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Head of AI Success

Broccoli
CompanyBroccoli
CategoryData & Analytics
LocationSan Francisco
RemoteOn-site (inferred)
EmploymentNot stated
LevelDirector
SalaryUSD 200k–300k
Posted23 Apr 2026
Last verified10 Aug 2026
SourceEmployer ATS (ashby)
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Description
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 → 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 HEAD OF AI SUCCESS @ BROCCOLI This is not a traditional Head of Customer Success role (and previous experience leading customer success is a plus, but not required). We’re not hiring someone to just manage relationships or coach people. We’re hiring someone deeply analytical, systems-driven, and AI-native — someone who can design and build a machine that drives retention and expansion at scale, not manage it manually. WHAT YOU’LL OWN Everything post-sale. Your goals are to 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 that scales from 500 → 5,000+ customers - Create systems for: - Account segmentation + ownership - Health scoring - Expansion and upsell playbooks - Turn 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, lower support load - Clear, repeatable expansion engine - A lean, high-leverage team powered by AI HOW YOU OPERATE Systems thinker - You design scalable systems, not manual processes - You’ve built (or can build) health scoring, segmentation, and playbooks Analytical - You live in metrics: NDR, churn, expansion, usage - You turn messy data into clear actions AI-native - You instinctively automate workflows using tools like Claude - You think leverage first, headcount last Revenue-driven - You see CS as a revenue function, not support - You’re comfortable owning expansion and NDR Builder - You want to create the playbook, not inherit one - You’ve scaled or want to 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 environment - 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.