Sr. Principal Sales Training Manager

The Senior Principal Sales Training Manager drives hands-on training, execution, and adoption of Keyfactor's global sales enablement programs. This role works directly with sellers and sales leaders to ensure the skills, methodologies, messaging, and tools introduced through enablement are consistently applied in the field.

A significant portion of this role focuses on delivering consistent, high-impact onboarding experience, guiding new sellers from initial training and certification through field readiness and productivity. This role also supports ongoing everboarding through live customer call observation, Gong reviews, and targeted coaching to reinforce skills and drive consistent field execution.

The Senior Principal Sales Training Manager plays a critical role in reinforcing Keyfactor’s Value Selling and MEDDICC methodologies, helping sellers improve discovery, qualification, business value conversations, multi-threading, executive engagement, and overall opportunity execution.

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

Job Responsibilities

Onboarding & Ramp Support

• Execute established onboarding programs for new sales hires and ensure consistent delivery across cohorts.
• Facilitate live training, workshops, role-playing, certifications, and practice sessions.
• Track new-hire progress against established 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 help new sellers close knowledge or skill gaps and accelerate their path to productivity.
• Communicate progress, risks, and coaching needs to Enablement and Sales Leadership.

Value Selling & MEDDICC Execution

• Reinforce consistent application of 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, strengthening why change, why now, and cost-of-status-quo conversations.
• Evaluate seller execution of MEDDICC within active opportunities and provide targeted coaching to strengthen business cases, customer conversations, and deal execution.
• Reinforce Keyfactor’s established messaging, sales plays, competitive positioning, and value propositions, helping sellers communicate effectively with both technical and executive audiences.
• Identify recurring gaps in sales skills, methodology, messaging, and technical-to-business translation and share insights with Enablement and Sales Leadership to drive targeted reinforcement.

Field Coaching & Insights

• Observe seller execution through live customer calls, Gong recordings, and field engagement, providing timely, actionable coaching to individuals and teams.
• Track seller competency and adoption of enablement programs, messaging, and sales methodologies using Gong, CRM data, enablement platforms, and direct observation.
• Reinforce skills introduced through onboarding and ongoing enablement through continuous coaching, practice, feedback, and field application.
• Identify recurring skill gaps, coaching needs, and field trends, providing actionable insights to Enablement, Sales Leadership, and frontline managers.
• Surface and share best practices and examples of strong execution, while measuring how enablement and coaching translate into improved seller performance.

Minimum Qualifications, Education, and Skills

• Experience: 8+ years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement, with significant experience coaching enterprise sellers.
• Field Coaching: Demonstrated ability to observe live sales interactions, diagnose skill gaps, and provide specific, actionable coaching.
• Methodology Expertise: Strong working knowledge of Value Selling and MEDDICC, with experience reinforcing methodology in active enterprise opportunities.
• Enterprise Sales Expertise: Strong understanding of complex, multi-stakeholder enterprise sales cycles and the behaviors required to successfully navigate them.
• Technical-to-Business Fluency: Ability to understand complex technical concepts and coach sellers on translating them into clear customer outcomes and business value.
• Facilitation: Strong facilitator comfortable leading onboarding sessions, workshops, role-playing exercises, certifications, and reinforcement sessions.
• Analytical Mindset: Ability to use Gong, CRM, enablement data, and direct observation to identify trends and measure seller progress.
• Coaching & Communication: Ability to build credibility with experienced sellers and sales leaders while delivering candid, actionable feedback.
• Cross-Functional Collaboration: Ability to work closely with Sales Leadership, Sales Engineering, Product Marketing, Product, Revenue Operations, and the broader Enablement team.
• Technology Fluency: Experience working with CRM, conversation intelligence, LMS/enablement platforms, and AI-powered sales tools.

 Travel Requirements

• Up to 40% travel required.