Head of GTM Strategy, Operations & AI

About Faire Faire is a technology wholesale platform built on the belief that the future is local. Independent retailers around the globe collectively represent a multi-hundred-billion-dollar wholesale market that has historically been fragmented and offline. At Faire, we're using the power of tech, data, and machine learning to connect this thriving community of entrepreneurs across the globe. Picture your favorite boutique in town — we help them discover the best products from around the world to sell in their stores. With the right tools and insights, we believe that we can level the playing field so businesses can grow and local communities can thrive. We’re looking for smart, resourceful and passionate people to join us as we power the shop local movement. If you believe in community, come join ours. About this role We're looking for a transformational leader who can use AI to help our teams work smarter and faster, so they can spend more time building real relationships with the independent retailers and brands at the heart of our mission. This isn't a traditional Revenue Operations role. Faire has already embraced an AI-first future. We have active initiatives underway, dedicated resources, and strong momentum. We're looking for a leader who can accelerate that journey, rethink what’s possible in today’s world, and help redefine how our Sales and Success teams operate internally and with customers. If you are someone who values moving fast, iteration over perfection, and trialing new ideas, you’ll fit right in. You'll lead a team of approximately 15 spanning multiple subfunctions under Rev Ops including GTM Engineering, Program Management, Enablement, and Analytics. Together, you'll own the systems, tooling, processes, training, and operating rhythms that power our revenue organization while helping shape the future of work through AI. What you’ll do Own the GTM Strategy & Execution Set the strategy, goals, and territory design across our sales and success teams - including how we set targets, prioritize accounts, and allocate resources across motions Own forecasting accuracy and pipeline diagnostics, and build the data and metric standards that the revenue function reports against Translate business strategy into GTM priorities; make tradeoffs visible and keep the org focused on the highest-leverage work Lead the AI Roadmap for Revenue Define and evolve the AI vision and roadmap for the revenue org - always anchored to business outcomes Decide where AI and automation belong in how we operate and analyze performance, and where human judgment is required, and build the review processes that make AI output reliable enough to act on Evaluate, build, and validate solutions and tools; this role is hands-on and leading from the front on AI building Measure what actually moved: rep time saved, conversion lift, pipeline quality Define and evolve the AI vision and roadmap for the revenue org - always anchored to business outcomes Decide where AI and automation belong in how we operate and analyze performance, and where human judgment is required, and build the review processes that make AI output reliable enough to act on Evaluate, build, and validate solutions and tools; this role is hands-on and leading from the front on AI building Measure what actually moved: rep time saved, conversion lift, pipeline qualityDrive Enablement and Adoption Drive Enablement and Adoption Own the enablement function for the revenue org - translating strategy, tools, new processes and sales skills into how reps and managers actually operate day to day Drive adoption and behavior change when new tools, processes, or AI workflows roll out; building something nobody uses isn't a win Build and Develop the Team Hire, coach, and develop a high-performing team with clear ownership, accountability, and career paths Foster a culture of experimentation, high standards, and the willingness to call things that aren't working We're looking for someone who Is a