About the Role
The Field Training & Enablement Sub Lead leads Billease's nationwide team of Sales Field Trainers (SFTs) under the Training Team. This role is responsible for ensuring that every SFT — regardless of region — trains, coaches, and evaluates Sales Associates (SAs) at the same high standard.
Beyond managing the trainer team, this role owns the continuous improvement of the field training function: standardizing materials and processes, certifying and calibrating trainers, accelerating the cascade of information, and building skill-development programs for both SFTs and Sales Network Area Supervisors (SNASs).
Key Responsibilities
SFT Leadership & Management
- Lead, supervise, and support Sales Field Trainers deployed nationwide
- Monitor SFT performance, field coverage, and deliverables across all regions
- Conduct regular coaching sessions, performance reviews, and field visits to observe SFTs during live training and SA engagements
- Support recruitment, onboarding, and deployment of new SFTs
SFT Certification & Calibration
- Design, implement, and maintain the SFT Certification Program covering product knowledge, facilitation, coaching, and evaluation skills
- Run regular calibration sessions to ensure all SFTs assess and coach SAs against the same standards
- Manage recertification cycles and remediation plans for SFTs who fall below standard
Standardization & Process Improvement
- Standardize training materials, delivery quality, training processes, and reporting trackers across all regions
- Maintain a single source of truth for all field training content and ensure nationwide adoption
- Continuously identify and implement improvements to make training programs more efficient and effective, in collaboration with the Training Lead and sales leadership
- Streamline field training workflows, from SA onboarding to refresher programs
Cascade of Information
- Own the nationwide cascade process for product updates, policy changes, and campaign launches — from HQ to SFTs to SAs
- Ensure cascades are fast, accurate, and verified through knowledge checks and standardized talking points
- Serve as the escalation point for field questions and feed insights back to the Training Team and product/sales leadership
Train-the-Trainer & Enablement Programs
- Develop and deliver Train-the-Trainer programs for SFTs covering not only product knowledge but core trainer skills: facilitation, adult learning, coaching, feedback, and field evaluation
- Build and roll out the Leadership Development Program for SNASs, covering people leadership, coaching, and performance management fundamentals
- Develop training materials, tools, and resources aligned with BillEase's objectives and values
Data, Reporting & Training Effectiveness
- Track training coverage, completion, assessment results, and post-training SA performance nationwide
- Prepare and present regular reports on trainer productivity, training effectiveness, and program impact
- Use data to identify skill gaps across the sales network and recommend targeted interventions
The Ideal Candidate
Experience
- Minimum 4 years of experience in training, with at least 2 years handling sales training, sales enablement, or field sales — sales financing or fintech background strongly preferred
- At least 1–2 years leading or supervising a team, ideally trainers or field-based staff
- Proven experience designing training programs, certification frameworks, or train-the-trainer curricula
Skills & Competencies
- Strong people leadership — able to manage, coach, and align a distributed, 100% field-based trainer team
- Strong process orientation with the ability to design and enforce structured, standardized training methodologies
- Analytical and evaluation skills to assess trainer performance, training impact, and program efficiency
- Excellent facilitation, communication, and interpersonal skills to engage diverse teams across regions
- Comfortable building and managing trackers, dashboards, and training documentation
Work Environment
- Willingness and ability to travel nationwide regularly, including field immersions with SFTs and SAs, and occasional weekends or non-standard hours
- Flexibility to adapt to different regional conditions and team dynamics
- Ability to coordinate effectively with cross-functional teams including sales, operations, product, and the broader Training Team
What Success Looks Like
- 100% of SFTs certified and calibrated to a single nationwide standard
- Standardized training materials, processes, and trackers adopted across all regions
- Product and policy cascades reaching all SAs quickly, accurately, and with verified understanding
- SFTs and SNASs demonstrating measurably improved training, coaching, and leadership skills
- Clear, data-backed visibility on training coverage and effectiveness for leadership