Sales Leadership Lessons from Datadog, to Drift, to Dooly | Michelle Pietsch, VP Revenue at Dooly

Sales Leadership Lessons from Datadog, to Drift, to Dooly | Michelle Pietsch, VP Revenue at Dooly

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From Datadog, to Drift, to Dooly, Michelle Pietsch has seen the PLG sales playbook over and over again. She says the most important thing sellers can do, especially in a product-led company, is get to know their product. After all, how are you going to present its value if you don't see it yourself first?

In this episode of the Product Led Revenue podcast, our host Breezy Beaumont welcomes Michelle Pietsch, Vice President of Revenue at Dooly. They discuss the importance of ease of use and ability for prospects to see the value of your product early on (read: it shouldn’t take multiple demos). Why everyone on the revenue team's goal should be to eliminate friction for customers and make their experience as seamless as possible. Also, Breezy gets Michelle’s perspectives on the power of data, pricing, and packaging models.


💡 Name: Michelle Pietsch

💡 What she does: She's the VP of Revenue at Dooly, a sales enablement platform that helps revenue teams win more deals.

💡 Company: Dooly

💡 Noteworthy: Before Dooly, Michelle was VP of Conversational Sales at Drift & Director of Sales at Datadog

💡 Where to find Michelle: LinkedIn

Key Insights 

Understand your product's features and benefits before you start selling it

Understanding your product is the first step to developing a sales cycle and building a successful sales team. What do your customers like about your product? Is it easy to use? These are all critical questions to keep in mind when developing a sales strategy. Michelle talks about her experience with Dooly. "We haven't actually been selling for a full year yet. I started at Dooly on March 1, 2021, and that's when we started building our sales team. So it hasn't been very long, and when we started in March, there were two sales reps that started with me, and we were very much in the learning mode of understanding what our customers like and what they don't like about the product because we were pretty much building from the ground up at that point and we still kind of are."

The more data, the better

Since Dooly is a data-driven company, there's always a need for more data. Whether it's understanding customer health, updating pricing deals, or converting a lead into a paying customer, data plays a significant role in the sales cycle. "We have amazing data analytics teams that are constantly updating us with where we should focus our time, and also a lot of that goes into pricing and packaging. So we're working on our pricing and packaging right now and trying to understand what is going to benefit Dooly, but also how we can appease our prospects and our customers to make it easier for them to understand which tier they actually fall into."

Using data to build pricing models

If you have enough data, you are better positioned to leverage it and analyze it to give customers what they need. For example, when it comes to pricing models, customers want to understand the criteria that make them fall into a particular tier. Michelle explains how Dooly operates. "We want to do the right thing for our prospects and our customers, so I’m doing a lot of research, and I personally don't want it to be a trick. So [I’ve been] listening to a ton of sales calls over the past few months where we're pitching our pricing. You have a lot of, “Why do I fall into that bucket?” Is it the sales rep that's positioning them into this specific bucket because it's going to make their commission higher, or is it best for the customer? So, I think it's understanding what levers you have to pull, and it goes back to that data question that you asked and what we look at."

Episode Highlights 

💜 Keep your customers in the loop

"Our CS team is made up of a director of CS, and they're focused on customer health, onboarding our customers, and making sure that they have everything that they need in order to be successful throughout their lifespan as a Dooly customer. And then part of that team is our enablement team and support, where they're doing a lot of educating on what Dooly is and how they can actually see the value relatively quickly, as opposed to leaving our customers in the dark. We want to be able to give them a resource and a guide and as many videos and how-tos and real people to reach out to."

💜 Why it's important for a product to be easy to use

"The most important thing that I took away was the ease of use and seeing the value of your product really early on. So, the fact that you didn't necessarily have to take three or four demos to walk someone through Datadog before they bought [the product] was amazing. So how can you replicate that in any other sales organization? It’s not easy. It really depends on the product, and can they [prospects] get to that ‘aha’ moment without necessarily having to go through multiple demos? And we are still very much learning how to do that at Dooly.

[...] That's my biggest learning: just ease of use, listening to your customer and trying to figure out how to make it as easy as possible for them to actually buy. Remove that friction."

💜 Time is money

"Time is money, right? Not to sound cliché, but if you continuously make your products more complex and they can't get to the ‘aha’ moment and see the value, then it's going to be more work for your sales team, which means longer sales cycles, and more competition is going to come up and get in your way."

Top quotes: 

[5:30] "Before I added a ton of people, I wanted to understand what our users were saying and how we were delivering that value really early on, and that starts with the product and understanding what they like about it. Is it easy to use? And you do that by listening to sales calls and listening to what your customers like and don't like."
[22:16] "It was exciting because you could see that the value of the product you're selling is resonating with individuals very quickly, as opposed to going through these daunting discovery calls and the old school Sandler pain funnels for people to actually understand the value that your product is going to give them."

Interested in learning about how Correlated can help your PLG company uncover expansion and upsell opportunities?

Sales and revenue leaders at PLG companies, like yourself, are faced with unique challenges. Using tools like Correlated can help sales and marketing teams identify new accounts that are ready to convert, or can help to notify your team for expansion and upsell opportunities.

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