Pre-Sales Engineer

Augment; Chicago (IL); Hybrid; USD 110,000 - 150,000; Full time

Benefits offered by this job

Competitive salary + equity

Comprehensive health, vision, and dent

Flexible PTO

Monthly stipend

Job summary

Augment is hiring a Pre-Sales Engineer to join the sales team and drive technical validation through live demos, RFP responses, and security reviews. You’ll work closely with Account Executives to convert complex logistics use cases into compelling technical narratives that close deals.

Expect heavy travel and a pivotal role in shaping the product feedback loop. You’ll be embedded with the AE team, handling a technical track from discovery to close, reporting to Head of Solutions with a dotted

Qualifications

• 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 technical and non-technical audiences.
• Strong written communication skills for crisp RFP responses.
• Comfortable navigating multi-stakeholder enterprise buying cycles (IT, security, ops, finance).
• Technically curious about APIs, integrations, and data flows.
• Experience collaborating with an AE team to push deals from technical validation to close.
• High ownership mentality over AEs’ pipeline.
• Familiarity with CRM tooling and structured deal tracking.

Responsibilities

• Run live product demos tailored to each prospect’s workflows, pain points, and tech stack.
• Partner with AEs on discovery calls to uncover what matters to the buyer.
• Own the technical track of the sales cycle: RFPs, security questionnaires, infosec reviews, vendor assessments.
• Map prospect requirements to Augment’s capabilities and flag gaps honestly.
• Field deep-dive questions from IT, operations, and engineering stakeholders at prospect accounts.
• Build proofs-of-concept, workflow mockups, or demo environments when needed.
• Provide product feedback to roadmaps with clear communication to product/engineering.
• Support deal strategy with leadership to decide when to push or pivot.
• Create sales enablement materials: battle cards, objection handling docs, teardowns, tech one-pagers.
• Travel up to 50% of the time for meetings, events, and deals.

Skills

Product demos

Stakeholder management

Technical storytelling

RFP responses

Sales enablement

Discovery calls

Cross-functional collaboration

Pipeline ownership

Tools

HubSpot CRM

Job description

About Us

Logistics 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.

Overview

As 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 Motion

Our 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 Do

• 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

• Travel up to 50% of the time — for customer meetings, industry events, team offsites, and strategic deals

What We're Looking For

• 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

Bonus Points For

• 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)

Benefits

• Competitive salary + equity

• Comprehensive health, vision, and dental benefits

• Flexible PTO

• Monthly stipend

About Augment

At Augment, we set out to create a fully autonomous AI platform that streamlines operations and reclaims the human element in logistics. Our founders recognized a pattern: talented professionals were stuck handling manual data entry, phone calls, and repetitive tasks, instead of focusing on high-impact problem-solving and strategic decision-making.

That insight became our mission -- to free logistics professionals from busywork so they can focus on what truly drives business growth. Augment isn't just about efficiency; it's about transforming an entire industry by empowering teams with AI-driven solutions that make logistics smarter, faster, and more adaptive.

Join us on this journey!

Augment is an Equal Opportunity Employer and values diversity at our company. We consider all qualified applicants without regard to race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, disability, or any other legally protected status.

Augment complies with federal, state, and local laws regarding equal employment opportunity and reasonable accommodation. If you need assistance or an accommodation during the application or interview process, please contact your recruiter.

We also consider qualified applicants with arrest and conviction records in accordance with applicable federal, state and local fair-chance / ban-the-box laws (for example, but not limited to, the California Fair Chance Act).

Our hiring process uses AI-powered tools to assist with screening and evaluating applications based on job-related criteria. All AI-assisted outputs are reviewed by human recruiters who make all decisions about which candidates advance in the process.