AffiniPay Holdings, LLC

Head of Sales Training and Enablement

AffiniPay Holdings, LLC • $125K — $150K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in Sales Enablement or Training in B2B SaaS
  • 5+ years leading an enablement or training team
  • Experience building in-house training programs from scratch
  • Strong foundation in instructional design and adult learning principles
  • Exceptional communication and facilitation skills
  • Experience leveraging AI tools to enhance workflows
  • Bonus: Prior quota-carrying sales experience in SMB or mid-market

Responsibilities

  • Own design and delivery of onboarding and ongoing enablement for sales teams
  • Create and maintain training content including playbooks and objection handling
  • Implement scalable coaching systems using performance analytics
  • Lead and develop a team for onboarding and training delivery
  • Own multi-year enablement strategy to improve sales performance
  • Partner with various departments to identify performance gaps
  • Define and report on key metrics to drive revenue outcomes

Benefits

  • Comprehensive health insurance options including a 100% company-paid HDHP plan
  • Competitive compensation with annual bonuses and equity options
  • Flexible Time Off and parental leave program
  • Wellness stipends and mental health support
  • Continuous learning opportunities through 8am.edu and professional development funds
  • Charitable matching gift program and paid volunteer time
  • Engagement through team-building events and recognition programs
Full Job Description
About the role

The Head of Sales Training and Enablement is the builder behind how our sales teams learn, sell, and win. We're looking for a charismatic, creative and inspiring sales training leader to help us build out a world-class sales training program.

You have built an in-house enablement program before, from content and curriculum to onboarding and coaching, and you know that the difference between good and great sales teams often comes down to how they were trained. This role sits at the intersection of craft and revenue: you turn strategy into curriculum, and curriculum into results seen across our sales teams.

What you'll do
  • Own the design, build, and delivery of new-hire onboarding and ongoing enablement for our sales teams, applying instructional design and adult learning principles to build role-based curricula and certifications in-house.
  • Create and maintain the content that powers the program: playbooks, talk tracks, objection handling, product enablement, competitive intelligence, and customer stories.
  • Implement scalable 1:1 and group coaching systems, using behavioral insights, call intelligence, and performance analytics to develop reps.
  • Lead, coach, and develop a team responsible for onboarding, training delivery, and program operations.
  • Own the multi-year enablement strategy and roadmap, tied to reducing time-to-ramp and improving conversion across sales roles.
  • Partner with Sales Leadership, RevOps, Marketing, and Customer Success to diagnose performance gaps, prioritize enablement investments, and prepare the field for new product launches.
  • Define and report on the metrics that matter, rep productivity, ramp times, certification pass rates, and translate insights into action plans that improve revenue outcomes.

About you
  • 10+ years of experience in Sales Enablement, Sales Training, or Revenue Enablement in a B2B SaaS environment, including 5+ years leading an enablement or training team.
  • You have built an in-house training program from the ground up, curriculum, content, certification, and onboarding.
  • You're a culture champion. You're the heartbeat of the sales floor, creating engaging programs and you know what it takes to motivate and inspire a team of SaaS sellers.
  • Strong foundation in instructional design and adult learning principles, with hands-on experience building multi-modal training curricula.
  • Exceptional communication and facilitation skills, with the ability to deliver executive-level presentations and coach reps one-on-one with equal comfort.
  • Demonstrated experience leveraging AI tools and technologies to improve workflows, enhance decision-making, or drive innovation.
  • Bonus points: Prior quota-carrying sales experience in the SMB or mid-market segment, so you understand the buyer, the deal cycle, and the daily reality of the reps you'll be enabling
  • Based in Austin, TX with the ability to work hybrid from our Austin office.

Why 8am:

At 8am, our culture is shaped by the people who bring it to life every day. Together, we build a company rooted in continuous learning, genuine community, holistic wellness, and meaningful engagement-values that empower us as individuals and unite us as a team. Our culture is grounded in our core values: Work Smart, Win Fast; Outshine Ordinary, and We Find a Way. These values drive how we serve our customers and work with each other in a collaborative, inspiring, and empowering environment, every day.

Here's how we support our 8Team:
  • Health Insurance Coverage: We offer our 8Team a variety of medical, dental, and vision plans, designed to fit your needs, including a 100% company-paid HDHP plan for employees.
  • Financial perks: We offer a competitive compensation and benefits package including annual bonuses, equity options and 401(k) or RRSP if in Canada, with a company match for all team members.
  • Time for what matters: Flexible Time Off, paid holidays, and a parental leave program for our new parents.
  • Wellness: Wellness stipends, mental health support, and one-on-one nutrition coaching.
  • Learning and Development: Continuous learning through 8am.edu, leadership programs, professional development funds, and individually focused talent development.
  • Giving back to the communities around us: Participate in our charitable matching gift program, paid time off for volunteer service, and company-sponsored volunteer events (both local and virtually).
  • Engagement: Virtual and in-person team-building events, quarterly award recognition through our Rise & Shine Award of Excellence Program, and our peer-to-peer appreciation platform.

About AffiniPay Holdings, LLC

AffiniPay is a financial technology company that provides payment processing solutions for professional services industries. The company's proprietary platform, designed specifically for the legal industry, streamlines the payment process, making it easier for clients to pay their bills and for law firms to manage their finances. AffiniPay has expanded its services to other professional services industries, including accounting, architecture, engineering, and healthcare. The company was founded in 2005 and is headquartered in Austin, Texas.
Learn more about AffiniPay Holdings, LLC
Size
500 employees
Industry
Net Income
$10 million
Founded
2005
5 Year Trend
+20%
Revenue
$1 billion
NASDAQ

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