About The Position

LRN is seeking an exceptional Enterprise Sales Executive to join our North America team. This role is designed for top-tier enterprise sellers, professionals who thrive in complex sales environments, consistently exceed expectations, and are motivated by competing at the highest level. Our team is intentionally small, highly collaborative, and built around high performers who take ownership of outcomes and deliver measurable results. The successful candidate will be responsible for driving new enterprise business across Fortune 2000 organizations, helping senior leaders strengthen their ethics, compliance, and culture initiatives through LRN’s Catalyst platform and advisory offerings. This role carries significant impact, visibility, and opportunity for those who want to build strategic relationships with C-level executives while delivering meaningful business results.

Requirements

  • 10+ years of enterprise B2B sales experience selling complex solutions
  • 5–8+ years selling SaaS or subscription-based platforms
  • Demonstrated success achieving $900K+ annual quotas within large enterprise environments (7,500+ employees)
  • Demonstrated success closing six-figure enterprise deals with multiple stakeholders
  • Strong executive presence and ability to engage senior leaders in meaningful business conversations
  • Deep expertise in consultative and solution-based selling
  • Experience managing long-cycle enterprise sales processes involving legal, procurement, and executive stakeholders
  • Consistently perform in the top tier of their sales organizations
  • Are comfortable operating in high-expectation, performance-driven environments
  • Take ownership of outcomes and approach challenges with resilience and creativity
  • Excel at building credibility with senior executives
  • Combine strategic thinking with disciplined execution
  • Disciplined pipeline management and forecasting using Salesforce
  • Highly motivated, competitive, and accountable mindset
  • Strong alignment with LRN’s values around ethics, integrity, and responsible business
  • BA/BS degree or equivalent experience

Nice To Haves

  • Experience selling into Corporate Legal, Risk, Compliance, or HR leadership
  • Background in compliance, ethics, governance, risk, or HR technology platforms
  • Experience selling SaaS or subscription-based enterprise platforms
  • Advanced degree is a plus

Responsibilities

  • Own and deliver against an annual enterprise sales quota of $900K+
  • Build, manage, and convert a strategic pipeline of Fortune 2000 opportunities
  • Lead the full enterprise sales cycle from qualification through negotiation and contract execution
  • Engage and influence C-level stakeholders, including General Counsel, Chief Ethics & Compliance Officers, and senior HR leaders
  • Develop trusted advisor relationships around emerging issues in ethics, compliance, culture, and risk management
  • Partner with Sales Development to drive proactive outbound prospecting and strategic account development
  • Lead complex deal orchestration involving legal, procurement, and executive stakeholders
  • Maintain accurate pipeline, forecasting, and opportunity management in Salesforce
  • Collaborate closely with marketing, product, onboarding, and delivery teams to ensure successful client outcomes

Benefits

  • Flexible PTO plus US public holidays and Sick Time.
  • Medical, Dental and Vision Benefits.
  • Excellent 401K with employer match
  • Life Insurance, short-term and long-term disability benefits
  • Health & Wellness reimbursements
  • Health Saving & Flexible spending account
  • Employee Assistance Plan.
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