Chief of Staff & Business Operations

Posted Yesterday
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San Francisco, CA, USA
In-Office
150K-200K Annually
Mid level
Agency • Artificial Intelligence • HR Tech • Professional Services
The Role
Serve as the CEO’s closest partner and first Business Operations hire. Own enterprise contracts, reporting infrastructure, revenue operations, pricing analysis, board materials, investor updates, operating cadence, partner relationships, and high-priority special projects. Build processes from scratch, solve ambiguous problems, drive commercial outcomes, and provide analysis that supports company and board decisions.
Summary Generated by Built In

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

Skills Required

  • 2-4 years of experience in consulting, investment banking, private equity, or venture capital
  • Business operations experience at a startup
  • Strong commercial instincts and ability to negotiate with enterprise legal teams
  • Clear and direct communication skills, including explaining business metrics
  • High agency and ability to independently identify and solve problems
  • Comfort working closely with a founder and solving ambiguous problems
  • Technical curiosity and willingness to understand how AI products work
  • Exposure to enterprise contracting, MSAs, or procurement cycles
  • Experience at a high-growth startup or in financial services, mortgage, or fintech
  • Familiarity with revenue operations tooling, business intelligence, or SQL
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The Company
6,000 Employees
Year Founded: 1998

What We Do

Rockstar is a full-service recruitment company that leverages a blend of human expertise and artificial intelligence to help businesses hire better and faster at a lower cost. They offer comprehensive recruitment services across a wide range of professional roles, utilizing proprietary AI to efficiently match candidates to job descriptions and conducting custom screening calls to ensure high-quality hires.

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