How To Enable Your Sales Team: Practical Tips for Sales Leaders

Last Updated December 17th, 2019

Joe Caprio,, enable your sales team


Listen to “51. How To Enable Your Sales Team: Practical Tips for Sales Leaders w/ Joe Caprio” on Spreaker.

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Joe Caprio is passionate about finding ways to enable your sales team to thrive. He was a loyal customer before joining the sales enablement software company as VP of Sales.

During his tenure running training and sales enablement at InsightSquared, he recognized the need to hire people into sales roles who are relatively new to sales. But they needed to execute a relatively complex sale in a way that required higher business acumen. That’s where Chorus came in.

Chorus, a sales intelligence and training platform for fast-growing tech companies, alleviated the skill gap and improved his team’s consistency in messaging. It also allowed them to figure out handoffs for the Account Executive team to enable the Customer Success team to serve the specific needs of each customer.

This cut the ramp time for new sales reps in half – and increased his win rate at the same time.

“I was a very happy customer of the software,” he says.

He knew everything about how Chorus worked as a user – and so did his wife because how much he gushed about it in the evenings. And now he’s a very happy employee of the company he admired so much.

“I just love what we do. My dopamine doesn’t come from closing deals, it comes from enabling new sales people to learn how to close deals,” he says. “I love the mission that we’re on right now of helping customers support their sellers with better training and enablement.”

On this episode of The Customer Experience Podcast, we drill into sales enablement with Joe. We talk about how we can best prepare our salespeople, and set them up to serve customers successfully. Because ultimately, sales isn’t just about quotas; it’s about pursuing our clients’ success.

Joe had spent 15 years in a variety of sales roles in Boston and San Francisco before making the move to Chorus.

He has seen how customer experience has really morphed to encompass the whole customer journey, and explains how in the video below…


This is because CX stretches from the first brand impression with customers all through the sales cycle. So, you need to be focused throughout the process to ensure your product or service is being utilized to its fullest potential, and that it’s earning your renewals and expansions.

It’s also essential for CX to have every employee on the team aligned to the same values of your business. And as a company, you all need to embrace what success means for your clients.

“Customer experience is every single customer-facing asset and employee on your team marching to the same tune with a unified message and a mission to help your customers succeed in their business,” Joe said.

Listen, read, and watch below as Joe details practical tips on how to enable your sales team and how to increase their impact on your business. We touch upon all of the following points…

Raising the business acumen of young sales professionals
Recognizing the importance of buyer personas
Prioritizing sales enablement for sales readiness
Keeping in mind areas of caution in sales training and promotions
Bringing attention to what marketing and customer success should know about sales



How To Enable Your Sales Team: Practical Tips for Sales Leaders

Video clips and highlights of The Customer Experience Podcast are available here in our blog posts, but you can also listen to this episode in your favorite player …

We also embed each episode in its companion blog post. Hear the entire conversation with Joe about how to enable your sales team with the skills and resources needed for success in today’s buying environment here…

Listen to “51. How To Enable Your Sales Team: Practical Tips for Sales Leaders w/ Joe Caprio” on Spreaker.


Teaching Sales Rookies to Be Veterans

Joe stressed the importance of sales training, especially with new sales professionals, by recalling his InsightSquared team’s experience with Outreach in the clip below…


“It really enabled my rookie BDRs to send the emails my veteran BDRs were sending,” he says. “So, folks that had a year or a year and a half in the seat had figured out what worked, what resonated and what the prospects liked to talk about.”

And this was all accomplished by taking email templates from the veterans and giving them to the rookies.

Maybe their phone work could use some growth, but the rookies were extremely successful with email. It’s not just about formatting emails, though. It’s about getting rookies straight off the bat to think about the key skills a seller needs to succeed at your company.

“That was the biggest ‘aha’ for me,” Joe said. “The number one way to enable your sales team is to get that tribal knowledge out of your veterans’ brains and distribute it across the rookies.”

Joe Caprio, sales training, sales knowledge,, sales enablement



The Importance of Developing Buyer Personas

It was easy for Joe to identify Chorus’ ideal customers because he was one – high-growth, rapidly scaling B2B sales teams. And this is because it shadows your sales teams, captures and analyzes their sales meetings, and puts together the best training program for them.

In turn, Chorus helps enable your sales team to understand their own buyer personas with more intimacy. Joe explains why these personas are essential to the success of your sales team in the following clip…


“As a customer, I don’t care about your features. I really don’t,” Joe said. “I don’t care about your technology and I don’t care about your reference customers. I care about how I should use your product and your service.”

Because customers are longing to know how you will help them do their jobs better and more effectively. So, salespeople need to take the time to understand the target buyers – not to trick or sell – but to comprehend what they aspire to accomplish and showcase areas of their product or service that will help them get there.

“The best way to service your customers is to make your buyer persona really successful in their function,” Joe explains. “If they’re successful in their career, they’re a high performer for their company.”

Joe Caprio, buyer personas, customer experience,



Focusing on Sales Enablement for Sales Readiness

The sales ops role has grown in importance with our ability to capture data, as companies realized they could have someone on staff to harness that data to help them make better decisions. Because the next frontier in efficiency is getting people skilled quickly and appropriately.

“A lot of companies are now starting to invest in enablement and readiness sooner,” Joe says. “They recognize that they’re building bigger teams with a data-driven approach. And they’re tying the coaching initiatives to behavior change and revenue improvement.”

Joe Caprio, sales productivity,


When working to enable your sales team in your high-growth business, there are two questions to keep in mind:

1. What will it take for a seller to be productive, autonomous, reliable, and consistent?

2. What are the elements that contribute to helping sellers acquire these traits (tech stack, training, etc.)?

Joe elaborates on both of these questions further in the following video clip…


“The ultimate measurement here is time to productivity and productivity per person,” Joe says. “And the mantra is to go out there and improve those two steps.”



Cautions to Consider for Sales Training and Promotions

In order to enable your sales team in an efficient and effective manner, Joe offers some points of caution for sales training and promotion in the video below…


His advice includes:

1. Don’t gather around the head of department for words of wisdom. This comes across like a philosophical teaching form Socrates or Plato.

“The world has changed,” Joe explains. “The way people interact and consumer information has changed, yet you’re still standing up and lecturing at people.”

Instead, do a weekly peer review or build out call libraries where new hires can go for information.

2. Don’t hire people based on their sales ability. Instead, hire them based on how their opinions align with your mission, pitch, and methodology. Also, make that information consumable for reps.

3. Don’t promote your best sales rep to be a frontline manager. Because, quite honestly, management and sales aren’t directly related, and someone who’s never been coached isn’t likely to be a good fit.

“The best sellers do not always make the best managers,” Joe says. “You really have to invest in this layer of front end managers because otherwise it’s the head of sales or the head of enablement telling the reps how to do things. But no one is out there after enforcing it and making sure reps understood it.”


What Marketing and CS Should Know About Sales

It’s a reality that salespeople are interviewed, tested, and hired with a personality profile that is not easy to change. They’re headstrong and determined. They’re confident in themselves and have conviction in their skills beliefs.

You can’t change people like that by sending a memo. Joe clarifies why in the clips below…


Joe asks that marketing and customer success professionals ask themselves, “How many times do you have to tell someone something before they really, truly learn it?” It’s more than one, right?

“Think about all the different ways you can support and enrich and enable your sales team members to do that versus just saying, ‘Well, we announced it at the Monday meeting, so what’s wrong now?’” Joe says.

Change, growth, and alignment require an active, ongoing conversation – with our sales team, throughout our entire organization, and across our customer base.



This post is based on an interview with Joe Caprio, VP of Sales at


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Enable Your Sales Team with Video

As you work to enable your sales team with more valuable training and tools for success, consider equipping them with the ability to send video emails to prospects.

Video can be used to create immediate empathy with the ideal customer, and you can send video emails as you connect with customers online and establish your own demand.

And “Rehumanize Your Business” offers your sales team the training and information to successfully integrate video into their sales motion.

The book is an Amazon #1 bestseller in Business Sales, Business Communication, and Customer Relations, the Porchlight Books #1 bestseller in its opening month of release, and a Barnes & Noble bestseller in its opening week of release.

Determine if it’s the sales enablement resource you need for your sales team to prosper with video by clicking right here.

customer experience, sales acceleration, rehumanize your business



Ethan Beute | About The Author

Chief Evangelist at BombBomb, host of The Customer Experience Podcast, and Wall Street Journal bestselling co-author of Human-Centered Communication and Rehumanize Your Business, Ethan Beute collects and tells stories of clearer communication, human connection, and higher conversion through simple, personal video messages. BA: University of Michigan. MBA: University of Colorado-Colorado Springs.

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