Role Overview
Loadsmart is hiring a Director, SaaS Sales ShipperGuide. This is a full-time remote role, with the team based in Chicago / Remote. posted 2 weeks ago. Full responsibilities, required qualifications, and the apply link are listed in the description below.
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Job description
ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?
Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!
We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.
With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.
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
DEPARTMENT: SaaS Sales - Shipperguide
LOCATION: Chicago IL or remote
About Loadsmart
Loadsmart
loadsmart.com
8 other open roles at Loadsmart on TryApplyNow.
Frequently Asked Questions
How do I apply for the Director, SaaS Sales ShipperGuide position at Loadsmart?
Use the Apply button above to submit your application directly to Loadsmart. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.
Is the Director, SaaS Sales ShipperGuide role at Loadsmart remote?
Yes. This is a remote role. The team is based in Chicago / Remote, but the position itself does not require relocating to that office.
What does a Director, SaaS Sales ShipperGuide at Loadsmart earn?
Loadsmart has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.
When was the Director, SaaS Sales ShipperGuide role at Loadsmart posted?
This role was posted on June 23, 2026 (19 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.
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