Business Operations & Strategy at Waystation AI
Location: Redwood City, CA (in-person, 5 days/week)
We're hiring across three levels in this track:
Business Operations Associate — 2–4 yrs
Business Operations Manager — 4–8 yrs
Chief of Staff — 6–10+ yrs
One posting, three different jobs. We're open to hiring at any of the three levels, and may hire more than one.
About Waystation
Waystation is building the operating system for consumer packaged goods.
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.
We're building an AI-powered procurement platform that turns email-driven chaos into structured data, visibility, and leverage. Our product sits directly inside 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: 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 it possible.
Led by repeat founder and CEO Ryan Caldbeck (previously founded CircleUp). 200+ customer interviews before writing a line of code. Paying customers, real usage, real impact. Backed by Founder Collective, Homebrew, Slow Ventures, and 87 Capital.
Why we're hiring this track
The CEO is personally running pipeline reviews, BDR founder screens, customer check-ins, demo prep, contract coordination, recruiting, and team logistics. That's not sustainable, and it pulls time away from closing deals and building the company.
We need help — but the shape of help we need depends on who we find. A great Associate runs the operational machine. A great Manager owns the functions and designs how the work gets done. A great Chief of Staff is a strategic partner to the CEO on what to do, not just how.
The three roles
Business Operations Associate — 2–4 yrs
You execute the operational machine.
You'll own:
CRM hygiene, pipeline reporting, weekly metrics
Daily BDR standups, activity tracking, sequence QA
Customer check-in coordination and follow-up
Inbound lead triage and routing
Recruiting pipeline logistics: sourcing, scheduling, first screens
Internal automations using AI tools, APIs, and no-code platforms
You're closest to the work. Your judgment shows up in what you flag, what you ship, and how clean your systems are. You'll take direction from the CEO directly today, and from the BizOps Manager when we hire one.
Path: Grow into a Manager or specialist role (RevOps, Customer Ops, Recruiting Ops) as the company scales.
You're a fit if: You were a top analyst at a consulting firm or bank, a top-performing BDR/AE who wants to move into ops, or BizOps hire #1 at another startup. You're AI-native, technical-leaning, and can't watch a manual process without trying to fix it.
Business Operations Manager — 4–8 yrs
You own the functions, build the systems, and eventually manage the Associate.
You'll own:
The GTM operations stack (HubSpot, Clay, Smartlead, Pendo): selection, implementation, hygiene
The BDR coordination function: standups, performance reviews, sequence reviews, coaching escalations
The customer success operation: health scoring, renewal tracking, expansion identification
The recruiting operation: pipeline design, interviewer training, offer process
The internal automation roadmap: what gets built, by whom, in what order
You're not just executing — you're designing how the work gets done and improving it quarter over quarter. You'll partner directly with the CEO on GTM motion, hiring plan, and operational metrics.
Path: Head of Operations or RevOps as the team scales past ~25 people.
You're a fit if: You've owned BizOps or RevOps at a growth-stage SaaS company, you've been Chief of Staff at a 50–200 person company and want to operate at smaller scale, or you've been a senior consultant who wants to stop advising and start owning.
Chief of Staff — 6–10+ yrs
You're a strategic partner to the CEO.
You'll own:
CEO leverage: calendar, priorities, decision queue — what hits his plate and what doesn't
Board prep, investor updates, fundraising support
Cross-functional strategic projects: pricing, packaging, GTM motion, ICP refinement, market expansion
Quarterly and annual planning
Org design and hiring plan
Senior leadership recruiting (often co-led with the CEO)
You'll partner with the CEO on what to do, not just how to execute. You'll write things he signs. You'll run meetings he's not in. You'll be the second-most-informed person at the company on every important decision.
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.
Path: COO, GM of a business unit, VP of a function, or founder of your next company.
You're a fit if: You've been Chief of Staff at a high-growth startup, a senior consultant at MBB with a strong operating bent, an ex-founder who wants to learn at scale before going again, or a senior product/strategy leader looking for a higher-leverage seat.
What's true across all three roles
AI-native from day one. You don't wait for someone to hand you tools. You build, automate, ship. If a task can be done by a model or an agent, you build it before anyone asks.
In-person in Redwood City, 5 days a week. No exceptions.
Judgment over pedigree. We care about what you've shipped and how you think.
High trust, low process. You can write a crisp email, run a meeting, and make a decision without waiting for permission.
Operational excellence. Details matter. You finish what you start.
What we offer
Direct mentorship from a repeat founder & CEO
Competitive base + meaningful equity (calibrated to level)
Full health, dental, vision; unlimited vacation
A real product with paying customers and a path to a category-defining outcome
Values
We are reliable, credible, and authentic
We are solution-oriented
We are proud of our work, our customers, and ourselves