Head of Global Sales

Overview A growth-stage logistics technology company is hiring a Head of Global Sales, based full-time in Chicago. This is a permanent, full-time, on-site role with a relocation package available for the right candidate. OTE is $500,000-$600,000, comprising a base salary of $225,000-$275,000 plus incentive bonus, with meaningful equity in a fast-growing business. Benefits include unlimited PTO, comprehensive medical, dental and vision cover, and a 401k match. This role exists because the business is scaling hard and needs a single leader to unify and own global enterprise sales, reporting directly to the CEO. The opportunity is straightforward: double revenue, build the kind of sales machine that makes the target look conservative, and grow into a CRO role as the business scales toward a major liquidity event. The person who thrives here is ambitious, hands-on, and on the ascent of their career - someone who has been in execution mode recently, knows how AI is reshaping the sales motion right now, and can back every claim with numbers. If you want a big title and a comfortable seat, this isn't it. If you want to own the outcome and build something that matters, it is. Key Responsibilities Lead and unify the global enterprise sales organisation, managing senior account executives directly in a flat structureReport to the CEO and present quarterly forecasts, GTM strategies, unit economics, and revenue performance to the boardAlign global sales execution and contract structures with the company's multi-year valuation and exit milestonesLead commercial due diligence and GTM integration for multi-product expansion and new international market entryTranslate sales data into strategic shifts across verticalization, inbound/outbound mix, ACV, and cost of saleMaintain rigorous pipeline discipline: forecast accuracy, stage progression, and individual rep performanceJoin key enterprise calls to guide deal strategy, coach in real time, and help close complex multi-stakeholder dealsBuild and drive the enterprise outbound motion with clear performance expectations and accountabilityIdentify operational and process gaps and execute self-directed fixes without waiting for directionDrive alignment across Sales, RevOps, Product, Marketing, and Customer Success to maximise net revenue retention and lifetime value Requirements Must-haves 12+ years B2B enterprise SaaS sales experienceProven track record as a VP or SVP scaling ARR from mid-stage growth through liquidity events or acquisitionsExperience presenting commercial strategy and revenue forecasts to boards and investorsDemonstrated expertise building global sales motions across complex, multi-product SaaS portfoliosExperience structuring multi-million-dollar enterprise contracts and strategic partnershipsBattle-tested through market shifts, failed playbooks, or GTM missteps, with the ability to spot execution risk earlyHigh agency: diagnoses problems and executes solutions independentlyPlayer-coach capable of managing flat teams with direct line-of-sight into rep executionHands-on in a sales execution role within the last 12 monthsFluent in modern, AI-era sales practices and pipeline engineeringBased in Chicago or willing to relocate (relocation package provided)Authorised to work in the US without visa sponsorship Nice-to-haves Experience taking a new product to market in an early or growth-stage companyTrack record at both a large scaled organisation and a smaller, scrappier oneDemonstrable experience hiring and developing high-performing sales talent What Success Looks Like Revenue doubled within the first year, with a pipeline and team structure that makes the next target look conservativeGlobal enterprise sales motion unified, with clear performance standards and accountability at every levelNew product GTM launched and gaining traction in target marketsSales process measurably improved, with forecast accuracy and stage discipline embedded across the teamA track record of results that can be told entirely in numbers, not narrative Team and Culture Flat structure with direct access to the CEO and board, no mid-management layer between you and outcomesHigh expectations, fast pace, and a bias toward execution over processA team that values curiosity, clarity, and results, and holds each other to high standardsThe kind of environment where ambitious people move quickly and are given real ownership Challenges This is a young, fast-moving company with high expectations: the pace is real and sustained, not a recruitment lineThe flat structure means there is nowhere to delegate upward - you own the problems you findThe role demands someone current and hands-on, not someone managing from a distance or relying on playbooks built in a different eraAmbition is a genuine requirement here, not a soft preference: the business wants someone whose best years are ahead of them, not behind