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Keyfactor

Senior Principal Sales Training Manager

Keyfactor

. Drive hands-on training, execution, and adoption of Keyfactor's global sales enablement programs.

Posted 11/5/2026full-timeRemote • United States, CanadaSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in B2B enterprise software sales enablement, with a strong focus on coaching sellers through complex sales cycles and reinforcing methodologies like Value Selling and MEDDICC. Proficient in using tools such as Gong and CRM systems to track seller performance and identify coaching needs.

Highest-signal resume keywords
B2B Enterprise Software ExperienceValue Selling MethodologyMEDDICC ExecutionSales CoachingGong Proficiency

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Sales EnablementOnboarding ProgramsSkill Gap AnalysisSales MethodologiesPerformance Measurement
Soft Skills
FacilitationCommunicationFeedback DeliveryCredibility BuildingCoaching
Tools & Technologies
GongCRMLMSEnablement PlatformsAI-Powered Sales Tools
Industry Keywords
CybersecurityEnterprise SalesMulti-Stakeholder Sales CyclesSales LeadershipSales Performance

Tech Stack

Tools & technologies
Cyber Security

About the role

Key responsibilities & impact
  • Drive hands-on training, execution, and adoption of Keyfactor's global sales enablement programs.
  • Work directly with sellers and sales leaders to ensure enablement skills, methodologies, messaging, and tools are consistently applied in the field.
  • Execute established onboarding programs for new sales hires across cohorts.
  • Facilitate live training, workshops, role-playing, certifications, and practice sessions.
  • Track new-hire progress against onboarding and ramp milestones.
  • Observe new hires in live selling situations and through Gong to evaluate field readiness and identify coaching needs.
  • Provide targeted reinforcement to close knowledge or skill gaps and accelerate seller productivity.
  • Communicate progress, risks, and coaching needs to Enablement and Sales Leadership.
  • Reinforce Value Selling and MEDDICC throughout the sales cycle, including discovery, qualification, multi-threading, champion development, and executive engagement.
  • Coach sellers to connect technical challenges to business initiatives, desired outcomes, measurable impact, and executive priorities.
  • Evaluate MEDDICC execution in active opportunities and provide targeted coaching on business cases, customer conversations, and deal execution.
  • Reinforce messaging, sales plays, competitive positioning, and value propositions for technical and executive audiences.
  • Observe seller execution through live customer calls, Gong recordings, and field engagement.
  • Track seller competency and enablement adoption using Gong, CRM data, enablement platforms, and direct observation.
  • Identify recurring skill gaps, coaching needs, and field trends; provide insights to Enablement, Sales Leadership, and frontline managers.
  • Share best practices and measure how enablement and coaching improve seller performance.

Requirements

What you’ll need
  • 8+ years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement, with significant experience coaching enterprise sellers.
  • Demonstrated ability to observe live sales interactions, diagnose skill gaps, and provide specific, actionable coaching.
  • Strong working knowledge of Value Selling and MEDDICC, with experience reinforcing methodology in active enterprise opportunities.
  • Strong understanding of complex, multi-stakeholder enterprise sales cycles and the behaviors required to successfully navigate them.
  • Ability to understand complex technical concepts and coach sellers on translating them into clear customer outcomes and business value.
  • Strong facilitator comfortable leading onboarding sessions, workshops, role-playing exercises, certifications, and reinforcement sessions.
  • Ability to use Gong, CRM, enablement data, and direct observation to identify trends and measure seller progress.
  • Ability to build credibility with experienced sellers and sales leaders while delivering candid, actionable feedback.
  • Ability to work closely with Sales Leadership, Sales Engineering, Product Marketing, Product, Revenue Operations, and the broader Enablement team.
  • Experience working with CRM, conversation intelligence, LMS/enablement platforms, and AI-powered sales tools.
  • Applicants must be legally authorized to work in the United States.
  • Up to 40% travel required.

Benefits

Comp & perks
  • Second Fridays (a company-wide day off on the second Friday of every month minus November and December due to the Holiday schedule). Please note that this benefit is subject to change.
  • Comprehensive benefit coverage globally.
  • Paid Parental Leave is available to new parents. Structure varies based on regional/government requirements. In regions where government-paid leave doesn’t exist, like in the U.S., the company offers generous paid parental leave, along with comprehensive adoption and fertility support.
  • Competitive time off globally.
  • Dedicated employee-focused ambassadors via Key Contributors & Culture Committees.
  • DIVERSE Commitment, a call to action for a more inclusive and diverse future in business, society, and technology.
  • The Keyfactor Alliance Program to support DEIB efforts.
  • Wellbeing resources, wellness allowance, mindfulness app free membership, Wellness Wednesdays.
  • Global Volunteer Day, company non-profit matching, and 3 volunteer days off.
  • Monthly Talent development and Cross Functional meetings to support professional development.
  • Regular All Hands meetings – followed by group gatherings.