Advanced Product Sales Trainer

Acrisure•Oklahoma City, OK

2d•Onsite

About The Position

We are looking for a seasoned Advanced Product Sales Trainer to elevate the performance of our sales organization across our Payroll and Human Capital Management (HCM) product suite. In this role, you will serve as a trusted advisor, coach, and performance partner to our Sales Representatives, Business Development Representatives, and Inside Sales Representatives — helping them sharpen consultative selling skills, deepen product knowledge, and drive sales success. Sales Training: Deliver one-on-one and group coaching sessions focused on pipeline development, discovery, objection handling, product demos, and closing techniques specific to Payroll and HCM solutions. Shadow live and recorded sales calls; provide structured, actionable feedback tied to measurable outcomes to ensure sellers can effectively position our products as a solution for our clients. Conduct personalized training for teams based on sales rep feedback and the specific needs of a division or region. Travel as needed to conduct in-person training at various sales events and meetings. Facilitate training workshops during 2-week new rep training and broader ongoing trainings, including selling season. Conduct product demo training to ensure sellers can effectively demonstrate the value of our products and link to meaningful discovery with prospects. Embed structured, advanced sales methodologies and skills across the sales organization. Partner with key stakeholders for cross-functional collaboration to align training objectives with organizational strategies. Equip new sellers with critical product knowledge to increase sales activity. Enablement & Curriculum Development: Design and deliver training programs for sales reps covering product knowledge, competitive positioning, and sales methodology focused on selling to core client categories and selling more than one product per client. Develop playbooks, talk tracks, objection-handling guides, and ROI frameworks tailored to Payroll and HCM buyer personas (CHROs, CFOs, Payroll Administrators, HR Directors, business owners, office managers, etc.). Collaborate with Product Marketing to translate product releases and competitive updates into sales-ready messaging and related sales training. Consult with sales teams and leaders to develop curated and targeted training. Performance & Analytics: Track rep performance metrics (ramp time, win rates, deal velocity, conversion rates) and use data to identify coaching priorities. Partner with Sales Leadership to identify skill gaps at the team and individual level. Report on training impact and enablement program effectiveness through defined KPIs. Culture & Community of Learning on the Sales Team: Foster a culture of continuous learning, peer accountability, and high performance. Facilitate peer learning sessions, deal reviews, and "win/loss" retrospectives. Serve as a subject matter expert and go-to resource for complex Payroll and HCM sales scenarios.

Requirements

7+ years of B2B sales experience as a trainer or sales representative
Minimum of 3 years selling Payroll, HCM, HRIS, or HR Tech solutions (e.g., ADP, Paylocity, Paychex, UKG, Ceridian, Paycom, or similar platforms)
Demonstrated track record of consistent performance as a trainer and meeting deadlines for content creation.
2+ years in a formal or informal sales coaching, training, or mentorship capacity
Deep fluency in consultative and value-based selling methodologies
Strong understanding of the HR and payroll buyer journey, common pain points, and competitive landscape
Exceptional facilitation, presentation, and written communication skills
Ability to diagnose performance gaps and tailor coaching approaches to different learning styles
Comfortable analyzing CRM data (Salesforce, HubSpot) to drive coaching decisions
Proficiency with sales enablement tools
A genuine passion for developing people — not just hitting numbers
High emotional intelligence; able to build trust quickly across diverse personality types
Growth mindset with a bias toward continuous improvement
Collaborative, patient, and direct
Expertise in varied adult learning methodologies

Nice To Haves

Experience selling into SMB
Familiarity with implementation cycles and integration considerations for Payroll/HCM platforms
Background in HR, workforce management, or benefits administration is a plus

Responsibilities

Deliver one-on-one and group coaching sessions focused on pipeline development, discovery, objection handling, product demos, and closing techniques specific to Payroll and HCM solutions.
Shadow live and recorded sales calls; provide structured, actionable feedback tied to measurable outcomes to ensure sellers can effectively position our products as a solution for our clients.
Conduct personalized training for teams based on sales rep feedback and the specific needs of a division or region.
Travel as needed to conduct in-person training at various sales events and meetings.
Facilitate training workshops during 2-week new rep training and broader ongoing trainings, including selling season.
Conduct product demo training to ensure sellers can effectively demonstrate the value of our products and link to meaningful discovery with prospects.
Embed structured, advanced sales methodologies and skills across the sales organization.
Partner with key stakeholders for cross-functional collaboration to align training objectives with organizational strategies.
Equip new sellers with critical product knowledge to increase sales activity.
Design and deliver training programs for sales reps covering product knowledge, competitive positioning, and sales methodology focused on selling to core client categories and selling more than one product per client.
Develop playbooks, talk tracks, objection-handling guides, and ROI frameworks tailored to Payroll and HCM buyer personas (CHROs, CFOs, Payroll Administrators, HR Directors, business owners, office managers, etc.).
Collaborate with Product Marketing to translate product releases and competitive updates into sales-ready messaging and related sales training.
Consult with sales teams and leaders to develop curated and targeted training.
Track rep performance metrics (ramp time, win rates, deal velocity, conversion rates) and use data to identify coaching priorities.
Partner with Sales Leadership to identify skill gaps at the team and individual level.
Report on training impact and enablement program effectiveness through defined KPIs.
Foster a culture of continuous learning, peer accountability, and high performance.
Facilitate peer learning sessions, deal reviews, and "win/loss" retrospectives.
Serve as a subject matter expert and go-to resource for complex Payroll and HCM sales scenarios.