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