Director, Revenue Enablement - Remote

Company Description

At PayNearMe, we’re on a mission to make paying and getting paid as simple as possible. We build innovative technology that transforms the way businesses and their customers experience payments. Our industry-leading platform, PayXM™, is the first of its kind—designed to manage the entire payment experience from start to finish. Every click, swipe or tap is seamless, fast and secure, helping non-commerce businesses boost customer satisfaction, accelerate payments, and reduce costs.

Our single platform handles it all: cards, ACH, digital wallets such as PayPal, Venmo, Cash App Pay, Apple Pay and Google Pay, and even cash at more than 62,000 retail locations nationwide. Today, thousands of businesses across consumer lending, iGaming and online sports betting, property management, and tolling trust PayNearMe to deliver a payment experience that drives real results.

In September 2025, we raised a $50 million Series E funding round to accelerate our growth. 

We’re a team of 200+ employees across 41 states, headquartered in Silicon Valley with satellite offices in Dallas, TX and Holmdel, NJ.

Join us and be part of a team that’s shaping the future of payments—one experience at a time.

Job Description

The Director of Revenue Enablement is responsible for building and scaling a buyer-centric enablement strategy that drives revenue growth, seller productivity, and predictable execution across the go-to-market organization. This role serves as the connection point between Marketing, Product, Sales, and Revenue Operations; ensuring that messaging, content, training, tools, and processes are aligned to how PayNearMe’s buyers evaluate, buy, and expand. You will lead enablement as a strategic function, not a support service, owning activation, adoption, and measurable business impact.

Responsibilities:

Enablement Strategy & Buyer Alignment

• Define and own the sales enablement vision and roadmap aligned to PayNearMe’s GTM strategy and growth priorities
• Translate buyer insights, personas, and journeys into actionable sales motions and messaging
• Ensure consistent value-based storytelling across segments, verticals, and deal stages

Cross-Functional Alignment & GTM Orchestration

• Act as a strategic partner to Marketing, Product, Sales Leadership, and RevOps
• Lead GTM readiness for product launches, new verticals, and strategic initiatives
• Establish clear operating rhythms (launch reviews, enablement councils, feedback loops)

Content & Messaging Enablement

• Partner with Marketing and Product to ensure content is buyer-relevant, easily discoverable, and clearly mapped to sales stages and use cases
• Own content activation—guidance on when, how, and why reps use assets
• Reduce noise by curating high-impact content and sunsetting what doesn’t perform

Training, Coaching & Onboarding

• Design and scale role-based enablement programs for new hire onboarding, product and solution launches and sales skills (discovery, challenger selling, objection handling, competitive)
• Partner with Sales Leadership to reinforce training through manager-led coaching
• Ensure learning drives behavior change, not just completion rates

Sales Process, Plays & Execution

• Partner with RevOps to align enablement with sales process and CRM stages
• Build and maintain sales playbooks (new logo, vertical-specific, expansion, competitive)
• Drive consistency while allowing flexibility for complex, enterprise deals

Tools, Technology & Adoption

• Own the enablement tech ecosystem in partnership with RevOps
• Ensure tools are embedded into seller workflows and adopted at scale
• Drive clear value realization for sellers—tools must help close deals, not add friction

Measurement, Analytics & Impact

• Define and track enablement success metrics tied to revenue outcomes, including ramp time, win rates, deal velocity and size, and content and training effectiveness
• Partner with RevOps to establish dashboards and a single source of truth
• Use data and field feedback to continuously iterate and improve

Change Management & Adoption

• Lead enablement as a change engine across the GTM org
• Communicate the “why” behind new initiatives and reinforce through multiple channels
• Build trust with Sales by incorporating field feedback and showing measurable impact

Leadership & Team Development

• Build, lead, and mentor a high-performing sales enablement team
• Establish clear roles, priorities, and career paths within enablement
• Serve as an executive-level voice for the seller and buyer experience

Qualifications

• 5+ years of experience in sales enablement, sales operations, revenue operations, or related GTM roles
• 3+ years in a senior leadership role building and scaling enablement programs
• Experience in B2B SaaS or fintech, supporting complex, consultative sales cycles
• Proven ability to influence without authority across Marketing, Product, Sales, and RevOps
• Strong executive presence with the ability to operate at both strategic and tactical levels

Preferred

• Bachelor’s degree in Business, Marketing, Finance or related field
• Experience supporting enterprise, mid-market sales teams and emerging markets
• Background in payments, financial services, lending, or regulated industries
• Familiarity with modern enablement and sales tech stacks (CRM, CI, LMS, enablement platforms)
   

Additional Information

Location: Flexible/Remote (within the US)

Great compensation package plus extensive benefits, including:

• 100% Remote (must be in US)
• Base salary per year (paid semi-monthly)
• Fast- paced and professional work culture
• Stock options with standard startup vesting - 1 year cliff; 4 years total
• $50 monthly communication expense stipend to go towards your phone/internet bill
• $250 stipend to enhance your WFH setup
• Reimbursement for peripheral equipment: monitor (up to $400), keyboard and mouse (up to $200)
• Premium medical benefits including vision and dental (100% coverage for employees)
• Company-sponsored life and disability insurance
• Paid parental bonding leave
• Paid sick leave, jury duty, bereavement
• 401k plan
• Flexible Time Off (our team members typically take off ~3-4 weeks per year)
• Volunteer Time Off
• 13 scheduled holidays
• 2x / year in-person team meet-ups (2-3 days, company paid)

Salary Range: $200,000 - $215,000

PayNearMe strives to create a workplace where all employees thrive. Our core values represent who we are today and we take pride in the way we work with each other as well as with our stakeholders.

We’re in this together to do the right thing. We deliver real results we are proud of while remaining respectful, transparent, and flexible.

PayNearMe is an equal opportunity employer. We are diligently and thoughtfully working towards cultivating a diverse workforce which in turn, enhances our products and services for the communities we serve. Applicants who represent all backgrounds are strongly encouraged to apply.

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Candidate information will be treated in accordance with our job applicant privacy notice found at: https://home.paynearme.com/ccpa-privacy-notice-jobs-employees/

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