Senior Proposal Manager leading complex RFP responses for D2L, a cloud company transforming education and the Future of Work. Coordinating global stakeholders, strategy, writing, and pursuit execution.
Responsibilities
Lead end-to-end management of complex, high-impact proposal responses, including RFIs, RFPs, and RFQs, for prospective and existing clients globally
Facilitate complex bid qualification discussions and support pursuit decisions, proposal readiness, and strategic alignment
Lead proposal planning, timelines, stakeholder coordination, risk identification, escalation management, and cross-functional contributor management
Independently manage multiple complex proposal pursuits simultaneously in deadline-driven environments
Apply strategic thinking, competitive awareness, and proposal management expertise to create compelling, differentiated, high-quality responses
Support proposal strategy discussions and recommend pursuit approaches, messaging, competitiveness, and proposal effectiveness improvements
Provide leadership guidance and influence across project teams
Identify opportunities to improve proposal processes, pursuit effectiveness, and operational approaches
Lead proposal development, writing, editing, and refinement
Review and guide executive summaries, cover letters, messaging, and other critical proposal components
Collaborate with Subject Matter Experts and senior stakeholders across Sales, Solution Engineering, Services, Finance, Legal, Security, Marketing, and other functions
Ensure submissions comply with brand, messaging, style, and audience requirements
Facilitate proposal reviews and align messaging, positioning, and response strategy
Act as a trusted advisor within the Proposal Management team, support onboarding, and mentor team members
Contribute to operational improvements, content enhancements, scalable proposal management approaches, knowledge sharing, and continuous improvement
Leverage proposal tools, AI-enabled technologies, operational processes, and best practices to improve quality, efficiency, and pursuit outcomes
Requirements
7+ years experience in a similar role in a fast-paced, high volume proposal writing environment
Direct experience in high-tech industry is preferred
Strong writing, editing, and storytelling skills
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
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
Bachelor’s Degree preferably in Business, Technical Writing, English, Communications, or Journalism
Benefits
Additional benefits may include a Wellness Subsidy, Equity Grants, Variable Incentive, and more
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
Impactful work transforming the way the world learns
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