Strategic Sales Trainer

The role

You will develop sales professionals within their first 12 months on the sales floor. You will design coaching, reinforcement, and skill assessments to help representatives deepen customer relationships and drive repeat business.

What you will do

• Design coaching, reinforcement, and skill assessments for representatives in their first 12 months
• Coach representatives to segment and prioritize books and reengage inactive customers
• Help representatives assess financing history and renewal readiness
• Refine personalized call, text, and email cadences
• Deliver hands-on sales coaching through live observation, call reviews, and role plays
• Build and scale AI-powered practice by designing role-play scenarios and coaching rubrics
• Use call insights and performance metrics to identify skill gaps
• Build financing and lender expertise and improve playbooks
• Equip frontline managers with insights and coaching practices

Required qualifications

• 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
• 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
• 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

Nice to have

• 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 development programs
• Experience designing and optimizing outreach cadences for existing customers
• Formal training or certification in Challenger, SPIN Selling, Sandler, MEDDICC, or a similar methodology

Benefits

• Medical, dental, and vision health care plans
• Flexible Vacation Time Off + 11 holidays + holiday company shutdown
• New Parent Leave
• Mental health support
• Paid sabbatical after 5 years
• Health and Dependent Care FSA and HSA Plan with monthly NerdWallet contribution
• Monthly Wellness Stipend
• Cell Phone Stipend
• Wifi Stipend (Only remote Nerds are eligible)
• Work from home equipment stipend and co-working space subsidy (Only remote Nerds are eligible)
• Employee Resource Groups
• Hackathons and team events

About the company

NerdWallet is on a mission to provide clarity for all of life's financial decisions. The Small Business Sales team helps entrepreneurs access the financing they need to start, grow, and succeed.