Episode TwoHundredTwentyOne

Become a 4-Time Founder & Sales CEO

Guest: Erik Kostelnik, Founder & CEO of Postal.io

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About This Episode

What if you could have the best of both worlds?

Creative and competitive.

A sales CEO and a product CEO.

Online and offline.

I was so happy to be able to interview Erik Kostelnik, Founder & CEO of Postal.io, about channeling his competitiveness and creativity into being a sales CEO.

With an artist mother and inside business father, Erik grew up combining those two seemingly opposite traits.

After selling everything from power tools to job postings during recessions, Erik decided to launch his own company. “I got fed up with making other people rich, honestly,” he said.

Join us as we discuss the pros and cons of being a sales CEO at a tech company.

From sales to entrepreneur

“I would say salespeople are probably set up the best to succeed as an entrepreneur  by how much of your day as a CEO is bent in some sort of selling fashion,” Erik said.

Being a sales CEO might have been viewed as negative 10 years ago, but that viewpoint has undergone a significant shift.

Now, we like CEOs that are revenue focused and understand how to build and optimize the sales and marketing gengine.

Erik calls himself especially fortunate because he co-founded Postal with Jed Danner.

Jed handled the engineering/product side, and Erik took the business building side. It couldn’t have worked out more perfectly.

“It was really important for me to find a business partner that truly understood where our values were. It’s hard to go it solo as a sales CEO,” Erik said.

Tips for cofounders

  • Know your weaknesses. You’ll need to do some self-reflection to understand where you need to rely on someone else’s expertise.
  • Know their weaknesses. Your cofounder will need to be equally upfront about their own challenges, too.
  • Invest in the relationship. Get comfortable talking to this person every single day — and probably seeing them more often than your family.
  • Align your goals. Make sure you share the same business objectives and core values and that you communicate those to your employees.

Leadership insights for sales CEOs

Ego has been known to destroy companies (and cofounder relationships).

Erik said that Uber’s Travis and Wework’s Adam let their ego get to their game. On the other hand, he named Marc and Parker at Salesforce as a great cofounding partnership.

In other words, great leaders check the ego at the door.

A couple of practical tips for how to do this:

  1. Healthy work/life balance. There’s nothing more ego-squashing than family life — and that’s ideal for reminding you that you’re actually pretty powerless in the grand scheme of things.
  2. Challenging hobbies. Taking your sports or musical instrument seriously will help put your abilities in perspective (others will always be better than you) and motivate you toward self-improvement.
  3. An outward focus. You might have founded a company for any of a dozen good reasons, but right now, your employees’ livelihoods depend on you. “It should be all about the employees,” Erik said.

This isn’t to say that ego is all bad. Actually, a good leader knows when to be moderate and when to let the ego out.

“Sometimes you need to be the guy, right?” Erik said. “But you need to know when to be the guy and then when not to be the guy.”

Sales transformation

Erik founded Postal because of the problems and challenges he saw facing salespeople. 

Despite the technological advances of the past 20 years, given the amount of tech poured into solving marketing and sales engagement and automation…

“What we’ve seen is that 100% of that effort was put toward digital,” Erik said.

And that’s actually a problem.

“We’ve now reached this critical mass of digital communication,” he added. “How do we change that? For me, it had everything to do with pattern interrupt.”

Postal applies the automation of digital to make the offline world just as seamless. “Inside of outreach sequences and sales loft sequences, you can automate any direct mail, gift, email, or donation automatically,” he said.

Merging the online and the offline world is what’s going to define the future-minded salesperson. 

Erik’s 3 takeaways

  1. Know when to let people shine and when to shine yourself.
  2. Ensure that you’re surrounding yourself with trusted people who can do the things you can’t.
  3. Take some time off and contemplate what is important to you.

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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