Principal Sales Trainer

About Us:
DailyPay is transforming the way people get paid. As a worktech company and the industry's leading on demand pay solution, DailyPay uses an award-winning technology platform to help America's top employers build stronger relationships with their employees. This voluntary employee benefit enables workers everywhere to feel more motivated to work harder and stay longer on the job while supporting their financial well-being outside of the workplace.
DailyPay is headquartered in New York City, with operations throughout the United States as well as in Belfast. For more information, visit DailyPay's Press Center.

DailyPay is seeking a Principal Sales Trainer — a senior-level individual contributor who will serve as a strategic driver of sales excellence across our go-to-market organization. This role is designed for a seasoned professional with deep expertise in sales methodology, coaching, and performance enablement. The Principal Sales Trainer will partner closely with senior sales leadership, enablement, and operations to embed a culture of mastery, accountability, and continuous improvement within our sales force.

This leader will elevate the effectiveness of both strategic, tenured Account Executives and early-career sellers, creating a cohesive learning environment that strengthens execution across the full sales lifecycle.

The role reports to the Director of GTM Enablement and will act as a key partner in operationalizing Sandler methodology and reinforcing core selling fundamentals across the field.

Sales Coaching & Methodology Leadership

• Serve as the primary champion of the Sandler sales methodology, ensuring consistent adoption through live and virtual coaching, deal simulations, and continuous reinforcement

• Lead advanced role-play sessions and "game film" reviews leveraging Gong conversation intelligence to analyze performance and identify opportunities for improvement

• Conduct targeted 1:1 and group coaching sessions that develop both the tactical skills (discovery, qualification, negotiation, closing) and the strategic mindset required for enterprise selling

• Translate coaching insights into actionable playbooks and enablement content that directly drive measurable improvements in conversion rates and sales velocity

Program Design & Continuous Enablement

• Design and own an annual sales coaching program anchored in core sales fundamentals — including prospecting excellence, value-based discovery, deal qualification (MEDDPICC), and executive engagement

• Build and facilitate immersive learning experiences tailored to different sales segments (e.g., new hires, ramping reps, enterprise AEs, and renewal specialists)

• Partner with Product Marketing and Sales Leadership to integrate new messaging, product updates, and competitive intelligence into ongoing training

• Maintain and update curriculum and resources in enablement systems (e.g., Seismic, Dochebo, Gong) to ensure field accessibility and ongoing relevance

Performance Measurement & Insights

• Use conversation intelligence, CRM data, and certification metrics to track adoption, skill progression, and performance impact

• Deliver quarterly coaching impact reports to senior leadership with insights and recommendations for sales process optimization

• Benchmark DailyPay's programs against industry best practices and continuously evolve training approaches to align with top-performing SaaS organizations

Strategic Partnership

• Act as a trusted advisor to senior sales leaders, shaping the strategy and priorities for skill development across all sales segments

• Collaborate with Enablement peers and GTM Systems to ensure training programs are aligned with process, tools, and data visibility

• Partner with RevOps and Sales Managers to identify skill gaps using performance metrics and pipeline analytics, ensuring coaching efforts align with business outcomes
  

• 10–15 years of experience in sales training, enablement, or coaching, preferably within high-growth SaaS or fintech organizations.

• Deep fluency in Sandler and MEDDPICC methodologies, with proven experience operationalizing them within complex sales environments.

• Demonstrated success training both tenured enterprise AEs and entry-level sellers, tailoring approach to diverse learning needs.

• Exceptional facilitation and coaching skills, both live and virtual, with the ability to drive engagement and accountability.

• Strong analytical skills with experience using Gong, Salesforce, and other sales intelligence platforms to inform coaching strategies.

• Excellent communication and executive presence, capable of influencing senior leadership and driving cultural adoption of best-in-class selling practices.

• Experience designing scalable learning paths and certification programs that drive measurable sales performance outcomes.

• A passion for developing sales talent and instilling a high-performance, learning-oriented culture across the GTM organization.
  

This is not a traditional "trainer" position — it's a strategic performance driver. The Principal Sales Trainer will be instrumental in elevating DailyPay's commercial excellence, ensuring every seller — from BDR to enterprise AE — is equipped to execute with precision, confidence, and consistency.

• Exceptional health, vision, and dental care

• Opportunity for equity ownership

• Life and AD&D, short- and long-term disability

• Employee Assistance Program

• Employee Resource Groups

• Fun company outings and events

• Unlimited PTO

• 401K with company match