About this role
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 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.