Chief of Staff

Chief of Staff

Location: Redwood City, CA (In-person, 5 days/week)

Experience: 6–10+ years

About Waystation

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.

"If you care about margin, availability, and speed, Waystation is a no-brainer." — Current customer

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.

Why This Role Matters

You're a strategic partner to the CEO—on what to do, not just how to execute.

Today, the CEO is the bottleneck on too many decisions. He's running pipeline, customer relationships, recruiting, fundraising prep, and planning all at once, and the company moves at the speed of his attention. Your job is to change that: be the second-most-informed person at the company on every important decision, and multiply what he can do.

You'll write things he signs. You'll run meetings he's not in. You'll own the projects that cut across every function and don't have an owner yet. And you'll be the filter that decides what actually needs him—and what gets handled before it ever reaches his plate.

This is not an EA role. It's not a junior-ops role. We're looking for someone who could plausibly be a VP or COO in 2–3 years.

What You'll Do

CEO Leverage

• 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

Board, Investors & Fundraising

• Own board prep, investor updates, and the data room

• Support fundraising end-to-end: narrative, materials, process, diligence

Cross-Functional Strategic Projects

• 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

Planning

• 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

Org & Talent

• Own org design and the hiring plan as the team scales

• Co-lead senior leadership recruiting with the CEO

What We're Looking For

We care far more about judgment, range, and ownership than pedigree. You should be someone who can 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.

You might be a fit if you:

• Are 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.

• 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.

Experience that helps:

• 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

Path: COO, GM of a business unit, VP of a function, or founder of your next company.

Values

• We are reliable, credible, and authentic

• We are solution-oriented

• We are proud of our work, our customers, and ourselves

What We Offer

• 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, VP, GM, or your own 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