Sr. Principal Sales Training Manager (Cybersecurity)

Location: Remote in the United States or Canada; CST/EST hours. Applicants must be legally authorized to work in the United States. Up to 40% travel is required.

Company

hirify.global, a Keyfactor company, provides security software and trust infrastructure for cryptographic identities connecting humans, machines, and AI.

What you will do

• Execute onboarding programs for new sales hires through live training, workshops, role-playing, certifications, and practice sessions.
• Track ramp progress, observe live selling situations and Gong recordings, and reinforce skills to accelerate field readiness.
• Coach enterprise sellers on Value Selling and MEDDICC, including discovery, qualification, multi-threading, champion development, executive engagement, and opportunity execution.
• Help sellers translate technical challenges into customer outcomes, measurable business impact, executive priorities, and compelling business cases.
• Use Gong, CRM data, enablement platforms, and direct observation to measure competency, identify recurring gaps, and share actionable insights.
• Collaborate with Sales Leadership, Sales Engineering, Product Marketing, Product, Revenue Operations, and Enablement.

Requirements

• 8+ years of experience in B2B enterprise software, cybersecurity, sales, or sales enablement, including 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 applied to active enterprise opportunities.
• Strong understanding of complex, multi-stakeholder enterprise sales cycles.
• Ability to understand complex technical concepts and coach sellers in translating them into customer outcomes and business value.
• Strong facilitation skills for onboarding sessions, workshops, role-playing, 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.
• Experience with CRM, conversation intelligence, LMS or enablement platforms, and AI-powered sales tools.

Culture & Benefits

• Entrepreneurial environment balancing autonomy and structure, with opportunities for professional and personal growth.
• Second Fridays company-wide day off, subject to change.
• Comprehensive global benefits, competitive time off, paid parental leave, adoption and fertility support, and wellbeing resources.
• Wellness allowance, mindfulness app membership, Wellness Wednesdays, Global Volunteer Day, nonprofit matching, and three volunteer days off.
• Talent development, cross-functional meetings, regular All Hands meetings, and employee-led diversity and inclusion initiatives.