Head of Global Sales

JOB TYPE: Exempt - U.S. Only

DEPARTMENT: Sales

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

• 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

• 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

• 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.