Waystation AI
Chief of Staff
Redwood City, CA · Exec
Sponsorship not specifiedDetected 42 days ago
ProcurementCadenceLeadership
About the role
- Every product starts with ingredients and packaging-and today, that work is still run through inboxes, PDFs, and spreadsheets.
- It slows innovation, hides costs, and quietly destroys margin.
- Waystation is the wedge-and ultimately the operating system-that makes that possible.
Responsibilities
- Own the CEO's calendar, priorities, and decision queue-what hits his plate and what doesn't
- Drive follow-through on his commitments across the team
- Own board prep, investor updates, and the data room
- Support fundraising end-to-end: narrative, materials, process, diligence
- Lead the projects that decide the company's trajectory: pricing, packaging, GTM motion, ICP refinement, market expansion
- Own org design and the hiring plan as the team scales
- Co-lead senior leadership recruiting with the CEO
- You'll own the projects that cut across every function and don't have an owner yet.
- The fastest path we know of to COO, VP, GM, or your own company
- A product and mission you'll be proud to build around-and a team you'll be proud to build with
Requirements
- Experience that helps:
- Be the company's escalation filter: triage what's real, handle what you can, and bring him only what genuinely needs him, decision-ready
Skills
- Want to be in the room, in person, close to the founder and the work.
Compensation
- Own quarterly and annual planning-goals, metrics, and the operating cadence that holds them
Benefits
- Competitive base salary + meaningful equity (calibrated to level)
- Full health, dental, and vision coverage
- Unlimited vacation
Company info
- Take an ambiguous, high-stakes question and turn it into a recommendation and a plan
- Own quarterly and annual planning-goals, metrics, and the operating cadence that holds them
- Keep the company honest about what it said it would do
- We're looking for someone who could plausibly be a VP or COO in 2-3 years.
- Waystation is led by repeat founder and CEO Ryan Caldbeck (previously founded CircleUp).
- Today, we have paying customers, real usage, and real impact.
- We are reliable, credible, and authentic
- We are solution-oriented
- We are proud of our work, our customers, and ourselves
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This listing is sourced directly from Waystation AI's careers page and normalized into a canonical job model.