Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowPosted 10 days ago

Strategic Sales Trainer

NerdWallet30 open roles

Pay
$96,000 – $132,000 a year
Where
New York, NY
Work mode
On site
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowStrategic Sales TrainerNerdWallet · New York, NY

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on NerdWallet's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

13.9% of postings close within 7 days. Measured by our own scanner across the market. NerdWallet postings stay open a median of 28 days.

Share of postings closed within
  1. 2.2%1 day
  2. 4.7%3 days
  3. 13.9%7 days
  4. 22.4%14 days
  5. 38.1%30 days
  6. 59.0%60 days
This job: posted 10 days ago

NerdWallet median: 28 days open

The posting

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

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 https://www.nerdwallet.com/privacy-policy.

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 https://www.sf.gov/sites/default/files/2022-12/FCO%20poster2020_0.pdf, as well as the Los Angeles Fair Chance Act, which requires this notice https://dcba.lacounty.gov/wp-content/uploads/2024/08/FCOE-Official-Notice-Eng-Final-8.30.2024.pdf.

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 https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf)

- Right to Work Poster (English) https://www.uscis.gov/sites/default/files/USCIS/Verification/E-Verify/E-Verify_Native_Documents/OSC_Right_to_Work_Poster.pdf / (Spanish/Español) https://www.uscis.gov/sites/default/files/USCIS/Verification/E-Verify/E-Verify_Native_Documents/OSC_Right_to_Work_Poster_ES.pdf

#LI-Onsite

From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against NerdWallet's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on NerdWallet's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    NerdWallet's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.