Sales Leader

Sales Leader LocationRemoteEmployment TypeFull timeLocation TypeRemoteDepartment2. Go To MarketAbout UsLogistics 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.OverviewWe'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 DoDirectly manage and coach our enterprise and strategic AE teamRun weekly 1:1s, pipeline reviews, and deal coaching — live call and email reviews, not just dashboard check-insOwn team quota attainment, forecast accuracy, and pipeline health in HubSpotCoach reps on discovery, objection handling, and demoing Augie's concrete automations (quoting, dispatch, tracking, billing, collections) rather than generic AI messagingPartner with Sales leadership on territory and account assignment and comp structure for the teamIdentify and escalate deal risk early; jump into strategic or stuck deals as neededPartner with Sales Enablement and RevOps on new-hire ramp plans, live coaching content, playbook gaps, comp and quota mechanics, and reporting needsFeed field intelligence — win/loss patterns, competitive intel, ICP fit signals — back to leadership and ProductCoach reps day-to-day on our GTM stack: HubSpot, LinkedIn Sales Navigator, Seamless.ai, and 6senseWhat We're Looking For8–10+ years of full-cycle B2B SaaS sales experience, including 5+ years in a first-line sales management roleTrack record of building and coaching a team to consistent quota attainmentComfortable being hands-on in deals — reviewing calls, joining critical meetings, coaching in real timeStrong forecasting discipline and CRM hygiene habits you can instill in a teamEnergized by an early-stage environment — you're building process, not just running one that already existsExperience selling and managing enterprise and strategic deals within freight, supply chain, or logistics techBonus Points ForExperience in logistics, freight, for-hire trucking, or supply chain techPrior individual-contributor success at an early-stage AI or automation companyFamiliarity with agentic AI or automation platformsWhy Join Us?Competitive Salary + Stock OptionsComprehensive Health, Vision, and Dental BenefitsFlexible PTOOn-site GymMonthly stipendAbout AugmentAt 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...