We9re 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 you9ll 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, you9ll teach representatives to uncover opportunities, reengage customers, and earn repeat business. Through live coaching, structured development programs, and AI-powered practice and feedback, you9ll develop more strategic sellers who turn stronger customer engagement into sustainable business growth.
Where you can make an impact:As a Strategic Sales Trainer, you9ll partner with Learning & Development and Sales Leadership to help representatives become confident, strategic sellers who deepen customer relationships and drive repeat business. You9ll:
- 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, you9ll help shape how representatives develop throughout their first year and become more strategic sellers who grow lasting customer relationships. You9ll 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, you9ll 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 coaching9s 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 you9ll know you9re successful:Success in this role will be measured by the impact you have on representative development and sales performance. You9ll 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. You9ll 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, you9ll 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 (Life9s 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
If you are based in California, we encourage you to read this important information for California residents linked here.
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