HEAD OF PRODUCT
Waystation AI | Redwood City, CA (5 days in office) | Full-time
ABOUT WAYSTATION
Waystation is an AI-native platform that helps food, beverage, supplement, and pet food manufacturers ($50M to $500M revenue) manage supplier communications and procurement data. Email is the UI: we connect to the accounts teams already use, structure every quote, spec, COA, and PO automatically, and give procurement, QA, and R&D one organized system of record with zero behavior change.
We're seed-stage, venture-backed, with paying customers including national bakery, supplement, and better-for-you brands. Ten people today: five engineers, three BDRs, a founding designer, and a founder who has done this before (CEO, prior venture-backed company through Series B+).
WHY THIS ROLE EXISTS
We have strong engineers, real customers, and a working AI extraction pipeline that is genuinely hard to replicate. What we don't have is a dedicated product leader. Until now, product has been carried part-time by a small team already wearing multiple hats, and we've grown past the point where that works. An experienced interim CPO (7 years as CPO of an email-native SaaS company) has spent the last month installing the operating system: a six-lane roadmap, weekly launch cadence, milestone discipline. It's working. He's interim.
You will inherit that system, make it yours, and become the Head of Product. This is not a caretaker role. We've learned firsthand what happens when a foundational project runs without a clear plan, and we've started building the discipline to prevent it. Your job is to make that discipline permanent.
WHAT YOU'LL OWN
The why-what-when chain. Every project should tie to a customer or business outcome, have a written plan, a DRI, and milestones with dates. Real dates. We want you to help the team make appropriate timing estimates.
Prioritization and the word "no." Our customers are vocal and our engineers are helpful, which means customer requests can eat the roadmap one "it's just an hour" at a time. You own the framework that decides what gets built, protects the product lanes, and keeps a run-the-business lane from swallowing everything.
Launch as a discipline. Product sign-off before deploy. Seeded demo environments the CEO can sell from with total confidence. Release notes, customer comms, and sales enablement for every launch. Something customer-visible ships every week.
One source of truth. We try to use Linear and should do a better job of using it consistently. You'll cut the AI-generated ticket noise, enforce triage, and make sure any engineer can look at the board and know what matters and why.
Discovery and the customer voice. You'll be in prospect and customer calls frequently, translating what buyers, QA leads, and R&D teams actually need into specs engineers can build against without guessing.
The hard conversations. You are the accountability layer between the CEO and the team. When something slips, you catch it in days, name it, and drive the fix.
YOUR FIRST 90 DAYS
- Days 1 to 30: Ride along on every customer and prospect call and internal cadence. Take ownership of the six-lane roadmap and weekly planning from the interim CPO. Ship your first launch end to end.
- Days 31 to 60: Every active project has dates, a DRI, and a one-page why. You've killed or consolidated everything that doesn't earn its lane. The CEO learns about slippage from you, before it slips.
- Days 61 to 90: The weekly launch cadence is routine. Sales knows what's shipping two weeks out. You've drafted the product hiring plan (design, PM, or forward-deployed) for the next stage of growth.
WHAT SUCCESS LOOKS LIKE AT 12 MONTHS
- No project runs longer than two weeks without a written plan and dated milestones.
- A customer-visible improvement ships every week, and the CEO can demo every one of them.
- Estimate accuracy is measurably improving because the team practices it.
- Customer-driven scope creep is governed by a framework, not by whoever asked loudest.
- The founder spends his product time on strategy and selling, not on chasing status.
WHO YOU ARE
- 6+ years in product, with at least one stretch as the senior-most product person at an early-stage startup (seed to Series B). You've operated without a playbook and without a team to delegate to.
- You've shipped B2B SaaS into unglamorous, workflow-heavy industries. Bonus if you've built on top of email, documents, or messy unstructured data. Extra bonus for supply chain, procurement, or CPG exposure.
- You're an excellent communicator, written and verbal. Clear and concise in a spec, a standup, a customer call, or a one-line Slack message. People never leave a conversation with you unsure of what was decided or what happens next.
- You build relationships and trust fast, across the org and with customers. Engineers want you in the room, and customers ask for you by name.
- You have real empathy for our customers. Procurement, QA, and R&D teams at food and beverage manufacturers do unglamorous, high-stakes work, and you want to build something big and impactful for them.
- You take ambiguity and create structure from it, and you've done it successfully before. Handed a mess, you produce a plan people can execute against.
- You're sharp analytically. You develop your own opinions, defend them with data and logic, and don't hold them too tightly when the evidence says you're wrong.
- You're fluent in AI-assisted building and clear-eyed about its failure modes. You know that AI-generated specs and tickets are only as good as the human who reviews them, and you actually review them.
- You run toward hard conversations. You can tell a talented engineer their estimate isn't credible, tell a customer no, and tell the founder he's wrong, all in the same week, and keep every one of those relationships strong.
- You have a chip on your shoulder. Something to prove. We'll ask about it
- Bonus if you have worked with products that also included a service model.
WHO YOU ARE NOT
- A product strategist who needs a PM team to execute. There is no team. You are the team.
- Someone who avoids hard conversations or needs consensus to make a call.
- Someone who treats process as the goal. Process here exists to ship faster, and you'll delete any of it that doesn't.
- Uncomfortable being in the office 5 days a week in Redwood City, on customer calls weekly, and occasionally on a plant floor in a hairnet.
COMPENSATION AND LOGISTICS
- Competitive salary plus meaningful equity for a foundational leadership hire. We pay for people we're betting on.
- Redwood City, CA. In person, 5 days a week. This team builds together.
- Reports directly to the CEO. Works daily with engineering leadership and our product advisor network.
PROCESS
1. Intro conversation with Ryan (CEO)
2. Working session: you'll review a real slice of our roadmap and tell us what you'd change
3. Team conversations (engineering, design)
4. Conversation with our product advisor
5. References, then offer
We move in days, not weeks. If this reads like the job you've been preparing for, tell us why: jobs@waystationai.com