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 energized by complex, technical enterprise sales who can partner closely with founders, product, and engineering 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 Lead complex enterprise sales cycles 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 prospecting and strategic account penetration into large private fleets and for-hire carriers 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 Comfortable operating in early-stage or growth environments, building pipeline and closing enterprise 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 Player-coach mentality with comfort building in early-stage environments Consultative, value-based selling mindset with strong discovery skills 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). 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.