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Program Director Jobs in Winnipeg, MB (NOW HIRING)

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Program Director information

What are some common challenges program directors face when overseeing multiple projects or initiatives?

Program Directors often encounter the challenge of balancing competing priorities across several projects, while ensuring alignment with the organization’s strategic goals. Managing diverse teams, coordinating resources, and addressing unexpected obstacles—such as shifting stakeholder requirements or budget constraints—are common aspects of the role. Effective communication, adaptability, and strong organizational skills are essential for navigating these complexities and ensuring successful program delivery. Collaboration with senior leadership and cross-functional teams is also crucial for resolving issues promptly and maintaining program momentum.

What are the key skills and qualifications needed to thrive as a program director, and why are they important?

To thrive as a Program Director, you need strong leadership, project management, and strategic planning skills, usually supported by a relevant degree and several years of management experience. Experience with budgeting software, project management tools like Asana or MS Project, and familiarity with compliance standards are often necessary. Exceptional communication, decision-making, and conflict resolution abilities are critical soft skills that set top Program Directors apart. These skills are crucial for aligning teams, driving program success, and ensuring organizational goals are consistently met.

What is a program director?

A program director is an upper-management position found within organizations across almost all industries. Your primary job duties include coordinating, implementing, and overseeing all details of a company’s operation and programs. You monitor the budget, create community programs, supervise other managers, and develop better business practices. The exact job duties vary widely depending on industry and employer. Some program directors oversee the entire organization while others oversee specific departments. Though almost all industries utilize program directors, the two most commonly seen are business and healthcare.

What is the difference between Program Director vs Project Manager?

AspectProgram DirectorProject Manager
CredentialsTypically requires a bachelor’s degree; often prefers PMP or similar certificationsRequires a bachelor’s degree; PMP or CAPM certifications are common
Work EnvironmentOversees multiple projects within a program, strategic focusManages individual projects, tactical focus
Employer & Industry UsageUsed in nonprofits, corporate, government sectors for large initiativesCommon across industries for specific project execution

The Program Director focuses on overseeing multiple related projects to achieve strategic goals, while the Project Manager handles the planning and execution of a single project. Both roles require similar credentials but differ in scope and responsibilities.

What degree do you need to be a program director?

A program director typically needs at least a bachelor's degree in a relevant field such as business, management, or a specific industry-related area. Many roles also prefer or require a master's degree or higher, along with experience in leadership, project management, or the specific sector they oversee.

What are the most commonly searched types of Program jobs in Winnipeg, MB?

The most popular types of Program jobs in Winnipeg, MB are:

What job categories do people searching Program Director jobs in Winnipeg, MB look for?

The top searched job categories for Program Director jobs in Winnipeg, MB are:

What cities near Winnipeg, MB are hiring for Program Director jobs?

Cities near Winnipeg, MB with the most Program Director job openings:

Infographic showing various Program Director job openings in Winnipeg, MB as of August 2026, with employment types broken down into 89% Full Time, and 11% Part Time. Highlights an 100% In-person job distribution.

Bilingual Director, Advanced Underwriting - Mentorship

Sun Life Financial

Winnipeg, MB • Hybrid

Full-time

Life, Retirement, PTO

Posted 2 days ago

New


Sun Life Assurance Company of Canada rating

8.6

Company rating: 8.6 out of 10

Based on 18 frontline employees who took The Breakroom Quiz

90th of 308 rated insurance


Job description

You are as unique as your background, experience and point of view. Here, you'll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. Every day, you'll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do.


At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring, and impactful.


When you join Sun Life, you'll work with passionate colleagues and empowering leaders who support your growth and celebrate your contributions, so you can make a meaningful difference in our Clients' lives.


Discover how you can make a difference in the lives of individuals, families and communities around the world.


Job Description:

Location: Hybrid, Work from Home

As a Director, Advanced Underwriting - Mentorship, you'll be joining one of Canada's top insurers. We're known for not only our strength in the market, but our commitment to our people. Underwriting goes beyond risk assessments here. We're focused on making thoughtful, well-informed decisions that provide financial security to Canadians and their loved ones.

By joining Sun Life, you become part of a high-performing team, led by passionate professionals with extensive experience in the field, industry knowledge, and a passion for mentorship. Our continuous learning pathways and skills development opportunities ensure endless growth for you as you advance in your career.

This role will be reporting to our Chief Underwriter and Claims Risk Officer.We're looking for an experienced underwriter with a passion for mentoring others and expertise in ultra-high net worth cases (>$25M). You'll partner with specialized case managers, advisors, reinsurance partners, and business leaders to assess medical, personal, and financial risk up to $200 million. A commitment to Client-first, proactive communication and partnership with our advisors and distribution team are critical aspects to this role.

What will you do?

  • Analyze insurance applications and evidence of insurability
  • Apply holistic underwriting expertise in all areas of underwriting (including medical, financial and lifestyle factors) to make sound and competitive underwriting decisions
  • Negotiate decisions with our reinsurers, in accordance with reinsurance treaties and internal rules
  • Effectively communicate and explain decisions to advisors and/or Clients' physicians, as required
  • Build strong relationships with business leaders, distribution teams, and advisors while delivering exceptional service and expertise
  • Identify continuous improvement opportunities and bring forward recommendations for solutions
  • Contribute to a positive environment through teamwork, a spirit of innovation, and professional development
  • Attend and contribute to regular HNW case reviews to share knowledge and support team development
  • Mentor and help employees reach the next levels in their careers

What do you need to succeed?

  • Decision Making Authority >$10,000,000 for Life and $1,000,000 of Critical Illness
  • Exceptional analytical, judgement, problem-solving and decision-making skills
  • Client and results focused, with proactive service orientation to support our business goals
  • Ability to influence and negotiate
  • Strong knowledge of medical and financial risk factors
  • The ability to work in a fast-paced environment, meet tight deadlines, and balance completing priorities
  • Interpersonal skills to work collaboratively with our internal and external partners
  • Strong attention to detail and accuracy
  • Ability to work independently and eager to take on responsibility
  • 10-15years of experience as an Individual Life Underwriter
  • Bachelor's degree or equivalent
  • Specialized training: ALU certificate and commitment to ongoing education with a goal of attaining the Fellow, Academy of Life Underwriting (FALU) and Fellow, Life Management Institute (FLMI) designations
  • Bilingualism (French, English, both oral and written) is required for the frequent interactions with English and French-speaking colleagues or internal partners across Canada and worldwide

Other Details

  • Some travel and representation at industry and sales events is required

What can we offer you?

Joining our team at Sun Life means you can expect:

  • A hybrid working environment, giving you the best parts of in-office collaboration and work from home flexibility
  • Flexible Benefits from the day you join, meeting the needs of you and your loved ones
  • Our stock ownership program and pension plan give you the chance to invest in Sun Life with company matching opportunities
  • An annual bonus based on company and individual performance
  • Paid vacation based on experience, 5 care days available for self-care or care of others (e.g. family or others you may support) and 10 personal illness days to support your well-being
  • Our unique sabbatical program gives you the opportunity to take up to 6 weeks off, every 5 years
  • Investment in not-for-profit organizations that are important to you
  • Maternity/Paternity top-up program so you can focus on your growing family

The Base Pay range is for the primary location for which the job is posted. It may vary depending on the work location of the successful candidate or other factors. In addition to Base Pay, eligible Sun Life employees participate in various incentive plans, payment under which is discretionary and subject to individual and company performance. Certain sales focused roles have sales incentive plans based on individual or group sales results.


Diversity and inclusion have always been at the core of our values at Sun Life. A diverse workforce with wide perspectives and creative ideas benefits our Clients, the communities where we operate and all of us as colleagues. We welcome applications from qualified individuals from all backgrounds.


Persons with disabilities who need accommodation in the application process, or those needing job postings in an alternative format, may e-mail a request to thebrightside@sunlife.com.


We are proud to be a hybrid organization that offers our employees the choice and flexibility to work from both the office and virtually based on the needs of the business, our Clients and you.


We may use artificial intelligence to support candidate sourcing, screening, interview scheduling.


We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted.


Salary Range:

110,000/110 000 - 180,000/180 000

Job Category:

Underwriting - Individual

Posting End Date:

04/09/2026

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