Sr. Principal Sales Training Manager

Keyfactor, Inc.

3h • Remote

About The Position

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

A significant focus is delivering a consistent, high-impact onboarding experience, guiding new sellers from initial training and certification through field readiness and productivity. The 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 reinforces Keyfactor’s Value Selling and MEDDICC methodologies, helping sellers improve discovery, qualification, business-value conversations, multi-threading, executive engagement, and overall opportunity execution. The position is remote in the United States and requires up to 40% travel. Applicants must be legally authorized to work in the United States.

Requirements

• At least 8 years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement, with significant experience coaching enterprise sellers.
• Demonstrated ability to observe live sales interactions, diagnose skill gaps, and provide specific, actionable coaching.
• Strong working knowledge of Value Selling and MEDDICC, with experience reinforcing methodology in active enterprise opportunities.
• Strong understanding of complex, multi-stakeholder enterprise sales cycles and the behaviors required to navigate them successfully.
• Ability to understand complex technical concepts and coach sellers on translating them into clear customer outcomes and business value.
• Strong facilitation skills and comfort leading onboarding sessions, workshops, role-playing exercises, certifications, and reinforcement sessions.
• Ability to use Gong, CRM, enablement data, and direct observation to identify trends and measure seller progress.
• Ability to build credibility with experienced sellers and sales leaders while delivering candid, actionable feedback.
• Ability to work closely with Sales Leadership, Sales Engineering, Product Marketing, Product, Revenue Operations, and the broader Enablement team.
• Experience working with CRM, conversation intelligence, LMS/enablement platforms, and AI-powered sales tools.
• Legally authorized to work in the United States.

Responsibilities

• 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.
• 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 established messaging, sales plays, competitive positioning, and value propositions for communication with 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.
• 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 onboarding and ongoing enablement skills 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.

Benefits

• Company-wide day off on the second Friday of each month, except November and December; subject to change.
• Comprehensive benefit coverage globally.
• Paid parental leave, with structure varying by region and government requirements.
• In the United States, generous paid parental leave and comprehensive adoption and fertility support.
• Competitive time off globally.
• Wellbeing resources, wellness allowance, free 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 support professional development.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed