Senior Sales Trainer

Hi, We’re AffiniPay! 

AffiniPay is a leading fintech company, based out of Austin, Texas. As the market leader in professional services payments and practice management software, AffiniPay’s tech products serve legal, accounting, architectural, engineering and construction firms. AffiniPay has been recognized as one of Inc. 5000’s fastest growing companies in the U.S. for 13 years in a row, and as a result, our teams continue to grow as well! 

As a Senior Sales Trainer, you’ll play a key role in helping our sales team close more deals—faster and more consistently. You’ll develop and lead impactful training and coaching programs that sharpen core sales skills, reinforce value-based selling techniques, and equip frontline managers with practical coaching frameworks. Your primary focus will be on making good reps great in our high-velocity, transactional sales environment.

This is a highly cross-functional role. You’ll collaborate closely with Sales Leadership, Enablement, and frontline managers to ensure training is relevant, adopted, and tied to measurable business outcomes. The ideal candidate is organized, proactive, and passionate about helping sellers grow. You know how to bring structure to fast-paced environments, earn credibility with reps and managers, and turn training into real performance improvement.

What You'll Do

• Build and deliver skill-based training sessions that improve core sales competencies—discovery, objection handling, demoing, negotiation, and closing
• Assess training needs and identify skill gaps within the sales team
• Apply value-based selling principles to teach reps how to move beyond feature pitching and tie their message to customer outcomes
• Lead role playing exercises and one-on-one coaching sessions to reinforce learning and provide personalized feedback on their sales techniques
• Create engaging live, asynchronous and just-in-time training formats that drive adoption and minimize time out of the field
• Track and report on training effectiveness by analyzing performance, gathering feedback, and using this information to continuously refine and improve the training program
• Build simple, repeatable coaching frameworks for managers to reinforce skills through call reviews and deal strategy sessions
• Support onboarding efforts with targeted skill modules and reinforcement that align to ramp milestones
• Collaborate closely with Sales Managers to align on priorities, gain feedback, and drive program adoption
• Proactively gather feedback and iterate training for impact
• Other duties as assigned

About you:

• 5+ years in sales training, sales enablement, or sales management in a high-velocity, B2B SaaS environment
• Expertise in value-based selling frameworks and the ability to translate them into actionable training
• Demonstrated success in coaching and improving sales performance through structured training programs.
• Strong facilitation skills with experience delivering both live and asynchronous training
• Exceptional organizational and program management skills—you bring clarity, structure, and consistency to complex environments
• Proven ability to build trust and gain buy-in from both individual contributors and sales leaders alike
• Strong team attitude and high standards of performance for self and others
• Passion for coaching and helping others grow
• Experience with sales processes and methodologies (Sandler, Value Selling, Solution Selling)
• Experience with tools like Salesforce, Gong and Outreach
• Sales Background: Strong track record as a former AE or frontline manager 
• This position is located in Austin, Texas

Our Story

Founded in 2005, AffiniPay’s mission is to build technology products that helps professionals focus on the work they love. As the leader in the professional payments industry, AffiniPay’s products serve legal, accounting, architectural, engineering and construction firms. Our portfolio of software solutions include MyCase (Legal Practice Management Software), CASEpeer (Practice Management for Personal Injury Firms), and Docketwise (Immigration & Case Management Software). Our portfolio of payment solutions include LawPay (Legal), AffiniPay for Associations (Associations), CPACharge (Accounting Professionals), and ClientPay (Architect, Engineer, and Construction). AffiniPay’s products serve over one hundred thousand users, and we are noted as one of the fastest growing tech companies in Austin, Texas. We are constantly looking for talent to join our team to continue playing a key part in unlocking our potential. 

 

Diversity, Equity & Inclusion at AffiniPay