About Owlery

Owlery is an AI-powered logistics platform built for shippers — the brands, manufacturers, and logistics teams whose product is actually moving. We're two things in one: a TMS that runs freight operations end-to-end, and an AI Logistics Teammate that actively manages those operations — resolving exceptions, communicating with carriers, and optimizing decisions around the clock. Think of it as replacing both the spreadsheets and the manual work that still dominate the industry.

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We were founded in 2022 by principal engineers from Uber Freight, and we're backed by institutional investors. Owlery is growing fast (>4x year over year) with a small team that punches well above its weight. We're remote-friendly with offices in the San Francisco Bay Area.

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The Opportunity

(To be clear up front: this is a customer-facing role, not a software engineering role. "Engineer" is in the title because we build technical products for our customers and you will find yourself debugging and reconfiguring that product for them.)

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Owlery runs real freight operations, and our AI Logistics Teammate makes real decisions inside them. So when something looks wrong to a customer, the answer is almost never on the surface. It could be an integration that silently stopped returning data, a stale configuration, a carrier API behaving badly, a prompt that steered the agent somewhere unhelpful, or the Teammate making a decision that was right and looked wrong. Some of those you fix. Some of those you explain. Telling which is which, quickly, is a key part of this job.

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We're making our first dedicated hire to own this scope of work. You'll be the person who interfaces with our customers and their partners to make sure Owlery is driving the full value they expect.

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You will report to one of our founders and work directly with our Customer Success Manager, who owns account strategy, renewals, and QBRs. As we grow, this role is what we build our support and CSM team around.

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We are a startup. This is a build-it role. Nobody is going to hand you a runbook. You get to write the first one.

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What You'll Do

• Own inbound support end to end. Email, slack, teams, and whatever other door customers knock on. You resolve the large majority of it yourself rather than routing it onward.
• Debug real problems. Trace an integration failure, read logs and dashboards, follow a load through the system, and determine whether the platform is wrong or the input was. Reproduce it before you escalate it.
• Explain Owlery and our AI Teammate. Tell customers why the agent did what it did, in language that builds trust rather than eroding it. This is harder and more valuable than it sounds, and it's the part of this job you won't find elsewhere.
• Fix data directly. Use internal tooling to correct customer data and system configurations carefully, with a trail of what you changed and why.
• Be the voice to our customers. If something breaks, you own customer communication: scope, impact, and status, delivered while the fix is still in flight.
• Be the voice to our product team. You'll see everything from all of our customers, so you'll know what we should build or do differently to make sure things work better. Your feedback and what customers tell you will directly shape our product roadmap.
• Build the function. Establish our escalation path to engineering, define our first support metrics (response time, first-contact resolution, backlog health), build out our knowledge base, and most critically, help us make our entire product and support experience automated and self service.

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Reactive work always feels more urgent than proactive work, and at most companies that means the proactive half quietly never happens. We expect you to be proactive in customer outreach, product feedback, developing documentation, and shaping our roadmap. We will carve out time to ensure reactive work does not get in the way of driving business value.

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Who You Are

• At least 2–4 years in technical or product support, solutions, or a similarly hands-on customer-facing role at a B2B SaaS company.
• You understand REST APIs — payloads, auth, error responses — and can work out whether an integration is failing on our side or theirs.
• You know how to change LLM prompts to get the results you need. The AI Teammate we're building for our customers is not the only agent in our stack. You'll be using, changing, and enhancing both internal and external AI agents on a regular basis.
• You've used observability or analytics tooling (Datadog, Grafana, Sentry, Cloudwatch) to investigate a live issue, and you're at home in an internal admin console.
• You write well under time pressure. Clear, calm, and specific, especially when the customer is none of those things.
• You have judgment about escalation. You know the difference between a problem worth two more hours of your own time and one that needs an engineer right now.‍
• You want to build a function, not join one. We are a small, nimble, and mighty team. You will have real ownership and no bureaucracy. Some people love that; it's worth knowing which you are before you apply.

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Nice to Have

• Logistics, freight, telematics, or supply chain experience. Think TMS, EDI, or API-based carrier integrations.
• You've stood up a knowledge base or a support process from scratch and have real opinions about how to actually deflect tickets.
• Comfort with light scripting (Python, JavaScript) and querying (SQL or Mongo) for bulk fixes and data pulls.
• Experience supporting an AI or automation product, where "why did it do that" is a routine question.

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What You'll Get

• Competitive salary based on experience and location. We care most about finding the right person for our team and there is flexibility on the role as a result.
• Access to premium AI tools including Claude Pro, plus the internal AI agents already running large parts of our operation.
• Periodic travel to get the remote team together face to face.
• Benefits vary by location.