Manager, Sales Training
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.
The Role:
We are seeking a dynamic and experienced Sales Training Manager to design, deliver, and continuously improve training programs that elevate the effectiveness of our go-to-market (GTM) Account Executives. This role is responsible for building engaging learning experiences, certifying teams on proven sales methodologies, and ensuring alignment between training initiatives and business goals. The Sales Training Manager will report directly to the Director of Enablement and will partner closely with Sales Leadership, Enablement, Product Marketing, and other cross-functional stakeholders to drive measurable performance impact.
If this opportunity excites you, we encourage you to apply even if you do not meet all of the qualifications.
How You Will Make an Impact:
Design & Delivery
Own the end-to-end design and delivery of the Sales Excellence program, including curriculum development, certification paths, and continuous learning experiences.
Facilitate engaging live and virtual training sessions tailored to sales
Incorporate adult learning principles and modern enablement practices into all programs, as well as Sandler and MEDDPICC sales methodologies
Build and deliver training on sales methodology, discovery, objection handling, closing strategies, and more
Partner with Sales Leadership to align programs with revenue goals and pipeline development
Create deal simulations, role-plays, and competitive battle cards
Ongoing rep coaching (1:1/1:few) via calls, game film sessions or tailored cohort skill development
Collaborate with GTM Content, Product Marketing, and subject matter experts to translate messaging, product updates, and best practices into actionable training
Maintain and update training assets in enablement platforms (e.g., Seismic, Dochebo)
Measurement & Continuous Improvement
Define and track key performance indicators (adoption, engagement, proficiency, performance lift) to measure training effectiveness
Gather feedback from participants, managers, and stakeholders to refine and enhance programs
Benchmark against industry best practices to continuously innovate training strategy
Cross-Functional Partnership
Act as the primary training lead for Sales and Sales Engineering within the Enablement function
Partner with GTM leaders to identify skills gaps and align training priorities with business objectives
Coordinate with other Excellence Managers to ensure consistency, scalability, and knowledge-sharing across programs
What You Bring to The Team:
5+ years of experience in sales training, enablement, or a related role
Strong facilitation skills for both in-person and virtual environments
Expertise in adult learning principles and modern enablement practices
Hands-on experience with sales methodologies (e.g., MEDDPICC, Sandler)
Proven ability to design engaging training content and deliver measurable results
Familiarity with enablement platforms (e.g., Seismic, Dochebo, WorkRamp, Gong)
Excellent communication, collaboration, and project management skills
What We Offer:
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