Head of Global Sales

Loadsmart; Chicago (IL); On-site; USD 225,000 - 275,000; Full time

Benefits offered by this job

Competitive base salaries

Equity package

Loadie Time Off — PTO and sick days

Medical, Dental, and Vision insurance

401k Match

Job summary

Loadsmart is seeking a high-agency Head of Global Sales to bridge executive strategy and day-to-day execution. You will unify the enterprise sales organization, manage senior contributors, and drive disciplined pipeline management in a flat-structure environment.

You will partner with the CEO and Board to present forecasts, align contracts, and steer multi-product expansion across international markets. Chicago-based, on-site with relocation possible.

Qualifications

• 12+ years of B2B enterprise SaaS sales experience; track record as VP/SVP scaling ARR
• Experience presenting to boards, investors, and exec committees on commercial strategy and forecasts
• Proven expertise architecting global sales motions across multi-product SaaS portfolios
• Experience structuring multi-million-dollar enterprise contracts and strategic partnerships
• Battle-tested in navigating market shifts and GTM missteps with proactive risk spotting
• High agency and autonomy; able to diagnose problems and execute without direction

Responsibilities

• Unify and lead the enterprise sales organization globally; manage Sales leadership and Senior Account Executives
• Partner with CEO and Board to present quarterly forecasts and GTM strategies
• Align global sales execution, contracts, and ACV growth with company valuation milestones
• Lead due diligence and GTM integration for multi-product expansion into new territories
• Translate sales data into strategic shifts (verticals, inbound/outbound mix, cost of sale)
• Maintain discipline over pipelines, forecasts, and rep performance
• Join enterprise calls to guide deal strategy and close complex multi-stakeholder deals
• Drive enterprise outbound motion with clear performance expectations and accountability
• Identify and fix sales process flaws with self-directed initiatives
• Drive alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize NRR and LTV

Skills

B2B enterprise SaaS sales

Board presentation

Global sales motions

Enterprise contract structuring

Autonomy and initiative

Flat-team leadership

Job description

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

$225,000 - $275,000 a year

Salary range:

Competitive Executive Compensation (Base + Incentive Bonus + Equity). The compensation offered for this role will be based on multiple factors such as location, the role’s scope and complexity, the candidate’s experience and expertise. In addition to your base compensation offer, this role is eligible for an incentive bonus, you will also receive stock options and benefits listed below.

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.