Sales Leader

Augment

2d•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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