• 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
• Applicants must be currently authorized to work in the United States on a full-time basis. Loadsmart will not sponsor applicants for work visas.