Enterprise Sales Director

Who We Are GoodShip is the AI engine powering modern transportation networks, empowering transportation teams to optimize spend and service while driving seamless collaboration across internal stakeholders and external partners. GoodShip unifies data from loads, tenders, contracts, real-time tracking, and market benchmarks to deliver a comprehensive, intelligent view of the transportation network. Embedded intelligence proactively recommends the highest-impact opportunities to save money, improve service, and reduce spot exposure. Teams can act instantly by renegotiating rates, refining routing guide logic, triggering carrier performance alerts, or running off-cycle bids and full-network RFPs through purpose-built procurement tools that blend automation and intelligence. The result is a continuously optimized freight network that remains agile and resilient in a dynamic market. We’re backed by A-list venture firms and founders of industry-leading FreightTech companies, and were recently recognized in the TechCrunch AI Disrupters 60. With ample financial backing and strong traction, we’re seeking a driven and experienced Enterprise Sales Director to join us on the ground floor and help bring ultra-modern transportation technology to market. About the Role As an Enterprise Sales Director, you will play a critical role in driving GoodShip’s revenue growth by building relationships with key enterprise customers and leading high-impact sales cycles. You’ll manage the full lifecycle from prospecting through close and partner cross-functionally with Solutions, Customer Success, and Product to ensure a seamless customer journey. This is a high-ownership role for someone who deeply understands the freight industry and can operate strategically while rolling up their sleeves to execute. What You’ll Do Generate Pipeline and Own the Sales Cycle Hunt for new business across the freight market, generate high-quality pipeline with shippers, carriers, brokers, and other enterprise logistics organizations, and take full ownership for converting outbound effort into closed-won revenue. Drive Opportunities with Urgency and Discipline Prospect consistently, qualify rigorously, create urgency with the right stakeholders, build compelling business cases, deliver tailored demos, and guide buyers through complex enterprise procurement cycles. Sell Strategic Platform Value Position GoodShip as a modern freight orchestration platform that helps enterprise teams improve transportation performance, uncover network opportunities, and make better decisions with data and AI. Navigate Enterprise Buying Teams Build relationships across Transportation, Logistics, Procurement, Finance, IT, and executive stakeholders to create urgency, align priorities, and move opportunities through enterprise decision-making processes. Partner Cross-Functionally to Win Customers Collaborate with Solutions, Product, Customer Success, and leadership to sharpen account strategy, validate customer needs, support clean handoffs, and set customers up for long-term success. Bring Market Insight Back Into the Business Translate prospect conversations, competitive dynamics, objections, and market feedback into actionable insights that influence GTM strategy, product priorities, and category positioning. What You Bring 5+ years of enterprise B2B SaaS sales experience, with a proven track record of generating pipeline, managing complex sales cycles, and closing new business in multi-stakeholder environments. Experience selling into transportation, logistics, supply chain, or similarly complex operational environments, with enough freight context to credibly engage buyers across shippers, brokers, carriers, and other logistics organizations. Strong understanding of enterprise sales motions, including account planning, discovery, qualification, business case development, executive alignment, procurement navigation, and mutual close planning. Proven experience closing multi-six-figure software deals, including opportunities that require selling into the C-suite, building executive alignment, and navigating senior-level approval processes. Ability to build relationships across Transportation, Logistics, Procurement, Finance, IT, and executive stakeholders, while identifying the people, pain, priorities, and process required to move a deal forward. Demonstrated ability to operate with ownership, urgency, and resilience in ambiguous, fast-moving startup environments, creating structure, driving activity, and staying accountable to outcomes. Strong commercial judgment and operating discipline, with the ability to balance strategic account thinking with consistent hands-on execution. Proven track record of operating in a metrics-driven environment and consistently meeting or exceeding quota. Experience selling freight, transportation, logistics, or supply chain technology solutions preferred. Familiarity with TMS, freight optimization, visibility, procurement, analytics, AI, or related supply chain technology platforms preferred. Why GoodShip Competitive compensation and meaningful equity ownership. 100% employer-paid health benefits. Unlimited PTO. Company-wide winter break during the December holidays. Fully remote work environment. Destination team off-sites.