Enterprise Sales Executive – Leadership Development & L&D Solutions

LifeGuides-posted 2 days ago

Full-time • Mid Level

Remote • Chicago, IL

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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.

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

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.

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

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