AI Strategy Senior Director

Today

• Hundreds of contractors rely on Broccoli every day.
• We've grown to $15M+ ARR in under two years.
• We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry.
• We're backed by Khosla Ventures and Y Combinator.

We're still just getting started.

The Role

If you've been on the value creation side of private equity, you know the job: find the operational levers, pull them across the portfolio, and turn them into EBITDA. AI is the largest lever to come along in a generation. Broccoli is how the trades pull it.

We're hiring a Senior Director of AI Strategy to lead AI value creation across our most strategic customers, which include PE-backed roll-ups and franchise groups with $1B+ revenue. You'll own the value creation thesis for these accounts and sit across the table from CEOs, CFOs, and PE partners as the person who makes the numbers move.

You'll have a team behind you. Every strategic customer has dedicated implementation, customer success, and forward-deployed engineers driving deployments and adoption on the ground. You oversee that team and own the outcome: ensuring every account gets the most from what it has today and has a clear path to realizing additional value over time across products and locations.

Expect travel to customers as needed to build executive relationships and ensure results.

What You'll Do

• Own the outcome on each account: make sure every location is getting the highest value from the AI products it runs today, quantify it in hard numbers (ROI, EBITDA impact, revenue, conversion, labor savings), and turn frontline results into board-level reporting.
• Diagnose why some locations outperform and others lag, then close the gap across technology, people, and process.
• Drive expansion into more AI products and more locations, growing each account toward our expanding platform.
• Direct the on-account team that owns execution (implementation, customer success, forward-deployed engineers) while you stay accountable for the outcome.
• Be the proactive partner to CEOs, CFOs, and PE partners, carrying the value story to the top.
• Feed learnings from the field back to Product, Engineering, and Operations to shape both the roadmap and our operating model.

What We're Looking for

• 10+ years across PE value creation or operating-partner roles, top-tier consulting (MBB), or senior operating roles in trades, industrials, or field services.
• A track record of measurable impact: EBITDA, margin, revenue, or operational improvement you drove through execution, not just recommended.
• Customer obsession. You measure yourself by whether the customer is better off, and you do what it takes to make sure they are.
• Credibility operating at the top, advising sponsors, boards, CEOs, and CFOs as a trusted partner.
• Comfortable in the data yourself. You can pull the numbers and build the model.
• You build polished, executive-ready slides that make complex work easy to follow.
• Deep operational knowledge of how roll-up businesses run, and where the leverage hides.
• An AI-native mindset. You use AI tools daily and have strong intuition for how AI reshapes how organizations operate.
• Excited to work in-person 5 days a week in San Francisco with the team

Bonus Points

• Experience at PE portco specifically in home services (e.g., HVAC, roofing, garage, pest control, etc.)
• Startup experience