Ed Roshitsh of Brightfin: Five Things You Need To Be A Highly Effective Leader During Turbulent Times

An Interview With Fotis Georgiadis

Practice extreme ownership and accountability for what you control as a leader. No, you cannot control inflation, or supply chain challenges, or what your competitors are doing, but you can control your response or strategy to take advantage of the opportunities.

As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Ed Roshitsh.

As a senior software company operational executive, Ed Roshitsh has helped create two billion dollars in increased shareholder value for six successive PE portfolio companies: Blackbaud, Vertafore, Granicus, Intelex, PointClickCare, and Dude Solutions. Over the last 20 years, Ed has built and coached high-performance teams that have increased sales, revenues, and profits. As well as being an operating executive, he has board experience and currently sits on the advisory board of a Bay Area SaaS SW company. Ed is also an active angel investor with investments in three start-up software companies. In addition to his role as CEO of brightfin, Ed also serves as Founder/CEO of Holidays for the Heroes, a 501c3 that sends active duty service members home for the holiday season through the contributions of patriotic donors. Holidays for the Heroes has helped hundreds of active duty heroes get home.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

First, thanks for being interested in brightfin and my story! The core of my story is that you are likely interviewing one of the luckiest people professionally that you will ever meet.

I grew up in northeast Ohio during a horrible recession. The lack of opportunity at the time as I was graduating high school pushed me into evaluating the Air Force as an option. Reagan had fired all of the air traffic controllers, and at the age of 18 I thought that it sounded cool to land planes. When I got to basic training, I was surprised that I had been diverted into computer repair. If that stroke of luck had not happened, we would not be talking!

After five years in the Air Force, I joined a mid-range computing manufacturer as an engineer. I watched the sales folks coming in and out of the office living life large and decided that would be a great route for me. One thing led to another, and I joined a networking integration company as a sales rep, working my way up to running sales, marketing, professional services and support. Things were going gangbusters!

The next stroke of luck was taking a call for a recruiter for a role at Blackbaud. This role led to a succession of gigs in SaaS as an operator as well as board member. I am now on my second software co-CEO role at brightfin.

On the personal side, I run a lot, read a lot, and spend some time helping active duty military folks get home for the holidays with a 501c3 I started. I have a full plate. I also published a book a while back that got a little traction.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I guess it is probably cliche to ask, but how much time do you have to run through the list?

Probably the funniest mistake I have made was answering an email about what to do about an office romance and hitting “reply all” without seeing who was on the email chain. I made some really dumb comments about how awesome one of the parties was and could not believe that she was dating so and so. And, I did it using some descriptors that were not professional. Yep, you guessed it, she was on the reply all chain. I am not proud of that moment, but I learned from it.

The easy learning was to not do dumb stuff like that. But the bigger learning was that as a leading executive, I need to do better, be better, and set a higher bar for professionalism for myself.

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?

I have been so lucky in this aspect as well. Everything I do or think today had its genesis from a key leader I worked for or from something I read. I have not had one original thought!

That said, I had two key leaders that have influenced me greatly. My first sales manager and the CEO at Blackbaud at the time I was there.

One story I still tell is the story of the first deal that I lost while working for the first sales manager. I had put a ton of time in on a small deal. I thought I had dotted my i’s and crossed my t’s, only to find out that the prospect decided to buy the product from somewhere else for a few dollars cheaper.

I went into the sales manager’s office to break the news and whine about the unfairness of it all. I started talking, and my boss quickly turned his head back to his computer and started typing away. After a few minutes, without even looking up, he says, “You can stand there whining all you want, but my advice to you, son, is to get on the phone and find a (bleeping) prospect.”

Life advice masked as sales advice — you can stand there whining, or you can get busy trying to make it better.

It has stuck with me to this day.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

We are a bit unique as we were formed by taking three companies and combining them together over the last year. Our purpose as a company is to provide visibility, recommendations, and execution assistance to Fortune 2000 IT and Finance leaders using ServiceNow who are responsible for managing the complexities of mobile devices, fixed telecom and cloud. In short, we want to create IT heroes!

We talk about this vision and our key moves to get there nearly every day in some way, shape, or form.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

We have all been in the crucible during the last 24 months. Personally and professionally, these have been anxious times. Imagine combining three globally distributed companies during these last 12 months! I, and the leaders I am partnered with on this journey, have agreed to lead with transparency, trust, collaboration, dignity, a commitment to being “snow white,” and a few other principles we put in front of the company in January of this year as we formed it. We also invested in Table Group training to bring the executive leadership team together under a single operating system for how we would function.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

Persistence is something I must have inherited from my ancestors. I think I have learned more about resilience and constant forward motion in my years of Ironman competitions and ultra-marathoning than anything else. When you are three days into an ultra with another two days to go, you find ways to stay motivated. If I can just get to the next house or telephone pole I will reward myself with another swig of water. Those telephone poles keep coming until the race is over.

Business is 100% like that. Life is 100% like that.

What would you say is the most critical role of a leader during challenging times?

I think during tough times Chief Executives need to be Chief Communicators. Receiving and transmitting 24×7. Clarity of mission, talking about wins and losses, and pointing to the next hill need to be in a constant loop. Here at brightfin, I send out a weekly email, sometimes a weekly video, conduct bi-weekly AMA sessions, hold monthly Town Halls, and have been pushing good news through our Teams channel. Our entire ELT does much of the same downstream as well as communicating to the company with monthly department newsletters.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

There is a good chance I am wrong here, but I think one of the things teams look for in CEOs during tough times is consistency and frequent communications. My perspective is that cheerleading, false optimism, and faux cheerfulness is a thin disguise soon seen through by most. What folks really want to see is realism, empathy, focused communications, and enough humor to take the edge off.

What is the best way to communicate difficult news to one’s team and customers?

One of our 10 principles at brightfin is “bad news shall travel faster than good.” And we mean it. I think the best way to communicate bad news begins with early communications of the issue. I am pretty old school on bad news. Own it. Explain what happened, what was learned, and how it will be corrected. Don’t hide behind corporate speak. Just get it out there and try to change the next chapter of the story.

How can a leader make plans when the future is so unpredictable?

As Mike Tyson has famously quipped, “Everyone has a plan for the fight until they get punched in the mouth.” It is hard to make long-term plans when things seem so discombobulated.

My view, almost like ultra-running, is you break bigger themes into smaller chunks and then smaller again to fit various time horizons.

At brightfin, we have four ongoing strategic moves that will serve us over the next three years. Every quarter we break the moves into quarterly progress goals and then keep track of the quarter, monitoring each initiative through 13 weekly sprints. We communicate these goals and progress ad nauseum to the company in several ways each quarter.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

I think the biggest idea I have about this works for me in my personal life and professional leadership role. Only worry and think about what you can control. I want to be the best I can be in comparison with myself the day before, and I think about corporations that way as well. What do we control? How can we do this better? What do we do if X happens or Y happens in response? Spending one minute of time worrying about anything out of a leader’s control is a waste of time and would turn that leader into a paralyzed blob over time.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

  • I will answer that in a positive frame and what I think business leaders should do versus avoid. I go back to communications. Listen hard and double down on keeping folks constantly in the loop.
  • Secondly, treat people like adults. Sure, there will always be a small number that don’t reciprocate, but I think most people just want to be treated with respect.
  • Make it a leadership mantra to expose reality. Make it easy for people to talk about issues, concerns, challenges, and problems. Most challenges are just puzzles to be solved.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

This last year for our team and likely many teams has been a battlefield MBA course. We are all experimenting and trying to figure out how to operate in these strange times. Anyone who thinks they have it all figured out is delusional!

My view on strategies is to:

  • Establish and communicate clear goals.
  • Get close to your team. They need to see you in the pit with them.
  • Stay close to clients and understand them more deeply.
  • If you are backed by investors, stay in constant dialogue, and report the good, the bad, and especially the ugly with equal weight.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

I think the most important first step is to acknowledge and communicate exactly where you are as a business regularly and honestly to all of the stakeholders. People will make up things they don’t know about and what they make up is never good. So get it all out front and fast.

I also believe that during hard times leadership teams need to be able to be authentically empathetic. Your teammates at all levels of the company are experiencing life challenges beyond the workplace. High organizational EQ is a must in times like these.

Practice extreme ownership and accountability for what you control as a leader. No, you cannot control inflation, or supply chain challenges, or what your competitors are doing, but you can control your response or strategy to take advantage of the opportunities.

Be available. Be accessible. Don’t hide.

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

I think this quote is a bit long, but Roosevelt’s “Man in the Arena” quote is one I continue to go back to in business, athletics, and my personal outlook. I also love another Roosevelt quote “We must all either wear out or rust out, every one of us. My choice is to wear out.”

These two quotes have sustained me on 260 mile running races, having beer bottles figuratively tossed at me on the business front, and when faced with something in my personal life.

How can our readers further follow your work?

Probably the best way to keep track of me is on LinkedIn, both under my name and through my 501c3 Holidays for the Heroes alias.

Thank you so much for sharing these important insights. We wish you continued success and good health!


Ed Roshitsh of Brightfin: Five Things You Need To Be A Highly Effective Leader During Turbulent… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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