Vice President of Sales, AI and Insights

Transflo Freight Technology SaaS

Position Summary

Transflo 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 Responsibilities

• Deliver 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 portfolio
• Originate, lead, and close transformational enterprise and multi-year opportunities with the freight industry’s largest carriers, brokers, factors, and LTL fleets
• Open and sustain C-suite and board-level relationships, using your own network and disciplined outbound pursuit to generate pipeline
• Serve as Transflo’s senior voice in executive conversations, positioning AI and insights as a strategic lever for our customers’ growth, margin, and competitive advantage
• Partner with Transflo’s C-suite on account strategy, deal structure, pricing, and executive engagement for the most important pursuits
• Run a high-performance team-selling motion with Solution Engineers, Subject Matter Experts, Product, Marketing, and Leadership
• Share your playbook by informally mentoring other sellers on enterprise pursuit strategy, executive engagement, and deal execution
• Provide market, customer, and competitive insight to Product and Executive Leadership to inform positioning, packaging, and roadmap priorities
• Represent Transflo at key industry events, customer forums, and executive meetings
• Travel 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 Agreement
• Maintain a clean, accurate pipeline in Salesforce to support executive and board-level reporting
• Travel as needed to support customer engagements, per the Transflo Employee Agreement
• Uphold Transflo’s core values, policies, and procedures

Qualifications

We are hiring the best. The ideal candidate combines elite, sustained results with polished executive presence, flawless follow-through, and relentless pursuit of the win.

Required

• 12+ years of enterprise SaaS sales experience, with deep, proven success within the freight or transportation industry
• Sustained history of top-tier performance, with consistent quota overachievement and recognition as a top performer at prior employers
• Record of independently originating and closing transformational new deals larger than $5M TCV
• Established senior relationships across the carrier, broker, factor, and LTL landscape, including the Transport Topics Top 500
• Demonstrated ability to lead credible, trusted conversations with CEOs and boards, and with frontline operators
• Hunter mentality, with a record of generating significant pipeline organically
• Exceptional team-selling skills and a record of working effectively with executives and cross-functional teams
• Outstanding written and verbal communication skills, with executive presence, tact, and diplomacy
• Ability to thrive in a highly competitive, highly visible environment
• Bachelor’s degree in Business, Marketing, Information Technology, or a related field

Strongly Preferred

• Experience selling data solutions, analytics, or market intelligence solutions, or other AI and logistics automation applications
• Familiarity with FMCSA requirements, telematics, and TMS software
• Experience selling in a private equity-backed environment

Why Transflo

This 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 importa…