Sales Trainer (Manhattan, NY)

NerdWallet•New York, NY

5d•$96,000 - $132,000•Onsite

About The Position

NerdWallet is hiring a Sales Trainer for its Small Business Sales team to develop sales professionals and improve customer outcomes. The role partners closely with Sales Leadership to onboard new Account Executives, coach existing team members, and reinforce effective sales behaviors. It is approximately 70% new-hire onboarding facilitation and 30% ongoing sales coaching. The trainer leads onboarding, observes live customer conversations, conducts coaching sessions, reviews performance trends, and helps representatives strengthen consultative selling skills. The position also develops and improves enablement materials, partners with cross-functional teams, and supports sales managers in building consistent coaching practices. Success is measured by faster new-hire ramp, better customer conversations and sales execution, improved conversion and funded revenue, fewer recurring performance gaps, and a strong coaching culture. The position is based in New York, NY and is an in-office role. After completing training, typically between months four and six, employees meeting minimum performance standards may work remotely up to 20% of the month from anywhere in the continental United States. Travel is approximately twice per quarter for in-person onboarding, training, and coaching.

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.
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.
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 for in-person onboarding, training, and coaching.

Nice To Haves

Experience selling or coaching in 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, master 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, identify coaching opportunities, and provide timely, actionable feedback.
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 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 five years.
Health and Dependent Care FSA and HSA Plan with monthly NerdWallet contribution.
Monthly wellness stipend and cell phone stipend; Wi-Fi stipend for remote employees only.
Work-from-home equipment stipend and co-working space subsidy for remote employees only.
Employee Resource Groups and team and company events.
Eight hours of volunteer time off per quarter and 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.