Director of Sales Enablement and Development

Director Of Sales Enablement & Development

NerdWallet Small Business is the go-to financial resource for small businesses. We're here to help entrepreneurs achieve their financial goals and grow businesses as big as their aspirations. As a catalyst for smart financial decisions, our combination of proprietary technology and financial expertise provides business owners with tailored solutions based on their unique needs and eligibility—helping them prosper, create more jobs, and, ultimately, grow the economy.

This is not a traditional L&D role.

You will own how our sales team performs—who we hire, how fast they ramp, how well they close, and how consistently they win.

You'll design the system that turns raw talent into top producers—and you'll be in the trenches making it happen.

If you're the type who:

• Gets frustrated watching average reps stay average
• Believes most training is too soft, too slow, and too theoretical
• Obsesses over conversion rates, talk tracks, and closing behavior
• Wants direct accountability for revenue outcomes

... this role is built for you.

Where You Can Make An Impact

Build a High-Performance Sales Engine

• Design and run a L&D strategy focused on revenue impact—not participation
• Raise the bar on what "good" looks like across the entire sales org
• Hold the line on performance standards

Upgrade Talent at the Source

• Partner with recruiting to define who gets in—and who doesn't
• Build interview processes that filter for closers, not talkers
• Continuously tighten hiring criteria based on real performance data

Create a Ruthless Onboarding & Ramp

• Build onboarding that produces productive reps fast—or exposes misses early
• Cut time-to-productivity without lowering the bar
• Make ramp a proving ground, not a checkbox

Coach in the Trenches

• Run live call reviews, deal breakdowns, and skill drills
• Give direct, actionable feedback reps can't ignore
• Work with underperformers until they improve—or clearly don't

Turn Data Into Pressure & Progress

• Track conversion rates, pipeline movement, and output like a hawk
• Identify exactly where reps lose deals—and fix it
• Build playbooks based on what actually works, not theory

Systematize Winning Behavior

• Extract what top performers do differently and scale it
• Build repeatable frameworks that drive consistent execution
• Eliminate randomness in performance

Build Stronger Sales Managers

• Turn managers into real coaches—not just forecast owners
• Create accountability systems that actually stick
• Push leadership to maintain high standards

Leverage AI & Tools for an Edge

• Use tools like Gong, ChatGPT, and Claude to sharpen messaging and feedback loops
• Continuously improve how reps learn, practice, and execute

Your Experience

• Experience in Business Lending/Lending required
• 5+ years in sales training, enablement, or sales leadership—preferably in high-volume environments
• A track record of measurably improving sales performance (not just delivering training)
• Strong instincts for diagnosing performance issues quickly and fixing them
• Comfort operating in high-pressure, high-accountability environments
• Experience working directly with reps—coaching, correcting, and pushing performance
• Deep understanding of sales execution (not just theory)
• What makes you stand out:

• Results-oriented mindset with a focus on impact and outcomes
• Strong communicator who delivers clear, constructive feedback
• Comfortable in fast-paced, high-accountability environments
• Bias for action—tests, iterates, and adapts quickly
• Ownership mentality with a proactive approach to problem-solving

What Sets You Apart

• You care about results more than process
• You're direct, honest, and not afraid of hard conversations
• You push people—and expect to be pushed back
• You move fast, test often, and adjust based on what works
• You take ownership when performance is off—and fix it

Bottom Line

This role is for someone who wants real ownership of sales performance—not just training programs.

If you want to build systems, raise standards, and directly impact revenue, you'll thrive here.

If you're looking for a softer, purely strategic L&D role—this isn't it.

Where

• This is a remote role open to candidates across the United States.
• We have a strong preference for candidates located in or near Scottsdale, AZ or New York City (Manhattan), as there will be opportunities for part-time, in-person collaboration with the team.
• We believe in the value of in-person connection—especially in a sales environment where real-time coaching and shared learning can accelerate development. While this role is remote, candidates may be asked to participate in occasional in-person collaboration (approximately once per quarter) in either our New York City or Scottsdale, AZ offices to support training and team performance.

What We Offer

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.

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