Sales Trainer (NY)

NerdWallet Small Business New York$96,000 - $132,0003+ years

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 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 onboard new Account Executives, coach existing team members, and reinforce the sales behaviors that drive exceptional customer outcomes.

You'll spend time where it matters most—embedded with the sales team—observing live customer conversations, facilitating coaching sessions, analyzing performance trends, and helping representatives sharpen their consultative selling skills. If you thrive in a fast-paced environment, enjoy helping others succeed, and love translating coaching into measurable business impact, we'd love to meet you.

Where you can make an impact:

As a Sales Trainer, you'll serve as a trusted partner to Sales Leadership while helping representatives build the confidence, skills, and product knowledge needed to succeed.

This role is approximately 70% new hire onboarding facilitation and 30% ongoing sales coaching. You'll:

Lead an engaging onboarding program that prepares new Account Executives to confidently navigate customer conversations, master our sales process, and achieve ramp expectations.
Deliver ongoing coaching through live call observation, call reviews, role plays, deal strategy sessions, objection-handling exercises, and pitch refinement.
Maintain a consistent presence on the sales floor, identifying coaching opportunities and providing timely, actionable feedback that improves performance.
Reinforce NerdWallet Small Business's Challenger-based and consultative sales methodology throughout every stage of the customer journey.
Coach representatives on discovery, objection handling, urgency creation, lender positioning, financing education, ROI articulation, follow-up strategy, and closing execution.
Become a subject matter expert on small business financing, alternative lending solutions, borrower profiles, lender programs, and deal positioning.
Partner closely with Sales Leadership, Business Development, Product, and Operations to ensure onboarding and coaching remain aligned with business priorities, market trends, and product updates.
Analyze call recordings, coaching observations, and performance metrics to identify recurring skill gaps and develop targeted coaching plans.
Create and continuously improve practical enablement materials including playbooks, talk tracks, call examples, role-play scenarios, and job aids.
Support frontline sales managers by reinforcing coaching best practices and driving consistency across teams.

Where you can grow:

At NerdWallet, learning doesn't stop after onboarding. As a Sales Trainer, you'll have the opportunity to influence the development of an entire sales organization while partnering closely with leadership to shape coaching strategy, improve onboarding programs, and continuously raise the bar for sales excellence. You'll build strong cross-functional relationships, expand your expertise in sales enablement, and directly contribute to the growth of both our people and our business.

Your experience:

3+ years of experience in sales training, sales enablement, sales coaching, or frontline sales leadership within a fast-paced, quota-driven organization.
A proven track record of onboarding new sales representatives and improving speed to productivity.
Experience coaching sales professionals through live observation, call reviews, role plays, and direct feedback.
A strong understanding of Challenger, consultative, and transactional sales methodologies.
Excellent communication, facilitation, and relationship-building skills.
The ability to deliver direct, actionable coaching while building trust and credibility across the sales organization.
Experience using sales and enablement technologies such as Gong, Salesforce, LMS platforms, or similar tools.
A data-driven mindset with the ability to connect coaching activities to measurable improvements in sales behaviors and business outcomes.
Willingness to travel approximately twice per quarter to support in-person onboarding, training, and coaching.

Preferred qualifications:

Experience selling or coaching within small business financial services, alternative lending, merchant cash advance (MCA), fintech, or another high-volume transactional sales environment.
Formal certification or experience with recognized sales methodologies such as Challenger, SPIN Selling, Sandler, or MEDDICC.

How you'll know you're successful

Success in this role will be measured by the impact you have on the development and performance of our sales organization. You'll help new hires ramp more quickly, improve the quality of customer conversations, strengthen sales execution, increase conversion rates and funded revenue, reduce recurring performance gaps, and build a culture where coaching is 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, confers great advantages owing to the spontaneous learning and collaboration opportunities that arise daily on a sales floor and that 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 from anywhere in the continental US starting after you complete training, typically between months 4-6.

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

If you are based in California, we encourage you to read this important information for California residents linked here.

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, as well as the Los Angeles Fair Chance Act, which requires this notice.

NerdWallet participates in the Department of Homeland Security U.S. Citizenship and Immigration Services E-Verify program for all US locations. For more information, please see: