Build a Sales Team from the Ground Up with Michelle Pietsch

In this episode of the Sales Hacker Podcast, we have Michelle Pietsch, VP of Revenue at Dooly, which streamlines sales workflow and saves reps 5+ hours per week. Join us for a standout conversation on building sales teams from the ground up at high-growth startups.

If you missed episode #181, check it out here: Facing Adversity with a Growth Mindset

What You’ll Learn

  • How to handle massive growth expectations
  • The importance of investing in infrastructure in the team
  • Hiring SDRs to create demand
  • Why the discovery process is always an improvement area

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Show Agenda and Timestamps

  1. About Michelle Pietsch & Dooly [2:10]
  2. Building sales teams from the ground up [8:08]
  3. Being in the early growth stage with sales [11:15]
  4. Effectively coaching reps for improved performance [16:40]
  5. Improving the discovery process [18:57]
  6. Paying it forward [25:10]
  7. Sam’s Corner [27:01]

About Michelle Pietsch & Dooly [2:10]

Sam Jacobs: We’re excited to have Michelle Pietsch on the show. She’s VP of revenue at Dooly, the rapid growth SaaS company that raised $80 million to pioneer the connected workspace for revenue teams. Michelle has a long history of developing and scaling sales teams for fast-growing startups. Prior to joining Dooly, Michelle served as the VP of sales at Drift and associate VP of sales at Datadog, where she successfully grew the sales team from the ground up.

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Michelle, welcome to the show. We like to start with your baseball card. Not everybody knows Dooly. What does Dooly do?

Michelle Pietsch: Sales reps don’t update Salesforce because there’s a lot of admin work, and that impacts the sales managers. With Dooly, reps take meeting notes and update Salesforce with one workflow and view, which eliminates duplicates and ensures that Salesforce is always up-to-date, saving sales reps over 5 hours per week. It eliminates all that busy work, all the noise. It helps with all of that grunt work and removes it.

Sam Jacobs: Where are you in your growth? How many people work there?

Michelle Pietsch: We have a big presence in the social media world. We’re around 50 employees today, and adding more to more engineering and product sides. We’re growing and have some pretty lofty goals ahead of us.

I realized that a larger organization really wasn’t for me because crushing goals, getting very little recognition, and not seeing that reflected in your paycheck wasn’t for me. I went to Applause where I got my experience in the startup world and took off from there. I had no idea what I was getting myself into. I didn’t know what a startup was. I learned very quickly about outbound prospecting, how to talk to prospects and close deals at a really young age, right out of school.

Building sales teams from the ground up [8:08]

Sam Jacobs: You’re at a well-funded company early in its growth, building sales teams from the ground up. Tell us about your philosophy for building out a sales team?

Michelle Pietsch: Every organization is different. It depends on what you’re selling, who you’re selling to. It starts with listening to your customers and the current employees that are there, and identifying superpowers and the value that we bring to the market. It’s important to understand what your customers are saying, what they love, what they hate about the product. What’s our lead flow look like? What type of sale is it going to be? Are we focusing on mid-market or enterprise? It’s identifying the top of the funnel.

Then putting the standard process in place from there. Knowing that the first few times might fail. Being okay with doing experiments and failing.

At the end of the day, we need to do qualification and proper discovery in order to make customers successful. Listen, learn, and identify those true superpowers for your customers in order for them to be successful.

Being in the early growth stage with sales [11:15]

Sam Jacobs: How are you balancing that tension now that you’re at Dooly? You’ve got this massive amount of capital on the balance sheet, which implies a couple of hundred million dollar valuation, but you’re pretty early in your growth stage.

Michelle Pietsch: It’s setting the right expectations with everyone involved at the strategic and board levels. We’re a seed company or early series A, but with a lot of money. We’ve been in learning mode since I started in March, and there were no sales reps. We had little resources or understanding of where this thing is going. When you have all of that capital and expectations to grow, you can fall on your face because you hire too fast and you don’t have the resources, the process, and the understanding of where you’re going. I said to our CEO that I will not throw bodies at a number just because we got a ton of funding.

We need to understand how we can be successful and map our priorities the right way. We’re still in the learning and growing phase. I spend most of my time coaching and listening to calls with my sales team to identify what our process is going to be. We’re starting to see more mid-market companies raise their hands.

Sam Jacobs: How are you thinking about building infrastructure as you hire the actual closers?

Michelle Pietsch: I hired a head of RevOps in June when I only had three sales reps at the time. The idea for her role is to understand our data and put the process in place for Marketing Ops, CS Ops, and Sales Ops so we can figure out where to focus, as opposed to bringing in a bunch of sales reps.

It’s really important to hire Sales Ops/ Rev Ops early on because you’re basically guiding light. They’re who I spend most time with to put the mechanisms in place. Without the actual tools needed in order to understand top of funnel metrics, top of funnel data, CS and customer success data, you can’t figure out where to go without that.

For the sales side, I hired an STR team earlier than I normally would as well. That’s for us to penetrate the market and get as many hands on leads and contacts as possible. It’s a one-to-one ratio right now, which you don’t typically see this early on.

Effectively coaching reps for improved performance [16:40]

Sam Jacobs: What are your keys to effectively coaching reps that drive improved behavior and performance?

Michelle Pietsch: It’s best to understand what the reps are doing every single day. What’s getting in their way, what’s working, what’s not working. Listening to calls and identifying coaching opportunities for each individual rep.

It’s important to figure out what they’re spending their time on. Figuring out how you can minimize that noise is really important. Build their trust in your ability to help them, especially when you’re identifying areas of improvement in their process. It’s really just about listening.

Improving the discovery process [18:57]

Sam Jacobs: You mentioned one thing that always bears improvement is the discovery process.

Michelle Pietsch: You’re 100 million in revenue. You’re crushing it. I guarantee there are reps that are still failing at the discovery process. I’m spending a lot of time listening to calls, to dig deeper and identify what I call a golden nugget. Discovery is super important to identify how you can position the value of the product, how you can actually help your prospect. Reps need to always be working on discovery. Even your top reps get super comfortable because they’re your top rep, they start to skate over some questions, and they miss the pain. They can’t tie value back. It’s something that I will always be working on with my team.

Sam Jacobs: You hear reps on the phone start asking so many questions and they lose the thread somewhere in the middle of the conversation. They’re not sure how to take the answers and tie it back to value. How do you coach people on that?

Michelle Pietsch: Less is more if you dig deeper and then identify answers in our demo. Once you get one thing really early on, stop there, ask a few more questions, know that you have ammo at the end of the call or the sales process to throw back at them.

It’s practice makes perfect and identifying, what else could you have asked with this one metric? Ask two or three more open-ended questions and then go to the part of our platform that ties back to that. People don’t want to be on a pain funnel call for 50 minutes where you’re drilling them with questions. You lose them in the demo because people’s attention spans are short.

Paying it forward [25:10]

Sam Jacobs: We like to pay it forward and figure out people or ideas that have had a big impact on your life that we should know about.

Michelle Pietsch: My previous CRO Josh Allen at Drift was a great mentor. He was one of the first leaders that provided feedback. We helped one another grow and learn. One of my favorite books is Patty McCord, Powerful. That was an awesome book — it ties back into what I’ve dealt with a lot with startups and the mentality of the employees from early on.

Sam Jacobs: What’s the best way to get in touch, what’s your preferred method of contact?

Michelle Pietsch: LinkedIn, MichellePietsch@Dooly.com

Sam’s Corner [27:01]

Sam Jacobs: Hey everybody, Sam’s corner. Michelle Pietsch is a talented early stage sales builder, and revenue leader. She’s at Dooly, and inherited a situation where they’ve raised $80 million, yet they’re early stage. With $80 million comes very high growth expectations.

Michelle has made smart decisions. The first is that she’s invested in infrastructure in the team first and foremost. She only had a small number of reps, yet she hired a head of Revenue Ops as one of her big hires, only a month or two into her journey there.

Secondly, she hired a bunch of SDRs. Instead of hiring 20 reps, they’ve got a one-to-one ratio. She’s creating demand through SDRs, focusing on creating infrastructure scalability. You’re going to have a smaller number of reps that feel supported. They’ve got infrastructure, they’ve got demand generation, and SDRs creating opportunities and leads. They’re far more likely to be successful.

She’s doing it the right way. Focus on creating demand, opportunities, and infrastructure through Revenue Ops. Then build out the sales team with scalability in mind.

Before we go, we want to thank our sponsors:

  1. Outreach. Save your spot at summit.outreach.io
  2. Pavilion. Apply today at joinpavilion.com
  3. Demostack. Accelerate revenue at demostack.com

You can email me at sam@joinpavilion.com. Talk to you next time.

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