Technical Chief of Staff

About RetailReady

We’re RetailReady (YC W24) — an AI-powered supply chain compliance engine shaking up an antiquated (and yes, unsexy) industry. After YC, we raised a $3.3M seed round and went heads-down building for our first enterprise customers. Fast forward: we’ve signed over 10 enterprise deals and have a strong pipeline — we’re officially in scaling mode.

We’re building world-class software that solves real problems for real people in the supply chain — the backbone of every business. From streamlining warehouse workflows to automating compliance for major retailers like Walmart, Target, and Amazon, RetailReady is where complex operations meet simple, scalable solutions.

What We Build

RetailReady is the first AI-powered compliance engine designed for retail supply chains. We automate the messy web of compliance requirements between brands, warehouses, and retailers — turning weeks of manual work into minutes of automation. Our platform integrates deeply with warehouse operations and connects with customer systems via EDI, APIs, and flat files.

We don’t just build dashboards. We build the nervous system of compliance inside a warehouse.

Why Retail Compliance Matters

• A massive problem: Retail compliance is fragmented, confusing, and costly — it’s also non-optional.
• Engineer’s playground: Complex workflows, messy data, and real-world impact.
• First to market: No one is solving this problem the way we are — we’re early and moving fast.
• Clear ROI: Customers see savings in weeks, not years.

About the Founders

We bring deep operational, product, and engineering backgrounds from Stord (supply chain unicorn) and Microsoft. We understand this space intimately, and in less then one year since launching, we've signed customers including Brümate, Natural Dog Company, and Ware2Go (a UPS company). Check out our Weekly Round Up Videos on LinkedIn to see our team culture.

The Role

We’re hiring a Technical Chief of Staff to work directly with our CEO and help scale RetailReady’s product, technical strategy, and go-to-market motion. This isn’t a generalist chief of staff role — it’s deeply technical, strategic, and cross-functional.

You’ll own the strategy and execution around complex customer workflows, help solution technical edge cases in enterprise deals, and drive internal product planning based on what’s happening on the ground.

This role is for someone who wants to sit at the intersection of technical architecture, product roadmap, and revenue strategy — and contribute meaningfully to all three.

What You'll Do

• Partner with the CEO on high-priority customer workflows and technical sales cycles
• Own solution design for complex implementations (EDI, APIs, retail compliance requirements, etc.)
• Drive clarity across sales, engineering, and product by translating customer chaos into technical requirements
• Project manage operational infrastructure to scale our go-lives, customer onboarding, and feedback loops
• Be the connective tissue between product, engineering, and sales 
• Get hands-on in the product where needed — this role is not purely strategic

What We're Looking For

• Strong technical background: You’ve written code, built systems, or deeply understand APIs/data flows
• High-context communicator: Can explain technical concepts to non-technical people (and vice versa)
• Obsessive about customer workflows: You love untangling messy edge cases and simplifying them
• Ruthlessly execution-oriented: You don’t just think — you drive things forward
• Comfortable in ambiguity: You can self-prioritize and carve structure out of chaos
• Bonus if you’ve worked with EDI, supply chain, or other enterprise integrations
• Bonus if you’ve worked at a startup or been in a Chief of Staff, Solutions Architect, or Sales Engineer-type role

Why Join Us Now

• Early team member: Join as one of the first 10 employees, and help shape the company culture and technical direction
• Proven traction: 10+ signed enterprise customers and a healthy pipeline
• Funded and stable: $3.3M seed round provides runway to execute on ambitious plans
• High-ownership, high-trust environment: You’ll work directly with the CEO, founding engineer, and customers
• Funded and focused: $3.3M seed, strong runway, clear goals

Location & Compensation

• Location: San Francisco (in-person team)
• Compensation: Competitive salary + equity
  • Range: $120k - $185k
  • Equity: .5 - 1.5%
• Benefits: Full health coverage, unlimited PTO, latest equipment

Ready to Join?

If you've gotten this far and are fired up about disrupting supply chain compliance with cutting-edge technology, we want to hear from you.

This isn’t a “wait to be told what to do” kind of role. We’re looking for someone who sees the whole board — and moves.