Senior Enterprise Account Executive

Logistics is broken. Let’s fix it.

We are a team of engineers, product designers, and customer champions using AI-powered automation to transform the $9T global logistics industry. Our AI agents reason and act like humans, revolutionizing freight brokerage workflows to drive efficiency and profitability.

Our team has scaled billion-dollar companies, built delightful products, and powered billions in commerce. Now, we’re solving logistics’ toughest challenges with AI.

If you thrive in fast-paced, high-impact environments and want to define how AI reshapes logistics, apply today.

Overview

We’re looking for a high-performing, consultative Senior Account Executive to drive revenue at Augment. You’ll own the full sales cycle—from outbound prospecting and discovery to demoing our AI platform and closing deals with top brokerages and logistics providers.

This role is ideal for someone who thrives in zero-to-one environments and is energized by complex, technical sales. You’ll work closely with our founders, product team, and solutions engineers to deliver tailored AI solutions that solve real customer pain.

We’re selling into an industry hungry for change—your ability to connect the dots, build trust, and close will directly impact the future of AI in logistics.

What You’ll Do

Enterprise Sales & GTM Execution

• Own the full sales cycle for named fleet accounts, from outbound prospecting through close

• Drive multi-threaded sales motions across operations, safety, IT, and finance leaders

• Run deep discovery to understand fleet workflows, operational bottlenecks, and economic impact

• Close complex, high-value enterprise deals with long sales cycles and multiple decision-makers

Pipeline Creation & Market Penetration

• Build and maintain strong pipeline coverage through outbound efforts and strategic account targeting

• Open doors at large private fleets and for-hire carriers, and expand footprint over time

• Develop account strategies that align Augment’s value to fleet KPIs such as utilization, safety, downtime, and cost per mile

Startup Impact & Ownership

• Operate with a builder mindset: help refine ICP, messaging, talk tracks, and sales process

• Create and improve sales assets as needed (collateral, ROI narratives, discovery frameworks)

• Partner with Product and Engineering to translate customer needs into roadmap input

• Share market insights and patterns that help shape Augment’s GTM strategy

What We’re Looking For

• 7+ years of experience selling enterprise software or technology solutions

• Proven success running complex, multi-stakeholder enterprise sales cycles

• Experience building a pipeline and closing deals without heavy inbound or enablement support

• Strong business acumen with the ability to tie product value to operational and financial outcomes

• Comfortable operating in early-stage or growth environments with ambiguity

Strongly Preferred

• Experience selling into fleet, transportation, or asset-based organizations

• Familiarity with buyers such as Fleet Operations, Safety/Compliance, Maintenance, Dispatch, IT, and Finance

• Background in adjacent markets such as telematics, fleet management, TMS, compliance, or operations software

Bonus Points

• Experience selling complex, AI-driven, or data-intensive enterprise platforms

• Comfort building in early-stage environments as a player-coach

• Consultative, value-based selling mindset with strong discovery skills

• Direct experience selling into logistics, supply chain, or asset-based fleets

• Technical curiosity across AI, ML, or systems-heavy workflows

• Background in consulting, solution engineering, or zero-to-one startups

Why Join Us?

• Competitive Salary + Commission + Stock Options

• Comprehensive Health, Vision & Dental Benefits

• Equity in a High-Growth AI Startup

• Flexible Work Environment

• Work on Cutting-Edge AI in a $9T Industry

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).