Global Head of Outplacement
Thrive Career Wellness Platform
Remote
Posted on Jun 2, 2026
Global Head of Outplacement
hybrid
Toronto, Ontario, Canada .
full-time . June 1, 2026
Toronto, Ontario, Canada .
full-time . June 1, 2026
Description
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. AI is at the center of how we do that: enabling personalized, high-quality career support at a scale that was never previously possible.
The Opportunity
The Head of Outplacement will own Thrive's global go-to-market execution in the outplacement space: defining strategy, building pipeline, closing enterprise deals, managing key partnerships, and holding commercial accountability for program deployments. You will inherit an active business — with established channels in Canada, Germany, and Australia, and two high-potential markets in active development in the United States and the United Kingdom — and be responsible for accelerating its growth.
This is not a role for someone who needs a fully built machine underneath them. It is a role for a commercially aggressive, credible market builder who can operate with a degree of ambiguity, partner effectively across Product, Delivery, and Customer Success, and earn increasing operational ownership as the business scales. The infrastructure is evolving. Your job is to help drive it forward.
The outplacement industry is ripe for disruption. Legacy providers are entrenched, expensive, and slow to adapt. Thrive has built a differentiated, AI-enabled platform and is growing. To compete with and displace long-standing incumbents, we need a leader with deep market credibility who can win buyer trust, shape category perception, and close.
What You're Inheriting
You are stepping into an active, revenue-generating business. Day one, you take commercial ownership of:
- Established outplacement channels in Canada, Germany, and Australia
- Developing market presence in the United States and United Kingdom, and broader Europe
- An existing base of employer relationships, active contracts, and delivery partnerships
- A product and technology platform with an active AI development roadmap
- A cross-functional team — spanning Product, Delivery, and Customer Success — that you will partner with closely
Key Accountabilities
1. Strategy & Market Expansion
You will define and execute Thrive's commercial strategy for outplacement.
- Develop the go-to-market strategy for active markets (Canada, Germany, Australia) and lead the commercial build-out of the US and UK.
- Identify and prioritize target employer segments — by industry, size, and profile — and build strategies tailored to each.
- Shape Thrive's category positioning as the leading AI-enabled outplacement platform — educating buyers, shifting market perception, and building confidence in a new delivery model.
- Stay close to the competitive landscape, tracking how incumbents are evolving and identifying where Thrive can create and widen its advantage.
- Bring market intelligence back into the business — informing Product, Delivery, and leadership on what buyers need and what the market is signaling.
2. Pipeline Generation & Sales Execution
You are a builder and a closer. You will own the outplacement pipeline from first conversation to signed contract, acting as Thrive's most credible voice in front of enterprise buyers.
- Build and manage a pipeline of enterprise employer relationships — with CHROs, HR Directors, and Total Rewards leaders as your primary buyer profiles.
- Lead proposals, RFP responses, and executive-level sales meetings as the domain expert.
- Partner with Thrive's Sales and Marketing teams to generate awareness, sharpen positioning, and convert inbound interest.
- Develop segment-specific sales approaches that reflect the distinct needs of different buyer types and geographies.
3. Partnership Growth
Distribution and delivery partnerships are a core growth lever for Thrive. You will own these relationships commercially — ensuring partners are activated, productive, and aligned.
- Grow Thrive's existing network of direct and channel delivery partners across active markets.
- Identify and develop new distribution partnerships — with HR consultancies, brokers, and service providers — that expand Thrive's reach in target markets.
- Define commercial terms and accountability frameworks for partner relationships, in collaboration with Finance and Legal.
- Act as the primary relationship owner for strategic partners, ensuring alignment on performance, quality, and mutual growth objectives.
4. Commercial Stewardship of Key Accounts
Once a deal is closed, your accountability does not end. You will hold commercial ownership of active client programs — ensuring Thrive;s most important client relationships are healthy, growing, and renewed.
- Partner with the Chief Customer Officer to ensure a strong handoff from sale to implementation, setting clients up for success from day one.
- Retain senior commercial ownership of key accounts - covering contract performance, renewals, and expansion conversations throughout the program lifecycle.
5. Cross-Functional Partnership on Delivery & Implementation
Thrive's delivery model spans Product, R&D, and operations teams. You are not expected to own delivery end-to-end — but you are expected to be a strong partner and advocate within it.
- Work closely with Product and R&D to ensure the platform roadmap reflects what the market requires — feeding in buyer feedback, unmet needs, and competitive gaps.
- Collaborate with Delivery and Customer Success to ensure program implementations meet client expectations and Thrive's quality standards.
- Support the development of scalable delivery frameworks as the operating model evolves — contributing a commercial and client perspective.
- Champion Thrive's AI-enabled workflows with clients — helping buyers understand, trust, and adopt a new model of outplacement delivery.
The Market Creation Imperative
One of the most distinctive aspects of this role — and one of the highest-leverage opportunities — is the chance to help define a new category.
Thrive is not selling a legacy outplacement product with a better price point. We are commercializing a fundamentally different approach: AI-enabled, scalable, and accessible to a far broader population of job seekers than the traditional model has ever served. That is a compelling story — but it requires a seller who can also be an educator.
Many HR buyers are accustomed to familiar models and familiar names. Part of this role is building confidence in something new: helping CHROs and HR leaders understand how AI-enabled career support works, why it delivers better outcomes, and why Thrive is the right partner to trust with their people through a difficult transition.
This role requires the ability to operate with authority in a space where Thrive is still earning its reputation at scale. You will need deep industry credibility to open doors, genuine intellectual curiosity about AI and technology to hold those conversations authentically, and the patience to build category trust over time — while still closing deals in the near term.
What Makes This Hard
We want to be direct: this role comes with real challenges. The right candidate will be energized by them.
Incumbent Competition
Our competitors have decades of market presence and deep enterprise relationships. Winning requires credibility, a genuine point of view, and the persistence to displace providers buyers have used for years.
Building While Running
You will grow the business while operating it — managing active accounts and partnerships, building pipeline, and closing new deals simultaneously. The infrastructure is evolving; you will help shape it.
Shaping a New Category
AI-enabled outplacement is differentiated — and unfamiliar to many buyers. Part of this role is winning trust and shifting perception, not just winning deals. That takes time and credibility.
Why This Role, Why Thrive
Thrive is at an inflection point. Here is what makes this opportunity worth your consideration:
- Real commercial ownership — not a managed quota with limited influence over the product or strategy.
- A meaningful mission: making premium career services accessible to every person going through a workforce transition, not just the privileged few.
- An AI roadmap that gives you genuine competitive advantages — and a story worth telling.
- Established revenue and active markets to build from, not a greenfield with nothing behind it.
- A leadership team invested in your success — and committed to increasing your scope as you build the business.
- The chance to help define what outplacement looks like in the AI era. Globally.
Qualifications
We are open to candidates who have built their careers at the intersection of this space — outplacement experience is valuable but not a prerequisite. What matters most is commercial credibility with senior HR buyers, enterprise deal ownership, and a genuine curiosity about AI-enabled services.
Required
- 10+ years of progressive commercial leadership — ideally with exposure to outplacement, career transition, workforce transformation, or HR consulting, though candidates from adjacent enterprise HR services backgrounds are strongly encouraged to apply.
- Deep understanding of employer pain points during restructuring and workforce transition, and a track record of building trusted relationships with HR and executive buyers.
- Demonstrated experience leading enterprise sales pursuits — from relationship development through proposal, negotiation, and close.
- Familiarity with digital career transition tools, coaching models, and the evolving HR tech landscape.
- Strong presence and communication skills — credible and compelling with CHROs, CFOs, and senior HR leadership.
- A collaborative working style alongside a strong bias for ownership, action, and commercial outcomes.
Valued
- Experience opening or expanding into new international markets.
- Exposure to AI-enabled HR or career services products — and comfort engaging buyers on the topic.
- An existing network within target organizations: enterprise employers, HR consultancies, advisory firms.
- Track record of building influence and driving outcomes in matrixed or cross-functional environments.
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.
Equal Opportunity & Accessibility
Thrive is an equal opportunity employer committed to building a diverse, inclusive team that reflects the communities and clients we serve. We welcome applications from all qualified candidates. Accommodations are available upon request for candidates participating in any stage of the recruitment and selection process.
