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Loadsmart

Posted 2 days ago

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Head of Global Sales

ChicagoOn-siteFull-time

AI Summary

Leads and unifies the global enterprise sales organization, managing senior leaders and individual contributors in a flat structure. Partners with the CEO and board on GTM strategy, forecasts, and unit economics, while driving pipeline discipline and operational improvements across a multi-product SaaS portfolio.

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

    • Skills

    ACVARRB2b SalesContract StructuringCRMEnterprise SalesForecastingGo-to-market StrategyGTMPipeline ManagementRevOpsSaaSSalesforceSales OperationsUnit Economics

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