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David Wallace: “Having confidence in your team”

Communicating, communicating, communicating: Just when you think you’re not communicating enough, communicate more. You might think what you’re doing is great, but is it effective? I don’t always know if people read my weekly blogs to my team, but when I announced the promotion of one of my managers, she got more than 120 reactions […]

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Communicating, communicating, communicating: Just when you think you’re not communicating enough, communicate more. You might think what you’re doing is great, but is it effective? I don’t always know if people read my weekly blogs to my team, but when I announced the promotion of one of my managers, she got more than 120 reactions on Slack. Even if you’re not getting responses directly, people are reading and want to hear from you.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing David Wallace.

As Chief Technology Officer, David leads the development of Greenphire’s innovative technology solutions that automate the payment life cycle the clinical trial industry, ensuring the infrastructure is secure, scalable and reliable. Leveraging a proven agile methodology, David and his team constantly refine and develop Greenphire’s solutions to support client needs. Additionally, he works closely with the product team to plan and execute the product roadmap strategy, anticipating “what’s next” and how to develop the right solutions to maintain the company’s strategic advantage.

With over twenty years of experience, David has an extremely valuable combination of technology strategy, architecture design, integration, and product development in the SaaS industry.

Previously, David was Senior Director of Information Technology at iPipeline, a leading SaaS provider used by the nation’s top life insurance companies, where he was responsible for global infrastructure, system and application security. Prior to that, David was Director of Information Systems at Procurian, where he managed networking and data center operations and lead the development of the company’s procurement infrastructure to support a Fortune 500 client base.

Born in Ireland, David holds a Bachelor of Science degree in Business Administration from Delaware Valley College. In his spare time, David enjoys adventure racing (that was pre-kids), and overall being active and engaged with his children


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I’ve been at Greenphire for eight years, from its infancy to where we are today with over 200 people. I have over 20 years in the technology industry, spanning strategy, application development, operations and more. I’ve worked in industries such as insurance, payment systems and healthcare — and at Greenphire, we are right where the intersection of where fintech and healthcare meet.

Personally, I spend a lot of time with my family and have two small children. I grew up in Ireland until I was in my early teens and still have a lot of family there, and I love to travel and do new experiences. I want to share those experiences with my children, just like my parents did for me. Expose them to as much as possible, and let those sponges of brains and personality absorb it all.

Can you share the most interesting story that happened to you since you started your career?

Well, this may both the most interesting and embarrassing! Several years ago, I was travelling for work and en route to Greenphire’s biggest client meeting ever, and forgot to check my bag. I had to wear my comfortable train clothes to this important meeting — just casual jeans instead of a suit. Thankfully we got the deal and my outfit didn’t matter anyway! (Sometimes its good to be an IT guy)

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One of my first jobs was as a developer and my initial project was working implementing direct deposit in the in-house payroll system — new and innovative at the time. I was responsible for calculating the 401K contributions for the company’s executives, and made a huge mistake in their calculation. Thankfully, my manager helped smooth out the situation, but it was uncomfortable at the time. I learned to take responsibility for my actions and to own up to my mistakes, but also to put checks in place to lessen the chances for manual error.

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

I’ve found that when you don’t have the right personal outlets, life can get out of balance. I personally love being active and any sports (basketball, tennis, occasional run), but admittedly I don’t get to do those things as much as I’d like with work and having small children. However, hobbies don’t necessarily need to be all exercise — it’s whatever makes you smile and decompress. One thing that I love is taking my seven-year-old daughter to gymnastics class (well, pre-COVID19). Spending time with her in the car, watching her tumble and listening to her excitedly talk about the class on her way home is special to me.

In recent months, I’ve joined the legions of DIY-ers and have spent time working with my hands — finishing the basement, building a garden. I enjoy working with my hands and don’t usually have time do so under normal circumstances. I learned that from my father and from a job I had through college, where I drove a truck and helped a furniture store re-finish furniture — a general building of knowledge of how to work with my hands.

I suggest to my teams and other executives to find time to what makes you happy. After all, only you can look after you — no one else can do it. It’s something important you need to figure out and work towards balancing. If you reach a tipping point, you’re likely to get frustrated, blame your company (or others around you). Remember — it’s not the company. Balance starts with you. Find what works to help bring both personal and professional satisfaction to your life.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Just one! Typically I’ve worked face-to-face with my teams and colleagues. Even though I’ve spent my career in IT, I haven’t done much offshoring or remote work, and enjoy the comradery of being in an office. It’s been an adjustment, but I’ve been pleased with how well our IT and engineering team has remained connected and productive.

Some of the things I’ve done differently include:

Weekly blogs — these are internal updates to the IT and Engineering team that highlight our team’s wins, company news and some personal stories. I’ve shared conversations as personal as my love and care for my mom.

Lunches — I’m dedicated to having lunch with different teams, to hear what they’re up to and just socialize. It’s been a lot of fun.

Office hours — I’ve also dedicated hours for when individuals can come to me with questions, suggestions, problems and more. It lets employees know that I’m available to them and prevents my calendar from getting overrun with meetings.

Breakfasts with the offshore team — We have a small team in Vietnam. Given that they’re on the other side of the world, I want to make sure that we’re doing everything possible to make sure we’re in constant communication and in the loop with our team in the US.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

Managing a team remotely certainly requires a shift. Rather than just highlighting the challenges, I’ve listed out some challenges and solutions to managing in this environment:

  1. Lack of transparency: Since you don’t see people face to face, it’s more difficult to know when people are working or how busy they are.
  2. Having confidence in your team: One way to confront the lack of transparency is through trust. When you have confidence in your team and managers, it gives them the opportunity to demonstrate leadership and professionalism to deliver on key projects. We look at metrics all the time, and We validate that we haven’t lost SDLC effectiveness by looking at metrics, building ownership and pride amongst our IT department.
  3. Understanding where their challenges are: Right now, employees working from home have challenges, many of them. Whether just feeling stir crazy, having a bad at-home work set up or having little children interrupting their work day, there are many distractions that can frustrate employees. I feel it myself. Recently I spent lots of time cleaning my garage top to bottom. All it took was my two kids playing with Styrofoam for a few minutes to turn it upside down again. I had to remind myself that they were just playing. Their world is upside down right now too.
  4. Creating that facetime with employees: Since we’re apart, it’s essential that you get comfortable with your webcam. You want to see each other, read your colleague’s body language, even during remote meetings.
  5. Communicating, communicating, communicating: Just when you think you’re not communicating enough, communicate more. You might think what you’re doing is great, but is it effective? I don’t always know if people read my weekly blogs to my team, but when I announced the promotion of one of my managers, she got more than 120 reactions on Slack. Even if you’re not getting responses directly, people are reading and want to hear from you.

Based on your experience, what can one do to address or redress each of those challenges?

To address the lack of togetherness that we all face right now, I can’t stress the importance of communication and encouraging facetime with your colleagues and teammates.

Some additional things we can do to overcome challenges are:

  • Flexibility: People working from home may have personal responsibilities to tend to. For example, we have several folks on our team who have shifted their schedules so they can alternate taking care of children with their spouse.
  • Empowering Managers: I lean a lot on my team’s managers right now, so it’s not just my leadership that’s important — but theirs as well. I make sure that they’re talking to employees regularly about projects and about their personal health also. First time managers are taking on a lot right now, learning to be managers, in a 100% remote workplace. They need our support and guidance
  • Taking time off: It may seem silly to take a day off (especially if you’re not going away on vacation), but taking time to decompress is essential right now to avoid physical and mental fatigue.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

I’ve had several instances of giving constructive feedback while working remotely. There are a few no brainers — ensuring that you’re face to face as we’ve already covered, and when live, being careful of your body language. It’s essential to make sure that your facial expressions and posture don’t give the wrong impression — especially in a group meeting.

However, remote or not remote, lead with the heart first. You don’t know what individuals may have going on personally, so I start by asking if there’s anything the individual wants to tell you about. He or she may have a scenario at home that may be weighing on them, and impacting their performance. Without asking about their personal well-being, you may lose credibility and damage the relationship.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

In my opinion, email is just factual and really shouldn’t be used for giving constructive feedback. People may misconstrue being direct for being critical, but in my case, an effective email should tee up either an action or a conversation. Always start cordially, and include what you need as well the “why” you need it (will it help with a client interaction? Will it improve internal efficiency?). Provide a due date and ask if there are any reasons why it might not be able to be completed on time.

By providing all the details and facts, you help the individual know exactly what’s needed to be successful.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

As I mentioned earlier, our team was used to working on location together prior to being forced to work remotely due to the pandemic. In addition to communicating more frequently and face to face, here’s another tip for leading employees through a new way of working.

Be sure to watch team dynamics, especially in group meetings. You want to make sure that those who are introverted don’t just fall to the background and get overlooked by extroverts in conversations. Make sure you engage everyone and ask others for their contributions who may not be as vocal.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

When our IT department is in the office, we have a lot of fun. We’re 70 people strong and do a lot of group activities such as a chili cook off, volunteer projects and more.

Now that we’re remote, it’s even more important to make sure that people are healthy and that we’re providing an empowering work culture.

We talk about personal happenings a lot — even I do as the head of the department. We all have the same problems — family, house, finding time to decompress.

Greenphire has been planning a lot of fun virtual activities that we as a team participate in, including Quizzo happy hours, talent shows and online workouts.

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. 🙂

The obvious answer right now would be to wear a mask! If I could trigger everyone to wear a mask, I would.

But, I’d also encourage everyone to remember that everyone has a story and we’re all going through a stressful time. On my team, I have two colleagues whose significant others are seven months pregnant. It is stressful to consider having a baby right now with so much going on in the world.

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

My father (and really my entire family) has had a tremendous influence on my life. Growing up in Ireland, he learned the value of hard work and my parents passed that along to us. In fact, the lesson I learned most from him is that no one will outwork me. Other people in a room may be smarter, but if you stand by your principles and remain inquisitive, you will succeed. Whether it was when I was just getting started or today, I advise others to “manage up;” share what you can do for them and the organization instead of why you deserve something of something. If you put forth the effort, hard work and dedication, you’ll go far in life. Opportunities may come along, but success is based on you!

Thank you for these great insights!

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