Cartage

Cartage is building infrastructure for an autonomous supply chain.  Wilson is Cartage's AI logistics coordinator.  Wilson works for the shipper — embedded inside their logistics team, representing them to carriers, consignees, and internal stakeholders. Wilson runs freight for some of the most demanding shippers in North America, across ERPs, email, platforms and carrier networks. Wilson is largely autonomous. He runs the freight. Autonomy Managers are the bridge between Wilson and the buyer. You make sure the humans who bought Cartage understand what Wilson is doing, trust that it's being done well, and see measurable value from the partnership. You step in on the rare moments Wilson needs human judgment. And you make sure the signal from your accounts flows back into the team making Wilson better. You work internally with Autonomy Operations, Engineering and sales to close gaps you find. The people who brought Cartage in — CEO’s, COOs, VPs are counting on you to prove they made the right call. What you’ll own The buyer relationship post-activation: you're the senior point of contact from go-live through renewal Making Wilson's work legible to the customer: regular business reviews, clear reporting on performance, honest conversations when things break Partnering with Sales during the sales cycle so the customer meets you early and the handoff is seamless Partnering with Product and Engineering during onboarding to get Wilson configured and representing the customer correctly The handful of moments that need a human: escalations, edge cases, sensitive stakeholder conversations The feedback loop into Autonomy Operations and Engineering: you surface the patterns you see across your accounts, they improve Wilson, you verify Retention and expansion across your accounts What we’re looking for 5+ years in LTL and FTL logistics — brokerage / 3PL, shipper-side, or receiver  Deep fluency in the freight lifecycle: pickup, in-transit, delivery, exceptions and claims You’ve worked with shippers, brokers, or carriers in environments where things break You can talk to a dispatcher and a CEO in the same hour and switch registers cleanly High ownership. Comfortable with ambiguity. Direct communicator. You want to work alongside AI, not around it Startup or high-growth experience What success looks like Wilson's autonomy level climbs on your accounts quarter over quarter Customers see Wilson as part of their team, not a vendor Buyers walk into every business review confident in the partnership Customers renew and expand because they can't imagine going back Sales trusts you in the room pre-close; Product trusts your feedback post-launch You become one of the most trusted operators at Cartage Why this role A role that didn’t exist three years ago, at a company defining the future of freight Direct impact on revenue, autonomy, and customer outcomes from day one Clear path to growth as the Autonomy Management function grows

Autonomy Operations Architect Location: Vancouver (preferred) / San Francisco Team: Autonomy Operations Reports to: Head of Autonomy Operations (Kolby) About Cartage Cartage is building an autonomy-first logistics AI called Wilson. Wilson acts as a 24/7 logistics team for manufacturers and distributors — behaving closer to a human employee than traditional software. Our goal is not to help humans do logistics better. Our goal is to build an AI that actually does the work. We believe autonomy is a measured capability, not a marketing claim. That belief shapes how we build product, how we sell, and how we run the company. This role exists to keep that belief true. What Autonomy Operations Does Autonomy Operations exists to answer one question: “What is Wilson actually capable of today — and where does he break?” This team does not run logistics. It does not quietly fix things. It does not hide human work. Instead, it: Surfaces reality Enforces boundaries Turns failures into signal for Product and Engineering The Role As an Autonomy Operations Architect, you sit at the boundary between real-world logistics and Wilson. You will monitor live workflows, identify where autonomy breaks, and step in only when necessary — not to take over the work, but to manage Wilson’s execution and make failures visible. You are not doing the work yourself. You are ensuring Wilson either does it correctly — or that the system clearly records when he cannot. This is a technical, analytical, logistics-native role — not customer support and not day-to-day operations. What You’ll Own Monitoring live shipments and workflows Identifying when and where autonomy breaks Assigning and adjusting autonomy levels when humans intervene Stepping in to manage Wilson when required (not replacing him) Classifying failures and exceptions with precision Enforcing supported vs unsupported workflows Producing clear, actionable signal for Product and Engineering Maintaining the autonomy matrix and weekly reality reports You are successful when: Failures surface quickly Nothing is “quietly handled” Product and Engineering are never surprised by reality What You Will Not Own Making workflows succeed at all costs Long-term manual execution Running accounts end-to-end Custom customer workarounds “Saving” deals or shipments Writing production engineering code If a workflow can’t run autonomously, your job is to expose that, not mask it. Who This Role Is For This role is a strong fit if you: Have worked in logistics operations at a shipper, distributor, or freight brokerage Understand how shipments actually move — and how they fail Enjoy finding where systems break Are comfortable saying “this doesn’t work yet” Care about correctness more than optics Think clearly under ambiguity Like being close to real operations without owning outcomes You don’t need to be a traditional engineer, but you do need: Strong systems thinking Comfort with data, workflows, and edge cases Clear written communication Who This Role Is Not For This role is not a fit if you: Want to run logistics day-to-day Prefer to quietly fix problems Measure success by “things got done” Want to promise customers anything it takes Are uncomfortable with failure being visible Why This Role Matters Most companies hide human labor behind AI. We don’t. Autonomy Operations is how we stay honest — and how the system actually improves. If this role is done well, the company compounds. If it isn’t, we become a services business. That’s how important this role is. Compensation Competitive salary + meaningful equity. Exact numbers depend on experience, scope, and location.

What is Cartage? Cartage is building Wilson, an AI that coordinates freight for manufacturers and distributors—handling the tedious work of booking, tracking, and managing shipments end-to-end. Our customers range from lumber mills to furniture manufacturers. With Wilson, teams can offload their entire logistics function and scale infinitely at a fraction of the cost of a human team. Backed by Y Combinator (S24), Paul Graham, and a $3.3M seed round, we’ve hit an inflection point in revenue growth. We closed $200K ARR in 3 hours earlier this month and are scaling the team to meet accelerating demand. This is a rare opportunity to build foundational systems that will define the future of how goods move. As a Full Stack Engineer, you’ll work side-by-side with the founders and take ownership of critical infrastructure, architecture, and AI design decisions from day one. Our Culture Cartage is a startup for builders who want full ownership. No PMs. No middle managers. Engineers own the customer experience end-to-end—from “what should we build?” to “it’s live and customers love it.” Our Core Values: Taste: Companies win on taste. Engineering is a creative discipline—part logic, part art—and we care deeply about how things feel, how they’re named, and how they scale. We sweat the small stuff because it compounds. Extreme Ownership: Everyone runs their domain like a founder. You own problems end-to-end. No handoffs, no waiting—just clear goals and the autonomy to build. Radical Transparency: You’ll see everything—from product decisions to monthly investor updates. We move faster when everyone has full context. We’re an in-person team in San Francisco, CA and Vancouver, BC, and believe deeply in building together in real life. What You’ll Do Build autonomous agents: Design and scale AI systems that can reliably automate complex, data-intensive workflows—handling everything from quoting to tracking—so customers can fully offload their logistics. Automate AI evaluation loops: Own the tooling to monitor, evaluate, and retrain AI models in production—ensuring performance improves automatically as new edge cases arise. Own the product: You won’t get a Linear ticket—you’ll get a problem and talk to the customer directly. You’ll design the solution, write the code, and ship it. Integrate everywhere customers work: Build deep integrations across enterprise systems (SAP, Oracle, ERPs, TMSs), messaging platforms (Slack, Teams), and browser automation—so Wilson fits seamlessly into any workflow. Who You Are Builder at heart: You don’t just write code—you build products. You think in terms of customer impact, not just technical elegance. You take pride in shipping real things that solve real problems. High-agency problem solver: You don’t wait for direction. You move fast through ambiguity, seek clarity on your own, and hop on the phone with customers to get to the root of issues and solve them directly. Full-stack executor: You get handed a problem like “get this customer live,” and do whatever it takes—build the UI, extend the API, fine-tune the agent—to make it happen. Preferred Experience 3+ years of professional software development with a proven track record of building and scaling production systems. YC startup background—you’ve thrived in fast-paced, zero-to-one environments where speed and ownership matter most. Agentic applications—experience designing or building AI systems that act autonomously, adapt to context, and improve through feedback loops. What We Offer Meaningful equity – 0.5% - 2% ownership as an early team member Competitive salary – $150K - $250K depending on experience Full health/dental/vision – 100% covered High trust, high ownership environment – Zero micromanagement A real shot at something big – Help define the future of AI in logistics

About Cartage Cartage is building Wilson, an AI that orchestrates shipments for manufacturers and distributors. Our customers range from lumber mills to furniture manufacturers. If you’re looking to make a difference in an industry that’s ripe for change, Cartage is the place for you. Our culture is built on high ownership and autonomy – we trust each team member to take initiative and drive projects forward. We also value collaboration and transparency at all levels, empowering everyone to do the most meaningful work of their careers as we build the future of logistics. About the Role As a Sales Development Representative, you will be at the forefront of Cartage’s growth, acting as the first point of contact for prospective customers and the driving force behind our sales pipeline. In this role, you’ll combine persistence, creativity, and communication skills to turn cold prospects into valuable clients. No two days will be the same – one day you might be cold calling a list of prospects, and the next you could be crafting a thought-leadership post on LinkedIn to engage new leads. This is a high-impact, high-autonomy position, perfect for a self-starter who loves challenges and wants to grow their career in tech sales. Location: San Francisco, CA. This role offers flexibility for remote or hybrid work arrangements based out of our San Francisco office. Key Responsibilities - Prospect and generate leads: Proactively identify and create new sales opportunities through high-volume cold calling and other outbound outreach methods. - Book meetings and drive pipeline: Consistently book at least 10+ meetings per month with qualified prospects by effectively pitching Cartage’s value proposition and following up on leads. - Multi-channel outreach: Leverage an omni-channel approach – phone calls, emails, video conferencing, and social media – to engage and nurture prospective clients. - Content engagement: Create and share engaging content (e.g. LinkedIn posts) to build awareness, demonstrate thought leadership, and attract potential customers to Cartage. - Qualify and hand off leads: Qualify inbound and outbound leads to determine fit, and set up meetings or product demos between prospective customers and the Account Executive team. - Collaborate with the team: Work closely with sales and leadership on targeting strategies and ensure a smooth handoff of qualified opportunities. - Manage data & follow-up: Maintain accurate records of prospect interactions and activities in our CRM system, and regularly follow up with leads to drive engagement. - Own your goals: Take ownership of your pipeline and consistently meet or exceed your monthly targets for meetings booked and opportunities created. Continuously refine your approach based on feedback and coaching. Qualifications - Experience: 1–2 years in a sales, business development, or other customer-facing role (SDR/BDR experience is a plus). - Communication skills: Excellent communication skills via phone, email, and social media, with the ability to engage prospects and clearly articulate value propositions. - Cold-calling prowess: Comfortable making cold calls and reaching out to new prospects daily, turning cold introductions into warm opportunities. - Track record of success: Proven ability to meet or exceed sales targets or activity quotas, and a strong motivation driven by results. - Drive and resilience: High-energy, results-driven attitude with a desire to succeed in a fast-paced, startup environment. Able to handle rejection and persist with a positive mindset. - Ownership & autonomy: Solution-oriented mindset, with a strong sense of ownership over your work – you take “extreme ownership” of your goals and thrive in an environment with high autonomy. - Team player: Collaborative and coachable, eager to learn from others and share knowledge. Values transparency and open communication within the team. - Tech savvy: Familiarity with CRM software and sales tools (e.g. Salesforce, Link