Director of Sales Training and Enablement

Summary

Join Pindrop, a leader in voice authentication and deepfake detection, and own the long-term go-to-market (GTM) enablement strategy. You will define requirements, create enablement materials, and equip the sales team with the resources to sell effectively. Develop and evolve programs for sellers, sales engineers, and customer success managers, covering onboarding, product launches, and ongoing readiness. Support sales leadership in establishing a coaching program and design scalable enablement initiatives across various audiences and geographies. Drive measurable performance improvements, translate product updates into learning modules, and champion the MEDDIC/MEDDPICC methodology. Guide enablement managers, manage enablement platforms, support GTM tool adoption, and benchmark success via KPIs. Collaborate with Marketing and Sales Operations to create content and track performance. This role requires a strategic leader with experience in shaping GTM strategies and a deep understanding of the cybersecurity buyer journey.

Requirements

• You are a strategic enablement leader with a track record of shaping and advancing multi-year, company-wide go-to-market strategies to accelerate revenue and organizational capability at scale
• You understand the cybersecurity buyer journey and simplify complexity into clear, impactful enablement programs
• You drive adoption of MEDDIC/MEDDPICC with confidence, coaching both technical and non-technical teams, enabling executive and field leadership to champion these practices
• You are an excellent program builder—skilled in instructional design, facilitation, and cross-functional collaboration
• You collaborate effectively across Product, Sales, Marketing, and Customer Success to align stakeholders and drive shared success
• You’re resilient and adaptable, energized by ambiguity, and comfortable leading in evolving, high-growth environments
• You are a proactive, self-motivated executor with the ability to prioritize, focus, and deliver measurable business impact
• You thrive in fast-paced, solution-driven sales environments and love building from the ground up
• You stay optimistic under pressure, turning challenges into opportunities for learning and growth
• 7+ years of experience in Sales Enablement, Revenue Operations, GTM Strategy, or related roles in cybersecurity, SaaS, or complex enterprise/B2B sales environments
• Strong hands-on experience enabling field and technical teams (AEs, SEs, CSMs) with instructional design, facilitation, and training delivery
• Proven success rolling out sales methodologies (MEDDIC/MEDDPICC) and training multiple functions on structured, value-based selling
• Demonstrated ability to communicate and influence across technical and commercial audiences
• Experience using and administering sales enablement tools and CRM platforms (e.g., Salesforce, Highspot/Notion, Gong, Clari, LMS)
• Experience creating short, targeted training that supports sellers in the moment—like deal prep guides or product refreshers before key calls or demos
• Exposure to security, authentication, or risk tech
• Deep familiarity with the cybersecurity buyer journey and field enablement best practices

Responsibilities

• Own the full long-term GTM enablement strategy
• Help define requirements and guide the team’s creation of enablement materials for training, documentation, and other internally-facing enablement uses
• Responsible for providing the sales organization with the information, content, expertise, and tools to help sales people sell more effectively
• Develop, deliver, and continuously evolve programs for all sellers, sales engineers (SEs), and customer success managers (CSMs) across onboarding, product launches, and ongoing field readiness
• Support frontline Sales Directors and extended sales leadership team in establishing and carrying out a sales coaching program
• Design and implement scalable enablement programs that blend onboarding, continuous education, certifications, and field-readiness across multiple audiences and geographies
• Be accountable for multi-year planning in alignment with Sales, Product Marketing, Product, and Security SMEs to enable initiatives with revenue goals, product priorities, company objectives and evolving buyer needs
• Drive measurable seller performance improvements, with a focus on increasing the percentage of reps attaining quota through targeted enablement interventions, coaching programs, and field-readiness initiatives
• Translate product updates, roadmap innovations, and cybersecurity threat trends into clear, actionable learning modules, ensuring all field teams are “product- and market-ready.”
• Champion the MEDDIC/MEDDPICC methodology across the sales cycle—delivering programs on qualification, deal progression, pipeline inspections, forecast reviews, and opportunity management
• Guide, mentor, and coach enablement managers and key field leaders on pipeline hygiene, sales execution, and best practices—enabling rigorous, data-driven selling
• Own development and governance of enablement content (playbooks, talk tracks, competitive intel, objection handling) in collaboration with cross-functional partners
• Manage enablement platforms (Learning Management Systems) for content delivery, training engagement, and self-serve learning
• Support readiness and adoption of essential GTM tools (e.g., Salesforce, Gong, Clari) and coordinate rollout or training for new systems and processes
• Benchmark success via enablement KPIs and impact reporting and continuously close knowledge gaps and translate data into actionable insights for commercial and executive leadership
• Collaborates with Marketing and Sales Operations to create content and track and measure operations and performance

Benefits

• Competitive compensation, including equity for all employees
• Unlimited Paid Time Off (PTO)
• Generous health and welfare plans to choose from - including one employer-paid “employee-only” plan!
• Best-in-class Health Savings Account (HSA) employer contribution
• Affordable vision and dental plans for you and your family
• Employer-provided life and disability coverage with additional supplemental options
• Paid Parental Leave - Equal for all parents, including birth, adoptive & foster parents
• One year of diaper delivery for your newest addition to the family! It’s our way of welcoming new Pindroplets to the family!
• Identity protection through Norton LifeLock
• Recurring monthly Phone and Internet allowance
• One Time home office allowance
• Remote first environment – meaning you have flexibility in your day!
• Company holidays
• Annual professional development and learning benefit
• Pick your own Apple MacBook Pro
• Retirement plan with competitive 401(k) match
• Wellness Program including Employee Assistance Program, 24/7 Telemedicine