[Hiring] Senior Proposal Manager @D2L

Role Description

As a Senior Proposal Manager, you will work in a high-impact, fast-paced, deadline-driven environment and be responsible for leading complex proposal response efforts for prospective and existing customers globally. You will manage highly visible and strategic Requests for Proposals (e.g., RFIs, RFPs, RFQs), driving cross-functional collaboration, pursuit readiness, proposal quality, and strategic alignment throughout the proposal lifecycle.

This role requires advanced communication, writing, organizational, strategic thinking, and project management skills, along with the ability to influence stakeholders, navigate ambiguity, and lead complex pursuits under pressure. Successful candidates will demonstrate strong business judgment, proposal management expertise, competitive awareness, and the ability to act as a trusted advisor and mentor within the Proposal Management team. You will play a key role in supporting proposal effectiveness, operational excellence, and continuous improvement across the function.

How Will I Make an Impact?

• Strategic Pursuit Leadership
  • Lead the end-to-end management of complex, high-impact proposal responses (e.g., RFIs, RFPs, RFQs) supporting prospective and existing clients globally.
  • Facilitate and drive complex bid qualification discussions, supporting informed pursuit decisions, proposal readiness, and strategic alignment.
  • Lead proposal planning activities including timelines, stakeholder coordination, risk identification, escalation management, and management of cross-functional contributors.
  • Independently manage multiple complex proposal pursuits simultaneously within fast-paced, deadline-driven environments.
  • Apply strategic thinking, competitive awareness, and proposal management expertise to support compelling, differentiated, and high-quality proposal responses.
  • Support proposal strategy discussions and contribute recommendations related to pursuit approach, messaging, competitiveness, and proposal effectiveness.
  • Provide leadership guidance and influence across project teams to support strong pursuit execution, stakeholder alignment, and proposal quality outcomes.
  • Identify opportunities to improve proposal processes, pursuit effectiveness, and operational approaches based on lessons learned and evolving business needs.
• Proposal Development & Strategic Communication
  • Lead the development, writing, editing, and refinement of proposal responses to ensure submissions are compliant, strategically aligned, compelling, and error-free.
  • Review and provide guidance on executive summaries, cover letters, messaging approaches, and other critical proposal components.
  • Work cross-functionally with Subject Matter Experts and senior stakeholders to coordinate and enhance proposal responses while maintaining a strong understanding of D2L’s products, services, value propositions, and competitive positioning.
  • Apply proposal management best practices, strong business judgment, and audience awareness to support high-quality and differentiated proposal responses.
  • Ensure proposal submissions align to established brand, messaging, and style standards while adapting approaches to suit varying audiences, opportunity types, and pursuit complexity.
  • Facilitate proposal reviews and support alignment on proposal messaging, positioning, and response strategy.
• Operational Excellence & Team Influence
  • Build strong partnerships with Sales, Solution Engineering, Services, Finance, Legal, Security, Marketing, and other stakeholders involved in proposal pursuits.
  • Act as a trusted advisor and experienced resource within the Proposal Management team, sharing expertise, supporting onboarding activities, and mentoring team members on proposal best practices and complex pursuits.
  • Contribute to operational improvements, proposal management best practices, content enhancements, and scalable proposal management approaches.
  • Support knowledge sharing initiatives and contribute to continuous improvement efforts across proposal operations and team effectiveness.
  • Leverage proposal tools, AI-enabled technologies, operational processes, and proposal management best practices to support proposal quality, operational efficiency, and pursuit effectiveness.
  • Contribute positively to a collaborative, high-performing, and solutions-oriented team environment while fostering a culture of continuous improvement and operational excellence.

Qualifications

• 7+ years experience in a similar role in a fast-paced, high volume proposal writing environment.
• Direct experience in high-tech industry is preferred.
• A work ethic that thrives in a fast-paced, high volume proposal writing environment.
• Strong writing, editing, and storytelling skills, with the ability to develop compelling, strategically aligned, audience-focused proposal responses and executive-level communications.
• Proven ability to develop processes and content to support new business areas and growth.
• APMP (Association of Proposal Management Professionals) certification or equivalent.
• Excellent knowledge of Microsoft Office applications, Salesforce, Adobe applications, and proposal automation software.
• Demonstrated ability to apply and promote AI-enabled tools and evolving proposal management best practices to improve proposal quality, team effectiveness, operational efficiency, and pursuit outcomes.
• Ability to work independently and as part of a team.
• Ability to adhere to strict deadlines.
• Experience writing proposals for education or other key verticals an asset.

Education Recommendations

• Bachelor’s Degree preferably in Business, Technical Writing, English, Communications, or Journalism.

Benefits

• Impactful work transforming the way the world learns.
• Flexible work arrangements.
• Learning and Growth opportunities.
• Tuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program.
• 2 Paid Days off for SkillsWave-related activities like exams or final assignments.
• Employee wellbeing (Access to mental health services, EFAP program, financial planning and more).
• Retirement planning.
• 2 Paid Volunteer Days.
• Competitive Benefits Package.
• Home Internet Reimbursements.
• Employee Referral Program.
• Wellness Reimbursement.
• Employee Recognition.
• Social Events.
• Dog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices.