Taking It One Day At A Time: Introducing Jacob Stelmack

Sky Inc
5 min readMay 19, 2023

Growing up, our team member Jacob Stelmack dreamt of being a truck driver. Like his dad, he wanted to drive across the country and live out his dream. At twenty-five years old, his dream has shifted, but his desire to follow his dad’s advice hasn’t.

“One lesson my dad taught me was to be cultured. No matter what, no matter where I end up, no matter who I become, he said to be cultured. Be a person that people can look to for answers, guidance, and culture.”

Starting here at Sky Inc this past June, Jacob has put all his energy into thriving in our Management Training Program. His adaptable mindset and natural team-oriented personality have aided his growth as a salesperson and leader, making him an asset to our business and his colleagues. Today, we want to honor this Chicago native’s grit, consistency, and determination with a Q&A session geared towards shining a light on his winning attitude and goals!

Jacob, you have a lot going on right now. Between hitting your stride at work and preparing for your wedding this October, you’re juggling a lot. We’re thrilled to be a part of this exciting chapter in your life and are eager for readers to delve into how you manage to continually hit the mark in and out of the office.

You attended Illinois State University with plans to teach high school history. While it’s clear that you enjoy working in sales more, how did your college experience change you for the better?

My college experience changed me by bringing accountability into my life. If something needs to be done right, I need to do it myself.

With the goal of working in our industry long term, we’re interested in learning more about your leadership style and how you plan to inspire others.

My leadership style consists of creating personal relationships. If I’m going to spend the next couple years of my life setting myself up for success, setting my finances up for success, then I have to have friends and not just coworkers.

What a great thought! Speaking of coworkers, when meeting with interview candidates, what qualities are you searching for?

Work ethic, manners, and honesty.

While you are clearly a wonderful leader focused on helping your peers thrive, let’s switch gears slightly and talk about your growth journey. How do you handle criticism and constructive feedback?

Criticism is a necessary effort to not only grow as a leader, but it has given me the opportunity to grow in all aspects of my life. When it’s done correctly, the difference between offensive and critical conversations is obvious.

“Never settle. I let Jonathan know, even in my interview, what my expectations were of this career. I wish more people wouldn’t settle. The power of one more — one more interview, one more attempt, one more risk, can get somebody on the right track to earn everything they’ve wanted out of life. I didn’t settle.”

What drew you to work with us?

What drew me to the company was the opportunity to surround myself with the people I strive to live like. Being around Jonathan Perry every day is a blessing that will help guide me into many years of success.

Tell us about your favorite thing about working at Sky Inc.

My favorite thing about the company is the culture. I told Jonathan in my interview that if there weren’t a good culture, I wouldn’t work here.

Share some insight into your short-term and long-term goals.

I’m a huge planner. I use a planner to rate my emotions every day on a scale of 1–10 based on many factors. They consist of family, friends, freedom, and career. It also helps me list the actions I can take to improve in any of those options that are lacking. Short-term goals involve opening an office in another market. Long-term goals involve owning my own mechanic shop and eventually franchising it. The “mechanics” of the opportunity for my repair shop are there. Now I just need to get the capital.

We know you deem your relationship with your fiance, Keegan, your greatest accomplishment. It’s also clear that on top of being the best partner, they also serve as an unlimited well of motivation.

“My greatest accomplishment in life was finding my fiancé Keegan. I found someone who puts up with me, my schedule, and my shortcomings and failures in the last six years. I found someone who celebrates me, who celebrates my success and puts me at the top of the world when I don’t even deserve it.”

We are sure that it was your extrovert personality that piqued her interest, but it was your good heart and drive to succeed that contributed to your relationship’s success. Just like you did with us, it’s your effortless ability to connect with others that sets you above the competition.

Who inspires you?

Until I had this career, it was me who inspired me. I’ve been on my own since I was 17, and the things I’ve accomplished are second to none for people my age in my position. Now, Jonathan Perry inspires me the most. He’s the perfect example of success without corruption. Success with morals. Success with everything I stand for. If I need anyone to set an example in and out of the office, whether it be for me or my peers, it’s Jonathan Perry.

How do you measure your rate of success?

Everything is a game that can be won or lost. Coach Tom Thibodeau, former coach of the Chicago Bulls, said he couldn’t stress it enough to take things one game at a time. Having that mentality eliminates anxiety, depression, and the thought of “what if” after a bad day. The Compound Effect is one of my favorite books that I’ve ever read. The smallest actions daily may not look like success, but stacking those actions over the course of a year, ten years, or twenty years will make success look like it happened overnight. It’s going to be the best feeling ever.

Jacob, we are thrilled that you chose to interview with us last summer and decided Sky Inc was the perfect fit for your professional journey. You are a shining example of what happens in our business when you are willing to put in the work to produce great results! Thank you for all you do. Here’s to making 2023 the year you level up your career!!

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Sky Inc

Nashville's face-to-face marketing experts since '07. Integrity-driven campaigns, partnering with the largest US telecom. 10+ years of expanding success.