Episode Summary
In almost all companies, there are top sales representatives who are also capable of leading teams and achieving excellent results in their field. They not only know how to position the company and create qualified potential clients, but they also have the skills to build trust within their teams.
But most sales representatives do not know how to reach the position of a leader (even if it is handed to them), and they are often afraid to take the next step. Should I ask for a promotion? Am I even ready for that kind of responsibility?
In this episode of Taking the Lead, Christina Brady welcomes Michelle Pietsch, the VP of Revenue at Dooly. Christina and Michelle get into how to get to your desired position and advance in your career and emphasize that the most important thing is to work meaningfully on your development path.
Guest Profile
- Name: Michelle Pietsch
- What she does: Michelle is the VP of Revenue at Dooly.
- Company: Dooly
- Noteworthy: She's an experienced Vice President of Sales with a demonstrated history of the building, scaling, and developing sales teams for fast-paced growing startups. She has experience in building high-performing sales teams; hiring, coaching, developing, and motivating sales teams; implementing sales process and strategy; and consistent revenue growth.
Key Insights
- A deliberate step in your career is always a step forward. Michelle believes that every well-thought-out step, even though it may be a step back, is a step towards success if you know what you want to achieve. She’s taken this kind of risk twice. "Especially my move to Datadog because we were super small, with only 13 employees at the time. And we were in a new space trying to sell this new idea and product. We had really early success, but being an account executive, trying to sell something new, is extremely scary. I had so much success in my previous role as an inside sales manager, but I looked at the founders, and I looked at the opportunity to grow the team and told myself that I will do it again. I will be able to prove that I have the ability to not only be a top sales rep but also lead a team again."
- It's vital to take on opportunities. Michelle is a successful VP of Revenue, and her career shows that her work is exemplary. But that doesn't involve working more, but working meaningfully. "Identify areas where you can have a positive impact within your team or organization without having to be asked to do that. And that is what I have done. I have also had unbelievable leaders on my team that did that. I promoted them to those roles because I didn't ask them to take on working on our sales methodology or process. They just identified an area that we needed to improve, and they ran with it without me asking them to do it."
- It is not shameful to take a step back in your career. When you take a step back in your career, you may feel embarrassed. According to Michelle, you have to have an internal drive to understand what you need to do to get back to that level, or even higher, and understand why you're making a move in the first place. "So for me, looking at the product itself and the founders and who I'm going to learn from [is important]. Are they going to coach me? Will they challenge me? Can I check off those boxes and feel confident that ‘Yes, I will learn. I will be challenged. I will also grow as an individual, not only in my career but in anything that I learned throughout this step-down. I will be able to take it to another company and get back to the level that I was at.’"
Episode Highlights
The Non-linear Career Path
“I started as a BDR at a startup, right out of school. And I did the grunt work and was qualifying meetings in a space that we really didn’t know, or we were creating a category, and then a new idea. So it was really a lot of experimenting and trying to understand how to position this company and also create qualified leads and then ship them over to the sales reps.
[…] And then I decided to leave that company after five years, which was super hard because it was basically my first role, and I moved up very quickly. And I went back to an individual contributor role, which a lot of people at the time thought was crazy because I had been a manager for three-plus years. And I did that because there are only 13 people in the organization. This was Datadog. […] Nine months later, I was promoted to a director because we had a business need, and we were growing.
[…] I was at Datadog for four years, and I love the startup space. They’ve plateaued; it was a well-oiled machine, I was getting bored, and so I jumped to another startup. Again, I don’t want to say I took a step down, but I went from AVP to the Senior Director of Sales at Drift. […] Totally out of the blue, I got promoted to Vice-President of Sales again, without raising my hand saying, ‘Hey, can I have this or I deserve this, or can I interview for this?’ And with that, with every promotion and change in my role came a lot more responsibility. And that was my role at Drift. And I am now VP of Revenue at Dooly. So I have worked at very fast-paced and very high-velocity startups, and built out their sales.”
Identifying How to Place an Individual or How to Transition Them Into the Right Position Is Very Important
“That’s another conversation or multiple conversations, in fact. Okay, they’re great at this role, and they know the company. It wasn’t really their fault that we ripped them out of their position and put them into the position that they shouldn’t have been in, in the first place. So let’s make sure that this is a smooth transition. Also, how you handle those difficult conversations reflects on the upper management team because people want to be respected. They want to make sure that they feel safe in their role. Not just the managers but also the reps.”
Your Progress Depends on the Business’s Need As Well As Your Performance
“Just because you have one great month in sales doesn’t necessarily mean you need to be a director of sales, all of a sudden. And it’s really hard for some people to grasp that we need to see repeated success. It really depends on the stage and the company. But the beauty of working at a startup is that we have a number of opportunities. The business needs you to grow within your career. But there are guidelines. So I just put together a career path with specific levels, and it’s really metric-driven. And once you hit those metrics, there are other aspects of that career path and more responsibilities that I want you to take on before we have the conversation of getting to the next level. I know right off the bat if someone is going to be a senior account executive or manager, more specifically manager and team lead. There are specific traits that I look for early on, like in your first few months, because it depends on how you handle a lot of change and stepping into a new organization, how you handle identifying people to talk to, and the onboarding process.”
Different Motives for Promotion
“I’ve had two different conversations with people. ‘I want more money; I don’t care about the title’ and ‘I want a title; I don’t care about more money.’ More recently, it’s ‘I just want the title. I don’t even care about it.’ They just have this idea, ‘I need to be in a director role, or I need to be an inside sales manager by 28.’ Okay, but I can’t get you there. But you know what? We’re leveling everyone up, and here’s a bump in your salary.”
