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 Required
- 12+ years of B2B enterprise SaaS sales experience
- Proven track record as a VP or 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
- Expertise architecting global sales motions across complex, multi-product enterprise SaaS portfolios
- Experience structuring multi-million-dollar enterprise contracts and strategic partnerships
- Experience navigating market shifts, failed playbooks, or go-to-market missteps and identifying execution risks early
- High agency and autonomy, with the ability to independently diagnose problems and execute solutions
- Player-coach mentality and willingness to manage flat teams without mid-management layers
- Must be based in or willing to relocate to Chicago, Illinois for on-site collaboration
- Currently authorized to work full-time in the United States
Loadsmart Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Loadsmart and has not been reviewed or approved by Loadsmart.
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Leave & Time Off Breadth — Unlimited PTO (“Loadie Time Off”) and sick time are described in postings as available without a limit, broadening flexibility for time away. Availability is noted across many U.S. roles, though exact application can vary by position and location.
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Healthcare Strength — Comprehensive medical, dental, and vision coverage is consistently cited in job postings, indicating a solid core health offering. This breadth forms a standard tech-style benefits baseline for U.S. employees.
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Equity Value & Accessibility — Stock options are frequently offered and positioned as competitive alongside base pay and other benefits. This ownership component is presented as a meaningful part of total rewards.
Loadsmart Insights
What We Do
We are industry veterans and data-scientists using innovative technology to fearlessly reinvent the future of freight. As the ‘nerds of logistics’, we seek intelligence in data to solve deep-rooted inefficiencies in the industry. We give shippers, brokers and carriers access to our data connections (linking supply and demand) and suite of award-winning solutions to strike the perfect balance of cost and service. We’re creating a more efficient and environmentally responsible way to move more with less. For more information, please visit: https://loadsmart.com
