibility and control over facility services
Education
- Bachelor of Commerce – University of Alberta
- Diploma in Management Studies – Red Deer College