Head of Global Sales
Description
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:
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Unify and lead the enterprise sales organization globally, directly managing Sales leadership and Senior Account Executives in a flat-structure environment
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Partner directly with the CEO and Board of Directors to present quarterly sales forecasts, go-to-market strategies, unit economics, and revenue performance metrics
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Align global sales execution, contract structures, and predictable ACV growth directly with the company’s multi-year valuation and strategic exit milestones
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Lead commercial due diligence and go-to-market integration for multi-product expansion and market entry into new international territories
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Translate raw sales operational data into actionable strategic shifts (verticalization, inbound/outbound mix, unit economics, ACV, and cost of sale)
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Maintain extreme tactical discipline across account pipelines, forecast accuracy, stage progression, and rep performance
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Join key prospective enterprise calls to guide deal strategy, provide real-time coaching, and help close complex multi-stakeholder deals
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Build and drive our enterprise outbound motion, establishing clear performance expectations and accountability
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Proactively identify operational and sales process flaws, designing and executing self-directed initiatives to resolve them
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Drive top-level strategic alignment between Sales, RevOps, Product, Marketing, and Customer Success to maximize net revenue retention and lifetime customer value
REQUIRED QUALIFICATIONS:
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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
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Experience presenting to boards of directors, investors, and executive committees on commercial strategy, GTM investment, and revenue forecasts
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Proven expertise architecting global sales motions across complex, multi-product enterprise SaaS portfolios, as well as highly regarded AI products and autonomous agents
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Demonstrated experience structuring multi-million-dollar enterprise contracts and strategic partnerships that drive long-term valuation and enterprise value
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Battle-tested experience navigating market shifts, failed playbooks, or GTM missteps, with the ability to spot execution risks early
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Demonstrated high agency and autonomy, with the ability to independently diagnose problems and execute solutions without waiting for direction
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Player-coach mentality with the willingness to operate without mid-management layers, managing flat teams with direct line-of-sight into rep execution
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Must be based in or willing to relocate to Chicago, IL for on-site collaboration
Skills
As published by lever · 16 questions · 8 written answers
Basics
Resume/CV, Full name, Pronouns, Email, Phone, Current location, Current company, LinkedIn URL, Twitter URL, GitHub URL, Portfolio URL, Other website, What is your age range?, I identify my ethnicity asSelect all that apply, What gender do you identify as?, Are you a veteran or current military service member?, Are you a member of any underrepresented groups? (e.g., LGBTQ+, Religious minorities), Do you have a dissability? The ADA defines a person with a disability as someone with a physical or mental impairment that substantially limits a major life activity, has a record of such an impairment, or is regarded as having such an impairment.
Pick from a list (8)
- We like to know where great talent comes from. Please select the option that best applies to how you heard about our company or this opportunity.
- Are you legally eligible to work in the U.S.?
- Will you now or in the future require sponsorship for employment visa status (e.g., H-1B visa status)?
- Are you currently using AI in your work? optional
- Are you located in the Chicagoland area? optional
- Are you open to being onsite?
- Have you directly built or scaled a global new business (hunting) motion into new international territories? optional
- Do you have 12+ years of B2B enterprise SaaS sales experience leading teams that sell multi-million dollar contracts? optional
Written answers (8)
- What is your target compensation (USD/Year)?
- What tools are you using and how often? optional
- Give a concrete example of impact (e.g. time saved, quality improved) optional
- Any limitations or concerns you’ve encountered optional
- IF YES, what international markets or regions have you sold into?
- Please state your numbers for your most recent VP/SVP sales leadership role: 1, Starting ARR vs. Peak ARR Scaled
- 2, Average Enterprise Deal Size (ACV)
- 3,% of Quota Achieved (New Business ONLY)