Customer Success Specialist - Overroute Lowell

Overroute builds AI agents for freight operations. Our agents work inside the tools operators already use, such as email and chat, to track shipments, answer operational questions, communicate with drivers, set appointments, and draft customer communications for freight carriers.

As Customer Success Specialist, you are the person our users know by name. You work onsite at J.B. Hunt headquarters in Lowell, alongside the dispatchers, customer service reps, and managers who use our agents every day. You make sure every user is set up correctly, knows how to use the agents in their own workflow, and gets fast help when something breaks.

You work across all of our customer's business units and report to the Head of Customer Success. You partner closely with our forward-deployed engineers and product team: you bring back what users need, what is working, and what is not, so they can spend their time bringing new agents and new teams live. As we add customers, you help turn what we learn into the playbook we use everywhere.

• Setup and onboarding. Get new users access, install and configure the Outlook and Teams add-ins, and check in during their first weeks so nobody stalls.
• Training. Run live sessions, office hours, and one-on-one coaching. Own the training library, including guides, quick-reference sheets, and short videos, and keep it current as features ship.
• Adoption and value. Sit with users to learn their workflows and show them where the agents fit. Capture the use cases that work and share them as repeatable plays. Follow up with users who have gone quiet.
• Support and bugs. Be first-line support. Triage issues, reproduce them, document what happened with clear evidence, route them to the right team, and close the loop with the user when the fix ships.
• Voice of the customer. Turn what you hear into structured feedback for Product and Engineering, and help prioritize what matters most to users.
• Reporting. Track usage and adoption with our dashboards, and contribute to regular updates for customer stakeholders and our leadership team.

• Be in the room. The best support happens next to the user, not in a ticket queue.
• Adoption is the job. A user with access who isn't using the agents is a problem to solve, not a number to report.
• Evidence over anecdotes. Every issue you raise names the user, the time, and what happened, so an engineer can act on it without a follow-up call.
• Close the loop. When something gets fixed, the user who reported it hears about it from you.
• Clear ownership. Engineering owns fixes and integrations. Product owns priorities. You own the user's experience: setup, training, support, and follow-through.
• Protect customer information. You handle confidential operating data and treat it that way.

• 2–5 years in customer success, account management, implementation, support, or operations.
• Confidence training a room and coaching one person at a time.
• Comfort learning enterprise software quickly, and strong Excel skills.
• Organization and follow-through. You close loops without being chased.
• Clear writing. You can explain a problem so an engineer can act on it.
• The ability to work onsite in Lowell most of the week. Must be authorized to work in the US.

supply chain experience, especially logistics or transportation; hands‑on experience using AI tools in your work; experience at an early‑stage company; an undergraduate degree.

• Early ownership of how customer success works at a growing AI company.
• Daily work with real users on live freight operations.
• Hands‑on experience deploying AI in the enterprise.
• A path to Customer Success Manager as we add customers.
• Competitive compensation and meaningful early-stage equity.
• Healthcare, standard benefits, and flexible PTO.