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David Careers

Director of Sales, AI and Insights

Posted 12 days ago

transfloPortland (ME)
Sales ManagersFreight Transportation Arrangement

SENIORITY

Manager

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About the role

Transflo | Freight Technology SaaSAbout 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 $8MHistory of independently leading and closing new enterprise deals larger than $3M TCVDemonstrated 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.

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