---
title: 'Head of AI Success at Broccoli AI'
canonical: 'https://feeny.ai/job/head-of-ai-success-broccoli-ai-san-francisco-c14y33x8hhr4'
type: 'job'
last_seen: '2026-09-14'
---

# Head of AI Success at Broccoli AI

- **Company:** Broccoli AI
- **Location:** San Francisco, CA
- **Compensation:** $200k–$300k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-04-23
- **Last confirmed live:** 2026-09-14
- **Apply:** https://jobs.ashbyhq.com/broccoli/c11599b9-56c3-4dc6-95f8-c263b7d4e55a/application

**Skills:** AI, Data Analysis, Customer Success, Product Management, Operations, Customer Success processes, Startup experience

> The Head of AI Success will design and build scalable AI-powered systems to drive customer retention, expansion, and net revenue resolution for Broccoli AI. This role focuses on creating automated, AI-first workflows and teams rather than manual relationship management, aiming to scale the customer success function...

## Job description

## 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, the hardworking businesses that keep homes and communities running, and 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, all while integrating seamlessly with platforms like ServiceTitan. Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built. Today:

- Hundreds of contractors rely on Broccoli every day.
- We've grown to $15M+ ARR in under two years.
- We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry.
- We're backed by Khosla Ventures and Y Combinator.

We're still just getting started.

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.

## About Broccoli AI

## Company Overview
- **One-liner**: Broccoli AI builds an AI-native operating system for home service businesses, using voice agents to automate customer service, scheduling, and revenue operations for plumbing, HVAC, and electrical contractors.
- **Entity Type**: Private (Series A)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2021
- **Founders**: AJ Jain (CEO) and Aditya Ketkar (CTO)

## Core Business
- **Primary industry/industries**: Home Services Technology, Artificial Intelligence, Customer Service Automation
- **Target customers**: B2B — plumbing, HVAC, and electrical contractors (from single-location operators to PE-backed roll-ups)
- **Mission or purpose statement**: "To democratize great customer service so every contractor, no matter their size, can give customers the experience they deserve."

## Products & Services
- **AI Voice Agents**: AI-powered phone agents that answer every call 24/7, book jobs in real time, and provide empathetic customer support for trades businesses. Type: AI Agent / SaaS.
- **Revenue Automation (Outbound & Follow-ups)**: Automated outbound calling and follow-up sequences to drive more revenue for contractors. Type: AI Agent / SaaS.
- **Operations Automation**: AI agents that handle scheduling, dispatch, and alerting for emergencies, integrated with systems like ServiceTitan. Type: AI Agent / SaaS.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed.
- **Key Metric**: Raised $25M+ in Series A funding led by Khosla Ventures, with participation from Y Combinator (Winter 2022 batch). [ycombinator.com](https://www.ycombinator.com/companies/broccoli-ai/jobs)
- **Notable Investors/Partners**: Khosla Ventures (lead, Series A), Y Combinator (W22 batch), Gustaf Alstromer (YC partner).
- **Growth Signals**: Grew from 0 to 800+ contractors in under 2 years; grew from $0 to millions in ARR in under a year; headcount grew 272.7% year-over-year to 31 employees; 22 active job postings (monthly job postings up 46.7%, yearly up 2,100%). [linkedin.com](https://www.linkedin.com/company/broccoli-com)

## Competitive Advantages
- **Deep vertical focus**: Built specifically for trades (plumbing, HVAC, electrical) rather than a generic AI voice agent, allowing for industry-specific workflows and integrations (e.g., ServiceTitan).
- **Founder-market fit**: Founders spent 9 years working together and went door-to-door meeting 100+ contractors to understand the market before building, leading to a product that truly fits the workflow.
- **Rapid traction**: Grew from 0 to 800+ contractors and from $0 to millions in ARR in under a year, indicating strong product-market fit.
- **Full-stack automation**: Unlike point solutions that only handle calls, Broccoli automates the entire front office (calls, scheduling, dispatch, follow-ups, marketing) in one platform.

## Strategic Focus
- **Scale the contractor base**: Continue onboarding plumbing, HVAC, and electrical businesses, targeting both single-location operators and large PE-backed roll-ups.
- **Deepen the operating system**: Expand automation beyond voice to cover the full workflow of home service businesses (scheduling, dispatch, marketing, operations).
- **Expand into new verticals**: The company is hiring for a "Strategy & Operations Lead, New Verticals," indicating plans to expand beyond the core trades.
- **Hire aggressively**: With 22 open positions and massive job posting growth, the company is in a major scaling phase across engineering, sales, marketing, and operations.

## Why Work Here
- **High-growth environment**: The company is growing extremely fast (272.7% headcount growth YoY, millions in ARR in under a year), offering employees the chance to have outsized impact in a rocket ship.
- **Founder-led with strong pedigree**: Founders AJ Jain and Aditya Ketkar have worked together for 9+ years, have backgrounds at Adobe and Microsoft, and are backed by top-tier investors (Khosla Ventures, Y Combinator). [ycombinator.com](https://www.ycombinator.com/companies/broccoli-ai)
- **Culture of deep customer empathy**: The company was built by going door-to-door and meeting 100+ contractors, and that customer-first ethos permeates the engineering and product culture.
- **Work policy**: Hybrid/In-Office — the company has two offices in San Francisco (300 Brannan St) and roles are listed as "Hybrid" or "In-Office" on Built In. [builtin.com](https://builtin.com/company/broccoli-ai)
- **Notable perks**: Backed by top-tier VCs (Khosla, YC); opportunity to work on a high-impact AI product that directly helps small businesses; fast-paced environment with significant ownership.
- **Engineering culture**: Heavy emphasis on AI and full-stack engineering; the team is building a complex, real-time voice AI system integrated with legacy field service software. Open roles include Staff Software Engineer, Director of Engineering, and Senior Product Manager. [ycombinator.com](https://www.ycombinator.com/companies/broccoli-ai/jobs)

## Sources
1. [broccoli.com](https://www.broccoli.com/)
2. [linkedin.com](https://www.linkedin.com/company/broccoli-com)
3. [ycombinator.com](https://www.ycombinator.com/companies/broccoli-ai)
4. [ycombinator.com - Jobs](https://www.ycombinator.com/companies/broccoli-ai/jobs)
5. [builtin.com](https://builtin.com/company/broccoli-ai)

## Other roles at Broccoli AI

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- [Office Manager (SF)](https://feeny.ai/job/office-manager-sf-broccoli-ai-san-francisco-zdx0kagdg281) — San Francisco, CA
- [People Operations Coordinator](https://feeny.ai/job/people-operations-coordinator-broccoli-ai-san-francisco-hdkmvwjfatnk) — San Francisco, CA
- [Director of Technical Success](https://feeny.ai/job/director-of-technical-success-broccoli-ai-lehi-jx3vwews73k9) — Lehi, UT
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