Pre-Sales Engineer

Augment•Chicago, IL

About The Position

As a 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. Our GTM is primarily outbound-led, targeting two ICPs: freight brokerages, for-hire carriers, and private fleet operators. Deals are complex, multi-stakeholder, and land in the $500K--$1M ARR range. 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.

Requirements

3--6 years in a pre-sales, sales engineering, or customer-facing technical role, ideally supporting enterprise deal cycles
Proven ability to run compelling product demos for both technical and non-technical audiences
Strong written communication -- you can turn a 40-question RFP into a crisp, confident response
Comfortable navigating multi-stakeholder enterprise buying cycles involving IT, security, operations, and finance
Technically curious -- you don't need to write production code, but you understand how APIs, integrations, and data flows work
Experience working closely with an AE team and understanding what it takes to push a deal from technical validation to close
High ownership mentality -- you treat your AEs' pipeline like your own
Familiarity with CRM tooling (we use HubSpot) and structured deal tracking

Nice To Haves

Background in freight brokerage, TMS, fleet management, or logistics SaaS
Experience with AI or automation platforms -- especially anything agentic or LLM-powered
Familiarity with security and compliance frameworks (SOC 2, GDPR, vendor security reviews)
You've handled deals where the buyer was skeptical of AI -- and you turned them around

Responsibilities

Run live product demos of Augie tailored to each prospect's specific workflows, pain points, and tech stack -- no canned slideshows
Partner with AEs on discovery calls to ask the right technical questions and uncover what really matters to the buyer
Own the technical track of the sales cycle: RFPs, security questionnaires, infosec reviews, and vendor assessments
Map prospect requirements to Augment's capabilities and be honest when there's a gap
Field 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 it
Capture and clearly communicate product feedback and feature gaps to our product and engineering teams -- you're a critical input to the roadmap
Support deal strategy with Sales leadership -- helping decide when to push, when to pivot, and when to bring in more firepower
Help create sales enablement materials: battle cards, objection handling docs, competitive teardowns, and technical one-pagers