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“We need to support the movement to expand growth in science and technology beyond the traditional male audience”

Lessons in Leadership with Joe Karbowski, CTO and COO of Asure Software


Lessons in Leadership with Joe Karbowski, CTO and COO of Asure Software


I am super excited to see the continued emphasis on growth in science and technology beyond the traditional male audience. Seems to me like the fastest way to double the intellectual growth of our planet is to open it up unfettered to 49.6% of the population.


I had the pleasure to interview Joe Karbowski. As CTO and COO of Asure Software, Joe focuses on using the best technology approaches that allow our solutions to sit atop the industry. He joined Asure in 2012 when the company he co-founded was acquired by Asure. Joe has also served as Director of Development at ERP vendor CMI. With more than 25 years of experience in product development and management, Joe shares his expertise to bring enterprise-scale software solutions to market. He is a featured speaker and has published numerous articles on software development techniques and methodologies. Joe earned a BS degree in Computer Science from Michigan Technological University, Houghton. While Joe may be a tech head, he has an artistic side to him as well. He can often be found playing percussion with his wife, recording artist Angela Josephine. When not pounding out code or a wicked beat, Joe and his wife can be found traveling the world, bagging state high points and finding fabulous local fare.

Thank you so much for doing this with us! What is your “backstory”?

I was a huge sports fan growing up and spent every waking hour outside playing whenever the weather allowed. I’d get on the landline or my bike, doing whatever was necessary to organize the neighborhood games. My Dad called me the “Lone Arranger” because I was constantly fitting activities into any available time slice.

I suppose it was only natural that I’d create a software scheduling product. The first iteration was “O.A.R.S. — Office and Administrative Resource Scheduler.” This was the early 90’s when one person owned the conference room calendars in a book on their desk. Coordinating a meeting would mean calling my colleagues from my office phone or sending an email using Eudora (the email client back then); I would then walk over to the book and, if the room wasn’t available, it was rinse and repeat, ad nauseam. I wrote OARS on my own time for personal sanity and put it up on Compuserve as a client server app. I don’t remember how many copies I sold, but there were some decent sized companies that took interest. Someone at (then) Smithkline Beecham commented, “You aren’t charging enough for this,” which lingered in the back of my mind.

Fast forward a few years to the late 90’s. Jeff Roof, a former co-worker and Michigan Tech alum and I were looking for something to do. We thought, “This Internet thing has legs”, so we turned my client server OARS app into a web product called Resource Scheduler and hung out our dot com shingle. I’d love to say we knew what we were doing, and though we did many things right, as with most startups it was more about hard work and fortunate timing than personal genius.

We put a decent amount of time into our web presence (such as it was back in the day), and generated orders and interest well in advance of product. That made for an intense period of software development. We were using Agile before we knew there was a Manifesto, creating an MVP (Minimum Viable Product) and used early buyers to fund co-development of features and new versions. Sort of text book today, but back then it was all new, at least to us.

We had some great early clients, including MSNBC, Chevron and Proctor & Gamble — still a client today. It is kind of cool, that the little OARS Compuserve shareware download turned into Resource Scheduler, which is ultimately part of the backbone of Asure’s Digital Workplace platform in use in over 80 countries today. Combined with our Time & Attendance, and HR/Payroll solutions, we are excited about enabling more workplaces to become the adaptable environments that attract and retain top talent.


Can you share the funniest or most interesting story that happened to you since you began leading your company?

Two years ago, a group from Asure rang the opening bell for Nasdaq. It marked a transition for us, from our past products and strategies, to our go-forward vision. I don’t think I fully appreciated what the experience would be like beforehand. Put on the suit, take some photos — part obligation, part fun (as much as an introvert can have in such circumstances). But the folks at Nasdaq really made it a special experience. The energy and orchestration were fantastic, and there is nothing quite like seeing pictures of you and your peers, multi-stories tall, displayed in Times Square. Well-placed motivators like that can move the needle for an entire company.

What do you think makes your company stand out? Can you share a story?

I was recently in London for a conference / customer tour talking about the Digital / Agile Workplace. We were high up in one of our client’s buildings, looking out over Canary Wharf, where you can see all of the buildings branded with the logos of their respective owners. The individual we were with said “See all of those companies out there? We are all competing for the same employee — how do we make our company stand out?”

That moment validated our decision to transition from a Scheduling solution to HR/Digital Workplace. The job market is tight globally — companies are really fighting to draw in and retain the best talent. They need a partner to help make that a reality, without building it from scratch. I want to save companies money with our technologies, so they can ultimately invest it back into their employee base and communities to create the best possible workplace.


Are you working on any new or exciting projects now?

I kicked off our recent customer event by doing an Amazon Alexa demo, integrated into our AWS backend platform. While that isn’t perhaps groundbreaking, I then went on to share about what we think of as “AI.” I look at it as Actionable Information vs. true Artificial Intelligence. Employees are really expecting the same kind of ease of use technology in the workplace that they have access to in the consumer / retail world. Voice recognition. Intelligent recommendations based on patterns. Where is my co-worker at so we can collaborate on this project? And employers to want to better understand their employee base, whether to nurture and grow strong staff or identify at-risk employees.

What advice would you give to other CEOs or founders to help their employees to thrive?

As a leader, your personality will permeate the culture of the organization. You got to where you are through intelligence, hard work, and treating others with respect. It’s important to remember to always be authentic, honest, and fair — if you can do this, people will continue to believe with you and work with you to accomplish a mission.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are many, many people that come to mind. My wife for sure. All of the teammates I’ve worked with over the years — it takes a village. Jeff, noted above as we started the company together. My current CEO, Pat Goepel, has been immensely helpful in helping me navigate from the domain of a smaller software company to what is now close to $100m public company — I can’t thank him enough.

One thing I remember as clear as the day it happened 40-ish years ago… My Dad was driving my cousin and I to an abandoned ski hill where he’d drop us off to go sledding for hours. We were in the back seat being obnoxious adolescents — making fun — and our comments made my dad very upset. He said, “You can’t put yourself up by putting other people down.” He didn’t get mad often. That observation has remained with me to this day and is part of who I am.

How have you used your success to bring goodness to the world?

This is a very interesting question because one of our employees brought this up on a team call the other day. Whom are we serving? We do feel as a company the need to serve Clients, Employees, Investors and the Community. I remember reading one of your interviews and the gentleman said ultimately you have to pick one (paraphrased). Perhaps true, but I would like to see the “Community” as a priority constituent of every company out there, if not in the product it creates, then via paying it forward in some fashion, direct or via employees. If any company is not thinking about Community as part of its values, I do think they are going to have trouble hiring in the future. Potential employees make decisions on more than just money.

Our VP of HR, does a great job creating employee programs. Asure uses gamification and incentive packages for employee well-being and healthy choice programs. We have a current step challenge program, and I think about one-third of the company were signed up for teams in a week. That is great participation! With that said, sometimes it is harder to get Engineers to participate in such activities. To that end and true to my inner nerd, we are also doing something in one of our Engineering offices to eliminate waste and improve health. In a “Make Magazine” like effort, we are going to build out our own flavored seltzer water machine. Cuts down on cans/plastic, and replaces perhaps more frequented sugar drinks with a healthier alternative. Assuming that succeeds, we’ll role it out at the other sites. John Pickard, one of our senior developers, is helping with this — the same guy that organizes our bi-weekly barbeques and monthly board game night. Work hard, play hard right?

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why.

Half vs. Half-Assed. I first saw the phrase in Jason Fried’s book (the quote was actually “Build half a product, not a half-assed product”), but we’d been living it already with our Resource Scheduler development. It dovetails with the MVP product philosophy — don’t over-engineer what may or may not resonate with your target market.

Trust but Verify. I have to admit, this one has been a little painful. Intrinsically, this is something I have done throughout my career, both as a software developer and as a leader of organizational units. As our company has grown, noise and competing priorities have shown their potential to disrupt work. Not intentional. Not political. Just human nature. So… trust your teammates to do what they say they can do, but always verify.

Numbers Matter. Moving from a private to a public company has been able to provide opportunities on any number of fronts, and has challenged my competing duality of Cynic and Learner like few other experiences. The Cynic in me is perplexed at the market perception of ours and other companies, having a seemingly arbitrary report card handed out on a quarter by quarter basis. Why is three months a magic number? Executives don’t become incompetent in 90 days and visions may take time bake. Products don’t obsolesce that quickly…. However, the Learner in me has come to respect and understand more about this interesting subset of the corporate world. There are over 4,000 public companies in the U.S. and the world is no longer flat. Markets. Technology. Everything is within reach, and there is no shortage of content by which to satisfy one’s bent to invest. So, numbers matter — they are the only language the broader audience has time to consume.

Failing is Still Failing. Not sure where the line is here, but you need to intuit the difference between the en vogue “Fail Fast” vs. the pedestrian “Sure but Steady.” The inertia in pivoting a $1M vs. $10M vs. $100M vs. $1B company is not the same. Perhaps the old saying of measure twice, cut once, is applicable no matter what size company, and if you do fail, that is ok — just take stock and learn.

Talent Matters. Sometimes you can’t always promote up. In the same way you may, from a product development perspective, “buy vs. build” or utilize a third-party in order to achieve time to market or domain expertise, you will need to do the same with your strategic hires. This should not be perceived as a slight if you’ve taken the time to develop strong communication with your team and everyone is striving towards the same goals.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I am super excited to see the continued emphasis on growth in science and technology beyond the traditional male audience. Seems to me like the fastest way to double the intellectual growth of our planet is to open it up unfettered to 49.6% of the population.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s easier to ask forgiveness than it is to get permission — Grace Hopper

Or some similar variant. Point being, a bias towards action is going to lead to either success or learning opportunities. Inaction can have value to be sure, but there is definitely a correlation between the 2014–15 Golden State Warriors being the only team to average over 100 possessions per game and their future success.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the U.S. with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this 🙂

It’s funny, my wife is a singer-songwriter and just had a similar question in one of her press questionnaires and we discussed how we struggle to answer questions like that. Favorite three people, living or dead. One person to have at your birthday party… It’s not that I am aloof or uninspired by others, it’s just that the years have convinced me that I need to pay attention and learn from whomever I am with at the moment. So what’s for lunch, Yitzi?

Originally published at medium.com

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