Strategic Sales Trainer

At NerdWallet, we're on a mission to provide clarity for all of life's financial decisions. Every small business has a unique story, and we're passionate about helping entrepreneurs access the financing they need to start, grow, and succeed. As part of our Small Business Sales team, you'll play a critical role in developing the sales professionals who make that mission possible.

We're looking for a Strategic Sales Trainer who is passionate about developing people, elevating sales performance, and building a culture of continuous learning. This is a highly collaborative, hands-on role where you'll partner closely with Sales Leadership to help Account Executives translate foundational training into consistent execution—with a strategic focus on representatives who have completed boot camp and are within their first 12 months on the sales floor.

A key focus of this role is helping representatives engage more of their existing book of business and deepen customer relationships. Through proactive outreach, thoughtful account prioritization, and discovery of evolving financing needs, you'll teach representatives to uncover opportunities, reengage customers, and earn repeat business. Through live coaching, structured development programs, and AI-powered practice and feedback, you'll develop more strategic sellers who turn stronger customer engagement into sustainable business growth.

WHERE YOU CAN MAKE AN IMPACT:

As a Strategic Sales Trainer, you’ll partner with Learning & Development and Sales Leadership to help representatives become confident, strategic sellers who deepen customer relationships and drive repeat business. You’ll:

• Build development beyond boot camp. Design coaching, reinforcement, and skill assessments for representatives in their first 12 months. Partner with onboarding facilitators and managers to support the transition to the sales floor, address performance gaps, and establish clear milestones.

• Deepen customer relationships and book-of-business engagement. Coach representatives to segment and prioritize their books, reengage inactive customers, uncover evolving financing needs, and develop relationship strategies that generate repeat business.

• Strengthen renewal and lender strategy. Help representatives assess financing history, renewal readiness, and existing obligations while weighing current-lender and alternative options based on eligibility, timing, financing structure, and customer needs.

• Improve outreach and sales execution. Refine personalized call, text, and email cadences and help representatives balance prospecting within their books, relationship building, follow-up, and active offers.

• Deliver hands-on sales coaching. Maintain a consistent sales-floor presence through live observation, call reviews, role plays, and deal strategy sessions. Reinforce Challenger-based and consultative selling across discovery, objection handling, urgency, financing education, lender positioning, ROI, and closing.

• Build and scale AI-powered practice. Design and refine role-play scenarios, customer profiles, coaching rubrics, and feedback tools using real call insights. Integrate practice into development plans, drive adoption, and evaluate its impact on sales execution.

• Turn data into targeted development. Use call insights, book coverage, outreach engagement, and performance metrics to identify skill gaps and connect coaching to stronger customer engagement, applications, funded units, and revenue.

• Keep enablement practical and aligned. Build financing and lender expertise, improve playbooks and job aids, and partner with Sales, Business Development, Product, and Operations to reflect business priorities. Equip frontline managers with insights and coaching practices that strengthen consistency across teams.

WHERE YOU CAN GROW:

As a Sales Trainer, you'll help shape how representatives develop throughout their first year and become more strategic sellers who grow lasting customer relationships. You'll have the opportunity to expand AI-powered coaching, strengthen book-of-business management, and build development programs that increase existing-customer engagement and repeat business across the sales organization. Along the way, you'll deepen your lending expertise, build strong cross-functional relationships, and directly contribute to the growth of both our people and our business.

YOUR EXPERIENCE:

• 2+ years in sales training, enablement, coaching, or frontline sales leadership within a fast-paced, quota-driven organization.

• Demonstrated success improving sales ramp and performance through structured development plans, live observation, call reviews, role plays, and actionable feedback.

• Experience selling to or coaching teams serving existing customers, including book-of-business prioritization, reengagement, renewals, and personalized multichannel outreach.

• Strong understanding of Challenger, consultative, and transactional sales methodologies.

• Excellent communication, facilitation, and relationship-building skills, with the ability to earn trust and deliver direct coaching.

• Experience using sales and enablement technologies, such as Salesforce, conversational intelligence tools, sales engagement platforms, or learning management systems.

• A data-driven approach to identifying skill gaps and measuring coaching’s impact on customer engagement, sales behaviors, and business results.

• Comfort using AI tools and interest in developing AI-powered sales practice and feedback.

• Willingness to travel approximately twice per quarter for in-person onboarding, training, and coaching.

Preferred qualifications:

• Experience in small business financial services, alternative lending, MCA, fintech, or a comparable high-volume transactional sales environment.

• Knowledge of repeat financing and strategies for positioning existing and alternative lenders.

• Hands-on experience building AI role-play scenarios, coaching rubrics, or AI-enabled