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 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.
HOW YOU'LL KNOW YOU'RE SUCCESSFUL
Success in this role will be measured by the impact you have on representative development and sales performance. You'll help representatives reach productivity milestones sooner, sustain progress after boot camp, and build stronger skills throughout their first 12 months.
Your impact will also show up in deeper book-of-business penetration: more existing customers reached, a greater share engaged in meaningful conversations, and more inactive relationships reactivated. You'll help representatives translate that engagement into qualified opportunities, applications, repeat funded units, and revenue growth.
Stronger discovery, account prioritization, renewal and lender conversations, and conversion rates will demonstrate their development into more strategic sellers. AI coaching adoption will be paired with evidence of skill improvement and stronger execution on live calls—helping make coaching an everyday part of winning.
WHERE
This role will be based in New York, NY.
We have found that working in person, alongside peers and more senior members of the team, offers significant advantages through the spontaneous learning and collaboration opportunities that arise daily on a sales floor and cannot be easily replicated in a remote environment.
We also understand the importance of flexibility to work remotely, both for personal and professional reasons. While this is an in-office role, as long as you are meeting our minimum performance standards, you'll have the option to work remotely 20% of the month (4 days)
WHAT WE OFFER
Pay Transparency: $96,000 - $132,000 base + equity
Work Hard, Stay Balanced (Life’s a series of balancing acts, eh?)
Industry-leading medical, dental, and vision health care plans for employees and their dependents
Rejuvenation Policy – Flexible Vacation Time Off + 11 holidays + 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 for Nerds to recharge, gain knowledge, and pursue their interests
Health and Dependent Care FSA and HSA Plan with monthly NerdWallet contribution
Monthly Wellness Stipend, Cell Phone Stipend, and Wifi Stipend (Only remote Nerds are eligible for the Wifi Stipend)
Work from home equipment stipend and co-working space subsidy (Only remote Nerds are eligible for these stipends)
Have Some Fun! (Nerds are fun, too)
Nerd-led group initiatives – Employee Resource Groups for Parents, Diversity, and Inclusion, Women, LGBTQIA, and other communities
Hackathons and team events across all teams and departments
Company-wide events like NerdLove (employee appreciation) and our annual Charity Auction
Our Nerds love to make an impact by paying it forward – Take 8 hours of volunteer time off per quarter and donate to your favorite causes with a company match
Plan for your future (And when you retire on your island, remember the little people)
401K with 4% company match
Be the first to test and benefit from our new financial products and tools
Financial wellness, guidance, and unlimited access to a Certified Financial Planner (CFP) through Northstar
Disability and Life Insurance with employer-paid premiums
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NerdWallet is committed to pursuing and hiring a diverse workforce and is proud to be an equal opportunity employer. We prohibit discrimination and harassment on the basis of any characteristic protected by applicable federal, state, or local law, so all qualified applicants will receive consideration for employment.
NerdWallet will consider qualified applicants with a criminal history pursuant to the California Fair Chance Act and the San Francisco Fair Chance Act, which requires this notice https://www.sf.gov/sites/default/files/2022-12/FCO%20poster2020_0.pdf, as well as the Los Angeles Fair Chance Act, which requires this notice https://dcba.lacounty.gov/wp-content/uploads/2024/08/FCOE-Official-Notice-Eng-Final-8.30.2024.pdf.
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