Episode OneHundredFortyOne

4 Enterprise Engagement Strategies for Training Reps

Guest: Ryan Barry, CRO at Zappi

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About This Episode

That one rep who earns 300% of plan?

That thing they have that everyone else doesn’t is the drive to improve their game.

That, plus short, killer messaging.

I recently got to chat with Ryan Barry, CRO at Zappi, about enterprise engagement strategy with a little touch of ABM.

Zappi has nailed a few important concepts around engagement — meaning their sales engagement platforms like outreach help with sequencing and cold outreach. They’ve also got a multichannel system (email, social, and phone) as well as ABM.

“Zappi is a consumer insights platform, so our customer base is big brands bringing new products to market,” Ryan said.

Meaning, their customer’s backdrop isn’t software. Their tools and capabilities are pretty analog.

Where to start?

Defining Enterprise

Everyone defines enterprise differently. “There’s been this navigation of that simple concept in and of itself,” Ryan said. 

A company like Pepsi that sells snacks and drinks in 30 countries, each one with separate brands, is a really hard sell for enterprise software. “You’re creating a land-and-expand play while trying to build an efficient business model as you go, so that makes the outreach fairly difficult,” Ryan said.

What makes the consumer insights space so crowded? And what to do about it?


So much messaging hitting these buyers every day — and it’s all littered with buzzwords.

Customers are getting 30+ cold emails a day. They’ve all but disconnected their work phones.

“We’ve tried to take buzzwords out of our messaging completely and be really focused on the vertical we’re talking to and thinking about their business and problems we could actually help them solve,” Ryan said.

Cadence tools

You don’t blast the same email to 20,000 buyers. “There’s something about using cadence tools like Outreach to guide the salesperson into what their steps should look like,” Ryan said.

Teaching reps about the domain their buyers live in, teaching them to be experts in the business… then reps can do the desk research to make the outreach relevant to that buyer. 

Simple communications

“Our best players in terms of getting in front of people are writing 2 to 3 sentences at most — but they’re fire sentences,” Ryan said.

It’s fine to spend half a day thinking through a super short message if it gets you a killer hit rate. 

Doing 3 things well is better than 100 things badly. (This is why Ryan doesn’t remunerate on calls per day.)

4 Sales Reps Strategies

1 — Value before ask

Ryan explained how he applies Gary Vaynerchuk’s Jab, Jab, Jab, Right Hook. “This is an outbounding sales principle I preach about internally,” Ryan said. “The notion of jab, jab, right hook is value, value, then an ask.”

It could look like this:

  • Connect on social
  • Mention something we think is interesting
  • Share another interesting thing.
  • Make an ask that’s clearly delineated from value.

This requires patience… and a lot of touches… like, 8 to reach a meeting.

“Let’s build some credibility through that process so that we get somebody to agree to a discovery call,” he said.

2 — Long sales cycle

Zappi has a 6 month sales cycle so sales reps can…

  • Be diligent
  • Optimize
  • Take it easy
  • Pay attention

…you know, do quality work instead of quantity work. It’s okay, even preferred, to make a long play.

3 — Reps training reps

“Anything that we want to get our reps to do, we point to success others are having,” Ryan said.

Their best sales rep is 300% of plan for the year, about to win the sales championship belt for the fourth straight quarter. So they’ll analyze the cadence software and show other reps the components of why that rep’s messaging is working.

Sharing data-driven techniques provides more credibility to operationalizing adjustments. 

You’re being successful at this when the sales leader isn’t the essential cog — the best reps are.

4 — Hiring for curiosity

“Our reps have to know what they’re talking about or they will just get smoked,” Ryan said. “It’s not negotiable.”

That thing that the best reps at Zappi do? They spend the most time on training courses.

It’s no accident that the ones who perform the best keep striving to improve themselves. They put in the work. They make the money.

“You can’t train people to give a shit,” Ryan said. That’s why he interviews for curiosity, coachability, and a desire to keep learning.

Reach out to Ryan on LinkedIn or email him at ryan@zappistore.com. He’ll take a discovery call with anyone who gives a thoughtful touch.

For more engaging sales conversations like this one, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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