Chief of Staff to the CRO

HockeyStack is building the agent infrastructure for enterprise revenue. We spent five years building the only data architecture that preserves causality across the full revenue stack — every interaction, every signal, in sequence. On top of that foundation, we built Nex-lm, a purpose-built AI engine that compiles natural language into deterministic agent workflows. The result is a platform that can extract the revenue blueprint from a company's data, encode it into repeatable automations, and execute it across sales, marketing, and customer success — consistently, at scale.

We are not building a dashboard tool with an AI feature. We are building the operating layer that replaces the human bottleneck in enterprise revenue organizations. This is a category being defined right now, and we intend to own it.

We have raised $50M+ from Bessemer Venture Partners, General Catalyst, Y Combinator, and others.

We operate fully in-person in San Francisco. We move fast and we hire people who want to win.

Since launching late 2023, we have grown to 8-figures in ARR, process over 60 TB of revenue data monthly, and we are working with some of the largest B2B companies in the world like Microsoft, Harvey, New Relic, Collibra, etc.

The CRO is running a transition. HockeyStack is moving from a GTM intelligence company to the agent company for enterprise GTM. That means a new sales motion, a new positioning, a new buyer, a new demo, and a new category narrative — all being built and proven simultaneously, while the existing business continues to grow.

The Chief of Staff is the force multiplier that makes this possible without the organization falling apart.

You will sit at the center of Sales, Marketing, RevOps, and CS. You will own the operating cadence of the GTM organization. You will translate the CRO’s priorities into structured execution. You will be the person who makes sure the most important things actually get done.

This is a high-trust, high-visibility role. You will have direct access to the CRO, the CEO, and the board-level narrative. You will see everything. You will be expected to operate with the judgment of a senior leader from day one.

GTM Operating Cadence

Pipeline reviews, forecast calls, QBRs, weekly revenue meetings, hot account reviews, launch coordination. Right now these happen inconsistently. You design the cadence, run it, and hold the organization to it. When the CRO walks into a room, everything is already in motion.

State of the Business

The CRO needs to know at any point — not weekly, not at QBR — exactly where the business stands. Pipeline coverage by segment. Conversion rates by stage. Agent motion metrics versus attribution motion metrics. Ramp progress. Deal velocity. Churn signals. You own the unified metrics framework. You own the narrative. You are the person who sees a number moving wrong and raises it before it becomes a crisis.

OKR Execution

Quarterly goals at HockeyStack are not aspirations. They are commitments with owners, milestones, and accountability structures. You run the OKR cycle end-to-end — translating CRO priorities into workstreams, tracking execution, and surfacing what is off track before it is too late to fix.

Cross-Functional Alignment

The agents motion touches every team. Product is building the cockpit and the blueprint discovery layer. Marketing is repositioning the company. Sales is running founder-led conversations to prove the motion before scaling it. RevOps is rebuilding the data model. Finance needs the story for the fundraise. All of these teams need to move in the same direction at the same time. That coordination does not happen by accident. You own it.

Strategic Projects

New segment design. Pricing architecture. Competitive positioning analysis. Partner strategy. Launch playbooks. The CRO initiates projects that do not fit neatly into any existing team’s remit. You lead them end-to-end — from framing the problem through execution — and you deliver outputs that are ready for high-stakes decisions.

You have 3 to 6 years of Chief of Staff experience inside a high-growth B2B SaaS company. You know what a GTM organization looks like when it is working and when it is not. You have built operating cadences, run OKR cycles, and managed cross-functional initiatives that required you to influence without authority.

Beyond the resume, a few things will determine whether this is the right role:

• You think in systems. You do not just solve the problem in front of you — you build the infrastructure that prevents the next ten problems.

• You move fast and you are comfortable with ambiguity. The agents motion is being built in real time. The playbook does not fully exist yet.

• You have strong opinions and you will share them. The CRO does not want a coordinator. He wants a thought partner who pushes back when something is wrong.

• You are deeply organized without being bureaucratic. Process exists to create speed, not slow things down.

• You can hold a strategic conversation with a CRO and a tactical conversation with an AE in the same afternoon. The range is required.

• You want to build something genuinely important. Not a feature. Not a vertical SaaS tool. The category-defining infrastructure for the next generation of enterprise software.

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.