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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 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.
Job Responsibility
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
Stay close to the competitive landscape
Bring market intelligence back into the business
Build and manage a pipeline of enterprise employer relationships — with CHROs, HR Directors, and Total Rewards leaders
Lead proposals, RFP responses, and executive-level sales meetings
Partner with Thrive's Sales and Marketing teams
Develop segment-specific sales approaches
Grow Thrive's existing network of direct and channel delivery partners
Identify and develop new distribution partnerships
Define commercial terms and accountability frameworks for partner relationships
Act as the primary relationship owner for strategic partners
Partner with the Chief Customer Officer to ensure a strong handoff from sale to implementation
Retain senior commercial ownership of key accounts
Work closely with Product and R&D to ensure the platform roadmap reflects what the market requires
Collaborate with Delivery and Customer Success to ensure program implementations meet client expectations
Support the development of scalable delivery frameworks
Champion Thrive's AI-enabled workflows with clients
Requirements
10+ years of progressive commercial leadership — ideally with exposure to outplacement, career transition, workforce transformation, or HR consulting
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
Nice to have
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