Head of AI Success
Broccoli · San Francisco
About this role
## About Broccoli AI At Broccoli, we’re building **AI teammates** for the people who build and maintain our world. We partner with **plumbing, HVAC, and electrical contractors** to replace fragmented software and repetitive manual work with AI that actually gets the job done. Our AI teammates **answer phones, book appointments, follow up with customers, recover missed revenue,** and help contractors deliver exceptional customer experiences—while integrating seamlessly with platforms like **ServiceTitan**. Before writing code, we visited **140+ contractors** to understand how these businesses truly operate. Today: - Hundreds of contractors rely on Broccoli every day - **$15M+ ARR** in under two years - Trusted by independent contractors and large private equity–backed operators - Backed by **Khosla Ventures** and **Y Combinator** --- ## Head of AI Success @ Broccoli This is **not** a traditional Head of Customer Success role. Prior customer success leadership is a plus, but not required. We’re looking for someone **deeply analytical, systems-driven, and AI-native**—who can **design and build a machine** that drives **retention and expansion at scale**, not manage it manually. --- ## What You’ll Own (Post-Sale) Your goals: maximize **customer happiness, product usage, and NDR**. You’ll own: - **Retention + Expansion** - **Customer outcomes** (bookings, revenue, efficiency) - **Deployment speed** (time-to-value in **days**, not weeks) - **Support** (AI-first, proactive, scalable) --- ## What You’ll Do - Build the **AI-powered success engine** scaling from **500 → 5,000+ customers** - Create systems for: - Account segmentation + ownership - Health scoring - Expansion and upsell playbooks - Turning customer data into revenue opportunities - Redesign onboarding to be **fast, repeatable, and low-touch** - Automate support and success workflows using **AI** - Hire and lead teams across **Success, Deployment, and Support** --- ## What Success Looks Like - **Best-in-class NDR** (expansion becomes predictable) - Faster deployments and **lower support load** - A clear, repeatable **expansion engine** - A lean, high-leverage team powered by AI --- ## How You Operate - **Systems thinker:** design scalable systems, not manual processes; can build health scoring, segmentation, and playbooks - **Analytical:** live in metrics (NDR, churn, expansion, usage) and turn messy data into clear actions - **AI-native:** instinctively automate workflows (e.g., Claude); think leverage first, headcount last - **Revenue-driven:** CS as a revenue function; comfortable owning expansion and NDR; want to create the playbook, not inherit one; can scale messy systems into machines --- ## Your Background - **8+ years** of strategy, product, or operations experience (e.g., product manager, engagement manager, consultant, founder, etc.) - Strong interpersonal and relationship-building skills - Experience developing new AI solutions in fast-moving, ambiguous environments **Bonus:** - Knowledge of Customer Success processes, systems, and best practices - Experience at a high-growth startup - Background in computer science or AI product management --- Broccoli is an **equal-opportunity employer** and complies with all applicable federal, state, and local fair employment practice laws.
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