Vice President of Sales, AI and Insights

Transflo | Freight Technology SaaSPosition SummaryTransflo is seeking an elite, top-tier Vice President of Sales to lead new business for our AI and insights portfolio, including Workflow AI (WFAI) and the Transflo Intelligence Suite. This is a senior individual contributor role for a proven closer who has delivered exceptional sales results over a sustained period and wants to operate at the highest level of enterprise selling.You will serve as one of Transflo’s most senior sellers, pursuing the industry’s largest and most strategic accounts. You will lead the strategic pursuits and often partner directly with Transflo’s C-suite on strategic pursuits, working alongside our Solution Engineers, Product, Marketing, and Leadership teams to win complex, enterprise-level deals. You will open doors at the top of the largest freight organizations, win transformational multi-year deals, and set the standard for how Transflo sells AI and insights to the market.Key ResponsibilitiesDeliver against the highest individual quota on the sales team, per the comp plan, by selling WFAI, the Transflo Intelligence Suite, and the broader Transflo/ATI SaaS portfolioOriginate, lead, and close transformational enterprise and multi-year opportunities with the freight industry’s largest carriers, brokers, factors, and LTL fleetsOpen and sustain C-suite and board-level relationships, using your own network and disciplined outbound pursuit to generate pipelineServe as Transflo’s senior voice in executive conversations, positioning AI and insights as a strategic lever for our customers’ growth, margin, and competitive advantagePartner with Transflo’s C-suite on account strategy, deal structure, pricing, and executive engagement for the most important pursuitsRun a high-performance team-selling motion with Solution Engineers, Subject Matter Experts, Product, Marketing, and LeadershipShare your playbook by informally mentoring other sellers on enterprise pursuit strategy, executive engagement, and deal executionProvide market, customer, and competitive insight to Product and Executive Leadership to inform positioning, packaging, and roadmap prioritiesRepresent Transflo at key industry events, customer forums, and executive meetingsTravel 25 to 50% of the time for customer onsites, executive meetings, trade shows, and industry events, representing Transflo at the highest level, per the Transflo Employee AgreementMaintain a clean, accurate pipeline in Salesforce to support executive and board-level reportingTravel as needed to support customer engagements, per the Transflo Employee AgreementUphold Transflo’s core values, policies, and proceduresQualificationsWe are hiring the best. The ideal candidate combines elite, sustained results with polished executive presence, flawless follow-through, and relentless pursuit of the win.Required12+ years of enterprise SaaS sales experience, with deep, proven success within the freight or transportation industrySustained history of top-tier performance, with consistent quota overachievement and recognition as a top performer at prior employersRecord of independently originating and closing transformational new deals larger than $5M TCVEstablished senior relationships across the carrier, broker, factor, and LTL landscape, including the Transport Topics Top 500Demonstrated ability to lead credible, trusted conversations with CEOs and boards, and with frontline operatorsHunter mentality, with a record of generating significant pipeline organicallyExceptional team-selling skills and a record of working effectively with executives and cross-functional teamsOutstanding written and verbal communication skills, with executive presence, tact, and diplomacyAbility to thrive in a highly competitive, highly visible environmentBachelor’s degree in Business, Marketing, Information Technology, or a related fieldStrongly PreferredExperience selling data solutions, analytics, or market intelligence solutions, or other AI and logistics automation applicationsFamiliarity with FMCSA requirements, telematics, and TMS softwareExperience selling in a private equity-backed environmentWhy TransfloThis is a rare opportunity to sell differentiated, market-leading technology at a pivotal moment for freight, with direct access to the C-suite and a real voice in how Transflo wins the industry’s most important accounts.Physical demands: sit, stand, listen, hear, read, talk, use a computer and phone, and travel up to 50% of the time.