Director of Sales, AI and Insights

Transflo | Freight Technology SaaS

About the Role

Transflo is seeking a proven, hunter-minded Director of Sales to drive new business for our AI and insights portfolio, including Workflow AI (WFAI) and the Transflo Intelligence Suite. This is an individual contributor role for a seasoned enterprise seller who has already built a track record of landing complex, high-value deals in freight technology.

You will lead pursuits at the largest carriers, brokers, factors, and LTL fleets. 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 be as credible with a CEO as with a frontline operator, and relentless about turning pipeline into Closed Won revenue. You will be capable of opening 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.

What You’ll Do

• Deliver against an enterprise-level quota, per the comp plan, by selling WFAI, the Transflo Intelligence Suite, and the broader Transflo/ATI SaaS portfolio
• Build pipeline organically through disciplined outbound prospecting and a network of senior industry relationships
• Own strategic enterprise pursuits end to end, from first conversation through negotiation and close
• Map each target account and build multi-threaded relationships, from frontline operators to the C-suite
• Lead executive-level discovery that ties Transflo’s AI and insights solutions to each customer’s operational and financial priorities
• Run a team-selling motion with Solution Engineers, Subject Matter Experts, Product, Marketing, and Transflo executives, and bring in the C-suite at the right moments to move deals forward
• Shape complex deal structures, pricing, and multi-year agreements in partnership with Transflo leadership
• Include the full Transflo/ATI and partner solution set in the initial sales cycle (post-contract expansion belongs to Account Management and Customer Success)
• Provide market and competitive feedback to Product and Marketing to sharpen positioning and roadmap priorities
• Maintain a clean, accurate pipeline in Salesforce, with correct stages, dates, and commitment levels, to support executive reporting
• 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
• Uphold Transflo’s core values, policies, and procedures

What We’re Looking For

We are hiring A+ talent. The ideal candidate combines a proven record of enterprise results with polished professionalism, flawless follow-through, and relentless pursuit of the win.

Minimum Qualifications

• 8+ years of consultative sales experience in a SaaS business model, including significant SaaS sales experience within the freight or transportation industry
• Proven record of consistent quota overachievement, with annual quotas typically ranging from $3M to $8M
• History of independently leading and closing new enterprise deals larger than $3M TCV
• Demonstrated ability to lead conversations with confidence and credibility at every level, from CEO to front line
• Hunter mentality, with a record of building pipeline organically
• Strong team-selling instincts and a track record of working effectively with executives, technical resources, and cross-functional partners
• Outstanding written and verbal communication skills, with tact, diplomacy, and executive presence
• Ability to manage a heavy workload in a highly competitive, highly visible environment
• Bachelor’s degree in Business, Marketing, Information Technology, or a related field

Preferred Qualifications

• Experience selling data, analytics, or market intelligence solutions, or other AI and logistics automation applications
• Established relationships within the Transport Topics Top 500, carriers, brokers, factors, and LTL fleets
• Familiarity with FMCSA requirements, telematics, and TMS software

Why Transflo

You’ll sell differentiated technology in a category where AI is reshaping freight, with direct access to senior leadership and a meaningful voice in how we pursue and win 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.