Head of Global Sales

loadsmart· Executive Team
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📍 ChicagoFull Time💰 USD 225K–275K

About this role

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 looking for a high-agency, hands-on Head of Global Sales to join our team! We are seeking an experienced, battle-tested sales leader who thrives in a flat structure, rolls up their sleeves to manage pipeline discipline, and uses data to drive strategic GTM decisions. Reporting directly to the CEO, you will bridge the gap between high-level go-to-market strategy and day-to-day tactical execution. You will unify our enterprise sales organization, lead senior individual contributors, and proactively identify and fix operational gaps. This is a very exciting and lucrative opportunity for the right leader.

 

JOB TYPE: Exempt - U.S. Only

DEPARTMENT: Sales

LOCATION: Chicago, IL (On-site / In-office requirement; Relocation package provided)

WHAT YOU GET TO DO:

  • Unify and lead the enterprise sales organization globally, directly managing Sales leadership and Senior Account Executives in a flat-structure environment

  • Partner directly with the CEO and Board of Directors to present quarterly sales forecasts, go-to-market strategies, unit economics, and revenue performance metrics

  • Align global sales execution, contract structures, and predictable ACV growth directly with the company’s multi-year valuation and strategic exit milestones

  • Lead commercial due diligence and go-to-market integration for multi-product expansion and market entry into new international territories

  • Translate raw sales operational data into actionable strategic shifts (verticalization, inbound/outbound mix, unit economics, ACV, and cost of sale)

  • Maintain extreme tactical discipline across account pipelines, forecast accuracy, stage progression, and rep performance

  • Join key prospective enterprise calls to guide deal strategy, provide real-time coaching, and help close complex multi-stakeholder deals

  • Build and drive our enterprise outbound motion, establishing clear performance expectations and accountability

  • Proactively identify operational and sales process flaws, designing and executing self-directed initiatives to resolve them

  • Drive top-level strategic alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize net revenue retention and lifetime customer value

REQUIRED QUALIFICATIONS:

  • 12+ years of B2B enterprise SaaS sales experience, with a proven track record as a VP/SVP scaling ARR from mid-stage growth through major liquidity events or acquisitions

  • Experience presenting to boards of directors, investors, and executive committees on commercial strategy, GTM investment, and revenue forecasts

  • Proven expertise architecting global sales motions across complex, multi-product enterprise SaaS portfolios 

  • Demonstrated experience structuring multi-million-dollar enterprise contracts and strategic partnerships that drive long-term valuation and enterprise value

  • Battle-tested experience navigating market shifts, failed playbooks, or GTM missteps, with the ability to spot execution risks early

  • Demonstrated high agency and autonomy, with the ability to independently diagnose problems and execute solutions without waiting for direction

  • Player-coach mentality with the willingness to operate without mid-management layers, managing flat teams with direct line-of-sight into rep execution

  • Must be based in or willing to relocate to Chicago, IL for on-site collaboration

 


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.

Frequently Asked Questions

What is the salary for the Head of Global Sales role at loadsmart?
The listed salary for this Head of Global Sales position at loadsmart is USD 225K–275K. This is an Full Time role.
Where is the Head of Global Sales position at loadsmart located?
This Head of Global Sales role at loadsmart is based in Chicago. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the Head of Global Sales role at loadsmart full-time or part-time?
This is listed as a Full Time position. It is posted as a Head of Global Sales role in the Executive Team department at loadsmart.
Which team or department does the Head of Global Sales at loadsmart belong to?
This Head of Global Sales position is part of the Executive Team department at loadsmart. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Head of Global Sales position at loadsmart?
Click the "Apply Now" button on this page. You will be redirected to loadsmart's official application portal hosted on lever where you can submit your application directly.
When was the Head of Global Sales job at loadsmart posted?
This Head of Global Sales position at loadsmart was posted on Sep 22, 2026. Apply as soon as possible — early applications are often reviewed first.
Head of Global Sales
loadsmart · 💰 USD 225K–275K
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