Head of Customer Success

Head of Customer Success / Founding Customer Success Lead

Location: San Francisco, CA (In-Office, 6 Days/Week)
Compensation: Top of Market + Equity

About Broccoli AI

Broccoli AI builds AI voice agents that act like real employees—answering phones 24/7, booking jobs in ServiceTitan, alerting techs when emergencies hit, and following up on missed calls or open estimates.

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.

Why This Role Matters

Our AI agents already power mission-critical customer communications for contractors nationwide. Now we need a world-class Customer Success leader to ensure every customer—from small HVAC shops to multi-location franchises—gets value from day one and stays for the long run.

This is a founding role : you’ll be the first Customer Success hire, working directly with the founders to design the systems, playbooks, and culture that define how we scale customer happiness and retention.

What You’ll Do

• Own the customer journey: Build onboarding, training, and retention processes that turn new users into advocates.

• Be the voice of the customer: Translate feedback into actionable insights for product and engineering to improve the AI experience.

• Drive adoption and outcomes: Help customers understand how Broccoli AI transforms their operations and measure success through real ROI.

• Design and lead processes: Create scalable CS systems—from health scoring to renewal workflows and playbooks.

• Hire and lead: As we grow, build and manage a world-class Customer Success team from the ground up.

• Partner with founders: Work cross-functionally with Product, Growth, and Engineering to shape the roadmap based on what customers actually need.

• Set the standard: Establish the metrics and rhythms for success—NPS, churn, time-to-value, expansion, and more.

What We’re Looking For

• 3–8 years of experience in Customer Success, Account Management, or Operations (preferably at a SaaS or AI company).

• You’ve built or scaled CS programs before—or you’re ready to.

• Exceptional communication and empathy—you can explain technical products clearly and connect with both business owners and operators.

• Analytical mindset: you’re data-driven, comfortable with dashboards, and can identify patterns in churn, retention, and usage.

• Comfortable with ambiguity and rapid growth —you like building structure where none exists.

• Deep curiosity about AI, automation, and voice technology , and how these tools impact real-world industries.

• 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: Own customer success at one of the fastest-growing AI startups in the country.

• Founding Role: Define how we support and retain our customers from the ground up.

• Direct Collaboration: Work shoulder-to-shoulder with the founders and leadership team.

• Fast Feedback Loop: What you build this month shapes what thousands of users experience next month.

• Top-of-Market Pay + Equity: Meaningful ownership in a company growing 40% month-over-month.

• Beautiful South Park Office: Collaborative, high-energy, and surrounded by builders