Starting a new sales job can be thrilling—but let’s face it, it can also feel like drinking from a firehose. New product? New industry? New team? Whew! The training and support you receive during onboarding (and beyond!) can make all the difference between thriving and just barely surviving.

At NextRoll, one of our core values is to “hire great people and help them grow,” and our Revenue Enablement team lives and breathes this mantra. They’ve built an exceptional onboarding and enablement program designed to empower our Sales, Customer Success, and Marketing teams to shine. We sat down with Caroline Estrada, Senior Manager of Revenue Enablement, to dive into what makes an enablement program truly stellar—and what to watch out for. Whether you’re job-hunting or looking for ways to take your learning journey into your own hands, you’ll want to bookmark this one!

What traits should I look for in a company’s onboarding or enablement program? And what red flags should I watch out for?

Starting with a new company can feel like a whirlwind. The right onboarding program should act as your anchor, helping you navigate the storm with confidence. Look for programs that:

• Offer multiple ways to learn—because let’s be real, we all absorb information differently! A great program embraces a variety of formats, repetition, and time to master key concepts.

• Have a clear roadmap—from day one, you’ll want to know exactly what’s expected of you, what goals you’re aiming for, and how success will be measured.

• Include role-specific support—whether it’s through role-specific training, manager check-ins, or a buddy system, you should feel supported and ready to hit the ground running.

Red flags? If the company’s approach is “sink or swim,” you might want to reconsider. A lack of guidance or poor communication can leave you floundering. When interviewing for new job, ask thoughtful questions like:

• “Do you have a dedicated Sales Enablement or Learning & Development team?”

• “What will my onboarding program look like? How long does it last?”

• “What learning formats are offered?”

What role do coaching and mentoring play in enablement programs? How does NextRoll incorporate these into its approach?

Coaching and mentoring aren’t just “nice-to-haves”—they’re game-changers! Both are invaluable elements of your success because they help you understand the role from people that have been in it, learn best practices, and contribute to your confidence in your role. Coaching focuses on refreshing and refining best practices, while mentoring allows an employee to develop a personal relationship and learn from someone who's been in the role before.

At NextRoll, we weave these elements into our onboarding from day one. New hires participate in hands-on activities, like mock presentations and guided worksheets, and are paired with teammates for role-specific learning. The result? A combination of real-world practice, valuable feedback, and relationship-building that sets you up for success.

How has NextRoll’s program measurably improved performance for new sales hires?

Let’s talk results! Here are just a few highlights:

• Faster deal creation thanks to established milestones during ramp.

• Increased confidence through virtual mock sales processes.

• Enhanced tool adoption and strategy-building via peer mentoring through our RollMate peer-to-peer mentorship program.

What if my company’s enablement program isn’t hitting the mark? How can I take charge of my success?

Sometimes, you need to fill in the gaps yourself to get the knowledge you need! Here’s how you can take the reins:

1. Share Feedback—Your manager and enablement team want to help you succeed, so don’t hesitate to voice your concerns and suggestions.

2. Explore External Resources—Webinars, podcasts, industry publications, and online courses from resources like Linkedin Learning can be invaluable. Lifelong learning is a habit that will benefit you in any role!!

3. Ask About Tuition Reimbursement—Many companies offer tuition support for job-related certifications or degrees. NextRoll will help pay for your graduate degree!

Closing Thoughts

At NextRoll, we’re all about setting our team members up for success—from day one and beyond. Our enablement programs are designed to help you grow, thrive, and crush your goals. With thoughtful support, coaching, and mentorship, we’re not just onboarding employees—we’re empowering our team’s success.

Interested in more great content like this?

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