Loadsmart

Real-time freight booking and pricing platform

Head of Global Sales

Account ExecutiveConfirmed live in the last 24 hours

Full-timeChicago, IL, USA

About the Job

Requirements

12+ years of B2B enterprise SaaS sales experience, with a proven track record as a Vice President or Senior Vice President scaling annual recurring revenue from mid-stage growth through major liquidity events or acquisitions.
Experience presenting to boards of directors, investors, and executive committees on commercial strategy, go-to-market investment, and revenue forecasts.
Expertise architecting global sales motions across complex, multi-product enterprise SaaS portfolios, including artificial intelligence products and autonomous agents.
Experience structuring multi-million-dollar enterprise contracts and strategic partnerships that drive long-term valuation and enterprise value.
Experience navigating market shifts, failed playbooks, or go-to-market missteps, with the ability to identify execution risks early.
High agency and autonomy, with the ability to independently diagnose problems and execute solutions without waiting for direction.
A player-coach mentality and willingness to operate without mid-management layers, managing flat teams with direct visibility into representative execution.
Must be based in or willing to relocate to Chicago, Illinois for on-site collaboration.
Must be currently authorized to work in the United States on a full-time basis.

Responsibilities

Unify and lead the global enterprise sales organization, directly managing Sales leadership and Senior Account Executives in a flat-structure environment.
Partner directly with the Chief Executive Officer 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 annual contract value growth 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 involving verticalization, inbound/outbound mix, unit economics, annual contract value, and cost of sale.
Maintain tactical discipline across account pipelines, forecast accuracy, stage progression, and representative performance.
Join key prospective enterprise calls to guide deal strategy, provide real-time coaching, and help close complex multi-stakeholder deals.
Build and drive the enterprise outbound motion, establishing clear performance expectations and accountability.
Identify operational and sales process flaws, and design and execute initiatives to resolve them.
Drive strategic alignment between Sales, Revenue Operations, Product, Marketing, and Customer Success to maximize net revenue retention and lifetime customer value.

Salary Range: 225000 to 275000 (Currency: USD) (Pay period: per-year-salary)

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, as well as highly regarded AI products and autonomous agents

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

• 401k Match

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

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.

About the Company

Loadsmart

Real-time freight booking and pricing platform

Loadsmart provides a logistics technology platform for shippers, carriers, and brokers to manage freight. It offers instant booking, real-time pricing, and access to intermodal capacity (truck, rail, ship) through a single interface. The platform supports iOS/Android apps and TMS integrations, enabling lane pricing, carrier matching, and mini bids. Its goal is to make freight management faster, cheaper, and more scalable by using data science, managed transportation services, and automated workflows.

Company size: 501-1,000
Company stage: Series D
Total funding: $343.7M
Headquarters: Chicago, IL
Founded: 2014

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