Director of Enterprise Workshops

About the Role

Section helps organizations build AI-powered workforces – our software (Section HQ and Section Coach) coaches employees to become AI-powered and measures the progress and ROI of employee AI use. Our workshops are often the first thing a client experiences with Section – live sessions that take executive teams and practitioners from AI-curious to AI-capable.

We are looking for a Director of Enterprise Workshops to own and run our workshop business end to end. This is a player-coach role: you'll run workshops like a business – owning quality, the instructor bench, and the content library – while also being one of our best people in the room, designing and delivering sessions yourself. One week you're facilitating an AI strategy session for a Fortune 500 executive team; the next you're building hands-on content that teaches practitioners to work in tools like Claude and Claude Code.

What You'll Own

• Run the workshop business day to day: capacity, scheduling, instructor staffing, and delivery operations, supported by a full-time program manager who reports to you

• Own workshop quality end to end – define what excellent looks like, build the systems that make it repeatable (presenter prep, content standards, post-session debriefs), and act fast when a session falls short

• Build and manage the instructor bench: develop the core instructors we use regularly, recruit and vet new ones, match the right presenter to the right room, and make the hard calls when someone isn't meeting the bar

• Own the workshop content library – what we teach, how it's structured, and how it stays current in a market that moves monthly – including building new sessions from scratch, from executive strategy formats to technical hands-on builds

• Personally design and deliver workshops, including our highest-stakes sessions: C-suite audiences and flagship client moments

• Partner with sales and account teams on scoping and shaping workshop engagements that fit what clients actually need

What Success Looks Like

• Quality is consistent – clients and account teams trust that any session, with any instructor, will land

• The instructor bench is deeper, better developed, and less dependent on any single person (including you)

• Workshop content stays ahead of the market, with new formats shipping as the technology and client needs evolve

• The workshop business runs without your manager in the loop day to day

What We're Looking For

• A proven room presence with senior executives – you can hold a room of skeptical CEOs, CFOs, and VPs and leave them convinced, and you've done it many times

• Genuinely technical with AI: you use frontier tools daily, can build a live demo or agent yourself, and can teach practitioners to do the same in tools like Claude Code – you don't need an engineer to make your content work

• Able to work high-low – deciding workshop strategy and portfolio direction while also prepping an instructor for Thursday's session, often in the same day

• Experience managing people and a distributed or contract talent bench – you hold a high bar without burning relationships

• A systems builder, not a hero: when something breaks, your instinct is to fix the process, not just the session

• Plain, fast communicator – no jargon, no theater

Details

• Full-time, remote-first (US), with travel for on-site deliveries

• Reports to the Chief AI Enablement Officer