SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Loadsmart is a growth-stage logistics technology unicorn (valued over $1B) reinventing freight through innovative technology for shippers, brokers, warehouses, and carriers. The company operates with headquarters in Chicago and a globally distributed remote team.
You will join as Head of Global Sales, reporting directly to the CEO in a high-agency, hands-on role. This is a VP-level position leading the enterprise sales organization globally. You will unify sales leadership and senior individual contributors in a flat-structure environment, partnering directly with the CEO and Board to present quarterly forecasts, go-to-market strategies, unit economics, and revenue performance.
Key responsibilities include:
- Unify and lead the global enterprise sales organization, directly managing sales leadership and senior account executives
- Partner with CEO and Board on quarterly sales forecasts, GTM strategies, unit economics, and revenue metrics
- Align global sales execution, contract structures, and ACV growth with multi-year valuation and strategic exit milestones
- Lead commercial due diligence and GTM integration for multi-product expansion and new international market entry
- Translate sales operational data into actionable strategic shifts (verticalization, inbound/outbound mix, unit economics, ACV, cost of sale)
- Maintain tactical discipline across account pipelines, forecast accuracy, stage progression, and rep performance
- Join prospective enterprise calls to guide deal strategy, provide coaching, and close complex multi-stakeholder deals
- Build and drive enterprise outbound motion with clear performance expectations and accountability
- Identify and resolve operational and sales process flaws through self-directed initiatives
- Drive strategic alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize net revenue retention and customer lifetime value
The role requires on-site presence in Chicago with relocation package provided. This is an exempt, full-time U.S. position.
REQUIREMENTS:
- 12+ years of B2B enterprise SaaS sales experience with proven track record as 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 ability to spot execution risks early
- Demonstrated high agency and autonomy with ability to independently diagnose problems and execute solutions
- Player-coach mentality with 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
- Must be currently authorized to work in the United States on a full-time basis (no visa sponsorship)
