Head of GTM Strategy, Operations & AI

Faire•San Francisco, CA

1d•$285,000 - $357,500•Hybrid

About The Position

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.

Requirements

10+ years of experience in GTM Operations, Revenue Operations, Strategy & Operations, Business Operations, Management Consulting, or related fields
Experience using AI tools and workflows to drive measurable improvements in team productivity or business outcomes
Experience building and leading high-performing teams
Strong analytical and operational skills
Experience in high-growth technology companies preferred

Nice To Haves

Is a Builder: You're a builder at heart — whether that means designing a better workflow, structuring a team from scratch, or prototyping a tool to test an idea. You're curious about what's possible and energized by turning that curiosity into something that actually works for the people using it. You follow AI developments closely and know how to apply them — but you're just as energized by a well-designed process or a sharp insight as you are by a new tool.
Has Exceptional Judgment: You understand where AI can create meaningful leverage and where it can't. You can tell the difference between a solution that saves a rep an hour a week and one that just looks impressive in a demo. You make thoughtful tradeoffs and focus on what matters most.
Knows Go to Market Deeply: You understand sales and the levers to move outcomes. You don’t just implement a playbook, you dig deep on each motion, ask good questions, form hypotheses, and develop first-principle strategies.
Builds Strong Teams: You raise the performance of the people around you. You coach effectively, are not afraid to have difficult conversations, and help individuals and teams reach their full potential.
Moves Fast and Creates Clarity: You're good at figuring out what matters most, communicating it clearly, and getting things done quickly and effectively.
Cares about who you are building for: You care about the mission and the team. You want to build a world where independent retailers thrive and help create vibrant communities. And you get true fulfillment from making the lives and roles of the reps who make that happen better and more impactful.

Responsibilities

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
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