Sr. Principal Sales Training Manager

The role

The Senior Principal Sales Training Manager drives the execution and adoption of global sales enablement programs. This role focuses on onboarding new sellers and providing ongoing coaching through live observation and Gong reviews to reinforce sales methodologies.

What you will do

• Execute established onboarding programs for new sales hires.
• Facilitate live training, workshops, role-playing, and certifications.
• Track new-hire progress against onboarding and ramp milestones.
• Observe new hires in live selling situations and through Gong.
• Provide targeted reinforcement to help new sellers close skill gaps.
• Reinforce Value Selling and MEDDICC methodologies throughout the sales cycle.
• Coach sellers to connect technical challenges to business outcomes.
• Evaluate seller execution of MEDDICC within active opportunities.
• Identify recurring gaps in sales skills and share insights with leadership.
• Track seller competency using Gong, CRM data, and enablement platforms.

Required qualifications

• 8+ years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement.
• Significant experience coaching enterprise sellers.
• Demonstrated ability to observe live sales interactions and provide actionable coaching.
• Strong working knowledge of Value Selling and MEDDICC.
• Strong understanding of complex, multi-stakeholder enterprise sales cycles.
• Ability to translate complex technical concepts into customer outcomes and business value.
• Strong facilitator for onboarding sessions, workshops, and role-playing.
• Ability to use Gong, CRM, and enablement data to identify trends.
• Ability to build credibility with experienced sellers and sales leaders.
• Experience working with CRM, conversation intelligence, LMS/enablement platforms, and AI-powered sales tools.

Benefits

• Second Fridays (a company-wide day off on the second Friday of every month minus November and December).
• Comprehensive benefit coverage globally.
• Paid Parental Leave.
• Comprehensive adoption and fertility support.
• Competitive time off globally.
• Wellbeing resources.
• Wellness allowance.
• Mindfulness app free membership.
• Wellness Wednesdays.
• Global Volunteer Day.
• Company non-profit matching.
• 3 volunteer days off.

Before you apply

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

About the company

Keyfactor is a leader in trust infrastructure for AI and machines, helping enterprises and government agencies manage cryptographic identities. The company is a global team that moves fast and thinks big.