Pre-Sales Engineer

Augment•Chicago, IL

About The Position

Augment is hiring a Pre-Sales Engineer to support its sales team in selling its AI platform for logistics operations. The role is the technical force behind the sales team: Account Executives lead customer relationships and deals, while the Pre-Sales Engineer makes the product tangible through tailored demonstrations, technical discovery, responses to security and technical questions, and proofs of concept. The position is embedded with the AE team and supports opportunities from discovery through close, primarily across freight brokerages, for-hire carriers, and private fleet operators. The role reports to the Head of Solutions, with a dotted line to Sales leadership, and includes travel of up to 50% for customer meetings, industry events, team offsites, and strategic deals.

Requirements

3–6 years of experience in pre-sales, sales engineering, or a customer-facing technical role, ideally supporting enterprise deal cycles.
Demonstrated ability to deliver compelling product demonstrations to technical and non-technical audiences.
Strong written communication skills, including the ability to produce clear, confident RFP responses.
Comfort navigating multi-stakeholder enterprise buying cycles involving IT, security, operations, and finance.
Technical curiosity and understanding of APIs, integrations, and data flows; production coding is not required.
Experience working closely with an Account Executive team and understanding how to advance a deal from technical validation to close.
High ownership mentality and willingness to treat Account Executives’ pipeline as one’s own.
Familiarity with CRM tooling and structured deal tracking; Augment uses HubSpot.

Nice To Haves

Background in freight brokerage, TMS, fleet management, or logistics SaaS.
Experience with AI or automation platforms, especially agentic or LLM-powered platforms.
Familiarity with security and compliance frameworks such as SOC 2 and GDPR, and with vendor security reviews.

Responsibilities

Run live product demonstrations of Augie tailored to prospects’ workflows, pain points, and technology stacks.
Partner with Account Executives on discovery calls, asking technical questions to uncover buyer needs.
Own the technical track of the sales cycle, including RFPs, security questionnaires, infosec reviews, and vendor assessments.
Map prospect requirements to Augment’s capabilities and communicate capability gaps honestly.
Answer in-depth technical questions from IT, operations, and engineering stakeholders across both target customer segments.
Build proofs of concept, workflow mockups, or demo environments when a standard demonstration is insufficient.
Capture and communicate product feedback and feature gaps to product and engineering teams.
Support deal strategy with Sales leadership, helping determine when to push, pivot, or bring in additional support.
Help create sales enablement materials, including battle cards, objection-handling documents, competitive teardowns, and technical one-pagers.
Travel up to 50% for customer meetings, industry events, team offsites, and strategic deals.