Enterprise Sales Executive – Leadership Development

Enterprise Sales Executive – Leadership Development & L&D Solutions

Location: Remote (United States)

Employment Type: Full-Time or Contractor

Company: LifeGuides

About the Role (Read This First)

LifeGuides is hiring a senior Enterprise Sales Executive to sell PMQ+ — a leadership development and professional mentoring solution designed to drive real behavior change in people managers.

This role is not for generalist SaaS sellers or HR-adjacent sales backgrounds.

We are specifically seeking someone who has already sold leadership development, coaching, executive education, or L&D solutions to HR and L&D buyers at the enterprise level.

If you have not personally owned deals selling leadership development or learning solutions, this role will not be a fit.

What You Will Do

• Own the full enterprise sales cycle for PMQ+, from outbound prospecting through close
• Sell leadership development and mentoring solutions into HR, L&D, Talent Development, and OD teams
• Lead discovery with CHROs, CLOs, VPs of Talent, Heads of L&D, and HR Business Partners
• Position PMQ+ as a solution for:
• manager effectiveness
• leadership behavior change
• retention and burnout reduction
• performance and accountability
• Navigate and close complex, multi-stakeholder sales cycles (4–9 months)
• Build pipeline independently through relationships, referrals, partnerships, and targeted outreach
• Collaborate with SHRM's sales team on select opportunities (supporting deals, not owning the partnership)
• Develop new strategic partnerships outside SHRM to expand PMQ+ distribution
• Accurately manage pipeline, forecasting, and deal progression in HubSpot

Required Experience (Non-Negotiable)

Applicants must meet all of the following:

• 7+ years of enterprise B2B sales experience
• Direct experience selling one or more of the following:
• Leadership development programs
• Coaching or mentoring solutions
• Executive education or learning platforms
• L&D or talent development solutions
• Proven experience selling to HR and L&D buyers (CHRO, CLO, VP Talent, Head of L&D, OD)
• Demonstrated success closing $30K–$250K+ deals for leadership or learning solutions
• Experience selling outcomes such as behavior change, retention, engagement, and performance
• Comfort selling "soft ROI" alongside business outcomes
• Strong consultative selling skills in multi-stakeholder enterprise environments

If your background is primarily in recruiting, staffing, HRIS, ATS, HCM, payroll, compliance, background screening, or PEO services, this role is not a fit.

Preferred Experience

• Experience selling leadership or learning solutions through partnerships or associations
• Background with companies such as:
• BetterUp, AceUp, CoachHub, Torch
• FranklinCovey, CCL, ExecOnline, BTS
• Udemy Business, LinkedIn Learning
• Familiarity with SHRM, professional associations, or L&D communities

Compensation

• $100,000 base salary
• Commission based on closed revenue
• Senior individual contributor role — no people management

Who Will Succeed in This Role

• You have already sold leadership development or learning solutions and want to go deeper
• You are comfortable challenging HR buyers and reframing "we already have training"
• You enjoy selling human-centered solutions that require trust, credibility, and patience
• You want ownership, autonomy, and the ability to directly impact growth
• You prefer execution over managing teams

About LifeGuides

LifeGuides is redefining leadership and professional mentoring by combining digital learning, cohort experiences, and human mentoring to drive lasting behavior change. PMQ+ is delivered in partnership with SHRM and is rapidly expanding across enterprise organizations.

Why Join Us?

PMQ+ is redefining how organizations develop their managers by combining digital learning + human mentoring + real-world application.

We partner with SHRM, the largest HR association in the world — giving you access to trusted branding and a rapidly growing marketplace while still empowering you to build new channels and direct enterprise opportunities.

This is a rare opportunity to help shape a breakthrough product, work with world-class partners, and impact tens of thousands of people leaders.

Apply today to help transform the future of leadership.

About LifeGuides

LifeGuides is pioneering a new category in Peer & Professional Mentoring and Non-Clinical Mental Health, providing personalized support for employees and their families. The platform connects individuals with trained and certified Professional Mentors who have firsthand experience navigating the same life event or leadership challenge.

Equal Opportunity Employer

LifeGuides is an Equal Opportunity Employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, national origin, ancestry, familial status, age, disability, pregnancy, sexual orientation, gender identity, genetic information, or veteran status.