We are seeking an experienced, results-driven Director of SaaS Sales to lead our ShipperGuide TMS team. This is a player-coach role where you will personally carry and be accountable to an individual sales quota while simultaneously leading, developing, and scaling your team. You own end-to-end sales strategy, execution, and revenue growth for the product; driving alignment, building scalable processes, and consistently exceeding both personal and team targets.

A key focus will be maximizing cross-sell opportunities by positioning ShipperGuide’s complementary solutions, increasing customer lifetime value, both through your own book of business and through the deals your team closes. This role will work closely with marketing to ensure timely, persistent, high-quality follow-up on inbound leads, resulting in closed deals through disciplined outreach, consistent cadences, and a consultative, value-selling approach.

The ideal candidate is a hands-on SaaS sales leader with experience in multi-product, high-growth environments selling logistics tech/ TMS. You’ll balance strategy and execution, while shifting from competing on features or price to selling business value and ROI.

Job Type: (Exempt) - U.S. Only 

LOCATION: Chicago IL or remote

 

• Competitive base salaries - we believe in rewarding top talent 

• Extremely competitive Equity package - become a shareholder in our company!

• Loadie Time Off - PTO and sick days without a limit

• Comprehensive Medical, Dental, and Vision insurance plans

• 401k Match 

 

*Applicants must be currently authorized to work in the United States on a full-time basis. Loadsmart will not sponsor applicants for work visas.

 

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

 

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.