Director, SaaS Sales ShipperGuide

Loadsmart
Loadsmart

Sales & Business Development

Chicago, IL, USA · Remote

USD 157k-200k / year + Equity

Posted on Jun 24, 2026
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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

WHAT YOU GET TO DO:

  • Carry and achieve a personal annual sales quota, directly owning a pipeline of net-new and expansion opportunities across ShipperGuide

  • Actively prospect, develop, and close strategic deals, modeling best-in-class selling behaviors for the team

  • Own and manage a personal book of business, including key accounts and high-value prospects, with full accountability for forecasting and pipeline health

  • Develop and execute a unified go-to-market strategy for both ShipperGuide and OpenDock that maximizes market penetration and revenue growth

  • Drive full-funnel sales execution, from lead qualification to closing and onboarding

  • Establish repeatable sales processes and ensure consistent adoption of tools, CRM hygiene, and reporting standards

  • Partner with marketing to define and refine ICPs, messaging, and campaign strategies

  • Align with Customer Success to ensure a smooth handoff from sales to onboarding and retention initiatives

  • Collaborate with Finance on pricing strategies, discount approvals, and revenue forecasting

  • Work with the Account Management team to proactively identify and execute account growth strategies, including upsells and cross-sells

  • Work closely with Managed Transportation and Brokerage sales leadership to identify cross-sell and upsell opportunities

REQUIRED QUALIFICATIONS:

  • 7+ years in SaaS TMS sales with at least 5 years in a leadership role, including direct quota-carrying responsibility at the Director level or above

  • Experience in public speaking and events

  • Proven track record of personally closing multi-million-dollar deals while simultaneously leading a team to exceed ARR targets

  • Strong operational discipline with the ability to build scalable, repeatable sales processes

  • Proven track record of leading teams to exceed multi-million-dollar ARR targets

  • Exceptional communication, negotiation, and presentation skills

  • Proficiency in Salesforce, SalesLoft, and sales analytics tools

  • Experience selling into supply chain, logistics, transportation, or similar industries

  • Experience managing multi-product sales teams or selling a platform with complementary offerings

  • Familiarity with both SMB/mid-market and enterprise SaaS sales motions

  • History of working closely with marketing and product to refine GTM strategy

WORKING AT LOADSMART:
• 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.

157000 - 200000 USD a year

The compensation offered for this role will be based on multiple factors such as location, the role’s scope and complexity, the candidate’s experience and expertise. In addition to your base compensation offer, this role is eligible for an incentive bonus and you will also receive stock options and benefits listed below.
Apply now
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