Location: Redwood City, CA (In-person, 5 days/week)
Experience: 2–5 years (versatility > specialization)
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 top-tier investors, including Founder Collective, Homebrew, Slow Ventures, and 87 Capital.
Why This Role Matters
This is not a back-office ops role.
You will be the CEO’s operational right hand—the person who makes the entire company move faster by taking ownership of the systems, processes, and coordination work that doesn’t belong on any one team’s plate yet. You’ll sit at the intersection of sales, product, recruiting, and customer success, and you’ll context-switch constantly.
Today, the CEO is personally running pipeline reviews, doing BDR founder screens, handling customer check-ins, prepping for demos, coordinating contracts, and planning team events. That’s not sustainable—and it’s pulling time away from closing deals and building the company. Your job is to take that weight off the plate, run it at a higher standard than it’s running today, and only surface what truly requires the CEO’s attention.
We expect you to be AI-native from day one. That means you don’t just use AI tools when someone hands them to you—you actively seek out ways to automate, accelerate, and scale your work with AI. If a task can be done by a model, an agent, or a workflow, you should be the person who builds that before anyone asks.
If you do this well, there is a clear path to Head of Operations or RevOps as the company scales.
Sales Operations & Pipeline Support
Own CRM hygiene, pipeline reporting, and weekly sales metrics—surface insights, not just data
Run the weekly pipeline review and daily standup when the CEO is on calls or traveling
Prepare prospect briefings, demo decks, and follow-up materials for active deals
Manage contract and MSA workflows through legal review to signature
Track and triage inbound leads; coordinate handoffs to BDRs or directly to the CEO
BDR Team Coordination
Run daily BDR standups and weekly performance reviews
Review outbound sequences and call recordings; flag coaching opportunities to the CEO
Track BDR activity metrics and pipeline contribution; own the reporting cadence
Be the first filter on BDR questions, blockers, and process improvements
Customer Success & Support
Run weekly customer check-ins; escalate only what requires the CEO’s involvement
Triage customer issues and coordinate responses across product and engineering
Track customer health signals, adoption metrics, and renewal timelines
Gather and synthesize customer feedback to inform product direction
Recruiting & People
Own the recruiting pipeline: source candidates, manage scheduling, run first screens
Conduct first and second interviews for non-executive roles
Coordinate team events, offsites, and culture-building logistics
Help build lightweight onboarding processes as the team grows
AI, Automation & Systems
Build and maintain internal automations using AI tools, APIs, and no-code/low-code platforms
Identify manual, repetitive work across the company and proactively automate it
Evaluate, implement, and manage internal tools (CRM, analytics, project management, AI agents)
Be the team’s go-to resource for “how do we use AI to do this faster and better?”
What We’re Looking For
We care far more about drive, judgment, and adaptability than pedigree.
You should be the kind of person who sees a messy process and can’t help but fix it—and who reaches for an AI tool or script before a spreadsheet.
You might be a fit if you:
Thrive in ambiguity and can context-switch between sales ops, recruiting, customer calls, and systems work in the same day
Are genuinely curious about AI and already use tools like ChatGPT, Claude, Cursor, Zapier AI, or similar in your daily work
Lean technical—you’re comfortable with APIs, light scripting (Python, SQL, or similar), and building workflows that don’t require an engineer
Have strong judgment about when to solve a problem with process vs. tooling vs. just doing it yourself
Can run a meeting, write a crisp email, and make a decision without waiting for permission
Take pride in operational excellence—you care about the details others overlook
Prefer being in the room, in person, solving problems together
Experience that helps (but isn’t required):
Biz Ops, Sales Ops, RevOps, or Chief of Staff experience at a startup or high-growth company
Experience in B2B SaaS, supply chain, or CPG industries
Comfort with HubSpot, Clay, Pendo, Smartlead, or similar GTM tools
Background in top-tier consulting, finance, or engineering with a pivot toward operating roles
Demonstrated ability to build automations, internal tools, or AI-powered workflows
We are reliable, credible, and authentic
We are solution-oriented
We are proud of our work, our customers, and ourselves
Competitive base salary + upside
Meaningful equity
Direct mentorship from a repeat founder & CEO
Clear path to grow into a Head of Ops or RevOps role
Full health, dental, and vision coverage
Unlimited vacation
A product and mission you’ll be proud to build around
A team you’ll be proud to build with every day
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