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Josh Mallamud of Cartegraph: “Slow down”

Slow down. You generally have more time than you think. Sometimes you don’t, but those situations are very rare, in my experience. Uncertainty generally is reduced over time, so try to maximize optionality and don’t make immediate, rash decisions. Slow down and process what’s going on. Then, as time begins to show you the best […]

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Slow down. You generally have more time than you think. Sometimes you don’t, but those situations are very rare, in my experience. Uncertainty generally is reduced over time, so try to maximize optionality and don’t make immediate, rash decisions. Slow down and process what’s going on. Then, as time begins to show you the best path, feel empowered to make those decisions.


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 Josh Mallamud.

Attorney turned technologist, Josh Mallamud is a global SaaS veteran with over 20 years’ experience. As the CEO of Cartegraph, an infrastructure management software company, Josh and his team provide a comprehensive cloud-based software platform that helps critical infrastructure owners prioritize maintenance, spend smarter, and improve the quality of life of their residents by driving data-driven decision-making. Josh is inspired by Cartegraph’s goal to help local governments and educational institutions become stronger, more sustainable and more resilient communities through better stewardship of their critical infrastructure assets. Hailing from Philly, he currently lives outside of Chicago, Illinois with his wife and three sons.


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’m a “recovering” attorney and management consultant who made the move to operating software companies a little over a decade ago. I jumped in with both feet by starting an e-commerce business in China. It was a bit more challenging than I anticipated to say the least, but we made a run of it and ended up scaling the business to a successful exit in just 15 months to over 200 people and 20MM dollars in revenue with operations in multiple countries across Asia. Since then, I’ve focused on leading software as a service (SaaS) businesses in the U.S. and have more recently focused on infrastructure and government technology.

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?

About a year out of college, I was working as a management consultant and was put in charge of managing a strategic technology implementation engagement with a major client of the firm. After months of building the relationship and listening to their challenges, I developed a comprehensive strategy which I thought was elegantly designed to address what ailed them. I probably pulled 3 or 4 all-nighters getting the deck done and then printing and binding copies — yes, I’m that old. We had about 10 people, including my boss and several key partners in the firm, fly up to pitch this solution to the client’s executive leadership team. They politely listened to our entire pitch, nodding at the pain points, and interacting with the presentation which led me to believe everything was going great — until our champion, the most senior person in the room, said, “Josh, this is great. You really nailed our pain points. Unfortunately, we could never implement all of this change and don’t have the budget to do a project of anywhere near this size. We appreciate the work though. Thanks for coming up.” Obviously, I was embarrassed and felt terrible for wasting the time and resources it took to prepare for a pitch that we never had a chance of winning.

That said, I took a lot from that experience. First, my boss, instead of lambasting me, opted to treat it as a “teaching moment.” He emphasized the significance in understanding the fundamental importance of implementation and execution. It’s not just about getting to the right answer, but equally, if not more importantly, we needed to develop solutions that the organization could digest, implement and execute against. This is one of the things we focus on at Cartegraph: providing solutions that are implemented successfully 100% of the time in a way that’s helpful and impactful to our customers and their constituents.

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?

There are too many to count. One in particular would be Kevin Meehan, my boss at my first job out of college: a consulting firm that is now Willis Towers Watson. He taught me about empathy, servant leadership and the importance of having a growth mindset. Another boss at a different consulting firm helped shore up my “voice” in the otherwise intimidating boardrooms of some of the country’s largest companies.

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?

Cartegraph started off like many other software companies: with a few folks in a basement, looking to grow and change an industry. It was 1994, and after seeing local governments struggling to manage their assets with note cards and paper maps hanging on their office walls, the founders knew they had to build a better way. First, they started by answering the question: what assets do I have — and the company has grown from there. More than two decades later, that inspiration and drive to change an industry remains.

Cartegraph’s purpose is to help create sustainable, resilient communities through the better stewardship of critical infrastructure. When infrastructure is well maintained leveraging data-driven decision-making, constituents are safer, happier, healthier and more prosperous.

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?

The pandemic is easily the most recent and relevant experience I can point to. When COVID-19 first started, there were a lot of unknowns in every aspect of life, not just with businesses. In these unfortunate situations, it’s extremely important to lead with empathy and communicate through the uncertainty. Not having all of the answers can make leaders hesitate, but it’s important to stay connected to your team during difficult times. It’s okay to say, “We don’t know everything, but here’s what we do know and here’s what we’re going to do next.”

I made a point to keep in touch with our employees as the pandemic unfolded. I shared in their uncertainty and asked them to prioritize their health, their families and, of course, our customers — and to focus on the things we could control. I also shared personal experiences of how I was affected by COVID, sharing a story about the first person I knew that passed away from it, how I was managing working from home with my wife and three young children, and how the changes I was experiencing were challenging me personally. These anecdotes opened the door to conversations with many team members and helped us navigate the unknown together, which I hope provided some degree of foundation and stability at a time when the world felt like it was anything but.

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

I never seriously considered giving up, though the thought certainly crossed my mind several times when I was building my start-up in China. I am naturally energized and motivated by learning new things, overcoming challenges and building relationships. So that keeps me going in this always-changing SaaS world.

At Cartegraph, I’m uniquely motivated by the work we’re doing. Infrastructure touches all aspects of our lives and stewardship of that infrastructure is important work. It shapes everything from the economy to the health and safety of our families and our environment. Ultimately, I know that when Cartegraph wins, constituents win — which means society wins. That’s a powerful reason to get up and come to work every day.

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

During challenging times, a leader needs to gather all of the information available and develop the best possible plan to protect the business, employees and customers. And as I mentioned before, it’s critical to lead with empathy and be intentional about communicating with your entire organization.

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?

I think authenticity goes a long way to boosting morale and bringing a team together. A leader needs to be realistic and honest about the situation, but also point to reasons to be optimistic about the future.

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

Directly, transparently and without delay.

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

When the future is unpredictable, seek to understand the situation as much as possible and think dynamically about the future. I like to think in terms of real options: Take actions today to maximize options in the future so as more information becomes clear, the company is positioned to take advantage of or react to those eventualities, whatever they may be.

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

Always learn, listen and seek to maximize options while staying focused on core values, vision/strategy and serving customers.

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?

A common mistake I see is business leaders failing to share information with employees in a timely manner, or keeping the team in the dark during uncertain times. It leaves a lot of room for folks to spin false and inflammatory narratives that can result in damaging misunderstandings.

Another would be companies trying to rush back to a sense of normal too soon. Right now, it’s becoming evident that things may never go all the way back to the way they were, but companies are pushing for it anyway, probably because they know that’s what people want to hear. It’s a square peg round hole problem and can create friction throughout the organization. Businesses need to remain agile and recognize that ‘the way it always was’ may be changing — but that’s not necessarily a bad thing.

Finally, during difficult times organizations may need to lay off some of their staff and I have seen businesses suffer when this is done poorly. If you have to make cuts, to the maximum extent possible, try to cut only once to prevent lingering anxiety in your organization. Be appropriately respectful and empathetic through the process, err on the side of generosity and make a point to set the exiting team members up for success in their next move.

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?

Focus on value and serving customers. Remember: they’re experiencing many of the same challenges you are. During this particular crisis, we leaned in to help our customers find opportunities to supplement their budget with CARES Act funding. We also hosted virtual user groups to connect customers with one another and share ideas on how they’re dealing with the pandemic and resulting budget constraints in their communities. Those examples are certainly specific to the nature of our business, but you can never go wrong by focusing on your customers and taking care of their needs.

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.

  1. Stay focused on the basics. Use your company’s vision, mission, and values as a guide when making decisions and motivating your team. For Cartegraph, our customers are the most important aspect of what we do. So, when the pandemic started and everyone across the globe felt powerless and in the dark, we banded together to create and offer our free Cartegraph for COVID-19 Response software solution. It helped our team feel like we were making a difference and more importantly, it addressed a pain point for many communities and, quite simply, was the right thing to do under the circumstances.
  2. Lead with empathy and over-communicate. As I mentioned before, being transparent and staying in touch with your team is the most effective way to create a productive work environment in the face of uncertainty.
  3. Don’t go it alone. As a CEO, you have a wide variety of resources available to you — your team, your Board, peer CEOs, partners, the list goes on. When I’m facing difficult times, I reach out to these resources. In the spring of 2020, I took long walks around my neighborhood while calling my network for their advice and feedback.
  4. Seek first to understand. The best way to reduce uncertainty is to learn. Learn as much as you can to get the best possible handle on a situation and resist the impulse to act reactively and prematurely because you feel the need to do something to gain control. Other than reaching out to my network, I’ll read about whatever the topic is to get more insight. You need to gather as much information as possible to make an educated decision.
  5. Slow down. You generally have more time than you think. Sometimes you don’t, but those situations are very rare, in my experience. Uncertainty generally is reduced over time, so try to maximize optionality and don’t make immediate, rash decisions. Slow down and process what’s going on. Then, as time begins to show you the best path, feel empowered to make those decisions.

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

I appreciate these two maxims from the Temple of Apollo at Delphi: know thyself and nothing in excess.

Truly knowing yourself — understanding and accepting your strengths and weaknesses — is really important for leaders. You need to be open and transparent about your weaknesses so you can plan, and build a team, to “cover” them and complement your leadership.

Nothing in excess — which I generally rephrase as “all things in moderation” — is something we’ve integrated into the Cartegraph culture with our emphasis on having a healthy work-life balance. If you’re doing something in excess, like constantly working, then what is happening with the other elements of your life? We empower our employees to work hard, but also to take time for themselves.

How can our readers further follow your work?

You can follow my professional journey through my LinkedIn profile: https://www.linkedin.com/in/joshmallamud

To follow Cartegraph or come join our incredible team, visit our website: https://www.cartegraph.com

You can also connect with us on our social channels:

https://www.linkedin.com/company/cartegraph
https://www.facebook.com/cartegraph

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


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