--- title: 'Head of Global Sales at Loadsmart' canonical: 'https://feeny.ai/job/head-of-global-sales-loadsmart-chicago-9t37ntc8ds7h' type: 'job' last_seen: '2026-10-15' --- # Head of Global Sales at Loadsmart - **Company:** Loadsmart - **Location:** Chicago, IL - **Compensation:** $225k–$275k - **Employment:** full-time - **Work type:** onsite - **Posted:** 2026-09-22 - **Last confirmed live:** 2026-10-15 - **Apply:** https://jobs.lever.co/loadsmart/c165cd34-9891-4fab-a22b-2ea3c96a7368 ## 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 ## 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 Loadsmart ## Company Overview - **One-liner**: Loadsmart is a digital freight platform that uses AI-powered agents, transportation management software, and brokerage services to help shippers, carriers, and warehouses move freight more efficiently. - **Entity Type**: Private (Late‑stage venture‑backed) - **Headquarters**: Chicago, Illinois, USA - **Founded**: 2014 - **Founders**: Ricardo Salgado, Felipe Capella ## Core Business - **Industry**: Transportation, Logistics, Supply Chain & Storage (with a strong AI/software component) - **Target customers**: B2B – enterprise shippers, carriers, and warehouse operators; small to large businesses in retail, manufacturing, consumer goods, etc. - **Mission / Purpose**: To become “the nexus of moving freight” by combining technology and human expertise to reduce freight spend and increase service levels [loadsmart.com/about](https://loadsmart.com/about/). ## Products & Services - **ShipperGuide (AI‑native TMS)**: Cloud‑based transportation management system that plans, procures, executes, and settles freight across all modes. AI agents embedded in the TMS handle tendering, tracking, document collection, auditing, and claims. [loadsmart.com/about](https://loadsmart.com/about/) - **Opendock (Dock, Gate & Yard Management)**: Digitizes freight entry, movement, and exit at facilities. Carrier self‑service scheduling, gate automation, and yard management across 4,500+ warehouses and 230,000+ carriers. The scheduling agent automatically reschedules when a pickup slips. [loadsmart.com/about](https://loadsmart.com/about/) - **AI Agents (Logistics Automation)**: Six specialized agents that run repetitive freight tasks end‑to‑end (document collection, tracking, retendering, load audits, claims, scheduling). Claimed to auto‑resolve 80%+ of work, with the remainder escalated to human Freight Experts. [loadsmart.com/about](https://loadsmart.com/about/) - **Freight Brokerage**: Technology‑enabled brokerage backed by 100,000+ vetted carriers. Execution is governed by the user’s routing guide and carrier preferences. [loadsmart.com/about](https://loadsmart.com/about/) - **Managed Transportation**: End‑to‑end transportation management as a service, combining the Loadsmart platform with dedicated specialists and forward‑deployed engineers. [loadsmart.com/about](https://loadsmart.com/about/) ## Market Standing - **Valuation / Market Cap**: Not publicly disclosed. - **Key Metrics**: - *Annual Revenue*: USD 250 M (as of latest fiscal year) [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) - *Total Funding*: USD 346.4 M (company site) / USD 368.1 M (LinkedIn) – both figures appear in search results; the company site reports $346.4 M. [loadsmart.com/about](https://loadsmart.com/about/) - *Headcount*: ~400 employees (LinkedIn reports 392, Built In 495; company site says 400+). [loadsmart.com/careers](https://loadsmart.com/careers/) - *Year‑over‑Year Headcount Growth*: +10.2% [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) - **Notable Investors / Partners**: BlackRock, Maersk Growth, Ports America, TFI International, Chromo Invest, Connor Capital, SoftBank Latin America Fund, CSX Corp. [loadsmart.com/about](https://loadsmart.com/about/) - **Growth Signals**: - Acquired Opendock and Kamion in November 2021. - Workforce distributed across 25 countries (United States, Brazil, Philippines, Colombia, El Salvador, etc.). - Active job postings up 100% year‑over‑year (14 open roles as of search date). [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) - LinkedIn followers: 34,627 (+12% yearly). [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) ## Competitive Advantages - **AI‑native platform**: AI agents are embedded in both the TMS and dock/yard system, not bolted on, enabling high automation rates (80%+ of repetitive tasks auto‑resolved). - **Unified data model**: ShipperGuide, Opendock, and the brokerage service share one data set, eliminating data silos. - **Large carrier network**: 100,000+ vetted carriers for brokerage; 230,000+ carriers connected through Opendock. - **Strategic backing**: Investors include global logistics players (Maersk, TFI International, Ports America) and financial heavyweights (BlackRock), providing both capital and industry credibility. - **Proven revenue base**: $250 M in annual revenue demonstrates market traction with enterprise clients. ## Strategic Focus - **Expanding AI capabilities**: Continuous development of AI agents to handle more freight tasks and compound auto‑resolution rates. - **Platform integration**: Driving adoption of the full suite (TMS + dock/yard + brokerage) to create stickiness and cross‑sell opportunities. - **Global scaling**: Maintaining offices in Chicago, New York, and across Latin America while enabling remote work; hiring across engineering, sales, and AI roles globally. - **Customer success**: Shifting user role from “operating the system” to “supervising results” through automation. [loadsmart.com/about](https://loadsmart.com/about/) ## Why Work Here - **Culture**: Described as “the nerds of logistics” – a mix of industry veterans, data scientists, and innovative engineers focused on reinventing freight. Emphasis on collaboration, fun, and celebration of achievements. [loadsmart.com/careers](https://loadsmart.com/careers/) - **Work model**: Hybrid/remote‑first; headquarters in Chicago (West Jackson) with additional offices in Latin America. Most roles open to remote within the US and select countries (Brazil, Philippines, etc.). [jobs.lever.co/loadsmart](https://jobs.lever.co/loadsmart/) - **Employee ratings**: 3.7/5 on LinkedIn (322 reviews) – Work‑Life 4.0, Compensation 4.0, Culture 3.6, Career 3.5. [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) - **Growth opportunities**: Rapidly growing (10%+ YoY headcount), recent job posts include senior engineering, AI automation, sales, and director‑level roles. - **Total rewards**: Formal “Total Rewards” program – details not fully listed but implies competitive compensation and benefits. [loadsmart.com/careers](https://loadsmart.com/careers/) ## Sources 1. [loadsmart.com/about](https://loadsmart.com/about/) 2. [loadsmart.com/careers](https://loadsmart.com/careers/) 3. [jobs.lever.co/loadsmart](https://jobs.lever.co/loadsmart/) 4. [linkedin.com/company/loadsmart](https://linkedin.com/company/loadsmart) 5. 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