Head of Global Sales

Join Loadsmart as the Head of Global Sales, where you will lead our enterprise sales organization, drive strategic go-to-market decisions, and collaborate directly with the CEO and Board of Directors. This is an exciting opportunity for an experienced sales leader with a proven track record in B2B enterprise SaaS sales.

• Unifier and leader of the global enterprise sales organization, directly managing sales leadership and senior account executives.
• Partner with the CEO and Board of Directors to present quarterly sales forecasts, go-to-market strategies, unit economics, and revenue performance metrics.
• Drive top-level strategic alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize net revenue retention and lifetime customer value.

• Experience presenting to boards of directors, investors, and executive committees on commercial strategy, GTM investment, and revenue forecasts
• Player-coach mentality with the willingness to operate without mid-management layers, managing flat teams with direct line-of-sight into rep execution
• 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
• Battle-tested experience navigating market shifts, failed playbooks, or GTM missteps, with the ability to spot execution risks early
• 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
• Demonstrated high agency and autonomy, with the ability to independently diagnose problems and execute solutions without waiting for direction
• Must be based in or willing to relocate to Chicago, IL for on-site collaboration