Head of Go-to-Market 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 Revenue Operations 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
• 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 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.

Qualifications

• 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

Salary Range

San Francisco: the pay range for this role is $285,000 to $357,500 per year.

This role will also be eligible for equity and benefits. Actual base pay will be determined based on permissible factors such as transferable skills, work experience, market demands, and primary work location. The base pay range provided is subject to change and may be modified in the future.

Work Arrangement

Hybrid Faire employees currently go into the office 3 days per week on Tuesdays, Thursdays, and a third flex day of their choosing (Monday, Wednesday, or Friday). Additionally, hybrid in-office roles will have the flexibility to work remotely up to 4 weeks per year.

Why You’ll Love Working at Faire

• Move fast: You’ll own meaningful problems that serve customers around the globe with the agency to move fast and see your results clearly.
• Equipped to scale: We invest in what matters, including the latest enterprise AI tools, to help you work smarter and get more out of every day.
• Best in class: Our team is full of sharp, kind, and generous colleagues who care about their craft and about helping you grow in yours.
• Real rewards: Competitive pay, equity, and comprehensive benefits designed to support your life inside and outside of work.
• Belonging: We’re intentional about building an environment where every Faire employee has equal access to opportunities, growth, and success.

Faire was founded in 2017 by a team of early product and engineering leads from Square. We’re backed by some of the top investors in retail and tech including: Y Combinator, Lightspeed Venture Partners, Forerunner Ventures, Khosla Ventures, Sequoia Capital, Founders Fund, and DST Global. We have headquarters in San Francisco and Kitchener-Waterloo, and a global employee presence across offices in Toronto, London, and New York.

Faire provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or gender expression.