Career Counselling Winnipeg | Expert Career Coaching & Counselling
Navigate Winnipeg’s finance and insurance sector, government institutions, and growing tech scene with clarity. ICF-certified coaches with 20+ years helping Manitoba professionals find work that fits.
- Find a career that fits Winnipeg’s market — perfectly.
- Land the job you really want in Winnipeg — fearlessly.
- One-on-one coaching with ICF-certified coaches.
- Coaching via Practice Better — secure telehealth, scheduled around your day.
“I came in with a vague idea of what I wanted but left with a clear, actionable career plan. The clarity I gained was transformative for both my professional and personal life.”
“This service was a great help — and I landed a great new job within 4 weeks. The coaching gave me the focus and confidence I needed to move quickly.”
Career coaching that goes deeper than a résumé rewrite
“Most Winnipeg professionals come to us thinking they have a job search problem. What they actually have is a clarity problem — and once we solve that, the right opportunities in this city become obvious.”
— Shirin Khamisa, Founder & Practice LeaderOur methodology works on values, identity, and strategy together — not just tactics. That’s how Winnipeg clients move from stuck to certain.
We understand Winnipeg’s finance and insurance landscape, its government sector culture, and how to position you for the roles that actually exist here.
You get matched to the right coach for your situation — and the collective expertise of the whole team behind every engagement.
Meet the coaches who’ll guide your journey
Shirin Khamisa
Founder & Practice LeaderShirin founded Careers by Design over 20 years ago with a single belief: that career satisfaction requires connecting what you’re good at with what lights you up. Her Connect Head & Heart methodology has helped thousands of Canadian professionals — from Winnipeg’s finance and insurance sector to government and healthcare — build careers they’re genuinely proud of.
Linda Faucheux M.A. LPC
Career Coach & Leadership CounsellorWith 25+ years as a career coach and former Director of Career Services, Linda helps professionals identify their unique strengths and build resilience through career transitions. Her background in counselling psychology and executive coaching makes her especially effective with Winnipeg’s senior professionals navigating public-to-private sector moves or leadership roles.
Jen Davies RP CCC Ed.D
Registered Psychotherapist & Certified Canadian CounsellorJen holds a Doctorate in Counselling Psychology and is both a Registered Psychotherapist (RP) and a Canadian Certified Counsellor (CCC). Her sessions may be covered under your extended health benefits or Employee Assistance Program — including plans from Canada Life, Sun Life, and Blue Cross Manitoba. Jen is especially effective with professionals feeling stuck at a crossroads in their Manitoba career.
Your coaching may be covered by your plan
Jen Davies holds both the Registered Psychotherapist (RP) designation and the Canadian Certified Counsellor (CCC) designation — the CCPA credential recognized by benefit providers across Canada, including Manitoba.
Many extended health care plans and Employee Assistance Programs (EAPs) cover counselling sessions with a CCC. Check with your provider — sessions may be fully or partially reimbursed under your existing plan.
Benefit plans that commonly cover CCC counselling: Canada Life, Sun Life, Manulife, Blue Cross Manitoba, Desjardins, Chambers of Commerce Group Insurance, and many employer EAPs through Great-West Life, Homewood Health, and others.
The CCPA designation recognized by benefit providers across all Canadian provinces, including Manitoba benefit plans.
Many Winnipeg employers provide EAP coverage. Jen’s sessions often qualify — check with your HR team or benefit provider.
Canada Life (which administers many Manitoba public sector plans), MPI, Boeing, provincial government, and other large employers commonly offer eligible coverage.
All sessions are delivered via Practice Better, a regulated telehealth platform — the documentation your insurer needs is built in.
We know the industries that drive Winnipeg
Winnipeg’s economy is anchored in finance and insurance, government and public services, and a growing aerospace and manufacturing base. Our coaches understand how careers develop inside these sectors — and how to move between them.
Canada’s insurance capital — a sector that rewards clarity
Winnipeg is home to some of Canada’s largest insurers and financial institutions. Professionals here often face role overlap, unclear progression paths, and the challenge of moving from technical expertise into leadership. We help you position yourself for what’s next.
Navigating the public sector — or finding the exit ramp
Winnipeg’s government and public sector employs a significant share of the city’s workforce. Whether you want to advance within government, cross into the private sector, or finally make the move you’ve been considering for years — we help you do it with clarity and confidence.
Skilled industries that require a different kind of career strategy
From Boeing’s Winnipeg operation to Ubisoft’s growing studio and NFI Group’s transit manufacturing, Winnipeg’s technical and creative sectors are expanding. We help specialists translate deep expertise into leadership trajectories — or successful transitions into adjacent roles.
The Winnipeg career realities most coaches ignore
Salaries in Winnipeg are lower than Toronto or Vancouver — but so is cost of living. The real question is how to negotiate effectively in this market and avoid underselling your value. Most professionals leave 10–20% on the table.
Winnipeg has a large government workforce, and the jump to private sector — or vice versa — is harder than it looks. How you frame your experience, your resume, and your story matters enormously when crossing that line.
Ambitious Winnipeg professionals often feel they have to leave for Toronto or Vancouver to build a great career. That’s rarely true — but it does require a different strategy. We help you figure out whether to stay, go, or build something better here.
Many Winnipeg finance and insurance professionals hit a ceiling not because of skill, but because of how they present themselves internally. Leadership roles go to people who can tell a strategic story — not just execute well.
Every program built for where you are right now
Whether you’re figuring out your direction or ready to move fast on a job search, we have a coaching program that fits. All sessions are delivered via Practice Better — no commute, no disruption to your Winnipeg workday.
Find Your Career Fit
Get clear on who you are, what you want, and what your next chapter looks like — before you start applying. The clarity program Winnipeg professionals come back to refer their friends for.
Learn More →Land The Right Job
For professionals who know what they want and need expert support to land it: strategy, positioning, networking, and interview prep built for Winnipeg’s market.
Learn More →Interview Coaching
Walk into any interview at Canada Life, Boeing, or the Province of Manitoba with genuine confidence. We prepare you for the questions that actually get asked — and the ones you need to ask back.
Learn More →Resume Writing
A resume written to speak to Winnipeg’s employers and ATS systems — by writers who know what finance, insurance, government, and aerospace hiring managers actually look for.
Learn More →Executive Resume Writing
For directors, VPs, and senior leaders in Winnipeg’s major organizations. Your resume should reflect your strategic impact — not just your job history.
Learn More →Outplacement Services
For Winnipeg employers supporting team members through transitions. We help people land well — with clarity, dignity, and a concrete plan for what comes next.
Learn More →Three steps to career clarity
Tell us where you are and what you’re trying to figure out. We’ll listen carefully and let you know if — and how — we can help. No pitch, no pressure.
Book A Free ChatYou’re matched with the coach who fits your situation best. Sessions run via Practice Better — our secure telehealth platform — so you can meet from anywhere in Winnipeg or Manitoba.
Whether you’re changing direction, advancing in Winnipeg’s finance sector, or finally making the move you’ve been putting off — you’ll have a strategy and the confidence to act on it.
Winnipeg’s leading employers
We’ve helped professionals from across Winnipeg’s economy — from major insurers and government to aerospace, tech, and agri-food.
What clients say about working with us
“Linda guided me through the process of redefining my career path, helping me step back and assess my needs and priorities with clarity. Her support and expertise were invaluable in giving me the confidence I needed to approach this significant change. I landed the first job I interviewed for after working with her.”
Drew Robinson, M.Sc. Financial Advisor“This service was a great help — and I landed a great new job within 4 weeks. The coaching gave me the focus and confidence I needed to move quickly and decisively.”
“Coaching at Careers by Design helped me achieve the confidence and self-worth I always had but never was able to realize before.”
“Jen is an exceptional career development practitioner. Her authenticity, determination and heart in anything she undertakes is refreshing.”
“I was at a crossroads in my career and Careers by Design helped me gain the clarity and tools I needed. I highly recommend them to anyone feeling stuck.”
“Shirin and the team provided invaluable guidance at a pivotal point in my career. Their approach is thoughtful, structured, and genuinely effective.”
Questions about career coaching in Winnipeg
We start with a free 20-minute discovery call to understand where you are and whether we’re the right fit. Most clients begin with our Find Your Career Fit program — getting clear on what they want before jumping into job search mode. Sessions are delivered one-on-one via Practice Better, our secure telehealth platform, scheduled around your life in Winnipeg.
Yes. Many of our clients work at Canada Life, Wawanesa Insurance, IG Wealth Management, Manitoba Public Insurance, Boeing, the Province of Manitoba, the City of Winnipeg, and Shared Health Manitoba. We understand the career dynamics of these sectors — including how to move between them — and build coaching strategies around how Winnipeg’s labour market actually works.
A career change program typically runs 7 to 12 sessions over 3 to 4 months. A job search coaching program typically takes 4 to 7 sessions. We give you a realistic picture of what to expect after the initial discovery call — no vague timelines.
Possibly, yes. Jen Davies holds the Canadian Certified Counsellor (CCC) designation from CCPA — the credential recognized by many Canadian extended health and EAP plans. Plans from Canada Life, Sun Life, Blue Cross Manitoba, and many employer EAPs commonly cover CCC sessions. Check with your provider or HR team to confirm your coverage before you start.
Your next chapter starts with a conversation
Whether you’re figuring out your direction or ready to start your job search in Winnipeg, we’re here. Book a free 20-minute coaching chat — or, if you’d like to explore coverage under your benefits plan, book directly with Jen for a counselling session. Caroline can help you get started.
Career coaching across Winnipeg and Manitoba
We serve Winnipeg and all of Manitoba virtually via Practice Better. Whether you’re in the Exchange District, River Heights, St. Boniface, or working remotely across the province — we come to you. No commute required.
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