Vasyl Soloshchuk
2 July 2019

Working with a Remote Team. Tips from Christopher Daly, Chief Digital Officer at GeoWealth

Many FinTechs experience fear of hiring remote software developers because a number of risks may arise. The often mentioned fears include the following:

  • If you don’t watch developers, you can’t control the pace and quality of development.
  • It’s difficult to synchronize the work, considering time and language differences.
  • Remote developers are not engaged at creating the best-in-class product.

Chris Daly, GeoWealthWe talked to Chris Daly, chief digital officer at GeoWealth, a FinTech firm that has created a platform for financial advisors. The firm has an offshore team in Eastern Europe, and they have been successfully collaborating for about 10 years. Chris shared with us how they have established work with their remote team and what techniques he uses to make the work more efficient.

Pros and cons of a remote team

GeoWealth has two development teams: Chicago hosts the core business, including product and operations managers in addition to software developers. Chris says that the benefit of having a part of the team in the United States (particularly, product) is that they are closer to software users and thus better understand their pain points and can see how to make software suitable for their needs.

The second, larger software team is in Sofia, Bulgaria, and it includes front-end and back-end developers, development leaders, and the head of engineering.

Chris admits that, from time to time, some challenges arise, caused by time and geographic or language differences; however, having a remote team also brings many benefits. For example, cultural differences can bring a fresh look at issues.

“I think having an additional cultural influence and having different eyes on projects is a great benefit to the end product itself.”

Another benefit is the opportunity to work almost day and night on tasks.

“It’s five o’clock where I’m working, but I’m, instead of putting this down and picking it up 12 hours later, I can hand it off to my colleague in Sofia, and they can work on it for several hours ahead of me, and, by the time I come back in the morning, it’ll be more advanced than when I left it.”

Chris names one more benefit of having the offshore team: The company has access to multiple talent markets and can acquire the best experts in the field.

“We’ve got a real crackerjack squad of front-end developers and core Java developers there. The level of knowledge they have is really, really solid.”

Overcoming the problems

Chris is confident that, for efficient work, communication with both teams is critical. They also have multi-week check-ins.

At GeoWealth, they extensively use Slack for communication and Jira for tracking software development and QA.

“My mornings are dominated with Slack and phone conversations with our Eastern European team since it’s the tail end of their day, [and] it’s the beginning of our day. We can see what’s been worked on and when, watching the stream of Jiras come through on their side.”

There’s one more significant aspect for efficient work—documentation. Chris says that they have created a significant knowledge base that allows both teams to work faster because everyone knows the system inside and out.

“Knowledge sharing isn’t just how something is built and how it gets done but also it’s a mentality, and there’s a real sort of proactive way of thinking and seeing the landscape in front of you and being able to work together to get there. So, it’s absolutely critical to success.”

GeoWealth uses Confluence and Dropbox Paper to store documentation.

Time management

Any technical leader knows that there’s never enough time in the day. Time management becomes an even bigger challenge when you need to manage distributed teams. Chris also experiences this problem.

“I’ve tried a number of different techniques. Scheduling every minute of my day, not scheduling anything in my day, using road map-based software, using calendaring-based software.”

He has created his own approach, which is based on two aspects: First, he uses the statement “Yes, and?” which helps to define where they are at and create an agreement to move forward. Second, he creates a to-do list instead of scheduling time.

“I know by the end of the week I need to get X, Y, and Z done. That doesn’t mean I’m going to schedule an hour today and two hours tomorrow and 15 minutes that day. I just have a list of 10 things that I know need to get done this week and when we have open time we sort of chew at them as we go.”

Everybody in the team has their own to-do lists. Sometimes they even don’t line up. However, Chris believes this is not a problem.

“We try not to be overly dogmatic in terms of scheduling minutes, looking over everybody’s shoulders. I think the best project management styles are the ones that lean into the best parts of your people.”

Chris is confident that this gives the team a kind of freedom and responsibility. As a result, they have a strong software velocity and get things done in a “soft way.”

“It gives us room to breathe on any project, and it gives us an opportunity to absorb what comes in.”

Experience of being a speaker

Chris believes that there’s one more skill that may give a big advantage to a technical leader. It’s the experience of public speaking.

“There’s a very fine line difference between giving a presentation at a conference and leading a meeting with your colleagues. They are fundamentally the same thing. It’s just a question of scale.”

Chris gained considerable public speaking experience by taking part in college theater productions. He was also a speech and debate coach at the start of his career. Today, Chris is a popular conference speaker. Last year, he presented his ideas at the Product Innovation Summit and the Digital Design & Web Innovation Summit.

Chris often gives a piece of advice for those who have concerns about speaking in public. He says that you shouldn’t be afraid of it because the audience goes to conferences to learn from you, not laugh. That’s why people want the speaker to succeed. Chris says that he always feels that all the people who listen to him are his friends, and this attitude gives him positive energy.

“Nobody wants to laugh at you. Nobody wants you to feel bad. Everybody wants you to do well, and you can feel that energy when you’re speaking in front of them.”

Chris explains why the experience of being a speaker is beneficial:

“It’s the ability to communicate and to turn your ideas from mentally to verbally to actual action. It’s a critical part of any success as you move up in your career.”


The case of Chris Daly, chief digital officer at GeoWealth, shows us that working with a remote software development team may be beneficial in many cases; however, to achieve success, the technology leader and teams need to follow some established principles, such as tight communication, effective time management, mutual respect, and freedom together with responsibility and understanding the mission.

Summarizing his story, Chris says:

“I love the fact that we have a distributed team. It keeps our people within their own context, within their own head, within their own home, and that makes them more comfortable. That makes them better at what they do. It makes them better people.”

What do you think of distributed teams? Do you have experience managing remote teams? What benefits can they bring? Do these benefits exceed the risks? Share your experience with the community.