Director of Sales

About Us: Outpost is building the backbone of freight. We’re reinventing how supply chain infrastructure works in America with carrier agnostic truck terminals. As a vertically integrated real estate, operations, and technology company, we acquire and operate mission-critical real estate across the country to serve the largest logistics providers in the world. Backed by $1B from Greenpoint Partners, we’re scaling and building the most valuable logistics network in the country. We thrive on accountability, integrity, and a shared drive to raise the bar. If you’re excited to reshape the industry alongside a high-performance team with a championship mindset that executes relentlessly, welcome aboard. Role Summary: As Director of Sales, you will own revenue for Outpost Gate Automation™ and lead the team that delivers it. Outpost Gate Automation™ began as infrastructure we built to run our own terminals. Customers asked to license it, and the technology business spun out because the market pulled it out. The strategy and the playbook already exist. This role is about execution — hiring and leading a team of Account Executives, driving disciplined adoption of the playbook across every rep, building the outbound motion that complements our inbound demand, and delivering the number. You will carry a personal quota on strategic accounts alongside your team. This position is based on-site in our Austin, TX office and reports to Greg Mason, Vice President – Solutions Engineering. Key Responsibilities: - Own the US revenue target for Gate Automation — bookings, margin, and forecast accuracy; - Hire, onboard, ramp, and lead a team of Account Executives, managing performance directly and coaching to the number; - Drive consistent execution of the existing sales playbook, and refine it with evidence from the field; - Build and lead the outbound motion that complements inbound demand; - Run a weekly operating rhythm: pipeline review, deal inspection, forecast call, and one-on-ones; - Carry a personal quota on strategic and enterprise accounts, including the largest national logistics providers; - Lead complex, multi-stakeholder deals across operations, IT, security, facilities, and procurement, and approve the proposals and pricing strategies behind them; - Deliver and coach tailored live demonstrations of the Gate Automation platform, including both software and hardware components; - Own HubSpot as the system of record, and partner with Sales Ops on quotas, training, and enablement; - Coordinate with engineering, product, and operations to scope and deliver solutions; and - Travel to customer sites for on-site assessments, and represent Outpost at trade shows and industry events. Qualifications: - Hardware-enabled SaaS experience. Selling, or leading teams that sell, software with a physical hardware component — IoT, access control, industrial automation, connected devices, or comparable. We prioritize this over logistics industry experience. - 8+ years of full-cycle B2B sales experience in enterprise software, industrial automation, or access control - 3+ years directly managing quota-carrying Account Executives, including hiring, ramping, and performance management - A proven track record of closing six-figure deals with complex stakeholders - Experience building an outbound motion, not only managing one that was already running - Experience working cross-functionally in fast-paced startup or growth-stage environments - Familiarity with CRM systems and data-driven pipeline management. HubSpot a plus - Based in Austin or willing to relocate, with 40–50% travel - Freight, logistics, or supply chain experience is a plus, but secondary to the hardware-enabled SaaS background Benefits: - Comprehensive Benefits Package including Health, Dental, and Vision Insurance - 401(k) Retirement Plan Matching - 18 Paid Holidays - Unlimited PTO - Friday Team Lunches Outpost is an Equal Opportunity Employer and Prohibits Discrimination of Any Kind.