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.
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
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)
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
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
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
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
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
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
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
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
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)
Location: Flexible/Remote (within the US)
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/
Alternative formats of this Notice are available to individuals with a disability. Please let us know if you need assistance.
All your information will be kept confidential according to EEO guidelines.
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$200,000 – $215,000
Base + Bonus · Stock Options
