Role description
Envoy AIEvery company now has two workforces: Human and AI. Enterprise software helped companies manage work. AI now enables companies to execute work. Envoy AI introduces the execution layer that transforms your existing technology stack into an AI-powered workforce.
With a current focus on AI agents that handle the booking process, including verifying carriers, autonomously communicating, negotiating rates, and booking freight via voice, SMS, and email. Ellie, our flagship agent, is already in market. We need someone who can make Ellie shine in front of the customers we're closing, and hold the room when the conversation turns technical.
What this role actually is
You're the person who takes a live sales conversation and makes it real. You'll configure demos on the fly, shape product to fit a prospect's world, and translate what our agents do into undeniable business value. If you've had exposure to FreightTech tooling, sales cycles, and learned tangibly bridge AI concepts to business impact - this is the role built for you.
WHAT YOU'LL DO
- Own the technical side of sales cycles - discovery, demo, proof of concept, and handoff - working in sync with the commercial motion
- Configure and customize Ellie demos using real customer data, lanes, and carrier scenarios to paint a credible picture of ROI
- Build and maintain a library of demo environments tailored to broker, 3PL, shipper, and other relevant use cases
- Respond to technical objections in the room - integration pathways, data flows, compliance questions - without breaking sweat
- Manage POC environments and assist prospects in reviewing data and insights
- Work with our product team to flag recurring prospect pain points and influence roadmap priorities
- Support technical evaluation steps including security questionnaires, and technical due diligence for enterprise prospects
- Help define the SE function from scratch - processes, assets, and playbooks - as our first SE hire
- Own Technical Handoff to implementation team to ensure customer receives value communicated during sales cycle
- Own integration conversations with prospect technical teams: how Ellie connects to McLeod, OTM, Truckmate, and custom TMS environments, what the data flow looks like, and what the implementation lift actually is
WHAT YOU BRING
- 2–5 years in a solutions engineering, sales engineering, or customer-facing technical role
- Hands-on exposure to freight brokerage, 3PL ops, TMS platforms, or carrier networks - you know the lingo and the pain
- Genuine comfort with AI tools and workflows - you've built or configured something with an LLM, not just read about it
- Ability to give a compelling, unrehearsed demo - you can adapt mid-call without losing the thread
- Strong written communication - you can explain complex systems simply and without filler
- Self-directed - you don't wait for someone to write you a playbook
NICE TO HAVE
- Familiarity with voice AI, SMS automation, or outbound communication tooling
- Experience in an early stage startup environment is a plus
- Background in freight tech products (Convoy, Transfix, project44, Flexport, or similar)
- Enough technical range to wire up a demo environment yourself and hold your own in a conversation about API architecture, webhooks, and data mapping.
- Prior experience as a dispatcher, ops coordinator, or freight broker
WHAT WE OFFER
- Base salary depending on experience. We'll talk numbers early, we don't believe in wasting anyone's time.
- Direct exposure to the commercial strategy of a company that is actively closing and negotiating deals
- A seat at the table - we're small, decisions move fast, and your work shows up immediately
- Remote-flexible with async-first communication norms
Apply
Send your resume and a brief note. We don't need a formal cover letter - just tell us where you've been and why this makes sense.