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Open nowPosted 45 days ago

Chief of Staff & Business Operations

Workable (global search)108,016 open roles

Where
San Francisco, CA, United States
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Your applicationOpen nowChief of Staff & Business OperationsWorkable (global search) · San Francisco, CA, United States

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The clock on this job

Early applications get read.

7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

Share of postings closed within
  1. 1.6%1 day
  2. 3.6%3 days
  3. 7.9%7 days
  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 45 days ago

Workable (global search) median: 7 days open

The posting

Rockstar is recruiting for a market-leading AI voice agent for mortgage lenders. Founded in 2024, the company has grown rapidly, currently counting 5 of the 10 largest independent mortgage banks in the U.S. as enterprise customers. The company has raised $21M across Seed and Series A from top investors.

Why This Is a Huge Opportunity

Around 1% of the U.S. labor force works in phone sales, representing roughly $100B of annual salary, and the industry is poised at the brink of complete disruption. The company is at the cutting edge of this economic transformation, one of the first creating real, durable economic value through applied AI.

Buying a house is the largest financial decision most people make in their lives, and homeownership is tied to many other purchases, including life insurance, homeowners insurance, alarm systems, home renovations, solar panels, and more. By owning the mortgage vertical, the company will own the relationship with the consumer, allowing them to serve as the essential AI infrastructure for high consideration consumer sales.

Why Join

  • Crazy growth: The market pull is exhilarating — the company has grown 10x in the past 12 months and more than 100x since its seed round, all without a dedicated sales or marketing team. Building something that people want so badly is the best feeling you can have in a startup.
  • Team and Culture: The team is high-agency, with a high bar where everyone makes the people around them better. Collaboration and intensity are core team values: people truly care about their work and their coworkers. At the same time, the team does not take itself too seriously.
  • Challenging problems: Outperforming human sales teams on half a million daily calls is not easy. Low-latency, real-time infra. 99.9% uptime. Enterprise-grade privacy and security. Advanced simulation and evaluation systems. Flexible A/B testing. AI scheduler and dialer. The company owns the whole stack and does not compromise on quality.
  • Well-funded: The company has raised $21M+ in total funding, most recently a $15M Series A in June 2026.

The Role

The role will be the CEO's closest partner and the first Business Operations hire. The job has two halves. The hire will own a set of commercial functions outright — contracts, reporting, pricing — and will be the person the CEO hands whole problems to: the urgent, ambiguous, high-stakes ones that do not have an owner yet. Most of this does not exist today, so the hire will be building it rather than maintaining it. This role is for a generalist who wants scope instead of specialization. The specifics will change as the company changes. What stays constant is that the hire owns outcomes.

What the Role Will Own

  • The commercial engine, end to end: Driving customer contracts and MSAs through legal, negotiation, and redlines to signature, and keeping enterprise deals moving between executive touch points. The hire will not be doing this alone on day one — the CEO will be in the room through the early negotiations — but the hire will own the process and the outcome.
  • The operating and reporting infrastructure, built from scratch: Key operating metrics, revenue operations, and GTM reporting that give the team and the board a clear read on the business. Today, most of this lives in scattered spreadsheets and in the CEO's head.
  • Pricing: The analysis, the structure, and the reasoning behind what the company charges as it continues to move upmarket.
  • The CEO's leverage: The hire will take whole problems off the CEO's plate and hand them back finished: board materials and investor updates, the operating cadence that keeps a fast-growing team pointed in the same direction, follow-through on decisions that would otherwise sit, partner relationships, and the special projects nobody owns yet. Handed to the hire whole, not in pieces.

What the Company Is Looking For

Must-haves

  • 2–4 years in consulting, investment banking, private equity, or venture capital — the candidate has been trained to take a messy problem apart and build the analysis themselves
  • Business operations experience at a startup
  • Strong commercial instincts — the candidate can hold their own in a negotiation and across the table from an enterprise legal team
  • A clear, direct communicator — the candidate can explain what the numbers mean to someone who will not read the spreadsheet
  • High agency — the candidate does not wait for a defined scope; they find what is broken and go fix it
  • Comfort working closely with a founder — the candidate can take a half-articulated problem and come back with it solved, not with more questions
  • Technically curious — the candidate does not need to be technical, but should want to understand how an AI product actually works

Nice-to-haves

  • Exposure to enterprise contracting, MSAs, or procurement cycles
  • Experience at a high-growth startup, or in financial services, mortgage, or fintech
  • Familiarity with revenue ops tooling, BI, or SQL (Cursor can help with the rest)

Benefits

  • $150k–$200k base + equity
  • Top-of-market medical, dental, and vision coverage for the candidate and their dependents
  • 401(k) with a top-of-market employer match
  • Unlimited PTO
  • Hybrid in-office schedule: four days a week together in SF, with a flexible remote day on Wednesdays
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