Chief of Staff

Waystation AI • Redwood, CA

21d • 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

• Judgment, range, and ownership over pedigree
• Ability to sit in any room in the company—board, customer, candidate, engineering standup—and add value, then go build the thing that came out of it
• AI-native from day one. 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.
• Ability to 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.
• Ability to 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.
• Ability to 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.
• 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.
• 6–10+ years of experience

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

Benefits

• Competitive base salary + meaningful equity (calibrated to level)
• A front-row seat and a real partnership with a repeat founder & CEO
• The fastest path we know of to COO, GM of a business unit, VP of a function, or founder of your next company
• Full health, dental, and vision coverage
• Unlimited vacation
• A product and mission you'll be proud to build around—and a team you'll be proud to build with

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed