Senior Manager & Team Lead, GTM Training

• About Us:
• DailyPay is the leader in On-Demand Pay, helping employers modernize how people get their pay. DailyPay serves more than 1,900 employers and over 6 million employees, including many of the world's most recognized brands. By providing real-time access to earned pay and financial wellness tools, DailyPay helps employees manage their finances and helps employers attract and retain talent. DailyPay is helping define the future of pay, where money moves at the speed of work. Learn more at DailyPay's Press Center.

The Role:

We are seeking a strategic, hands-on Senior Manager, GTM Training to lead and evolve our onboarding & sales training function. This is a player-coach role responsible for overseeing a team of trainers while remaining actively engaged in the design, delivery, and continuous improvement of learning experiences across the Commercial organization.

Reporting to the Director of Enablement, this leader will oversee the Revenue Training Manager, BDR Trainer, and Principal Sales Trainer , ensuring a cohesive training strategy that scales across every stage of the seller journey. As the strategic bridge between Commercial Leadership and Enablement, this role will translate business priorities into high-impact training initiatives that improve seller readiness, productivity, and revenue performance.

The ideal candidate is equally comfortable leading people, influencing senior stakeholders, facilitating executive-level training, and building scalable enablement programs that drive measurable business outcomes.

How You Will Make an Impact:

Team Leadership & Coaching

Lead, mentor, and develop a high-performing team of trainers, fostering a culture of continuous learning, collaboration, and accountability

Establish consistent standards, best practices, and development plans across the training team

Coach trainers on facilitation, instructional design, stakeholder management, and program execution

Drive prioritization and resource planning across training initiatives to ensure alignment with business needs

Training Strategy & Program Leadership

Own the overall training strategy and roadmap across onboarding, continuous development, certifications, leadership enablement, and skill reinforcement

Translate business priorities into scalable learning programs that support seller productivity and revenue growth

Partner with Sales Leadership to identify capability gaps and proactively recommend learning solutions

Ensure consistency and quality across all training programs while tailoring learning experiences for different audiences and roles

Training Delivery & Facilitation

Personally design and facilitate high-impact training programs, workshops, leadership sessions, certifications, and strategic initiatives

Deliver onboarding, sales methodology, product, process, and skill development programs for GTM teams as needed

Facilitate role plays, deal simulations, certification sessions, and executive workshops

Provide one-on-one and cohort coaching to accelerate performance across new hires, tenured sellers, and sales leaders

Lead Gong-based call coaching sessions focused on reinforcing desired behaviors and improving execution

Stakeholder Partnership

Serve as the primary strategic training partner for Leadership

Partner with Product Marketing, Revenue Operations, and other cross-functional leadersto align learning priorities with organizational objectives

Influence stakeholders through data, insights, and recommendations that improve seller effectiveness

Act as the connective tissue between business strategy and training execution, ensuring organizational changes are effectively translated into learning experiences

Content & Enablement Alignment

Collaborate with Content, Product Marketing, and subject matter experts to transform messaging, product updates, and strategic initiatives into actionable learning

Ensure training content remains accurate, current, and aligned to GTM messaging

Oversee training assets within the LMS, Docebo + Articulate

Measurement & Continuous Improvement

Define and measure training success through adoption, proficiency, certification completion, behavior change, and business impact

Leverage qualitative and quantitative feedback to continuously improve learning programs

Benchmark industry best practices and introduce innovative approaches to modern sales enablement

What You Bring to The Team:

7+ years of experience in Sales Enablement, Sales Training, or Revenue Enablement

2+ years leading enablement professionals

Demonstrated success building and scaling sales training programs in a high-growth B2B SaaS or technology organization

Exceptional facilitation skills with experience delivering executive-level, virtual, and in-person learning experiences

Expertise in adult learning principles, instructional design, and enablement best practices

Strong knowledge of sales methodologies such as MEDDPICC, Sandler, Challenger, or similar frameworks

Experience coaching sales teams using Gong or comparable conversation intelligence platforms

Familiarity with enablement technologies such as Seismic, Docebo + Articulate, Salesforce, Gong, and related platforms

Strong executive presence with the ability to influence senior leaders and build trusted cross-functional partnerships

Excellent communication, project management, and organizational 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

High-performing cultures aren't built in silos, they thrive on partnership. At DailyPay, we Commit Together to an inclusive, professional environment where multifaceted perspectives are our greatest competitive advantage. We recognize that our team members don’t live “single-issue lives,” and we lean into the wide-ranging backgrounds and life stages that sharpen our collective decision-making.

In our high-trust environment, we empower you to Challenge Norms . We’ve created a space where it is safe to ask difficult questions, disrupt the status quo, and share bold perspectives without fear of professional fallout. We believe that by checking our own assumptions and staying curious about the experiences of others, we arrive at better, more innovative results.

We provide the space for you to do your best work through peer advocacy and transparent career development. If you are looking for a culture that values intellectual honesty, celebrates the unique lived experiences of its people, and thrives on collective success, you’ll find it here.

If you require reasonable accommodation for any aspect of the recruitment process, please send a request to [email protected] . All requests for accommodation will be addressed as confidentially as practicable.

DailyPay is an equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion or creed, alienage or citizenship status, political affiliation, marital or partnership status, age, national origin, ancestry, physical or mental disability, medical condition, veteran status, gender, gender identity, pregnancy, childbirth (or related medical conditions), sex, sexual orientation, sexual and other reproductive health decisions, genetic disorder, genetic predisposition, carrier status, military status, familial status, or domestic violence victim status and any other basis protected under federal, state, or local laws.