Sales Pitch Techniques
Sales Prospecting 10.29.2021

Sales Pitch Techniques

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On this episode of the Sunny Side Up podcast, Zack Ciesinski sits down with Anoop to talk about his time as a sales leader at Stripe. Zack has a wide variety of experience in sales and shares his advice about how to nail your sales pitch, the concept of transparency-based sales, and how the role of the seller is not to act as support—it’s to go after businesses and talk to them about the challenges they’re facing. The episode concludes with Zack’s word to managers about choosing which opportunities to spend the time on, plus a few resources he recommends to sellers and managers.

About the Guest

Zack Ciesinski has been in sales for the majority of his career. Zack started out as an SDR at Zendesk. He then helped build the consulting partner program at Xamarin (acquired by Microsoft), and he has spent the past ~4.5 years at Stripe in various sales roles. Currently, Zack leads a team of AEs who sell to large digitally native accounts. While Zack tries to avoid sales stereotypes, you’ll find him either on the golf course or tasting a new bag of coffee when not at his desk.

Connect with Zack Ciesinski

Key Takeaways

  • Making sure you nail your sales pitch is all about being a compelling storyteller.
  • When thinking about outcome-based sales engagement, it’s important to leverage your ROI materials and take those objectives and use them as an anchor point throughout the sales process.
  • The concept of transparency-based sales means we tend to buy from businesses with 4.3 to 4.7-star reviews instead of straight 5-star reviews. When businesses lead with 5-star reviews and accolades, consumers tend to be skeptical and think their pitch must be too good to be true.
  • Zack shares how Stripe leads with one of their main points of “weakness”: the fact that Stripe works with a lot of startups. This has turned into one of their strengths thanks to transparency-based sales.


“Our role as sellers is not to support, it’s not to answer questions. Our job is not to respond to all of these users, but instead to go after businesses and talk to them about the challenges they’re facing.”

Highlights From the Episode

How do you make sure you nail your sales pitch? 

Nailing a sales pitch is all about telling a story to a prospect, Zack says. Oftentimes sellers nail each slide of their pitch, but they don’t know how to transition to the next slide. Nailing those transition moments with details and flexion is important to being a compelling storyteller when it comes to pitching.

Why is the concept of transparency-based sales good for business?

Transparency-based sales disarm the prospect and help them know they’re not talking to a stereotypical salesperson. Zack says the way his team uses transparency-based sales techniques at Stripe is by leaning into the fact that Stripe does do a lot of business with startups, and not shying away from that. Leaning into that startup story disarms the user because Stripe isn’t trying to hide that part of their business.

As a sales manager, how can you know which opportunities you should spend the most time on?

Instead of filling up your calendar with support emails and calls, Zack advises sales managers not to be afraid of that dead time in their schedule. It’s better to spend time going after those new prospective businesses than to spend hours answering emails the support team is meant to be working on.

Do you have recommended resources for the audience?

Zack recommends checking out The Transparency Sale by Todd Caponi and Inbound Selling by Brian Signorelli. For managers specifically, he recommends reading Cracking the Sales Management Code by Jason Jordan and Michelle Vazzana and The First 90 Days by Michael D. Watkins.


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Sunny Side Up

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