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

We're hiring our first dedicated Customer Success Specialist to own the day-to-day experience for our active customer base. You'll be the go-to person when customers need help, ensuring they're getting maximum value from Owlery and that issues are resolved quickly and thoroughly. This role reports directly to one of our founders and works closely with our product and engineering teams, and our Customer Success Manager — your insights from the front lines will directly shape what we build next.

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This is a great fit for someone who loves solving problems for customers, thrives on being responsive, and wants to grow into a broader CS leadership role as we scale.

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What You'll Do

• Serve as the primary point of contact for active customers, fielding questions, troubleshooting issues, and making sure nothing falls through the cracks.
• Monitor customer health and usage to spot risks or opportunities early — then act on them.
• Drive regular check-ins and QBRs to keep customers engaged and informed.
• Collaborate with product and engineering to relay customer feedback and help prioritize what we build. You'll have a direct line to our roadmap.
• Document common workflows, FAQs, and support processes to build out our customer-facing knowledge base.
• Partner with our onboarding team to ensure smooth handoffs from implementation to active account management.

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Who You Are

• You genuinely enjoy helping people and take pride in being the person customers trust.
• You're organized and detail-oriented — you can manage multiple accounts without letting things slip.
• You're a clear, prompt communicator — in writing and on calls.
• You have 1–3 years of experience in customer success, support, or account management, ideally in logistics, supply chain, or B2B SaaS.
• You're proactive — you don't wait for a customer to escalate before stepping in.
• You're technically curious and comfortable getting under the hood — you don't need to be an engineer, but you're comfortable digging into data, navigating a complex product, and thinking like one when troubleshooting.

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What You'll Get

• Competitive base salary in line with experience, plus equity (ISOs) to share in our success.
• Premium healthcare coverage including medical, dental, and vision plans.
• Company-sponsored 401K plan and FSA.
• Access to premium AI tools like ChatGPT Plus and Claude Pro to keep your workflow sharp, plus the host of internal AI Agents we have running things.
• Unlimited PTO because we trust you to manage your time.
• Regular travel to meet face-to-face with the team — we invest in getting remote teammates together.