Top-rated career coaches in Winnipeg
Here are the leading career coaches working with professionals in Winnipeg. Each has been assessed for expertise, clear communication, and a strong track record of client success.
Dr John O'Dwyer
Leadership Coach
Leadership consultant, author, educator, and creator of the GettingItDone Toolkit. Known for blending practical wisdom, academic rigour, and humour, he helps teams and executives align vision, execution, and culture to deliver measurable results.
Sasja Winkels
Career Transition Specialist
Are you feeling stuck or unfulfilled in your career? Unsure which direction will truly energize you? I support professionals in finding the right career path and turn that into a realistic plan, so they can move forward with confidence, purpose, and momentum. With a background in HR and certifications in transformative coaching and yoga, I combine a holistic approach with very practical support. Once your direction is clear, we work on the steps that make change happen: building self-trust and resilience, removing inner and outer obstacles, and taking consistent action. 💼 And because clarity alone isn’t enough, I also support you with proven job-market strategies: creating a standout personal brand (CV, LinkedIn, USP), leveraging networking to access opportunities, crafting strong applications, and interview training that helps you stand out. ♥️ If you’re ready to step into a more fulfilling career, let’s talk! 🌐 You can read more about me and my coaching on my website: www.sasjazwinkels.com.
Benicia Jeulin
Leadership Coach
I am a leadership and career coach with a background in recruitment. I help professionals break through limiting beliefs and blockers to unlock their full career potential.
Michelle Hillier
Self-discovery Coach
As a TEDx speaker, educator, and published author, I've spent over two decades helping people unlock their hidden potential through movement, creativity, and radical self-discovery. From captivating large crowds to intimate coaching sessions, I've helped millions reclaim their power and move beyond their limits. I'm all about creating safe, transformative spaces for people to reconnect with their inner flame.
Working in Winnipeg
Employment Landscape
Job seekers in Winnipeg today will find a market that is stabilizing yet competitive. The unemployment rate sits around six percent, with full-time job gains in sectors such as construction and health care somewhat offset by declines in manufacturing. Major local players like Manitoba Hydro, NFI Group, Canada Life and IGM Financial continue hiring, particularly in operational, administrative and client-facing roles. At the same time, firms such as Bass Pro Shops have cut dozens of office positions, reflecting uneven demand across sectors. Health and social services, as well as trades and retail, remain areas where openings persist, but candidates must be adaptable and persistent in their approaches.
Dominant Industries
Typical Roles
Hiring Patterns
Health care and social services roles are growing steadily, and construction is beginning to pick up with public infrastructure and housing projects underway. Manufacturing employment is slightly declining, though food and machinery sectors remain somewhat resilient. Many employers favor contract or temporary hires that can evolve into longer-term roles.
"Finding work in Winnipeg now feels like fitting the right tool into the right slot—if your skills match a hiring niche, you stand a chance; if not, you’re stuck on the side."
Career developments in Winnipeg
Recent news and trends shaping the job market in Winnipeg. Stay informed about opportunities in your area.
Last available update: March 15, 2026
Sick and tired of theft, Winnipeg businesses consider IDing customers, making diners pre-pay
Two Winnipeg business owners are exploring new security measures in response to increased theft and dine-and-dash incidents. They are considering requiring customers to show identification upon entry and implementing pre-payment for dining. This reflects growing concerns among local businesses about financial losses due to theft.
New initiative ships beds to northern Manitoba communities to improve sleeping conditions
Winnipeg still short of housing target tied to $122M federal fund with less than 1 year to go | CBC News
The City of Winnipeg has not yet met its housing targets associated with over $122 million in federal funding, with less than a year remaining to fulfill these goals. This shortfall may impact local construction and housing-related job opportunities as the city works to address the housing shortage.
The hiring momentum in Winnipeg creates real opportunities for prepared professionals.
- 1Use the Career Audit to identify which growing sectors match your skills
- 2Work with a coach to position yourself for roles at expanding companies
- 3Get resume templates optimized for high-demand positions in your area
What is WORK-SELF?
Work Self is a career development system that helps people grow through coaching and daily habit support.
What Work Self provides
- One to one coaching for clarity and momentum
- Software that guides habits and simple next steps
- A structure that keeps progress moving between sessions
Why people choose it
- Builds confidence and better decision making
- Creates steady progress with small daily actions
- Makes career growth feel clear, guided, and achievable
How it works
- 1Meet with your coach to set goals and direction
- 2Follow daily guidance in the software
- 3Build habits that lead to long term improvement
A new way to grow your career
Innovative tools and coaching methods designed to transform how you develop professionally.
Career Audit Tool
Assess your professional path in Winnipeg with our comprehensive 360° audit.
Transition Blueprint
Map your move with structure and real momentum. Step-by-step guidance.
AI-Powered Coaching
Intelligent guidance available 24/7. Get instant answers to your career questions.
Rituals for Growth
Build clarity and confidence with intentional daily habits designed for you.
Personal Brand Builder
Tell your story clearly and powerfully to stand out in the local market.
Coaches available in Winnipeg
We select top coaches who understand the local market dynamics and global career trends.
Dr John O'Dwyer
Leadership Coach
Leadership consultant, author, educator, and creator of the GettingItDone Toolkit. Known for blending practical wisdom, academic rigour, and humour, he helps teams and executives align vision, execution, and culture to deliver measurable results.
Sasja Winkels
Career Transition Specialist
Are you feeling stuck or unfulfilled in your career? Unsure which direction will truly energize you? I support professionals in finding the right career path and turn that into a realistic plan, so they can move forward with confidence, purpose, and momentum. With a background in HR and certifications in transformative coaching and yoga, I combine a holistic approach with very practical support. Once your direction is clear, we work on the steps that make change happen: building self-trust and resilience, removing inner and outer obstacles, and taking consistent action. 💼 And because clarity alone isn’t enough, I also support you with proven job-market strategies: creating a standout personal brand (CV, LinkedIn, USP), leveraging networking to access opportunities, crafting strong applications, and interview training that helps you stand out. ♥️ If you’re ready to step into a more fulfilling career, let’s talk! 🌐 You can read more about me and my coaching on my website: www.sasjazwinkels.com.
Benicia Jeulin
Leadership Coach
I am a leadership and career coach with a background in recruitment. I help professionals break through limiting beliefs and blockers to unlock their full career potential.
Michelle Hillier
Self-discovery Coach
As a TEDx speaker, educator, and published author, I've spent over two decades helping people unlock their hidden potential through movement, creativity, and radical self-discovery. From captivating large crowds to intimate coaching sessions, I've helped millions reclaim their power and move beyond their limits. I'm all about creating safe, transformative spaces for people to reconnect with their inner flame.
Simple, transparent pricing
Invest in your career clarity today.