The roleWe're hiring a Chief of Staff to work directly with the CEO and extend the leadership team's reach. This is an operator's job: you'll own the systems that keep the company running, drive the cadence of board and investor communications, and lead how we deploy AI agents across our own operations. We build autonomous AI for our customers; we expect to run the company the same way. You'll sit close to every major decision and be expected to move them forward.
What you'll doOperations support
- Run the leadership team's operating cadence: staff meetings, OKRs, quarterly planning, and the follow-through that makes them stick
- Own the operational backbone across GTM, finance, and people: pipeline reviews, forecasting, reporting, and planning cycles
- Own HubSpot and our core internal tooling as systems: data quality, stage definitions, and the dashboards leadership and the board rely on
- Take on special projects the CEO would otherwise own, from diligence and RFP responses to market analyses and internal process design
- Identify what's breaking as we scale and fix it before it becomes a fire
Agentic implementation
- Map our internal workflows and identify where AI agents can take over work outright: pipeline hygiene, reporting, prospect research, RFP drafting, customer onboarding, investor updates, and more
- Build and deploy those agents yourself using tools like Claude, HubSpot, and our internal data, and own them in production
- Establish the standards for how the company uses agents: what gets automated, how outputs are reviewed, how we measure the hours and dollars recovered
- Be the internal evangelist and teacher; get every function running on agents, not just the ones you touch directly
Board and investor communications
- Own the board meeting cadence end to end: agenda, materials, pre-reads, and follow-ups
- Draft and refine investor updates, board decks, and ad hoc communications with the CEO
- Track commitments made to the board and investors through to completion
What we're looking for- 4-8 years in a role that rewarded both rigor and execution: bizops or strategy at a growth-stage company, consulting, banking, or a prior chief of staff seat
- Hands-on with AI tools. You've built real workflows with LLMs and agents, not just used a chatbot, and you're comfortable with light scripting, APIs, and CRM configuration
- Strong analytical chops. Comfortable building a model in Excel, pulling your own data, and turning it into a clear narrative
- Excellent writer. You can draft a board memo or investor update the CEO would send with light edits
- Systems thinker with a bias for action: you'd rather build the process than describe the problem
- High judgment and discretion with sensitive company, customer, and investor information
- Healthcare or enterprise SaaS experience is a plus; curiosity about revenue cycle and clinical AI is required
Why this roleYou'll get an unusually direct view into how a category-leading healthcare AI company is run and grown, and a mandate to rebuild its operations around AI agents. People who succeed here typically go on to lead operations, a business unit, or found their own company.
