Enterprise Sales Executive – Leadership Development

LifeGuides-posted 8 days ago
Full-time • Mid Level
Remote • Chicago, IL
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LifeGuides is expanding PMQ+ — a first-of-its-kind professional mentoring program that enhances SHRM’s People Manager Qualification (PMQ) by adding personalized mentoring, behavior-change support, and real-world application. This senior individual contributor role leads the full enterprise sales cycle—creating pipeline, driving strategic discovery, and closing complex deals with HR and L&D leaders. We’re looking for a seasoned enterprise seller with strong experience in HR, L&D, OD, Talent Development, Coaching, or Leadership Development solutions. If you thrive in consultative, multi-stakeholder environments and love helping organizations develop stronger people managers, you’ll excel here.

  • Sell PMQ+ into mid-market and enterprise organizations (500–5,000+ employees).
  • Own the full sales cycle from prospecting through close.
  • Conduct strategic discovery with CHROs, CLOs, VPs of Talent, OD leaders, and HRBPs.
  • Communicate the ROI of manager effectiveness, behavior change, retention, and productivity.
  • Manage a healthy pipeline of qualified HR/L&D opportunities.
  • Represent PMQ+ at industry events, conferences, webinars, and SHRM activations.
  • Collaborate with internal teams (enablement, delivery, marketing, leadership) to ensure smooth handoffs and long-term client success.
  • Partner directly with SHRM’s national salesforce to co-sell and accelerate adoption.
  • Support SHRM-led opportunities with PMQ+ expertise, demos, proposals, and strategic deal guidance.
  • Maintain alignment to ensure PMQ+ is positioned consistently in the field.
  • Design and execute a scalable strategy to expand PMQ+ reach through new strategic partnerships (e.g., HR associations, L&D firms, influencers, consultancies).
  • Identify, onboard, and support partners who can open new avenues for enterprise growth.
  • Collaborate with marketing and product teams to develop partner-specific materials, enablement, and campaigns.
  • Build new sales channels that complement — but do not replace — SHRM collaboration.
  • Provide regular updates on partner performance, pipeline health, and revenue forecasts.
  • Use CRM tools (HubSpot) to track activities, opportunities, and partner engagement.
  • Maintain accurate and strategic forecasts for leadership.
  • 7+ years of experience in enterprise sales selling into HR, L&D, OD, Talent, or leadership development buyers.
  • Strong track record selling leadership development, coaching, HR tech, or behavior-change solutions.
  • Deep consultative selling skills and comfort with multi-stakeholder, multi-month (4–9 month) sales cycles.
  • Ability to articulate business impact around retention, manager effectiveness, engagement, and performance.
  • Experience selling programs priced between $30K–$250K per cohort or annual engagement.
  • High EQ and strong executive presence — able to hold the attention of CHRO-level buyers.
  • Familiarity with modern sales tools (HubSpot, ZoomInfo, LinkedIn Sales Navigator).
  • Demonstrated ability to generate new business independently and build pipeline creatively.
  • Experience co-selling with partners or channel organizations.
  • Background in coaching platforms (BetterUp, AceUp, Torch, CoachHub, etc.) or executive education (INSEAD, CCL, FranklinCovey, ExecOnline, etc.).
  • Understanding of manager development challenges, behavior-change science, HR budget cycles, and adult learning principles.
  • Experience tailoring proposals and pricing for mid-market and public-sector clients.
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