Sr. Principal Sales Training Manager

About Keyfactor Our mission is to securely connect the world: humans, machines, and AI. Keyfactor is the leader in trust infrastructure for AI and machines, helping the world's largest enterprises and government agencies take control of the cryptographic identities that safeguard every digital interaction. Behind the platform is a global team of people who care deeply about the work and each other. We move fast, think big, and show up for one another every day. If you're looking for work that matters and a team that brings out your best, we hope you'll trust your future with Keyfactor! Title: Sr. Principal Sales Training Manager Location: United States (Remote) Experience: Senior Job Function: Business Transformation Employment Type: Full-time Industry: Computer Network Security About the position 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