Enterprise Sales Director

Job Description

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 stays 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. We're growing fast, and we're looking for an Enterprise Sales Director to carry our largest accounts: a closer with real freight fluency who owns the whole cycle, from the first cold conversation to signed.

About the Role

This is a high-ownership role for someone who's energized by the hunt, not just the close. We want a seller who deeply understands the freight industry and can operate strategically while rolling up their sleeves to run the full cycle themselves.

You'll own the pipeline end to end: prospecting, qualifying, building the business case, navigating the buying committee, and closing. But the job doesn't stop at quota. You'll be the trusted voice in the room when enterprise buyers ask why GoodShip and not the status quo, and you'll partner closely with Solutions, Product, and Customer Success to make sure every deal you win turns into a customer who stays. This is an individual contributor role, but the scope is real: you'll have the autonomy to build your book of business the way you think it should be built, and the accountability that comes with it.

If you love the chase, want to be the person prospects trust to tell them the truth about what GoodShip can and can't do, and get real satisfaction from turning a cold conversation into a signed enterprise deal, this is your seat.

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 insights that shape GTM strategy, product priorities, and category positioning.

A Typical Week Might Include

• Running discovery calls and tailored demos with shippers, carriers, and brokers
• Building and defending a business case for a champion who needs to sell GoodShip internally
• Mapping the buying committee on a multi six-figure deal and figuring out who actually owns the decision
• Working a deal through procurement, legal, and security review without losing momentum
• Strategizing with Solutions and Customer Success on how to set up a new close for long-term success

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 command 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.
• A bias toward ownership and action. You create structure in ambiguous, fast-moving environments and stay accountable to outcomes without waiting to be told what's next.
• 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.