The Ops Leader’s Role in Building an Effective Remote-First Team

Anne-Marie Kaden was not thinking of workflows, client engagements, or the bottom line when she flew the Tiny Paws Bookkeeping team out to Colorado for their first in-person retreat.

She rented an Airbnb, took everyone out to dinner, and got people who had only known each other through screens to spend a long weekend together.

They didn’t need to talk about work. In fact, Kaden says the goal was simply to bond. Before the retreat, everyone was friendly with one another. They showed up for their weekly staff meetings, collaborated on big projects, and communicated as much as necessary to get their jobs done. But that was it. They weren’t, in her words, “leaning on each other for extra help or seeing their teammates as resources.”

They walked into the building as strangers, and they left almost as siblings,” Kaden says.

Anne Marie

Most remote firms have some version of Kaden’s “before” team: cordial, but transactional. A retreat can help fix that—for a weekend. And that’s the tricky part.

Although the offsite changed the way Kaden’s team saw each other, it didn’t change the fact that, come Monday, everyone would go home. The screens would come back on. Slack messages would start flying. Work would need to be assigned, handoffs made, and problems surfaced, all without anyone sitting in the same room.

That is where remote culture is really built. Not in the occasional retreat or virtual happy hour, but in the everyday operating environment: how clearly work is assigned, how information moves between people, how easily someone can ask for help, and whether team members prioritize getting to know the humans behind the names on their screens.

Those things don’t happen by accident. Someone has to build the environment that fosters them. And while that responsibility may ultimately sit with the firm owner, ops leaders have a major hand in implementing the systems, routines, and expectations that determine how a remote team works together every day.

The question isn’t how to recreate a physical office online. It’s how to intentionally build the things an office inherently provides: connection, visibility, and a sense that you’re part of something bigger than your own individual workload.

The Daily Rhythm

When people aren’t sharing a physical space, the casual interactions that happen naturally in person have to be created deliberately. Many virtual firms default to meetings as a means of building that rapport and camaraderie, but it’s important to be mindful of the types of meetings you add to your team’s already-busy schedule.

Alisa McCabe, who runs a fully remote operation at First Steps Financial, does this with a daily standup that takes almost no time. Every workday, each person gets roughly 15 to 20 seconds to answer four questions: Did you win yesterday? What’s your win for today? Any heads-ups to share with your teammates? Are you stuck on anything?

The format is intentionally short, but it gives the entire team a daily pulse on what’s happening around the firm. Everyone sees everyone else. More importantly, everyone knows who might be able to help when something goes wrong.

If you’re stuck, somebody says, ‘I’ll help you,’” McCabe explains.

Alisa McCabe

The value lies in the cadence. The team probably wouldn’t get as much out of the meeting (or participate as honestly) if it were a once-a-week gathering.

Tyler Otto takes a slightly different approach at Specialized Accounting. He adapted the idea of a “morning lineup”—which came from his time working in five-star hotels—to his 100% remote team. The lineup happens twice a week:

• On Tuesdays, one of his teams takes about 10 minutes to present something useful to everyone else. That could be a new client, tool, process, or something they’ve learned.
• Thursdays are entirely social, with a question of the day that gets everyone talking about something outside of work.

These meetings are more than pure status updates. The small, recurring interactions give employees visibility into what other team members are doing inside and outside of work, while making it easier for people to reach across the firm when they need help.

You don’t have to copy the exact format of McCabe’s standup or Otto’s morning lineup. As an ops leader, you can start by simply looking at what the team is missing: do people know what their team members are working on? Is it easy to ask for help? Do they have opportunities to interact outside of client work?

From there, ops leaders can design a rhythm that addresses those gaps. It could be a daily standup or a twice-weekly lineup—or it could be something entirely different. What matters is creating recurring opportunities for remote employees to see one another, share what’s happening in their personal and professional lives, ask for help, and talk about something other than the task in front of them.

The In-Person Moments That Bring Teams Closer

Speaking of spending together in person, communication happens in lots of different ways: tone, body language, mannerisms, and other physical subtleties you only pick up on when you’re within the same four walls.

Kaden noticed this happening immediately during her team retreat in Colorado.

Just that experience of having them together made such a huge difference in how they communicate now,” she says. “Now they were a team. Now they knew each other. They were real people to one another.”

Anne Marie

She describes the shift as a complete “180,” saying, “they bonded together like they had been long-lost family.”

Lynn James-Young witnessed a different kind of breakthrough when she brought her team from Bring It Bookkeeping together for a weekend in Oklahoma. The retreat included a full day of discussions, a guest speaker, dinner, and team-building activities. And the benefits of being together went far beyond bonding.

I saw what their weaknesses were, I saw their strengths, I saw their fears,” she says.

Lynn James-Young

The gathering also gave her a chance to hear what the team was struggling with as a group—and, in the process, see what she needed to work on as an owner. She described it as a “real game changer” for both her and the business.

Even McCabe’s team—who spent years getting to know each other online—took their connection to a whole other level when they finally had the opportunity to meet in person at the Scaling New Heights conference.

They hung around together like a swarm of bees,” she says, explaining how they immediately gelled.

Alisa McCabe

They talked, competed in a team challenge, and spent their downtime together. McCabe was moved by how naturally they connected, especially considering how much time and effort she had put into building a team who would truly understand one another, rely on each other, and show compassion when someone needed help. Seeing that relationship play out in person felt like the culmination of that investment.

The Communication Architecture

A remote team can have all the chat tools and virtual meeting software in the world and still feel strangely disconnected.

After all, if every message is about a deadline, a missing document, or a client problem, employees may start to view the firm more as a collection of tasks than a group of people.

That’s why Otto made sure to create opportunities for his team to engage in non-work conversations as part of their daily workflow. His team has a “water cooler” Slack channel for random jokes and updates. There’s also a “wins and losses” channel where team members celebrate and comfort one another.

GIFs have become such a normal part of the firm’s communication culture that Otto jokes that “communicating well in GIF format will help people integrate with the rest of the team.”

None of this requires sophisticated technology. What matters is that Otto has intentionally created spaces for different kinds of team interaction. Not every conversation has to move work forward, he says—nor should it.

The key is giving people different outlets and pathways for different types of communication, and making sure there is a shared understanding around where to go for each. To help accomplish this, ops leaders can identify where communication breaks down, establish and document clear expectations, and create the spaces the team needs.

Start by asking:

• Where does urgent information go?
• Where can people ask for help?
• Where are wins celebrated?
• Where can someone share something completely unrelated to work?

Those spaces don’t have to live in separate tools. They just need to be clear enough that people know where to go for what—and feel comfortable doing so.

The Nuances of Hiring for Remote Roles

Hiring someone for a remote role means hiring for a work environment you can’t fully observe. You won’t see how team members approach a difficult task, whether they ask for help when they’re stuck, or how they communicate when something goes wrong.

All of that means you’re not just looking for a candidate who can do the job well. You also have to understand how they’ll do it when no one is sitting beside them.

James-Young, for example, looks for an ownership mindset—someone who constantly goes beyond simply completing tasks as assigned. She wants people she can teach, gradually give more responsibility to, and trust to think through problems and make informed decisions.

I want them to have an ownership mindset and not an employee mindset,” she says. “I’m there to help them think and solve problems.”

Lynn James-Young

A remote employee should be able to work fairly autonomously, moving work forward without constant supervision. But they also need to recognize when they should ask for help; communicate clearly enough that a manager doesn’t have to guess what they’re trying to say; and take initiative without always waiting for instructions.

Otto has learned some hard lessons about what to look for in potential team members—and how to set them up for success once they come on board. When his firm was smaller, he was so determined to create a flexible workplace that he gave employees near-total freedom to determine when and how they worked.

The problem? Many chose to work late at night when Otto wasn’t online. That made it harder for them to receive timely feedback or coordinate with the rest of the team. He eventually realized that flexibility without clear boundaries wasn’t helping anyone.

Today, his firm still offers flexibility, but with clearer guidelines and expectations. It’s not about monitoring remote employees, Otto argues. It’s just that autonomy works best when people understand what they’re responsible for and how the team best works together.

Kaden also approaches hiring decisions from a place that goes beyond technical skills. Her employees must be able to translate complex financial concepts into plain English, listen for context, and recognize when a conversation has gone too far into the weeds.

She also stopped making personnel decisions alone. Kaden brought her manager into the interview process so another person who understands the firm’s clients and work could assess the candidate alongside her.

I have somebody I can talk to about it,” Kaden says. “Somebody who’s going to see different aspects or different pieces that I might miss and vice versa.”

Anne Marie

For a growing remote firm, that’s a simple way to make hiring less dependent on one person’s judgment. The person who will manage the new hire—or work most closely with them—may notice something the owner misses, particularly in terms of communication style and day-to-day fit.

Dave Kersting, who runs Denver-based Capovario, looks at the other side of that equation, assessing not just whether a candidate fits the firm’s DNA, but whether the firm can actually support the way that person works.

What happens if I were to hire somebody who needs more structure?” he asks. “Can I give them that structure that they need? Or am I looking for somebody who can get out of bed in the morning and start working all by themselves?”

Dave Kersting

That mindset turns remote hiring into a two-way assessment. You’re evaluating whether the candidate can work effectively in your environment, but you’re also evaluating whether your environment gives them what they need to succeed.

For ops leaders, that means being honest about what remote work actually looks like at your firm, and recognizing that you have some influence over that environment, too. How much autonomy does each role require? How often should people communicate? Where do they go when they’re stuck? Are managers properly equipped to provide the necessary level of support?

If the answer to any of these questions is unclear, then as an ops leader, you should focus on putting definition around these items before the next person joins the team.

The Manager’s Role

The physical office used to give managers a steady stream of information about their team members without much effort. You could overhear a conversation that showed someone was struggling. You could see when two people were working through a problem together. You could walk past someone’s desk and notice when a project was falling behind. Remote work takes a lot of that visibility away.

Otto discovered another, less obvious remote work effect as his firm grew. Early on, when he was doing much of the work himself, he saw the wins firsthand: happy clients, successful projects, and problems that were getting solved.

As the firm grew and employees took over more of the day-to-day work, his field of view changed.

The only things that make it to your desk are the big problems,” Otto says. “The easy stuff is being handled at the front lines. The client wins are happening without you.”

Tyler Otto

That can create a distorted picture of the business. The work that reaches the owner or manager is the work that needs intervention, while much of what is going well never reaches them at all. Otto says this can make you start to “feel like the firm is falling apart when, in reality/actuality, most of the good and easy stuff is being taken care of.”

For remote ops leaders, that means making sure you have feedback structures in place that surface the good work and the problems that require your attention.

That might mean holding regular check-ins with team members, asking for project status updates, creating shared dashboards, or introducing simple rituals to recognize completed work and celebrate wins (like the aforementioned standups). The specific mechanism will vary by firms. The ops leader’s role is to notice where visibility is missing and create a reliable way for information to travel upward—even when things are going right.

Remote-First Is Not Second-Best

Remote-first is not a lesser version of working together in an office. It’s a wholly different operating environment—one that asks more of the people designing the infrastructure.

When there isn’t a hallway to bump into someone else, a desk to walk past, or a conversation to overhear, the things that keep teams connected as human beings have to be intentional. Someone has to decide how people communicate, where they turn for help, how they stay visible to one another, and what makes them feel like part of the same team.

That’s the real work of building a remote-first firm: not recreating a virtual version of a physical office, but designing an environment where people can do good work, access the support they need, know one another, and feel connected even when they’re miles apart.

The office creates that connection by default. A strong remote firm builds that connection by design.

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