Sales Enterprise Training, Director

Aventiv•,

5d•$123,854 - $141,193•Remote

About The Position

The Senior Sales Skills Enterprise Training Director is responsible for ensuring the Sales teams and Sales leaders are fully supported, equipped, and enabled through skills-based training that drives measurable business outcomes. This role partners closely with Sales Leadership to diagnose performance gaps, prioritize the most critical skills, and design and deliver training that translates into execution (e.g., better discovery and qualification, stronger customer conversations, improved win rates, increased pipeline conversion). Reinforcement is mandatory for every training: the Senior Sales Skills Enterprise Trainer owns the creation and operationalization of leader-ready reinforcement tools (coaching guides, observation checklists/scorecards, practice routines, reinforcement cadences, and measurement) so managers can consistently coach, verify proficiency, and sustain skill adoption across the organization.

Requirements

Knowledgeable in adult learning theory and skill-building methodologies (practice, feedback, reinforcement).
Ability to diagnose performance gaps, gather inputs from the field and leaders, and translate insights into outcome-aligned training plans.
Strong facilitation skills that drive participation, practice, and measurable skill progression in both in-person and virtual environments.
Demonstrated ability to build and operationalize reinforcement toolkits for every training (e.g., coaching guides, observation scorecards, practice plans, and 30/60/90-day reinforcement cadences) that drive manager-led coaching and retention of concepts.
Comfortable using metrics and qualitative feedback to evaluate effectiveness and communicate impact to Sales Leadership.
Ability to travel up to 20%
High School Diploma or GED
8+ years’ experience in sales, sales training, sales enablement, or a similar role—building skills programs that support sales execution and performance outcomes.
Demonstrated ability to partner with Sales leaders and frontline managers to identify needs, deliver training, and drive reinforcement/coaching.
Strong background in building skill content (role plays, scenarios, talk tracks) grounded in real customer conversations.
Excellent communication and presentation skills, with the ability to engage and motivate large groups.
Proficiency with CRM platforms, sales analytics, and data-driven decision-making to measure impact and guide continuous improvement.

Nice To Haves

Bachelor’s degree in Business, Education, Training, or a related field.
Sales experience selling B2B or B2G (Law Enforcement or Public Sector a plus)
Experience with instructional design and digital learning methodologies.
Familiarity with innovative training techniques such as gamification, microlearning, simulations and more.
Experience enabling leaders/managers (e.g., coach-the-coach, leader-led reinforcement, field coaching programs).

Responsibilities

Own the enterprise sales skills training strategy across sales roles and levels, ensuring every program clearly ties to agreed sales outcomes and field performance expectations and ensuring all business units are aligned with sales strategy and language.
Partner with Sales Operations, Sales and Sales Leadership to identify skill gaps using data and field insights (e.g., pipeline health, conversion, win/loss, ramp, quality reviews) and translate findings into prioritized training plans.
Design and deliver practical, skills-based learning (instructor-led and virtual) that centers on deliberate practice—role plays, simulations, talk tracks, and real-world scenarios aligned to current selling motions.
For every training delivered, produce a standardized Leader Reinforcement Toolkit that includes: coaching guide, observation checklist/scorecard, role-play/practice plan, reinforcement cadence ( and manager facilitation materials to drive ongoing coaching and skill adoption.
Operationalize reinforcement for every training by launching and managing required post-training transfer activities , including clear timelines, ownership, and completion tracking.
Measure training effectiveness and reinforcement adoption through skills assessments, role-play scoring, leader observations, surveys, business performance indicators, and reinforcement metrics (report insights to Sales Leadership and recommend actions.
Continuously improve programs based on performance results and stakeholder feedback—updating content, delivery, and reinforcement to increase impact.
Maintain scalable learning assets and documentation using standard templates, a centralized repository, version control, and a defined review/update cadence based on field feedback and performance data.
Collaborate with enablement, product, and training partners to align skills training with messaging, tooling, and other learning initiatives.
Manage and guide outside sales skills vendors to deliver high-quality experiences and measurable results.
Lead and evolve sales onboarding to accelerate readiness and time-to-revenue, partnering cross-functionally to integrate tools, processes, and solutions.
Work cross organizationally to ensure sales positioning, talk tracks, and skill expectations are aligned across outputs and reinforced through leadership routines.