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VP Enterprise Sales

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Jobtailor
Full Time position
Listed on 2026-08-02
Job specializations:
  • Sales
    SaaS Sales, VP of Sales, Director of Sales, Sales Manager
Salary/Wage Range or Industry Benchmark: 180000 - 260000 USD Yearly USD 180000.00 260000.00 YEAR
Job Description & How to Apply Below

Responsibilities

  • Develop and execute a comprehensive enterprise sales strategy aligned with Envoy’s growth goals and global priorities.
  • Drive aggressive but achievable revenue targets, ensuring consistent year-over-year growth.
  • Lead, mentor, and inspire enterprise sales executives; provide direct coaching in pitching, executive conversations, and closing.
  • Define and refine sales processes to ensure scalability, efficiency, and repeatability.
  • Work cross-functionally with Marketing, Product, Finance, Legal and Account Management to ensure alignment and deliver a seamless customer experience.
  • Oversee sales forecasts, pipeline health, and performance metrics, reporting regularly to the CRO and executive team.
Requirements
  • 10+ years of progressive B2B sales leadership with at least 5 years managing enterprise sales teams.
  • SaaS, HR Tech, or global mobility experience preferred (not required).
  • Proven ability to scale teams, build accountability-driven cultures, and manage through change and resistance.
  • Deep understanding of enterprise sales methodologies, executive-level negotiations, and complex deal cycles.
  • Obsessed with numbers—pipeline health, quota attainment, CAC, retention, and market share growth.
  • Ability to align long-term vision with tactical execution.
  • Confident, persuasive, and effective at engaging with C-level stakeholders and boards.
  • Track record of success working cross-functionally with CROs, CMOs, CFOs, and other executives.
  • Proficiency with Salesforce and sales enablement tools.
Core Competencies

Demonstrates extensive experience in enterprise sales leadership, with a strong focus on developing and executing sales strategies that drive revenue growth. Proven ability to mentor teams, manage complex deal cycles, and engage effectively with C-level stakeholders.

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