The Future of Sales: Leading with Levity and Authenticity

June 15, 2021

The Future of Sales: Leading with Levity and Authenticity

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The journey to leading sales at the executive level at a tech company is not always a straight path. For me, it started with facing my fears and then creating an approach to leadership that may be unconventional in the sales world.

Facing Fears

Early in my career as a young sales rep in NYC, I had to deal with some of the largest and most demanding clients on Wall Street. It was tough. And let me tell you, it was challenging. My boss noticed my nerves when it came to presenting at the executive level, and suggested I try Toastmasters – the usual cure for public speaking nerves. Never one to do things conventionally, I opted instead for stand-up comedy. There is no greater fear (or rush) than standing on a stage in a room full of complete strangers who are essentially daring you to make them laugh. While doing stand-up a few times was fun and a lifelong dream, I quickly noticed that I was not good enough to quit my day job. 

At its core, stand-up comedy is about being authentic and vulnerable while making people find the humor in that. Being able to show up and connect with an audience, while still being yourself, is such a fantastic thing. It changed my perspective on how to show up in sales meetings and eventually, influenced how I lead sales teams. 

Leadership Elements

My approach to leading the Sales Team and driving growth at Cologix is best summarized by lead with levity and authenticity. Here is what that means:

  • Find the silver lining in uncomfortable situations: Our profession is fueled by stress and high energy. Often, things do not go the way we plan, so it is important not to take ourselves too seriously all the time. Humor is a great way to break the tension between our teams, with clients or even with yourself.
  • Don’t do anything unnatural: I have been fortunate to work for and with some amazing people throughout my career. I remember one leader in particular who once said “let’s not burn the canoes.” What that means is don’t do something stupid that is going to jeopardize your relationship with a customer; instead, make decisions based on integrity. I’ve always led with an introspective lens of: How would I feel as a salesperson if I was being asked to do the same thing? If I wouldn’t be comfortable doing it, I wouldn’t expect or ask my team to do it.
  • Two ears, one mouth: Too often in sales, we think we have to do a lot of talking. But I coach my team to listen, listen again, and then listen more. Clients want to be truly heard.  When the Cologix Sales Team can do that, we establish trust with our customers.
  • Consistency in communication: Sales teams need to operate and communicate on a regular cadence. Nobody likes surprises. Especially during the pandemic, I have found that a consistent, weekly cadence of meetings, check-ins, and communication is extremely important.
  • Expect the unexpected: The past year of living through a global pandemic has driven home the need to be agile and flexible. When a roadblock pops up, adjust, pivot, and rely on your team.

The Role of Humor

I see the role of humor in selling not as an excuse to be the class clown, but as a way to connect with the client and the team. Remember my foray into stand-up comedy? The same principle applies when working with a client. Be authentic, be genuine, show some humor, bring some joy into the interaction to let the client know you are all human. I find a quick moment of levity during a stress-filled meeting or conference call can help bring things into perspective. We are all humans and make mistakes. The most important part is really how we, collectively, between the sellers and the client, work together to solve the problem at hand. All things can be resolved and it’s a matter of how we work together to accomplish this. Let’s not take things so seriously. Yes, we have numbers to hit and families to feed but at the end of the day helping to solve our customers’ business issues is the most important part of our jobs. The rest will take care of itself.

The Next Ten Years

The next 10 years at Cologix will be incredibly important as we continue to grow the business as well as the Sales Team. In the world of sales, leading with humor and authenticity are not common -but the world is changing. I see a shift in how sales leadership is viewed and executed, and I see the trend towards authenticity, humor and levity picking up speed. This means that I expect our approach to sales leadership to eventually become the norm, instead of the exception. We’ve been successful as a Sales Team thus far, and I predict we will continue to build relationships with clients, continue to meet them where they are headed and continue to offer world-class services and products, all while enjoying some levity as a part of the process.

I’m fortunate to have been able to lead the Cologix Sales Team for the past two and a half years and to have been able to share some humor along the way. The foundation of authenticity and trust that we have built with this team, combined with our approach to culture, and elevating women in leadership means that we have taken critical steps to set Cologix apart in the data and technology industry.

Together We Win

Together We Win is such a great approach to leading a team. To me and the Sales Team, it means: We don’t win or lose alone. Our Sales Reps – no matter the location in North America – all support each other. And our Sales Team is supported by Marketing, Operations, Finance, Customer Care, and many more of the Cologix team. There is confidence in the understanding that we are all in sales and we are all collectively working towards the same goal to solve our customers’ business needs.

by Chris Heinrich, Chief Sales Officer


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