[Hiring] Senior Principal Sales Training Manager @Keyfactor, Inc.

Role Description

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.

Qualifications

• 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.

Requirements

• Up to 40% travel required.

Benefits

• Second Fridays (a company-wide day off on the second Friday of every month minus November and December due to the Holiday schedule). Please note that this benefit is subject to change.
• Comprehensive benefit coverage globally.
• Paid Parental Leave is available to new parents. Structure varies based on regional/government requirements.
• Competitive time off globally.
• Dedicated employee-focused ambassadors via Key Contributors & Culture Committees.
• DIVERSE Commitment, a call to action for a more inclusive and diverse future in business, society, and technology.
• The Keyfactor Alliance Program to support DEIB efforts.
• Wellbeing resources, wellness allowance, mindfulness app free membership, Wellness Wednesdays.
• Global Volunteer Day, company non-profit matching, and 3 volunteer days off.
• Monthly Talent development and Cross Functional meetings to support professional development.
• Regular All Hands meetings – followed by group gatherings.

Company Description

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.