VP, Engineering

About Thrive

Thrive is transforming how individuals and organizations navigate career transitions. We partner with employers and service providers to deliver tech-enabled outplacement and career wellness solutions, helping people move into meaningful employment, faster.

We are building the future of outplacement. We are on a mission to democratize access to premium career services, making them available to every person facing a workforce transition, at every level, in every market.

The Opportunity

This is our first executive engineering leader below the CTO, and it is a seat with real authority rather than an administrative layer. You will own what we commit to and when, you will lead the people who build it, and you will be the person the business comes to when it wants to know what is possible and by when.

You will lead four engineering teams and sixteen engineers building a platform that governments and large enterprises depend on. We are reorganising around three business units, each with its own commercial owner, all drawing on that same platform. Deciding where engineering capacity goes, and holding those decisions when they are tested, is the heart of this role.

Key Accountabilities

1. Delivery Commitments and Dates. You own what we commit to and when, across four teams and three business units, including the authority to change a date or decline a commitment.
2. Commercial Partnership. You are the person sales and our business unit owners negotiate delivery with, so that what we promise has capacity attached to it before it is promised.
3. People Leadership. Line management for the engineering teams, including one-to-ones, performance, development and progression.
4. Hiring and Levelling. Engineering hiring, the bar we hire against, and a levelling framework you will build with our Head of People.
5. Team Structure and Platform Health. How the teams are shaped, how capacity is allocated against competing demand, platform reliability, incident response, and a technical debt allocation you propose and defend to the executive team each quarter.

Why This Role, Why Thrive

The authority is real. You will own delivery outright rather than administering someone else’s roadmap, and you will have the CTO’s backing when those decisions are challenged. Three business units will all want to be first, and you will be the person who decides.

There is room to build. This is a new seat, so you are not inheriting someone else’s process or working around a structure you did not choose. If you want a role where you set how engineering runs rather than maintaining how it already runs, this is that role, and you will build the levelling and progression framework alongside our Head of People.

And the work matters. Every release goes to someone in the middle of a job loss, which is one of the harder things that happens to anyone. We think that is worth building well.

Qualifications

We have kept this list short deliberately. If you meet most of it, we would like to hear from you.

• You have led engineering for a business software product at roughly 15 to 60 engineers
• You have owned delivery dates rather than reported them, and you can tell us about a commitment you changed or declined
• You have managed managers or team leads
• You are comfortable in a room with a customer, a procurement team or a security reviewer

Valued Experience

Enterprise or public sector delivery including security review and compliance evidence. Applied AI or machine learning products. Multi-tenant platform work. Experience somewhere that had to earn its budget rather than raise it. Building a levelling or progression framework somewhere that did not have one.

Compensation and Benefits

A competitive executive base salary commensurate with experience, with a premium for candidates who can be in Toronto regularly. An annual company performance bonus. Meaningful equity in a revenue-generating, privately held Canadian company. Our full benefits plan, on the same terms as the rest of the company.

Vacancy & Process

This is a posting for a new vacancy.

Thrive does not use artificial intelligence to screen, assess, or select applicants in our recruitment process.

Our process is five conversations: an introductory call, a discussion with our CTO about delivery ownership, a technical conversation with two of our engineers, a conversation with one of our business unit owners, and a final conversation with our CEO. If you interview with us, we will tell you where you stand within 45 days of your last interview.

Equal Opportunity & Accessibility

Thrive is an equal opportunity employer committed to building a diverse, inclusive team that reflects the communities and clients we serve.

Accommodations are available upon request for candidates participating in any stage of the recruitment and selection process.