About this role
Senior Sales Training Specialist – Field Enablement
Role Overview
The Senior Sales Training Specialist is a strategic field enabler responsible for translating global and centralized enablement programs into impactful, role-relevant experiences that drive seller behavior change and business outcomes. This role brings programs to life in the field by tailoring them to specific roles, regions, and segments, ensuring they resonate and are effectively adopted.
This individual is a confident facilitator and field presence—comfortable presenting to diverse audiences, from front-line sellers to senior sales leadership, and willing to travel to deliver high-impact, in-person enablement moments. As a senior individual contributor, they operate with autonomy, owning enablement workstreams end-to-end and partnering across all levels of the organization to drive execution.
Impact
This role is critical to ensuring that enablement programs translate into meaningful seller behavior change. By delivering engaging training, reinforcing learning in real selling situations, and partnering closely with the field, the Senior Sales Training Specialist drives measurable improvements in sales performance and productivity.
Key Responsibilities
Program Activation & Field Delivery
Deliver high-impact live and virtual training sessions to sales teams, with confidence presenting to small and large audiences
Travel as needed to support in-person field enablement, including regional trainings, kickoffs, and team sessions
Tailor global programs to align with regional, segment, and role-specific needs
Facilitate engaging, interactive sessions that drive skill development and practical application
Field Enablement & Reinforcement
Reinforce learning through structured follow-ups, coaching sessions, and field application exercises
Partner with frontline managers to embed consistent coaching practices and sustain behavior change
Participate in deal reviews, call coaching, and pipeline discussions to connect learning to active opportunities
Identify gaps in adoption and execute targeted reinforcement plans
Workstream Ownership & Stakeholder Management
Own enablement initiatives and workstreams end-to-end, from planning through execution and follow-up
Partner cross-functionally with sales, enablement, product, and leadership stakeholders to align priorities and execution
Build credibility and influence across all levels of the organization, including senior leadership
Ensure clear communication, alignment, and timely delivery of enablement initiatives
Data-Driven Execution
Track effectiveness of training and field activation efforts using defined metrics
Gather field feedback and performance insights to continuously refine programs
Use data to inform decisions, prioritize efforts, and improve enablement impact
Continuous Improvement & Thought Leadership
Apply best practices in facilitation, adult learning, and sales coaching
Share insights from the field to improve program design and delivery strategies
Contribute to building scalable, repeatable field enablement approaches
Qualifications & Experience
Required
4–5+ years of experience in sales enablement, sales, or project/program management
Proven ability and confidence presenting to groups of varying sizes, including senior stakeholders
Willingness and ability to travel regularly for in-person trainings and field engagement
Experience owning projects or workstreams end-to-end, with strong organizational and execution skills
Demonstrated ability to collaborate and influence cross-functional stakeholders at all levels
Strong communication, facilitation, and interpersonal skills
Preferred
Experience in payments industry or complex sales environments
Background delivering instructor-led and virtual training
Familiarity with sales methodologies (e.g., MEDDICC, Challenger, consultative selling)
Experience supporting frontline managers with coaching and enablement
Core Competencies:
Confident Facilitation: Engaging, credible presenter able to command a room and adapt to diverse audiences
Ownership & Accountability: Independently drives workstreams from strategy to execution and results
Stakeholder Influence: Effectively partners and collaborates across functions and seniority levels
Field Acumen: Understands real-world sales dynamics and tailors enablement accordingly
Execution Excellence: Balances speed, quality, and impact in a fast-paced environment
Adaptability: Adjusts approach based on field needs and evolving business priorities