Team Lead, Software Development

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.

AI Disclosure Statement

To ensure an efficient and fair review process, we utilize artificial intelligence tools to assist in the initial screening and assessment of applicants for this role.

Your role as a Team Lead, Software

The Provider Experience group is looking for a Software Team Lead to lead a new team within the Provider Stream, focused on accelerating the delivery of ServiceOS , Dialogue's tech-powered operating system that automates care coordination and shifts our model toward direct-to-care.

Reporting to Lauranne Sins, Director of Engineering, you will guide the team's delivery, support the growth of your engineers, and partner with Product to keep the team focused. The remaining technical portion of your time is dedicated to the foundations that make a team productive: developer experience improvements, services maintenance, observability, and platform health — work that is often deprioritized in feature-focused teams but is critical to sustained delivery velocity.

We're looking for someone who genuinely enjoys both sides of the role: a hands-on technical leader who is just as comfortable in a 1:1 as in a pull request review.

What you'll be doing

Hands-on technical contributions (~60%)

• Developer experience: Identify and lead improvements that make your team faster and happier — local dev setup, tooling, build/test pipelines, internal documentation.
• Services maintenance: Take ownership of the operational health of the team's services — dependency upgrades, technical debt reduction, performance tuning, and recurring maintenance work.
• Observability: Improve monitoring, logging, alerting, and on-call practices so the team has the visibility it needs to operate confidently in production.
• Technical guidance: Review designs and pull requests, weigh in on architectural decisions, and make sure the team is making sound technical trade-offs.

Team leadership (~40%)

• Guide the team: Lead 1:1s, planning, retros, and sprint rituals. Set clear expectations and keep your team focused on what matters.
• Ensure delivery: Track progress against commitments, surface risks early, and unblock your developers so they can ship reliably and predictably.
• Support your engineers: Coach team members, give regular feedback, and help each person grow in their role and career.
• Partner with Product: Work closely with your Product Manager to shape the team's backlog, scope work realistically, and keep priorities clear.
• Collaborate across teams: Coordinate with peer software teams in the Provider Stream to align on dependencies and shared standards.

We'd love to hear from you if you have

• Engineering Management Experience: 2+ years of experience leading a software engineering team, with a track record of consistent delivery.
• Strong Engineering Background: A solid technical foundation (typically 5+ years as a software engineer before management), with experience in backend or full-stack development. You should still feel comfortable contributing code when it matters.
• DevEx & Operational Mindset: Genuine interest in the work that keeps a team productive — tooling, CI/CD, observability, and service health. Experience with AWS, modern monitoring stacks, and CI/CD platforms is an asset.
• Delivery Focus: Comfort with agile practices and a pragmatic approach to planning, estimation, and execution. You know how to keep a team shipping without burning them out.
• People Skills: Genuine care for your team. You give clear feedback, run good 1:1s, and create the conditions for engineers to do their best work.
• Collaboration: Strong communication skills and the ability to work effectively with Product, Design, and other engineering leaders.
• Healthcare or Regulated Environments: Experience in healthcare, fintech, or another regulated industry is an asset.

Please note that as we serve customers across Canada, bilingualism is an asset 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

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