Location

Remote work in Ontario, Canada.

About EasyRoutes / Roundtrip.ai

Have you ever wondered what actually happens between the time when you make a purchase and a package shows up at your doorstep? It seems like magic but peel back the cover and you’ll discover a whole world of algorithms, geospatial analysis, machine learning, real-time data processing, and artificial intelligence.

At Roundtrip.ai we set out to build EasyRoutes to provide businesses with delivery superpowers. Our mission is to equip the millions of merchants both big and small give their customers that same magical delivery experience we’ve all come to expect. Before starting Roundtrip.ai to make EasyRoutes, our team (formerly at Google, Mozilla, Xtreme Labs/Pivotal Labs) worked on building internet browsers and making apps that are used by billions of people globally.

Our Values

• Customer-first: You can’t build a good product without deeply understanding who your customers are and what they’re trying to accomplish. Don’t take it from us: read any of our countless 5-star ratings.
• Bias for action: We value speed. We choose action over deliberation. We believe in continuous improvement, in shipping often and in iterating upon what we've shipped.
• Openness and Kindness: We value trust and build it by communicating openly, listening intently, and by acting consistently with kindness.

The Role

We’ve got support at EasyRoutes running smoothly with solid tools and processes in place . Now we’re looking for our first full-time Customer Experience Specialist to be the first point of contact for merchants, keep things fast and friendly, and spot improvements that help everyone. You’ll work side by side with our founders, content lead, and engineers to turn what we hear from merchants into real changes — all within a steady, focused flow of requests that let you prioritize giving merchants a great experience.

What you'll do / how you'll make an impact:

• Own and scale the merchant support experience – Take full ownership of front-line CX across chat and email (Help Scout) during 9–5 ET. Resolve most merchant requests directly with clear, empathetic replies. Escalate complex issues to engineering with clean repro steps. Handle key Tier-2 operational tasks like refunds, credits, trial extensions, and account verification.
• Off-hours “keep the pulse”: Brief, time-boxed scans (~4 h/week) for urgent merchant issues outside engineering’s on-call (e.g., blocked delivery, urgent billing/security). Non-urgent items wait for business hours.
• Build and improve our CX toolkit – Keep our playbook, macros, and SOPs fresh. Work with our content lead to turn your frontline knowledge into clear macros, Loom videos, and structured insights that improve onboarding, help-centre articles, and in-app guidance. Expand and refine our AI support assistant’s knowledge base so it can resolve more first-line requests on its own.
• Support merchant activation and retention – Partner with founders to guide trials to first driver invite and first completed route. Host 1–2 short “get started” demos weekly for merchants who need a boost to launch, delivering clear, personable walkthroughs over video calls and screen shares.
• Drive small-scale growth initiatives – Run repeatable outreach like reactivation, review requests, and upsell prompts. QA new features pre-launch, publish release notes, pilot new CX tools, and deliver a weekly CX snapshot with trends, risks, and wins.

What you'll bring to the table:

• 1–3 years in SaaS support, customer success, or customer experience.
• Crisp, empathetic communication skills and strong follow-through.