Larry Hipp of Brightwell: Five Things You Need To Be A Highly Effective Leader During Uncertain & Turbulent Times

Fintech company Brightwell's CEO Larry Hipp stands in a conference room, smiling right at the camera. He is wearing a light blue buttoned shirt and gray blazer.A person holding a tablet with icons on it.

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 Larry Hipp of Brightwell.

With more than 18 years in technology and product development, Larry serves as the CEO at Brightwell, global payments and financial service provider. As an experienced engineer, consultant, and sales manager, Larry has a proven track record of delivering digital products and leading groups to success.

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?

I started my career as a software engineer. It was my first job out of college and it just so happened to be in the banking industry. I was writing check imaging software at the time. It’s hard to remember now, but 20 years ago it was a novel concept to be able to see a check online.

From there I found my way to developing and leading teams to create software involving core banking, retail bankings, fed clearing, stocks, bonds and now cross-border payments at Brightwell. About the only financial products I haven’t worked with are gold and crypto and I have a feeling that one day crypto will be in my near future.

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?

During one of my early executive roles I had one of the most embarrassing days of my career. To fully grasp the horror of this story you need to understand Slack and GIFs. Slack is a chat tool used across many companies for internal communication, and GIFs are often funny animated images used to communicate humor in a text based world.

One day, I wanted to send a GIF to a chat channel of Loki from Guardians of the Galaxy putting his head in his hand in shame — but shuffle was not a feature option at this point in time. To share a GIF, you had to keep posting them in Slack until you found the one you wanted. I searched and searched for the perfect Loki GIF and for some reason I keep getting the wrong thing (ie. GIFs of Nicki Minaj rap videos, etc.)

I thought I was posting the GIFs in a private channel to myself, but in reality I was sending dozens and dozens of gifs to our company wide announcements channel, in the middle of the workday! Realizing my mistake, I quickly deleted the GIF spam and apologized but my team (rightfully) never let me live that one down.

My takeaway is you’re going to inevitably do something that makes you look stupid in front of others, but you have to roll with it and be able to laugh at yourself and the situation.

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?

When I first started writing software I had a manager named John. He was an experienced, professional software engineer and he took me under his wing to learn how to build business ready software. He taught me that complex software systems can’t be built all at once, they require breaking tasks into smaller pieces and assembling the pieces once you’re sure they all work individually.

This concept has lived with me since the day he taught me how to use it. Breaking tasks into smaller digestible pieces and reassembling them to solve complex problems is a framework for software, business and life.

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

Brightwell has been in business for 13+ years and has transitioned through a couple of different missions along the way. Like most businesses, prior to our user centric journey we were focused on the bottom line for us and our customers –but six years ago, that all changed.

Our “purpose driven” change was driven by building empathy for and understanding of the humans that use our product, most often they are migrants needing to send money back home to their families around the world. Our users are the most selfless and hard working people who have made the ultimate sacrifice to leave their home country in hopes of greater financial opportunities.

Turning our focus on solving their problems was truly transformation in our company, and that human/user centric element is now incorporated into everything we do.

Over the years, our core value of “Users First” has guided us into making difficult decisions and choosing what is best for our users instead of our bottom line. In turn, the trust we’ve created with them has helped Brightwell to become the leading product in the market.

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?

When the pandemic hit in 2020, I was appointed the CEO of Brightwell.

At the time, Brightwell’s only product helped to manage the global payroll distribution for some of the biggest names in the cruise industry. So when the industry came to a halt, so did the company’s revenue.

It’s hard to describe the level of uncertainty our teams were facing — our employees were worried that they wouldn’t be able to keep their jobs and we were all wondering how long could we last without the cruise ship industry running. Thankfully, our company already had a strong culture — we knew the days ahead would be very challenging but as a team, we banded together for our users and our colleagues.

This was one of the toughest times in my career, but our management team remained as transparent as possible and held ourselves to the promise that we were going to make it to the other side. While the cruise industry was shut down, we focused our attention to the future, went into R&D mode, and came out of the COVID-19 era with two new products, Arden and ReadyRemit, and additional markets for the company to do business in.

Those two years are the proudest of my career. The level of sacrifice and commitment from the team to not only hold the line throughout the cruise shutdown, but also build for the future, will always be a special moment in time for Brightwell.

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

If my wife were to answer this question she would probably say my biggest fear is failure — but for me, failure isn’t an option. This isn’t to say everything is always perfect — things fail, but that is when we have to regroup and start again. Ultimately, failure isn’t an option if you keep pushing forward.

I’m an author and I believe that books have the power to change lives. Do you have a book in your life that impacted you and inspired you to be an effective leader? Can you share a story?

If I had to pick one universal book on leaders, teams and perseverance I would recommend The Five Dysfunctions of a Team by Patrick Lencioni. One of the quotes from that book that fundamentally changed my perspective on leadership is: “If you could get all the people in the organization rowing in the same direction, you could dominate any industry, in any market, against any competition, at any time. ” ― Patrick Lencioni

The core concept that company culture is a leader’s responsibility and that when you can reach the highest level of organization your teams will be stronger than competition with more people, money and advantage is now a core part of my leadership strategy.

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

Communication. When times are challenging, people are often anxious about what is coming next. A leader should always clearly communicate what is happening and the potential outcomes with their team. In my experience, being authentic and real is the best way to move through challenging times.

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?

Uncertainty is inevitable. But the ability to boost morale during these times starts way before the uncertainty occurs.

A strong company culture with a defined “why” or “north star” is a prerequisite for success. If your team is all rowing in the same direction, or has the same “north star”, everyone will be focused on the end goal.The motivation becomes less about inspiring words from the leader, and more about everyone in the company pulling together for the benefit of the team.

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

Be direct, be out front, and be authentic. Most people can decipher corporate speech — and once we hear it, we automatically shut down because we know we’re being “worked”.

Whether you’re delivering bad news (ie. lost a big deal, missed deadline, etc.) or owning up to a mistake, in my experience it’s always best to be direct, take ownership and move towards improvement.

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

“Everyone has a plan until they get punched in the face” — Mike Tyson.

The path from A to B is always riddled with unexpected problems. It’s important to anticipate issues and be cognizant that they are an inevitability.

At Brightwell we often use the term “asteroids” to refer to problems that we can’t see yet. But knowing that the asteroid is heading our way, and once it shows up, the team is ready to respond quickly.. There is no delusion that the path to success will be smooth, but anticipating that asteroids are already on the way ensures you will be prepared when they show up.

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

Build a strong company culture. The stronger the culture, the stronger your team will be to weather the ups and downs. Company culture doesn’t just happen organically — and it’s more than a pizza party a few times a month. Culture must be a top-line management priority for an organization to be successful.

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?

Some common mistakes I see are:

  1. A lack of roles and responsibilities. Without clear roles and responsibilities, people tend to start politicking vs. fixing the problem. Leaders must be sure to plan ahead and assign roles to their team members to prevent distraction.
  2. Taking too long to react. Fear of making the wrong decision can be crippling — but if you don’t start, the problem often worsens. As a leader, you have to take the best information you have and jump in.
  3. Not communicating with your team. People want to hear from the top leaders in any organization. If you’re not upfront and transparent with your communication, the team may doubt your ability to lead them to success. Always be honest and proactive with your team.

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.

Build a solid company culture foundation

The most important thing a business leader can do is build a resilient company ahead of a turbulent time. With a strong company culture, core values, and mission, the hard days will be a little easier.

Solve for X

When a complex problem emerges, it’s often overwhelming to understand how to get to the other side. In my experience, breaking complex problems down into smaller, accomplishable pieces is the best framework for success. Focus on the things you can control, and build yourself up towards a solution.

Take ownership of the outcomes

Leaders own the outcomes on the way up and on the way back down.

Oftentimes, leaders want the credit when things are good, but pass the blame/responsibility down the ladder when things get hard.

If you’re on the way down, step out front and acknowledge the issue. Don’t be afraid to acknowledge you don’t have all the answers yet, but do acknowledge that you will do everything you can to solve the problem.

Communicate effectively to your teams

During turbulent times, clear communication is critical. If the leaders aren’t providing information, people will fill in the gaps with their own assumptions or rumors. Establish a communication cadence that your team can count on for the next batch of updates.

Celebrate wins along the journey

The path out of uncertain times often has many ups and downs. It’s easy to always focus on the lows, but remember to take the time to celebrate and communicate the small wins along the way.

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

The legendary former CEO of General Electric, Jack Welch, famously said: “There’s no such thing as work-life balance. There are work-life choices, you make them, and they have consequences.”

The idea that work-life balance was a choice changed my entire perspective on work. Work-life balance is a dial that can be turned up or down based on the outcomes you are seeking.

Ready to start a family? It’s ok to turn the dial towards life. Want to go for that promotion? It’s ok to turn the dial towards work.

It took me years to realize that a 60+ hour work week is not how it “has” to be to get ahead. Figuring out what I wanted at work and tuning the balance dials to match the season of life I’m in has created a much healthier relationship with work.

When I give leadership coaching advice I often quote Jack Welch:

  • What do you truly want from your work/career?
  • What do you want in your personal life?
  • Turn the work-life balance dial to match your goals.
  • Understand what you are trading off and sit well in that decision.
  • Reevaluate the dials often and don’t be afraid to return the dial to your new perspective of balance.

How can our readers further follow your work?

You can follow me on LinkedIn, or tune in to Brightwell’s website for company updates.

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

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