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Chief of Staff

Broccoli AISan FranciscoPosted Aug 31, 2026
Chief of StaffOn-siteExecutive
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Mirrored from Broccoli AI's own Ashby careers system · refreshed hourly

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Other open Broccoli AI roles
Aug 31
Posted
Ashby
Applicant system
Job description

About Broccoli 🥦

 

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.

The Role

We are hiring our first Chief of Staff to operate out of the founder's office, working directly with our CEO and partnering closely across the exec team. This is a broad mandate: part strategic thought partner, part cross-functional operator, part connective tissue for a fast-moving leadership team.

What You'll Own

Strategy and Special Projects

  • Drive strategic special projects end to end, from framing the problem to seeing execution through.

  • Bring structure to ambiguous, undefined problems that don't yet have an obvious owner.

  • Act as a thought partner to the CEO on prioritization, weighing trade-offs and pressure-testing plans before they go company-wide.

Cross-Functional Execution

  • Lead cross-functional initiatives that require coordinating across engineering, GTM, finance, and people.

  • Partner with the broader exec team (CTO, COO) on initiatives that span the founder's office.

  • Track ownership and follow-through across teams so priorities don't stall between functions.

Operating Cadence

  • Own the rhythm of how leadership operates, including planning sessions, leadership meetings, all-hands prep, and priority tracking.

  • Build and improve internal operating systems and processes as the company scales past its early-stage.

Board and Executive Support

  • Prepare board and investor materials, including decks, memos, and synthesizing input from across the company into something the CEO can walk into a room with.

  • Act as a force multiplier for the CEO's time, judgment, and follow-through across a wide range of priorities.

Nice to Have

  • Prior experience in a founder's office or chief-of-staff-adjacent role at a high-growth startup.

  • Strategy consulting experience before moving into an operating role.

  • Past founder experience.

  • Comfort picking up new internal tools quickly (we run on Ashby, Slack, and Google Workspace).

Broccoli is an equal-opportunity employer and complies with all applicable federal, state, and local fair employment practice laws.

View original posting on Ashby

What applying to Broccoli AI usually looks like

Based on publicly available information, candidates applying through Ashby can typically expect a structured online application process, often beginning with a resume and application form submission followed by an automated confirmation email. Ashby-based employers commonly use standardized workflows, which may include an initial recruiter screen, followed by additional interview stages such as hiring manager conversations, skills assessments, or panel interviews depending on the role. Response times vary by employer and position, and candidates should not assume a fixed number of rounds, as this can differ based on seniority and department, whether for technical, sales, or operational roles. Applicants to Broccoli AI may also encounter take-home assignments or case studies for certain functions. Communication is generally handled through the Ashby platform, and candidates are encouraged to monitor their email, including spam folders, for updates throughout the process.

Based on publicly available information. LandEarly does not verify interview process details.

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Chief of Staff
Broccoli AI · San Francisco
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