Strategic Sales Trainer

NerdWallet•New York, NY

4d•$96,000 - $132,000•Onsite

About The Position

NerdWallet is seeking a hands-on, collaborative Strategic Sales Trainer for its Small Business Sales team. The role develops sales representatives—especially those in their first 12 months on the sales floor after boot camp—into confident, strategic sellers who deepen customer relationships and generate repeat business. The trainer partners with Learning & Development and Sales Leadership to provide coaching, reinforcement, structured development, and skill assessments. The position is based in New York, NY and is primarily in-office, with the option to work remotely up to 20% of the month (four days) when minimum performance standards are met. Travel is approximately twice per quarter for in-person onboarding, training, and coaching. The trainer helps representatives improve book-of-business engagement through account prioritization, reengagement of inactive customers, discovery of changing financing needs, and strategies for repeat business. The role also strengthens renewal and lender conversations, personalized multichannel outreach, and execution across discovery, objection handling, financing education, lender positioning, ROI, and closing. Coaching methods include live observation, call reviews, role plays, and deal strategy sessions, with a focus on Challenger-based and consultative selling. The trainer designs and scales AI-powered practice, including role-play scenarios, customer profiles, coaching rubrics, and feedback tools informed by real call insights. They use sales, engagement, and performance data to identify skill gaps and measure the effect of coaching on customer engagement and business results. The role also improves financing and lender playbooks and job aids, aligns enablement with business priorities, and equips frontline managers with insights and coaching practices. Success is measured by representative development and sales performance, including faster progress toward productivity milestones, sustained progress after boot camp, stronger customer engagement and book penetration, reactivated relationships, qualified opportunities, applications, repeat funded units, revenue growth, improved sales skills and conversion, and adoption of AI coaching accompanied by demonstrable skill improvement.

Requirements

At least 2 years of experience 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.
Data-driven approach to identifying skill gaps and measuring coaching 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.

Nice To Haves

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.

Responsibilities

Design coaching, reinforcement, and skill assessments for representatives in their first 12 months; support their transition from onboarding to the sales floor and establish development milestones.
Coach representatives to segment and prioritize their books of business, reengage inactive customers, identify evolving financing needs, and build relationships that generate repeat business.
Help representatives assess financing history, renewal readiness, and existing obligations, and evaluate current-lender and alternative options in light of eligibility, timing, financing structure, and customer needs.
Improve personalized call, text, and email cadences and help representatives balance book-based prospecting, relationship building, follow-up, and active offers.
Provide hands-on sales-floor coaching through live observation, call reviews, role plays, and deal strategy sessions.
Reinforce Challenger-based and consultative selling in discovery, objection handling, urgency, financing education, lender positioning, ROI, and closing.
Design and refine AI-powered role-play scenarios, customer profiles, coaching rubrics, and feedback tools using real call insights; integrate practice into development plans, encourage adoption, and evaluate impact.
Use call insights, book coverage, outreach engagement, and performance metrics to identify skill gaps and connect coaching to customer engagement, applications, funded units, and revenue.
Build financing and lender expertise; improve playbooks and job aids; and partner with Sales, Business Development, Product, and Operations to align enablement with business priorities.
Equip frontline managers with insights and coaching practices that strengthen consistency across teams.
Travel approximately twice per quarter for in-person onboarding, training, and coaching.

Benefits

Industry-leading medical, dental, and vision health care plans for employees and their dependents.
Flexible vacation time off, 11 holidays, and a holiday company shutdown.
New Parent Leave for employees with a newborn child or a child placed with them for adoption or foster care.
Mental health support.
Paid sabbatical after 5 years.
Health and Dependent Care FSA and HSA plan with monthly NerdWallet contribution.
Monthly wellness stipend and cell phone stipend; wifi stipend for remote employees only.
Work-from-home equipment stipend and co-working space subsidy for remote employees only.
Employee Resource Groups and team events, hackathons, and company-wide events.
Eight hours of volunteer time off per quarter and a company match for charitable donations.
401(k) with 4% company match.
Access to new financial products and tools.
Financial wellness guidance and unlimited access to a Certified Financial Planner through Northstar.
Disability and life insurance with employer-paid premiums.
Base pay of $96,000–$132,000 plus equity.