Senior Sales Training Specialist

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