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.

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.

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

• 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

• 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