Freelance Program Manager Jobs in Ontario (NOW HIRING)

The salary range for this position is $120,000 to $140,000. Final compensation will be determined based on relevant skills, experience, qualifications, and internal equity. In addition to base salary, eligible employees may be entitled to other elements of total compensation, which may include group benefits, employer RRSP contributions, and discretionary bonus or incentive programs, where applicable to the role. We are committed to offering competitive compensation and comply with all applicable pay transparency legislation. Further details regarding our total rewards program will be shared by the Talent Acquisition team during the hiring process. Canadian work experience is not a requirement for this role. Please note that artificial intelligence–based tools may be used at certain stages of the recruitment and applicant screening process.

This is posting for an existing vacancy.

As Director, Proposal Development on the Growth Team, you will lead Compass Group Canada’s multidisciplinary team of proposal managers, content writers, marketing professionals and graphic designers. You will be a strategic partner to Sales and sector leadership, translating growth priorities and client insight into compelling proposals, presentations, campaigns and thought leadership that differentiate Compass in the marketplace. Strong performance in this Director-level role will create opportunities for broader scope and future progression as the function and its impact continue to grow.

Now, if you were to come on board as our Director, Proposal Development, we’d ask you to do the following for us:

• Strategic & Creative Leadership
  • Translate Compass Group Canada’s growth priorities into a clear creative and proposal services strategy, roadmap and measurable plan.
  • Partner early with Sales and sector leaders on priority pursuits to shape win themes, value propositions, executive narratives and differentiated client experiences.
  • Set the creative vision and quality standard across proposals, presentations, sales materials, campaigns and thought‑leadership content.
  • Bring original ideas and an outside‑in perspective to how Compass tells its story, reflecting client needs, market trends and our strongest competitive advantages.
  • Build a thought‑leadership agenda that turns enterprise expertise and market insight into credible points of view, executive content and sales enablement.
• Proposal Excellence & Growth Enablement
  • Own and continuously improve the end-to-end proposal process, from pipeline visibility and intake through strategy, storytelling, design, production, submission and post-project learning.
  • Guide high-priority pursuits and creative reviews, ensuring submissions are compliant, client‑centred, cohesive and clearly differentiated.
  • Establish effective standards for content governance, templates, reusable assets, brand alignment, accessibility, version control and quality assurance.
  • Work across Sales, Marketing, Operations, Analytics, Finance, Legal and sector teams to turn complex information into persuasive stories, visuals and proof points.
  • Serve as the primary liaison with the U.S. Creative Services team to share ideas and standards, collaborate on priority projects and access specialist capabilities when required.
• Team Leadership & Capability Building
  • Lead, coach and develop the proposal management, writing, marketing and graphic design teams, with clear accountabilities, performance expectations and career pathways.
  • Manage workload, capacity and project assignments across a high-volume portfolio; anticipate demand, resolve constraints and make informed resourcing decisions.
  • Build a structured capability‑development program across strategic storytelling, writing, design thinking, data visualization, project management, commercial acumen and technology fluency.
  • Ensure team skills and ways of working evolve in step with—and where possible ahead of—the needs of the Sales organization.
  • Foster a culture of curiosity, collaboration, constructive challenge, accountability, experimentation and continuous learning.
• Data, Operations & Innovation
  • Build reliable reporting across the project portfolio, including demand forecasts, project volume, capacity and utilization, hours by project, cycle time, on‑time delivery and stakeholder satisfaction.
  • Track proposal outcomes and win/loss trends and translate the findings into improvements to pursuit strategy, content, resource allocation and team performance.
  • Measure marketing performance using appropriate metrics, including reach, engagement, conversion, influenced pipeline and return on investment.
  • Own the function’s budget, external production spend, technology investments and vendor or freelance relationships, with clear forecasts and disciplined cost management.
  • Identify, pilot and responsibly scale AI, automation, knowledge‑management and workflow tools that improve productivity, quality, reuse and insight.

Think you have what it takes to be our Director, Proposal Development? We’re committed to hiring the best talent for the role. Here’s how we’ll know you’ll be successful in the role:

• Five or more years of progressive experience in proposal development, creative services, marketing, sales enablement or a related growth function within a complex organization.
• Demonstrated experience leading and developing multidisciplinary teams; experience overseeing proposal managers, writers, marketers and designers is strongly preferred.
• A strong portfolio or track record of differentiated proposals, presentations, campaigns and/or thought‑leadership content that supports business growth.
• Exceptional strategic storytelling, writing and editing judgment, with the ability to simplify complex information and connect client needs to a compelling value proposition.
• Strong creative direction skills and working knowledge of visual communication, brand systems and information design; familiarity with Adobe Creative Cloud and Microsoft 365 is expected.
• High data literacy, including experience defining KPIs, interpreting dashboards and using insight to improve operations and investment decisions.
• Experience with workflow or project‑management platforms, CRM and content or knowledge‑management systems; practical experience with AI and automation is an asset.
• Proven financial and resource‑management capability, including budgeting, forecasting, capacity planning and vendor management.
• Excellent executive presence, communication and influencing skills, with the confidence to challenge constructively and operate calmly under pressure.
• Post‑secondary education in business, marketing, communications, design or a related field—or an equivalent combination of education and experience.
• APMP certification is an asset; relevant project‑management, change‑management or marketing/creative credentials are also valued.
• Bilingualism (French and English) is an asset.