Senior Principal Sales Training Manager

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Lead hands-on training, implementation, and adoption of Keyfactor's global sales enablement initiatives.

• Collaborate directly with sellers and sales leaders to ensure the consistent application of enablement skills, methodologies, messaging, and tools in the field.

• Implement established onboarding programs for new sales colleagues across various cohorts.

• Conduct live training sessions, workshops, role-playing, certifications, and practice exercises.

• Monitor new-hire progress against onboarding and ramp-up milestones.

• Assess new hires in live selling scenarios and through Gong to evaluate field readiness and identify coaching requirements.

• Deliver targeted reinforcement to address knowledge or skill deficiencies and enhance seller productivity.

• Communicate progress, risks, and coaching requirements to Enablement and Sales Leadership.

• Emphasize Value Selling and MEDDICC throughout the sales process, including discovery, qualification, multi-threading, champion development, and executive engagement.

• Mentor sellers to link technical challenges to business objectives, desired outcomes, measurable impacts, and executive priorities.

• Assess MEDDICC implementation in active opportunities and provide focused coaching on business cases, customer dialogues, and deal execution.

• Strengthen messaging, sales strategies, competitive positioning, and value propositions for both technical and executive audiences.

• Observe seller performance through live customer calls, Gong recordings, and field interactions.

• Monitor seller competency and enablement adoption utilizing Gong, CRM data, enablement platforms, and direct observation.

• Identify recurring skill gaps, coaching needs, and field trends; share insights with Enablement, Sales Leadership, and frontline managers.

• Disseminate best practices and evaluate how enablement and coaching enhance seller performance.

⛳️ Requirements

• Over 8 years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement, with substantial experience in coaching enterprise sellers.

• Proven ability to observe live sales interactions, identify skill gaps, and provide specific, actionable coaching.

• Strong understanding of Value Selling and MEDDICC, with experience in reinforcing methodology in active enterprise opportunities.

• In-depth knowledge of complex, multi-stakeholder enterprise sales cycles and the necessary behaviors to navigate them successfully.

• Capability to comprehend complex technical concepts and guide sellers in translating them into clear customer outcomes and business value.

• Proficient facilitator who is comfortable leading onboarding sessions, workshops, role-playing exercises, certifications, and reinforcement sessions.

• Ability to utilize Gong, CRM, enablement data, and direct observations to identify trends and assess seller progress.

• Capacity to build credibility with experienced sellers and sales leaders while providing honest, actionable feedback.

• Ability to collaborate closely with Sales Leadership, Sales Engineering, Product Marketing, Product, Revenue Operations, and the broader Enablement team.

• Experience with CRM, conversation intelligence, LMS/enablement platforms, and AI-driven sales tools.

• Candidates must be legally authorized to work in the United States.

• Up to 40% travel may be required.

🏝️ Benefits

• Second Fridays (a company-wide day off on the second Friday of each month, excluding November and December due to the holiday schedule). Please note that this benefit is subject to change.

• Comprehensive global benefit coverage.

• Paid Parental Leave is provided for new parents, with structures varying based on regional or governmental requirements. In areas lacking government-paid leave, such as the U.S., the company offers generous paid parental leave alongside comprehensive adoption and fertility support.

• Competitive time-off policies worldwide.

• Dedicated employee-focused ambassadors through Key Contributors & Culture Committees.

• DIVERSE Commitment, a call to action for fostering a more inclusive and diverse future in business, society, and technology.

• The Keyfactor Alliance Program to advance DEIB initiatives.

• Wellbeing resources, wellness allowance, complimentary mindfulness app membership, and Wellness Wednesdays.

• Global Volunteer Day, company non-profit matching, and three volunteer days off.

• Monthly talent development and cross-functional meetings to promote professional growth.

• Regular All Hands meetings followed by group gatherings.