Senior Director, Sales Enablement & Technical Training

Dragos

7d•Remote

About The Position

Dragos is seeking a Senior Director of Sales Enablement & Technical Training to serve as the critical bridge between our Product Management and Product Marketing teams and the global sales force, partner ecosystem, and customer-facing teams that drive revenue. This is a high-impact, high-visibility role at the center of Dragos’ go-to-market engine. You will own the full enablement lifecycle, translating complex ICS/OT cybersecurity product capabilities, competitive intelligence, and market messaging from PM and PMM into role-specific, revenue-aligned enablement and training programs that equip sales teams, channel partners, SEs, and customer success to execute with precision and consistency. You will also lead technical training for customers and partners, ensuring they realize the full value of the Dragos Platform. The ideal candidate is a builder, translator, and performance-driven leader who can operationalize a structured learning and enablement model and deliver modular, continuously reinforced training programs tied directly to pipeline creation, win rates, deal velocity, and net revenue retention. This role is responsible for executing a fundamental shift in how Dragos enables its field; moving from broad, episodic training toward a product-first, revenue-aligned enablement model built on eight structured tracks.

Requirements

7+ years of experience in sales enablement, technical training, or revenue performance leadership roles, with demonstrated success in B2B SaaS or cybersecurity environments.
Proven track record of building and scaling multi-track enablement programs that directly impact win rates, deal velocity, ramp time, and pipeline.
Deep understanding of sales processes and methodologies (MEDDPIC/MEDDPICC required).
Experience building and delivering enablement programs for both internal sales teams and external partner/channel communities.
Demonstrated ability to translate complex technical product capabilities into clear, compelling, role-appropriate training content.
Exceptional cross-functional leadership and communication skills. Able to align PM, PMM, Sales, and Channel on a unified enablement strategy.
Proficiency with enablement platforms and LMS tools (e.g., Mindtickle, Articulate 360, Descript, Credly).
Strong data orientation: ability to define, measure, and report on enablement KPIs tied to business outcomes.
Ability to operate with autonomy, manage multiple stakeholder needs, and deliver high-quality programs under tight timelines.

Nice To Haves

Prior experience in tech, a must. Cybersecurity, OT/ICS security, or critical infrastructure industries strongly preferred.
Familiarity with product-led growth (PLG) motions and how product usage data informs sales qualification and expansion.
Background in building customer-facing technical training and certification programs.

Responsibilities

Serve as the primary conduit between Product Management, Product Marketing, and the field—converting product releases, roadmap updates, competitive intelligence, and GTM messaging into actionable enablement content.
Lead message certification programs that test and validate consistent narrative delivery across all customer-facing roles before and after major product launches or GTM pivots.
Own and execute the global Sales Enablement roadmap across 8 structured learning tracks, aligned to GTM priorities, revenue goals, and Dragos’ ICS/OT cybersecurity mission.
Design and deliver modular, role-based learning programs (onboarding, e-learning, in-person workshops, simulations, certifications) that accelerate seller productivity, shorten ramp time, and improve win rates.
Drive continuous reinforcement of messaging and positioning through short, repeatable modules rather than episodic one-time sessions.
Establish a PLG-aligned enablement model that teaches reps to read product signals, qualify from usage data, and accelerate pipeline through the funnel.
Extend the full enablement model to Dragos’ partner community by building partner-specific training tracks, certification programs, and co-sell playbooks that drive consistent partner-sourced revenue.
Develop scalable partner onboarding and ongoing education programs that enable channel partners to independently position and sell the Dragos Platform with the same confidence and accuracy as the direct sales team.
Collaborate with the Channel and Alliances team to align partner enablement with GTM priorities, partner tiers, and incentive structures.
Oversee the technical training curriculum for customers and partners, ensuring they have the knowledge to deploy, operate, and maximize the value of the Dragos Platform.
Build and manage product certification programs (leveraging platforms such as Credly) that create verifiable credentials and drive adoption milestones.
Translate complex OT/ICS cybersecurity concepts into accessible, outcome-based training content across multiple modalities inckuding virtual, in-person, hybrid, and self-paced.
Establish and manage KPIs that demonstrate enablement ROI across the full revenue funnel: influenced pipeline per cohort, certified vs. non-certified rep win rates, deal velocity, new hire ramp time, and NRR impact from CS-certified accounts.
Implement certification programs with clear pass/fail criteria and ongoing recertification requirements to maintain field readiness.
Use win/loss data, deal desk insights, and field feedback to continuously improve program content and delivery.
Build, lead, and develop a high-performing enablement team responsible for program design, content development, delivery, and performance reporting.
Operate with strong cross-functional alignment—partnering with Sales, SE, CS, Product, Marketing, and Channel leadership to prioritize the enablement roadmap and close critical skills gaps.
Drive high-speed, high-quality decision-making in a dynamic, fast-paced environment while remaining willing to be hands-on when required.