Solutions Engineer
United States
Solutions Engineer
Envoy AI - Remote-Friendly - Chicago Preferred
Every company now runs two workforces: human and AI. Enterprise software helped companies manage work. AI now lets companies execute it. Envoy AI is the execution layer that turns your existing stack into a working Digital Workforce for logistics operations.
Our Digital Reps own operational tasks such as verifying carriers, communicating autonomously, negotiating rates, and booking loads over voice, SMS, and email. Ellie, our flagship Digital Rep, is already in market and moving freight for real customers. We need someone who can put Ellie to work in front of the prospects we're closing, show what it means to add a Digital Rep to a team, and hold the room when the conversation turns technical.
To Apply
We're hiring through our network first. You need to be a first-ring connection of the team, or vouched for by one. If someone here knows you, or knows someone who does, that's your way in.
Send your resume and a brief note. No formal cover letter. Just tell us where you've been and why this makes sense. Send a direct message to Nate Puskaric or Robert Nathan.
What this role actually is
You're the person who makes the Digital Workforce tangible. Not a slide about AI, not a feature tour. A live Digital Rep doing the job in front of a prospect. You'll stand up Ellie against a customer's real lanes and carriers, show what she handles on day one, and translate "AI agent" into "a teammate who books 40 loads while your desk sleeps." When someone asks how she actually plugs into their operation, you answer without flinching.
WHAT YOU'LL DO
- Own the technical side of sales cycles - discovery, demo, proof of concept, and handoff - in sync with the commercial motion
- Configure Ellie against real customer data, lanes, and carrier scenarios so prospects see a Digital Rep doing their actual job, not a canned demo
- Build and maintain a library of demo environments that show the Digital Workforce in action across broker, 3PL, and shipper use cases
- Answer the real questions in the room: how the Digital Rep onboards, what she handles unsupervised, where a human stays in the loop, and what changes on the desk once she's deployed
- Handle technical objections live - data flow, oversight, compliance
- Run POC environments and walk prospects through the work Ellie produced and the results behind it
- Feed recurring prospect pain points back to product and help shape what the Digital Workforce learns to do next
- Support security questionnaires and technical due diligence for enterprise prospects
- Define the SE function from scratch - process, assets, playbooks - as our first SE hire
- Own the technical handoff to implementation so the customer gets the Digital Workforce they were sold
- Own integration conversations with prospect technical teams: how Ellie connects to systems like McLeod, OTM, Tai, and custom TMS environments, what the data flow looks like, and what standing up the Digital Workforce actually takes
WHAT YOU BRING
- 2-5 years in solutions engineering, sales engineering, or a customer-facing technical role
- Freight tech background: brokerage, 3PL ops, TMS platforms, or carrier networks. You know the lingo and the pain.
- Hands-on with AI agents and workflows. You've built or configured something with an LLM, not just read about it.
- Familiarity with voice AI, SMS automation, or outbound communication tooling
- Enough technical range to wire up a demo environment yourself and hold your own on API architecture, webhooks, and data mapping
- Can make a Digital Rep credible in the room: a compelling, unrehearsed demo, adapted mid-call without losing the thread
- The instinct to sell deployment, not software. You can explain what it takes to onboard a Digital Rep and what a team looks like once one is running.
- Strong written communication. You explain complex systems simply, without filler.
- Early-stage startup experience. You know how to operate when things move fast and the process isn't built yet.
WHAT WE OFFER
- A front-row seat to the shift from software that manages work to a Digital Workforce that does it. You're not selling a tool, you're deploying labor, and you'll help define how a company sells that, from the demo that illustrates it to the playbook we run.
- Direct exposure to the commercial strategy of a company that's actively closing and negotiating deals
- A seat at the table - we're small, decisions move fast, and your work shows up immediately
- We talk numbers early. We don't waste anyone's time.
- Remote-flexible with async-first communication norms