Sales Enablement Trainer: Onboarding & Coaching

NerdWallet, Inc; New York, Northern (NY, KY); Hybrid; USD 96,000 - 132,000; Full time

Benefits offered by this job

Health and wellness benefits

401K with 4% company match

Paid sabbatical after 5 years

Wellness stipend

Wifi stipend

Equipment stipend

Job summary

NerdWallet, Inc. is seeking a Sales Trainer to embed with the Small Business Sales team, developing and coaching sales professionals to improve performance and customer outcomes.

You will lead onboarding for new Account Executives, provide ongoing coaching, and reinforce a Challenger-based, consultative selling approach across the sales journey. This role offers a mix of in-office and remote work with travel as needed.

Qualifications

• 1+ 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.

Responsibilities

• 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.

Skills

Sales training

Sales enablement

Sales coaching

Frontline sales leadership

Communication

Tools

Gong

Salesforce

LMS platforms

Job description

NerdWallet, Inc. is seeking a Sales Trainer to embed with the Small Business Sales team, developing and coaching sales professionals to improve performance and customer outcomes.

You will lead onboarding for new Account Executives, provide ongoing coaching, and reinforce a Challenger-based, consultative selling approach across the sales journey. This role offers a mix of in-office and remote work with travel as needed.