Director, Revenue Enablement

Role Overview

• 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

Requirements

• 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)

Benefits

• 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)