AI Transformation Lead

About Broccoli AI

Broccoli AI is building the AI operating system for home service businesses.

We work with plumbing, HVAC, and electrical contractors — the people who keep homes running — and we replace fragmented tools and manual workflows with AI agents that actually do the work.

Our AI assistants answer phones, book jobs, follow up with customers, and drive revenue, fully integrated into systems like ServiceTitan.

We started by going door-to-door, meeting 100+ contractors, and understanding how these businesses actually run. That shaped everything we’ve built. Today:

• Hundreds of contractors use Broccoli to run their front office

• We’ve grown from $0 to millions in ARR in under a year

• We’re trusted by both single-location operators and the largest PE-backed roll-ups

• Raised $25M+ from Khosla Ventures and YC

The Role

We’re hiring an AI Customer Strategy Lead to get customers live on our platform and make it deliver real value in their business.

This is the work that turns a signed contract into a customer who runs their front office on our platform. You’ll own the rollout end to end: understand how each business operates, configure and launch the platform to fit it, drive adoption across the front office and technicians, and prove the impact in the customer’s own numbers. You won’t do it alone — you’ll partner closely with our forward-deployed engineers, who handle the deep technical build while you own the customer, the configuration, and the outcome. You’ll do this across a portfolio of customers at once, and you’ll help shape the playbook and delivery model that let us do it well at scale.

The best person for this has done implementation or deployment before at a company where getting customers live and adopting was the product. This is hands-on transformation work — you own the rollout and the outcome, not a set of recommendations. You understand SMB operators, you’re comfortable in the data, and you measure yourself by whether the customer is genuinely better off. It’s an early, high-ownership role with real room to grow as we scale.

What You’ll Do

• Own the rollout. Take customers from signed to fully live on the platform — scoping, configuration, launch, and adoption across the front office, technicians, and locations.

• Learn the business first. Understand how each customer actually operates, then set up the platform to fit the way they work.

• Drive adoption and value. Make sure customers are using the platform deeply and getting real results — and quantify it in hard numbers (ROI, revenue, conversion, labor savings).

• Manage a portfolio. Run multiple customer rollouts at once, keeping each on track to go-live and to value.

• Be the customer’s trusted partner. Build the relationship, run the day-to-day, and turn frontline results into reporting their leadership trusts.

• Partner with engineering. Work hand in hand with our forward-deployed engineers — they handle the deep technical build, you own the customer, the configuration, and the outcome.

• Influence the playbook and delivery model. Turn what works in the field into repeatable practices that shape how we deliver the platform as we scale.

• Feed the field back to Product. Turn what you learn on the ground into signal that shapes the roadmap and how we deliver.

What We’re Looking For

• 4–8+ years in implementation, onboarding, deployment, or platform migration at a high-growth software or ops-heavy company (e.g., ServiceTitan, Toast, Rippling, or similar).

• Also a fit: technology-transformation or systems-implementation consulting (e.g., Deloitte, Accenture) where you ran the rollout rather than advised, or an engineering/technical background you’ve turned toward customers and business outcomes.

• A track record of getting customers live and adopting — ideally across a portfolio, and ideally with SMB or multi-location operators.

• Measurable impact you can point to: adoption, retention, time-to-value, revenue, or operational improvement you drove through execution.

• Customer obsession. You measure yourself by whether the customer is better off, and you do what it takes.

• Comfort in the data yourself — you can pull the numbers, show the impact, and tell the story.

• Strong presence with both senior leaders and frontline operators; you can earn a shop owner’s trust as easily as an executive’s.

• An AI-native mindset. You use AI tools daily and have strong intuition for how AI reshapes the way a business runs.

• Excited to work in person 5 days a week in San Francisco with the team.

Bonus Points

• You’ve owned a platform migration or major product rollout across many customers or locations.

• Experience in home services, field services, restaurants, retail, or other multi-location / SMB-dense industries.

• Startup experience.

Broccoli is an equal-opportunity employer and complies with all applicable federal, state, and local fair employment practice laws.