VP Enterprise Sales

The Vice President of Enterprise Sales is a senior executive leader responsible for building, scaling, and managing Envoy Global's enterprise sales organization. This role is accountable for driving revenue growth, optimizing sales processes, and aligning sales strategy with the company's overall business objectives. As a core member of the leadership team, the VP of Enterprise Sales will balance strategic vision with hands-on execution, working closely with the CRO to align global targets, instill scaling discipline, and deliver predictable results. This leader will foster a high-performance, metrics-driven culture, raising the bar for execution and ensuring best practices are adopted - even through resistance.

This role can be located within the Chicago, IL area or Remote - Travel requirement 30%

Primary Responsibilities

Strategic Leadership & Alignment: Develop and execute a comprehensive enterprise sales strategy aligned with Envoy's growth goals and global priorities. Partner closely with the CRO to align targets, forecast accurately, and drive scalable, repeatable sales processes. Contribute to the executive leadership team in shaping go-to-market direction and overall company strategy.

Revenue Growth & Deal Execution: Drive aggressive but achievable revenue targets, ensuring consistent year-over-year growth. Actively participate in high-value, strategic opportunities - providing guidance on deal structure, executive positioning, and negotiations. Shorten sales cycles and improve win rates by instilling discipline around opportunity management.

Team Leadership & Culture: Lead, mentor, and inspire enterprise sales executives; provide direct coaching in pitching, executive conversations, and closing. Build and sustain a high-performance culture grounded in accountability, resilience, and continuous improvement. Recruit, develop, and retain top talent, building bench strength for future growth.

Process & Performance Management: Define and refine sales processes to ensure scalability, efficiency, and repeatability. Establish rigorous pipeline, forecasting, and performance management systems in Salesforce. Drive adoption of sales methodologies, playbooks, and enablement tools across the team.

Collaboration & Market Engagement: Work cross-functionally with Marketing, Product, Finance, Legal, and Account Management and Legal Professionals (Firm) to ensure alignment and deliver a seamless customer experience. Engage with industry trends, customer needs, and competitive dynamics to refine sales approaches. Build and maintain strong relationships with senior decision-makers and strategic partners.

Reporting & Accountability: Oversee sales forecasts, pipeline health, and performance metrics, reporting regularly to the CRO and executive team. Ensure transparency and accuracy in reporting, equipping leadership with data-driven insights for decision-making.

Skills & Qualifications

Experience: 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)

Leadership: Proven ability to scale teams, build accountability-driven cultures, and manage through change and resistance.

Sales Expertise: Deep understanding of enterprise sales methodologies, executive-level negotiations, and complex deal cycles.

Metrics Orientation: Obsessed with numbers - pipeline health, quota attainment, CAC, retention, and market share growth.

Strategic Thinking: Ability to align long-term vision with tactical execution.

Executive Presence: Confident, persuasive, and effective at engaging with C-level stakeholders and boards.

Collaboration: Track record of success working cross-functionally with CROs, CMOs, CFOs, and other executives.

Tech-Savvy: Proficiency with Salesforce and sales enablement tools.

Key Performance Metrics

Revenue growth (year-over-year increases)

Quota attainment across individuals and team

Pipeline health (volume, velocity, quality)

Sales cycle length and conversion metrics

Employee retention and talent development outcomes

Compensation includes an annual salary range $145,000.00- $170,000.00 with commission eligibility.

Notice at Collection for California Applicants:

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