Sr. Principal Sales Training Manager

Department

Business Transformation

Location

United States or Canada, CST/EST (Remote)

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 ever boarding 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…