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. 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 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.

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.

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.

Line management for the engineering teams, including one-to-ones, performance, development and progression.

Engineering hiring, the bar we hire against, and a levelling framework you will build with our Head of People.

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.

Three business units will all want to be first,



and you will be the person who decides.

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.

We think that is worth building well.

You have led engineering for a business software product at roughly 15 to 60 engineers

You are comfortable in a room with a customer, a procurement team or a security reviewer

Enterprise or public sector delivery including security review and compliance evidence. Building a levelling or progression framework somewhere that did not have one.

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. 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. Thrive is an equal chance 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. #

📌 Executive VP Engineering (Toronto)
🏢 Thrive Career Wellness
📍 Toronto