Chief of Staff

Waystation AI•Temecula, CA

22d•Onsite

About The Position

Waystation is building the operating system for consumer packaged goods (CPG). Every product starts with ingredients and packaging—and today, that work is still run through inboxes, PDFs, and spreadsheets. Procurement is mission-critical, but opaque, manual, and painfully inefficient. It slows innovation, hides costs, and quietly destroys margin. Waystation changes that. We're building an AI-powered procurement platform that turns email-driven chaos into structured data, visibility, and leverage. Our product sits directly in existing supplier workflows (no portals, no supplier logins) and delivers immediate ROI. Our vision is bold: a world where building a physical product is as simple as launching a website. Waystation is the wedge—and ultimately the operating system—that makes that possible. Waystation is led by repeat founder and CEO Ryan Caldbeck (previously founded CircleUp). Before writing a line of code, we conducted 200+ customer interviews to validate the problem. Today, we have paying customers, real usage, and real impact. We're backed by Founder Collective, Homebrew, Slow Ventures, and 87 Capital.

Requirements

You use AI to produce real work—analysis, drafts, models, decisions—not just to summarize. You raise the company's ceiling on what's possible with these tools.
Absorb ambiguity at the highest level. You take the messiest, least-defined problems the CEO has and return clarity, a recommendation, and a path forward.
Own the escalation filter for the whole company. You decide what reaches the CEO and what gets resolved before it does—and you're right often enough that he trusts the call.
Operate with founder-level agency and ownership. You act like it's your company, you don't wait for permission, and you carry things all the way to done.
Can write what the CEO signs and run what he's not in. Your judgment, voice, and standards are close enough to his that the company doesn't slow down when he's out of the room.
Have genuine range. Strategy and execution, numbers and narrative, people and product—you move between them without dropping quality.
Want to be in the room, in person, close to the founder and the work.

Nice To Haves

Chief of Staff at a high-growth startup
Senior consultant at MBB with a strong operating bent
Ex-founder who wants to learn at scale before going again
Senior product or strategy leader looking for a higher-leverage seat

Responsibilities

Own the CEO's calendar, priorities, and decision queue—what hits his plate and what doesn't
Be the company's escalation filter: triage what's real, handle what you can, and bring him only what genuinely needs him, decision-ready
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
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
Own org design and the hiring plan as the team scales
Co-lead senior leadership recruiting with the CEO