Proposal Specialist

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 accessibility@dialogue.co.

Your role as Proposal Specialist

Reporting to Cathie Beerman, Manager of GTM Enablement, the Proposal Specialist plays a key role in shaping compelling, high-impact proposals that help Dialogue win new business and expand existing partnerships.

In this role, you will lead the development of strategic RFP and RFI responses, translating complex information into clear, persuasive narratives that highlight Dialogue’s unique value. You will collaborate closely with cross-functional teams across Sales, Product, Clinical, Legal, and Strategy to deliver polished, high-quality submissions that support Dialogue’s go-to-market success.

You will thrive in this role if you take pride in your craft, bring structure to complex work, collaborate naturally with others, and are motivated by the impact your work has on winning together as a team.

What you'll be doing

• Own and elevate the end-to-end proposal process: Delivering high impact RFP and RFI responses that position Dialogue as the clear partner of choice
• Write bold, tailored proposals that bring Dialogue’s value to life: Combining strategic storytelling with precision to stand out in competitive evaluations
• Translate complexity into clarity: Turning detailed requirements into compelling narratives and executive summaries that focus on what matters most, connecting client priorities and deal strategy to create a clear path to winning
• Collaborate deeply across teams: Partnering with GTM, Product, Clinical, Legal and Strategy to deliver accurate, aligned and high-quality submissions
• Drive with speed and rigor: Managing timelines, stakeholders and procurement requirements to deliver compliant, polished proposals, on time, every time
• Continuously raise the bar: Improving tools, templates and ways of working to increase efficiency, scalability and overall proposal quality
• Strengthen our collective impact: Contributing to a high-performing, team-first environment and stepping in where it matters most to win together
• Build and refine reusable content: Ensuring our knowledge base is sharp, current and easy to leverage for consistent, high-quality outputs

We'd love to hear from you if you have

• A strong writer and operator who is organized, driven, and ready to take real ownership - experience level matters less than craft and hustle
• Strong writing and storytelling skills you can translate complex information into clear, compelling content
• Highly organized and detail-oriented with the ability to manage multiple priorities and deliver high-quality work under tight deadlines
• Comfortable in fast-paced environments where you adapt quickly, stay focused when things get busy and follow through
• Collaborative and team-oriented where you communicate clearly, work well with stakeholders and step in where needed to get things done
• Curious, proactive and eager to learn where you take initiative, seek feedback and continuously improve.
• Interest in healthcare or SaaS (nice to have, not required)
• Bilingual in English and French is a strong asset
  
  

Please note that as we serve customers across Canada, bilingualism is essential for this position. You may be required to communicate in French and English.

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

Recruitment Fraud Notice
Dialogue only contacts candidates through official @dialogue.co email addresses. We never request payment, gift cards, or personal financial information at any stage of hiring, and we never extend an offer without a structured interview process. All open roles are listed exclusively at dialogue.co/en/careers. If you receive a suspicious communication claiming to be from Dialogue, do not respond — report it to <jobs@dialogue.co> and verify the role on our official careers page.

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