Head of Software Sales

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 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. You will unify our enterprise sales organization, lead senior individual contributors, and proactively identify and fix operational gaps.

Sales
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
~ 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 Executive Compensation (Base + Incentive Bonus + Equity)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, you will also receive stock options and benefits listed below. Extremely competitive Equity package - become a shareholder in our company!

• Comprehensive Medical, Dental, and Vision insurance plans
• 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. 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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. If you would like more information about how your data is processed, please contact us.