Director of Sales, AI and Insights

Job Description

Transflo | Freight Technology SaaS

\n

\n

About the Role

\n

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.

\n

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.

\n

\n

What You’ll Do

\n

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

\n

\n

What We’re Looking For

\n

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.

\n

Minimum Qualifications

\n

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

\n

Preferred Qualifications

\n

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

\n

\n

Why Transflo

\n

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.

\n

Physical demands: sit, stand, listen, hear, read, talk, use a computer and phone, and travel up to 50% of the time.