Pre-Sales Engineer

Pre-Sales Engineer LocationChicago RemoteEmployment TypeFull timeLocation TypeHybridDepartment2. Go To MarketAbout UsLogistics is broken. Let's fix it.We are a team of engineers, product designers, and customer champions applying the most transformative technology of our time, AI, to one of the world's largest industries: logistics. Our mission is to streamline freight brokerage, carrier management, and 3PL operations through automation, freeing teams to focus on high-value strategic work.We're looking for a Sales Engineer who's equally at home in a discovery call as they are in a technical deep dive -- someone who makes our AEs unstoppable and helps prospects say yes faster.OverviewAs a Pre-Sales Engineer at Augment, you're the technical force behind our sales team. While our Account Executives own the relationships and drive the deals, you're the one who makes the product real. You'll run live demos of Augie, answer the hard technical questions, handle RFPs and security questionnaires, and translate what Augment does into language that makes a logistics buyer go "that's exactly what we need."This role lives in the sales cycle, not after it. You'll be embedded with the AE team, working deals from discovery through close. You'll report to our Head of Solutions with a dotted line to Sales leadership. The right person here isn't just technical; they're a persuader, a problem framer, and a natural closer-by-proxy.GTM MotionOur GTM is primarily outbound-led, targeting two ICPs: freight brokerages and for-hire carriers, as well as private fleet operators. Deals are complex and involve working with multi-stakeholders. You'll be the technical anchor across these cycles, working alongside AEs to run tailored demos, navigate IT and security reviews, and build the technical case that gets deals across the finish line.What You'll DoRun live product demos of Augie tailored to each prospect's specific workflows, pain points, and tech stack -- no canned slideshowsPartner with AEs on discovery calls to ask the right technical questions and uncover what really matters to the buyerOwn the technical track of the sales cycle: RFPs, security questionnaires, infosec reviews, and vendor assessmentsMap prospect requirements to Augment's capabilities and be honest when there's a gapField deep-dive technical questions from IT, operations, and engineering stakeholders at prospect accounts across both ICP segments (brokerages/carriers and private fleets)Build proofs-of-concept, workflow mockups, or demo environments when a standard demo won't cut itCapture and clearly communicate product feedback and feature gaps to our product and engineering teams -- you're a critical input to the roadmapSupport deal strategy with Sales leadership -- helping decide when to push, when to pivot, and when to bring in more firepowerHelp create sales enablement materials: battle cards, objection handling docs, competitive teardowns, and technical one-pagersWhat We're Looking For3-6 years in a pre-sales, sales engineering, or customer-facing technical role, ideally supporting enterprise deal cyclesProven ability to run compelling product demos for both technical and non-technical audiencesStrong written communication -- you can turn a 40-question RFP into a crisp, confident responseComfortable navigating multi-stakeholder enterprise buying cycles involving IT, security, operations, and financeTechnically curious -- you don't need to write production code, but you understand how APIs, integrations, and data flows workExperience working closely with an AE team and understanding what it takes to push a deal from technical validation to closeHigh ownership mentality -- you treat your AEs' pipeline like your ownFamiliarity with CRM tooling (we use HubSpot) and structured deal trackingBonus Points ForBackground in freight brokerage, TMS, fleet management, or logistics SaaSExperience with AI or automation platforms -- especially anything agentic or LLM-poweredFamiliarity with...