Head of Customer Success
Location: San Francisco, CA (In-Office)
Compensation: Top of Market + Equity
About Broccoli AI
Broccoli AI builds AI voice agents that act like real employees!!
In just 12 months, we’ve grown to 200+ contractors with 40% MoM growth. Backed by top-tier VCs, we’re building the AI native operating system for the trades—helping home service businesses run faster, smarter, and more profitably.
We move fast, experiment constantly, and ship products that change how real-world businesses operate.
Our Culture
At Broccoli, customer obsession and empathy are at the heart of everything we do. We’re proud to have a world-class Net Dollar Retention of 270% more than double the industry benchmark. That’s not just a metric; it’s a reflection of how deeply we understand, support, and grow with our customers.
Our Customer Success team is a critical part of that success. With six experienced CSMs already in place driving onboarding, implementation, and account growth, we’re now looking for a Head of Customer Success to lead this group through our next stage of rapid expansion.
Why This Role Matters
Our AI agents already power mission-critical communications for contractors across the country. As demand accelerates, we need a proven CS leader to scale our systems, elevate customer outcomes, and grow a world class team.
You’ll be responsible for driving adoption, retention, and expansion across a fast-growing customer base helping Broccoli AI set a new standard for what “customer success” means in AI-driven industries.
What You’ll Do
Lead and scale the CS organization: Manage and grow a team of 6+ CSMs responsible for onboarding, implementation, and retention.
Drive customer outcomes: Develop strategies that increase adoption, deliver measurable ROI, and maintain best-in-class retention metrics.
Champion customer empathy: Instill a culture of deep understanding and proactive support across every touchpoint.
Work with the industry leaders in the market .
What We’re Looking For
6+ years of experience in Customer Success, Account Management, or similar roles within SaaS or AI companies.
2+ years in leadership, managing and scaling CS teams during periods of rapid growth.
Proven track record of driving retention and expansion—ideally in high-growth, customer-centric environments.
Exceptional communication and executive presence—you connect with everyone from small business owners to enterprise leaders.
Strong operational acumen—you think in systems and know how to build processes that scale.
Deep curiosity about AI, automation, and the future of intelligent business operations.
Excited to work in-office in San Francisco, side-by-side with the team, talking to users, and driving impact daily.
Why Join Broccoli AI
Massive Impact: Lead Customer Success at one of the fastest-growing AI startups in the country.
Elite Retention: Join a team with an NDR of 270%—the strongest in our space.
High Growth, Real Scale: Step into a live operation with 6+ CSMs and hundreds of active accounts.
Leadership Opportunity: Shape the strategy, systems, and culture of a team that defines our customer experience.
Top Skills
What We Do
Broccoli AI is building the future of customer service for the trades. Our AI voice agents help plumbing, HVAC, and electrical businesses deliver fast, reliable, and empathetic support around the clock. Our mission is simple: to democratize great customer service so every contractor, no matter their size, can give customers the experience they deserve.
