Fast Facts

Degreed is seeking a Vice President of Sales to drive enterprise growth across North America, focusing on acquiring new relationships with Fortune 500 and Global 2000 companies while leading a team of Sales Directors.

Responsibilities: Lead, coach, and develop a high-performing sales team, own North America new business revenue targets, refine go-to-market strategies, and collaborate cross-functionally to enhance sales execution and customer value.

Skills: Enterprise sales leadership, familiarity with AI-enabled solutions, skills-based workforce transformation, proven track record in demand generation, and executive engagement.

Qualifications: Experience in scaling enterprise teams in complex SaaS environments, deep understanding of pipeline generation, and experience engaging C-suite leaders in workforce strategy discussions.

Location: Remote position based in the USA.

Compensation: $370000 - $400000 / Annually

Degreed is looking for a Vice President of Sales to lead enterprise growth across North America.

This role owns the strategy, execution, and results for net new enterprise revenue across NAMER, leading a team of Sales Directors focused on acquiring and expanding relationships with the Fortune 500 and Global 2000.

You will be responsible for defining how Degreed wins in the enterprise market; shaping territory strategy, building predictable pipeline generation, and ensuring consistent execution from first conversation through complex enterprise deal closure.

This role is both strategic and operational. You will partner closely with the CRO and commercial leadership team to refine our go-to-market strategy while building a high-performance sales organization capable of consistently winning complex, multi-stakeholder deals.

You’ll work directly with C-suite leaders at some of the world’s largest organizations, helping them navigate the shift to a skills-first workforce and AI-enabled learning ecosystem.

If you thrive in high-growth environments, enjoy building winning sales motions, and have a track record of scaling enterprise teams in complex SaaS markets, this is an opportunity to lead a critical growth engine for Degreed.

Key Skills

• Enterprise sales leadership
• Proven track record leading enterprise sales organizations responsible for multi-million-dollar quotas in complex SaaS environments with long, multi-stakeholder sales cycles.
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• AI-Enabled Enterprise Solutions
• Familiarity with positioning AI-enabled products and helping organizations adopt new technologies through workforce transformation initiatives.
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• Skills-Based Workforce Transformation
• Understanding of the emerging shift toward skills-based talent strategies and how enterprises approach reskilling and workforce capability development.
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• Category Creation & Value Selling
• Experience leading teams that sell strategic transformation solutions, where success requires building executive business cases and influencing enterprise priorities rather than fulfilling pre-existing budgets.
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• Go-to-market strategy
• Ability to design and execute enterprise territory strategies, align sales plays to product and marketing initiatives, and adapt the sales motion as the market evolves.
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• Pipeline Creation & Demand Generation
• Experience building sales organizations that generate significant pipeline through outbound prospecting, executive engagement, partner ecosystems, and coordinated marketing campaigns.
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• Data-Driven Sales Management
• Deep experience running a disciplined sales operating cadence including pipeline health reviews, forecast accuracy, deal strategy sessions, and performance analytics.
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• Competitive Enterprise Selling
• Track record of winning strategic deals against established competitors and incumbent solutions in mature SaaS markets.
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• Executive Engagement
• Credibility engaging and influencing C-suite leaders; particularly CHROs, CLOs, CIOs, and other senior stakeholders responsible for workforce strategy and transformation.
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• Talent Development
• Demonstrated ability to recruit, coach, and develop enterprise sellers, helping individuals consistently exceed quota and progress into leadership roles.
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• Cross-Functional Influence
• Ability to partner effectively with Product, Marketing, Client Experience, and Customer Success teams to improve pipeline generation, product positioning, and deal conversion.

Key Responsibilities

Sales Leadership

Lead, coach, and develop a team of Sales Directors responsible for acquiring new enterprise customers across the United States and Canada.

Build a culture of accountability, ownership, and continuous improvement focused on pipeline creation, disciplined deal execution, and predictable revenue outcomes.

Recruit, develop, and retain high-performing enterprise sellers while ensuring clear performance expectations and career growth opportunities.

Revenue Ownership

Own the North America new business revenue target and drive consistent attainment across the team.

Ensure forecast accuracy through structured pipeline reviews, deal inspection, and data-driven sales management.

Guide complex enterprise deal strategies, providing executive-level support for high-impact opportunities.

Go-to-Market Execution

Refine and execute Degreed’s enterprise sales strategy across target industries and accounts.

Develop territory and vertical strategies that maximize coverage of the Fortune 500 and Global 2000.

Align sales plays with product innovation, competitive positioning, and evolving enterprise buyer priorities; particularly around AI and workforce transformation.

Pipeline & Market Development

Ensure the sales organization maintains strong pipeline coverage through a combination of outbound prospecting, executive engagement, and marketing-driven demand generation.

Partner with Marketing to design account-based campaigns, industry programs, and executive events that accelerate enterprise pipeline creation.

Cross-Functional Collaboration

Partner with Product teams to translate market feedback into product innovation that improves competitiveness and deal conversion.

Work closely with Client Experience and Customer Success leaders to ensure a seamless transition from new logo acquisition to long-term customer value and expansion.

Serve as a key member of Degreed’s commercial leadership team, helping shape long-term strategy and growth initiatives.

Compensation

We are committed to fair and equitable compensation practices.

The total pay range for this role is $370,000 - $400,000.

Actual compensation packages are based on several factors that are unique to each candidate, including but not limited to: skill set, depth of experience, certifications, specific work location, and internal equity.