Strategic Sales Trainer

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

Job summary

NerdWallet, Inc. is recruiting a Strategic Sales Trainer in New York, NY to develop our Small Business Sales team and help Account Executives translate training into consistent, strategic selling.

You’ll partner with Sales Leadership to extend training beyond boot camp for reps in their first 12 months. The role emphasizes deeper customer engagement, renewal strategy, and AI‑powered practice, with hands‑on coaching and cross‑functional collaboration across Product, Operations, and Sales.

Qualifications

• 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 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 coaching’s 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.

Responsibilities

• Build development beyond boot camp by designing coaching, reinforcement, and skill assessments for reps in their first 12 months.
• Deepen book‑of‑business engagement by coaching reps to segment and prioritize their books and reengage inactive customers.
• Strengthen renewal and lender strategy by evaluating financing history and options for customers.
• Improve outreach and sales execution with refined call, text, and email cadences.
• Deliver hands‑on sales coaching through live observation, role plays, and deal strategy sessions.
• Build and scale AI‑powered practice with real call insights and coach rubrics.
• Turn data into targeted development using call insights and performance metrics.
• Keep enablement practical by updating playbooks and tools with cross‑functional collaboration.

Skills

Sales training

Coaching

Relationship building

Public speaking

AI in training

Tools

Salesforce

Conversational intelligence tools

Sales engagement platforms

Learning management systems

Job description

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 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 you'll 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, you'll teach representatives to uncover opportunities, reengage customers, and earn repeat business. Through live coaching, structured development programs, and AI‑powered practice and feedback, you'll develop more strategic sellers who turn stronger customer engagement into sustainable business growth.

Where you can make an impact:

As a Strategic Sales Trainer, you’ll partner with Learning & Development and Sales Leadership to help representatives become confident, strategic sellers who deepen customer relationships and drive repeat business. You’ll:

• 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, you'll help shape how representatives develop throughout their first year and become more strategic sellers who grow lasting customer relationships. You'll 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, you'll 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 coaching’s 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 you'll know you're successful:

Success in this role will be measured by the impact you have on representative development and sales performance. You'll 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. You'll 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, you'll have the option to work remotely 20% of the month (4 days)

What we offer:

Pay Transparency: $96,000 - $132,000 base + equity

• 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:

• E‑Verify Participation Poster (English+Spanish/Español)
• Right to Work Poster (English) / (Spanish/Español)