Principal Proposal Writer

Dialogue; Toronto; Hybrid; CAD 80,000 - 110,000; Full time

Job summary

Dialogue, Canada’s leading virtual care provider, is seeking a Principal Proposal Writer in Toronto. This role involves crafting winning proposals, collaborating cross-functionally, and managing project timelines to drive revenue growth. Ideal candidates have 5+ years of proposal writing experience in the healthcare sector, strong communication skills, and adaptability in fast-paced environments. The role offers benefits including hybrid work opportunities, comprehensive insurance, and support for learning and wellness.

Benefits

Access to virtual mental health support

Fully funded insurance and health spending account

4 weeks vacation and wellness days

Incentive plans and referral bonuses

Learning and training budgets

Qualifications

• 5+ years of experience in proposal writing with proven track record.
• Familiarity with insurance, virtual healthcare, or SaaS sectors.
• Exceptional communication and storytelling abilities.

Responsibilities

• Lead the writing of tailored RFP, RFI proposal responses.
• Collaborate cross-functionally with various teams.
• Manage timelines and ensure on-time delivery of submissions.

Skills

Proposal Writing

Communication

Project Management

Adaptability

Job description

Your role as Principal Proposal Writer

Reporting to Corey Klein, Director of Revenue Operations, the mission of the Principal Proposal Writer is to craft winning proposals that drive revenue growth by clearly articulating the impact of Dialogue’s health and wellness solutions.

What you’ll be doing:

• 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

We'd love to hear from you if you have:

• 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.

At Dialogue, your well-being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following benefits:

• 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

About Dialogue

Dialogue is the #1 virtual care provider in Canada. By developing our Integrated Health Platform, we provide exceptional online health and wellness programs (primary care, mental health, iCBT, EAP, and wellness) to organizations that want to improve the wellness of their employees and families.

When it comes to our work, we set the bar high. Together, we’re transforming health and helping millions improve their well-being. We’re firm believers that great people don’t settle on:

Impact Community Growth Excellence

Feel like you can make a difference? Good news, we saved you a seat!

Come as you are. As a proud equal-opportunity employer, Dialogue is dedicated to creating a diverse and inclusive workplace for everyone. Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants who require specialized accommodation are encouraged to contact [e-mail] .