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 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.
Compensation
Salary will be commensurate with experience.
Culture, Career Opportunities and Benefits
We build teams that continually strive to get better than the day before. You will be challenged daily and given opportunities to grow personally and professionally. We balance autonomy and structure to create an entrepreneurial environment to spur creativity and new ideas.
Here are just some of the initiatives that make our culture special:
- 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. In regions where government-paid leave doesn’t exist, like in the U.S., the company offers generous paid parental leave, along with comprehensive adoption and fertility support.
- 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.
Our Core Values
Our core values are extremely important to how we run our business and what we look for in every team member:
Trust is paramount.
We deliver security software and solutions where trust and openness are of the highest importance for our customers. We are honest and a trusted partner in every aspect of business.
Customers are core.
We strategize, operate, and execute through a customer-centric view. We prioritize the security interests of our customers, and we act as if their data were our own.
Innovation never stops, it only accelerates.
The speed of change is accelerating. We are committed, through investment and focus, to stay ahead of the innovation curve.
We deliver with agility.
We thrive in high-paced and continually changing environments. We navigate through newly added variables, adjust accordingly, while driving towards our strategic goals.
United by respect.
Respect for all is what unites us. We promote diversity, inclusivity, equity, and acting with empathy and openness, both in our business and in our communities.
Teams make “it” happen.
Vision and goals are not individually achievable – they require teamwork. We pride ourselves in operating as a cohesive team, creating promoters and partners, and winning as one.
Keyfactor is a proud equal opportunity employer including but not limited to veterans and individuals with disabilities.
REASONABLE ACCOMMODATION: Applicants with disabilities may contact a member of Keyfactor’s People team via [email protected] and/or telephone at 1.216.785.2990 to request and arrange for accommodations at any time.
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Keyfactor Toronto, Ontario, CAN Office
2225 Sheppard Ave E, Suite 1015, Toronto, Ontario M2J 5C2, CA, Toronto, Canada
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