Enterprise Freight AI Sales Director

Transflo; United States; Remote; USD 900,000 - 1,800,000; Full time

Job summary

Transflo seeks a proven Director of Sales to drive new business for our AI and insights portfolio, including Workflow AI and the Transflo Intelligence Suite. This is an enterprise role for a seasoned seller who has closed multi-million deals in freight technology.

You will lead pursuits at the largest carriers, brokers, and fleets, collaborating with C-suite and Solution Engineers to win complex, multi-year contracts. Travel 25–50% is expected.

Qualifications

• 8+ years of consultative SaaS sales in freight/transportation industry.
• Proven quota overachievement with annual quotas typically $3M–$8M.
• Experience closing enterprise deals larger than $3M TCV.
• Ability to engage with CEO to frontline leaders with credibility.
• Hunter mentality with strong pipeline development.
• Strong cross-functional collaboration with executives and tech teams.
• Excellent written and verbal communication with executive presence.
• Bachelor’s degree in Business, Marketing, IT or related field.

Responsibilities

• Sell WFAI, Transflo Intelligence Suite, and broader SaaS portfolio to enterprise accounts.
• Build pipeline through disciplined outbound prospecting and senior relationships.
• Own strategic enterprise pursuits from first conversation to close.
• Map target accounts and build multi-threaded relationships with C-suite and operators.
• Lead executive-level discovery tying AI solutions to customer priorities.
• Coordinate team-selling with engineers, product, marketing and executives.

Skills

Enterprise sales

SaaS sales

Quota attainment

Relationship building

Executive communication

Prospecting

Negotiation

Collaboration

Education

Bachelor’s degree in Business or related field

Job description

Transflo seeks a proven Director of Sales to drive new business for our AI and insights portfolio, including Workflow AI and the Transflo Intelligence Suite. This is an enterprise role for a seasoned seller who has closed multi-million deals in freight technology.

You will lead pursuits at the largest carriers, brokers, and fleets, collaborating with C-suite and Solution Engineers to win complex, multi-year contracts. Travel 25–50% is expected.