Chief of Staff

Broccoli; San Francisco (CA); On-site; USD 140,000 - 200,000; Full time

Job summary

Broccoli, an AI startup building teammates for trades, is hiring its first Chief of Staff to operate from the founder's office, working directly with the CEO and the executive team. This role blends strategic thinking with hands-on execution across a fast-moving leadership group.

You will drive strategic projects end to end, lead cross-functional initiatives, and help shape operating rhythms as the company scales. Prior founder experience or strategy consulting is a plus.

Qualifications

• Must have experience in a founder's office or CEO-facing role at a high-growth startup.

Responsibilities

• Drive strategic special projects end to end.
• Lead cross-functional initiatives across engineering, GTM, finance, and people.
• Own operating cadence and leadership prep, including board materials.

Skills

Cross-functional

Strategic thinking

Project management

Executive comms

Board prep

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.