Sales Trainer (Manhattan, NY)

NerdWallet•New York, NY

11d•$96,000 - $132,000•Onsite

About The Position

NerdWallet is hiring a Sales Trainer to develop sales professionals on its Small Business Sales team. The role partners closely with Sales Leadership to onboard new Account Executives, coach existing team members, and reinforce sales behaviors that support strong customer outcomes. It is approximately 70% new-hire onboarding facilitation and 30% ongoing sales coaching. The trainer is expected to work closely with the sales team, observing customer conversations, facilitating coaching, reviewing performance trends, and helping representatives improve their consultative selling skills. The role also collaborates with Business Development, Product, and Operations to keep training aligned with business priorities, market trends, and product updates, and supports frontline managers in maintaining consistent coaching practices. The position is based in New York, NY, and is primarily in-office. After training is completed, typically between months 4–6, employees meeting minimum performance standards may work remotely 20% of the month from anywhere in the continental United States. Travel is approximately twice per quarter. Compensation is $96,000–$132,000 base plus equity.

Requirements

At least 1 year 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.
Strong understanding of Challenger, consultative, and transactional sales methodologies.
Excellent communication, facilitation, and relationship-building skills.
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 and ability to connect coaching activities to measurable improvements in sales behaviors and business outcomes.
Willingness to travel approximately twice per quarter.

Nice To Haves

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.

Responsibilities

Lead an engaging onboarding program that prepares new Account Executives to navigate customer conversations, learn the sales process, and meet 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 and provide timely, actionable feedback to improve performance.
Reinforce NerdWallet Small Business's Challenger-based and consultative sales methodology throughout the customer journey.
Coach representatives on discovery, objection handling, urgency creation, lender positioning, financing education, ROI articulation, follow-up strategy, and closing execution.
Develop subject-matter expertise in small business financing, alternative lending solutions, borrower profiles, lender programs, and deal positioning.
Partner with Sales Leadership, Business Development, Product, and Operations to align onboarding and coaching with business priorities, market trends, and product updates.
Analyze call recordings, coaching observations, and performance metrics to identify recurring skill gaps and create targeted coaching plans.
Create and continuously improve 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.
Travel approximately twice per quarter to support 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.
Work-from-home equipment stipend and co-working space subsidy for remote employees.
Employee Resource Groups for Parents, Diversity and Inclusion, Women, LGBTQIA, and other communities.
Eight hours of volunteer time off per quarter and a company match for charitable donations.
401(k) with 4% company match.
Financial wellness guidance and unlimited access to a Certified Financial Planner (CFP) through Northstar.
Disability and life insurance with employer-paid premiums.
Equity.