Chief of Staff

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

Experience: 610 years

About Waystation

Waystation is building the operating system for consumer packaged goods (CPG).

Every product starts with ingredients and packagingand 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.

Were 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 wedgeand ultimately the operating systemthat 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. Were backed by Founder Collective Homebrew Slow Ventures and 87 Capital.

Why This Role Matters

Youre a strategic partner to the CEOon what to do not just how to execute.

Today the CEO is the bottleneck on too many decisions. Hes 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.

Youll write things he signs. Youll run meetings hes not in. Youll own the projects that cut across every function and dont have an owner yet. And youll be the filter that decides what actually needs himand what gets handled before it ever reaches his plate.

This is not an EA role. Its not a junior-ops role. Were looking for someone who could plausibly be a VP or COO in 23 years.

What Youll Do

CEO Leverage

• Own the CEOs calendar priorities and decision queuewhat hits his plate and what doesnt

• Be the companys escalation filter: triage whats 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 companys 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 planninggoals 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 Were 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 companyboard customer candidate engineering standupand 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 workanalysis drafts models decisionsnot just to summarize. You raise the companys ceiling on whats 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 doesand youre right often enough that he trusts the call.

• Operate with founder-level agency and ownership. You act like its your company you dont wait for permission and you carry things all the way to done.

• Can write what the CEO signs and run what hes not in. Your judgment voice and standards are close enough to his that the company doesnt slow down when hes out of the room.

• Have genuine range. Strategy and execution numbers and narrative people and productyou 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.

• We are reliable credible and authentic

• We are solution-oriented

• We are proud of our work our customers and ourselves

• 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 youll be proud to build aroundand a team youll be proud to build with

Have questions before you apply Reach out at and someone on the team will get back to you.

Required Experience:

Senior IC