Chief of Staff to the CRO

HockeyStack is an Applied AI company on a mission to automate sales, marketing, and customer success for B2B companies. We build the most complete and accurate picture of the B2B buyer by integrating with every tool your team uses, partnering with third-party data providers, and deploying custom AI research agents. We use this data to power applications that automate high-value, high-complexity workflows across the go-to-market and revenue teams. Our core products include:

• Marketing Intelligence – instantly answers questions like “What led to that sudden drop in pipeline?”

• Account Intelligence – surfaces next-best actions to help reps move target accounts toward conversion

Since launching in January 2023, we’ve come through Y Combinator, raised a $26M Series A led by Bessemer. We’re growing 3× year-over-year, have hit multimillion ARR, and process over 60 TB of GTM data monthly. Based at our San Francisco HQ, we operate fully in-person, move fast and hire people who are ready to win.

HockeyStack is growing fast — with 3× revenue in the past year, a breakout product, and customers scaling just as quickly. We are looking for an exceptional Chief of Staff to the CRO to bring structure, clarity, and operational excellence to a fast-moving GTM organization. This role acts as an execution force-multiplier for the CRO — ensuring priorities move forward, the revenue team is aligned, KPIs are tracked, and cross-functional initiatives operate smoothly.

You’ll sit at the center of Sales, Marketing, RevOps, and CS — driving alignment, operational rigor, and strategic focus. You should be highly organized, deeply analytical, able to manage ambiguity, and obsessed with making the GTM engine operate at peak performance.

This is a strategic, high-visibility role with direct exposure to executive leadership and high-impact special projects.

• GTM Operational Rigor & Structure

  • Build and maintain the operating cadence for the entire GTM org (weekly revenue meetings, pipeline reviews, forecast calls, QBRs, leadership syncs).

  • Create and enforce organizational structure across Sales, Marketing, CS, and RevOps.

  • Manage the GTM calendar and coordination across teams.

  • Ensure clear workflows, ownership lines, and handoffs exist across the revenue engine.

  • Identify bottlenecks and implement scalable, repeatable processes.

• KPI Tracking, Reporting & Insights

  • Own a unified GTM metrics framework across funnel, pipeline, revenue, retention, and productivity.

  • Partner with RevOps to ensure accurate reporting and dashboards.

  • Monitor KPIs against goals and raise risks proactively.

  • Turn data into narrative storytelling for CRO-level and board-level communication.

  • Maintain a constant “state of the business” perspective for leadership.

• OKR Planning, Accountability & Execution

  • Lead the quarterly GTM OKR cycle end-to-end.

  • Translate CRO priorities into structured workstreams with owners, milestones, and measurable outcomes.

  • Maintain cross-team accountability and ensure execution stays on track.

  • Provide weekly and monthly reporting on OKR progress.

• Cross-Functional Alignment & Communication

  • Act as an extension of the CRO in meetings, providing clarity and follow-through.

  • Ensure the GTM org is aligned with Product, People, Finance, and Ops.

  • Draft weekly updates, strategy docs, meeting agendas, and operational briefs.

  • Remove ambiguity across teams by defining expectations and success criteria.

• Special Projects With the CRO

  • Lead high-impact strategic projects that directly influence GTM performance.

    • Examples include:

    • Territory & segmentation design

    • GTM motion redesigns & playbook builds

    • New product launch strategy

    • Pricing & packaging analyses

    • Competitive intelligence & positioning

    • Strategic partnership research

  • Manage projects end-to-end: research → planning → cross-functional coordination → execution.

• Strategic Support for CRO

  • Act as a trusted partner to the CRO — providing leverage, clarity, and decision-support.

  • Build frameworks, business cases, and presentations for high-stakes conversations.

  • Anticipate operational risks and help the CRO stay ahead of issues.

  • Ensure the CRO’s priorities translate to real outcomes across the org.

• 3–6 years of experience as a Chief of Staff within high-growth B2B SaaS.

• Bring structure and operational rigor to the entire GTM org — meetings, cadences, processes, accountability.

• Own KPI and OKR systems — ensure accurate performance tracking, insight generation, and quarterly goal execution.

• Drive cross-functional alignment across Sales, Marketing, CS, RevOps, Finance, and Product.

• Lead special projects directly with the CRO on strategic initiatives that impact pipeline, revenue, or GTM efficiency.

• Act as a force multiplier for the CRO — ensuring priorities move forward, decisions are informed, and the org stays aligned.

We’re at an inflection point. The product is proven, the market is massive, and the opportunity is wide open. You’ll be joining a company with real traction, rapid growth, and meaningful backing—where every person still shapes the outcome. This isn’t just a job. It’s a chance to build something category-defining with people who care deeply about doing it right.

As part of our San Francisco, California-based team, the on target earnings range for this role is $120,000– $160,000 USD annually, depending on experience and qualifications.

HockeyStack is proud to be an Equal Opportunity Employer. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or any other legally protected status. We celebrate diversity and are committed to fostering an inclusive environment for all employees.