
Principal Proposal Writer
- Toronto, ON
- Permanent
- Full-time
- Own the proposal writing cycle: Lead the writing of compelling, tailored RFP, RFI, etc. proposal responses that position Dialogue as the partner of choice for large organizations across Canada
- Collaborate cross-functionally with Product, Clinical, Legal, and Strategy teams to gather inputs and craft clear, persuasive, and technically accurate responses.
- Project Management: Manage timelines and ensure on-time delivery of compliant, complete, and high-quality submissions across various procurement platforms (e.g., MERX, SEAO, Bids & Tenders).
- Continuously contribute to the improvement of our proposal process, templates, and messaging to boost win rates and alignment with sales strategy
- 5+ Years of Experience: Demonstrated expertise in writing proposals, with a proven track record of leading winning bids
- Industry Experience: Familiarity with the benefits provider, insurance, virtual healthcare, or SaaS sectors, with a deep understanding of these markets
- Exceptional communication and storytelling abilities, with a knack for translating complex ideas into clear, compelling messages
- Adaptability in Fast-Paced Environments: Highly organized, deadline-driven, able to pivot under pressure, and energized by fast-paced, high-impact work.
- Strong project management capability: Ability to lead RFP responses for high-value, complex deals with multiple stakeholders.
- Access to the Dialogue app and virtual mental health support for you and your family
- Fully funded insurance, a health spending account, dental coverage, and fitness reimbursement
- 4 weeks vacation, 9 wellness days, and 1 volunteer day
- Hybrid work: 3 days/week in our Montreal or Toronto offices, excluding remote roles
- Work abroad up to 4 weeks/year
- Incentive plans, referral bonuses & RRSP matching
- Learning via Coursera, external training budget & mentorship
- Optional parental leave top-up