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Broccoli AI is building AI teammates for contractors in plumbing, HVAC, and electrical services. The company has grown to $15M+ ARR in under two years and is backed by Khosla Ventures and Y Combinator. Broccoli's AI solutions handle phone answering, appointment booking, customer follow-up, and revenue recovery while integrating with platforms like ServiceTitan.
As the first Chief of Staff, you will operate out of the founder's office, working directly with the CEO and partnering closely with the executive team. This is a broad, high-impact role combining strategic partnership, cross-functional operations, and organizational leadership.
Key responsibilities include:
**Strategy and Special Projects**: Drive strategic initiatives end-to-end, from problem framing through execution. Bring structure to ambiguous, undefined problems without obvious owners. Serve as a thought partner to the CEO on prioritization, trade-off analysis, and pressure-testing plans before company-wide rollout.
**Cross-Functional Execution**: Lead initiatives requiring coordination across engineering, GTM, finance, and people functions. Partner with the exec team (CTO, COO) on initiatives spanning the founder's office. Track ownership and follow-through to prevent priorities from stalling between functions.
**Operating Cadence**: Own the rhythm of leadership operations, including planning sessions, leadership meetings, all-hands preparation, and priority tracking. Build and improve internal operating systems and processes as the company scales beyond early-stage.
**Board and Executive Support**: Prepare board and investor materials (decks, memos, synthesized company input). Act as a force multiplier for the CEO's time, judgment, and follow-through across diverse priorities.
**Requirements**: While not explicitly stated as hard requirements, the posting indicates preference for prior experience in a founder's office or chief-of-staff-adjacent role at a high-growth startup, strategy consulting background before moving into operations, founder experience, and comfort with internal tools (Ashby, Slack, Google Workspace).
