Sales Leader

About Us Logistics is broken. Let's fix it. We are a group of engineers, product designers, and customer champions applying the most transformative technology of our times, AI, to one of the largest industries in the world, logistics. In our prior lives, we have built multi-billion dollar companies with products that delighted thousands of merchants and powered billions of dollars of commerce. We are looking for intelligent, driven people with insatiable curiosity and a desire to make an impact. If you’re excited to build AI that can reason and take action, like humans, in one of the most complex industries in the world — apply below. Overview We're looking for a Sales Leader to manage a team of Account Executives at Augment. You'll coach our enterprise and strategic AEs covering freight brokers, 3PLs, for-hire carriers, private fleets, and distributors — on pipeline generation, deal execution, and forecasting. This isn't a role covering every segment; it's ownership of a defined team within our broader outbound-led motion, reporting into the Head of Sales. You'll be the first line of coaching on how reps position Augie and its automation of quoting, dispatch, tracking, billing, and collections to an ICP that's skeptical of generic AI claims. What You'll Do Directly manage and coach our enterprise and strategic AE team Run weekly 1:1s, pipeline reviews, and deal coaching — live call and email reviews, not just dashboard check-ins Own team quota attainment, forecast accuracy, and pipeline health in HubSpot Coach reps on discovery, objection handling, and demoing Augie's concrete automations (quoting, dispatch, tracking, billing, collections) rather than generic AI messaging Partner with Sales leadership on territory and account assignment and comp structure for the team Identify and escalate deal risk early; jump into strategic or stuck deals as needed Partner with Sales Enablement and RevOps on new-hire ramp plans, live coaching content, playbook gaps, comp and quota mechanics, and reporting needs Feed field intelligence — win/loss patterns, competitive intel, ICP fit signals — back to leadership and Product Coach reps day-to-day on our GTM stack: HubSpot, LinkedIn Sales Navigator, Seamless.ai , and 6sense What We're Looking For 8–10+ years of full-cycle B2B SaaS sales experience, including 5+ years in a first-line sales management role Track record of building and coaching a team to consistent quota attainment Comfortable being hands-on in deals — reviewing calls, joining critical meetings, coaching in real time Strong forecasting discipline and CRM hygiene habits you can instill in a team Energized by an early-stage environment — you're building process, not just running one that already exists Experience selling and managing enterprise and strategic deals within freight, supply chain, or logistics tech Bonus Points For Experience in logistics, freight, for-hire trucking, or supply chain tech Prior individual-contributor success at an early-stage AI or automation company Familiarity with agentic AI or automation platforms Why Join Us? Competitive Salary + Stock Options Comprehensive Health, Vision, and Dental Benefits Flexible PTO On-site Gym Monthly stipend About Augment At Augment, we set out to create a fully autonomous AI platform — Augie — that streamlines operations and reclaims the human element in supply chain. 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 supply chain 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 supply chain 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.