Inside the Risk & Insurance Education Alliance’s Workforce Strategy: What We Learned About Leading a Remote Team

This article is part of a sponsored series by Risk & Insurance Education Alliance.

In 2020, when the COVID-19 pandemic forced organizations around the world to rethink how work got done, the Risk & Insurance Education Alliance was no exception. Like many employers, we transitioned our workforce to remote operations almost overnight. At the time, it was a temporary solution to an unprecedented challenge. Six years later, we’re still remote and intentionally so.

What started as a necessity became an opportunity to evaluate how we worked, how we collaborated, and what truly mattered. As we looked at our performance, team member engagement, and ability to serve our customers, we realized something important: our people were succeeding without being in the same building. Rather than returning to the office simply because it was familiar, we chose to build a long-term remote workforce strategy rooted in trust, accountability, and communication. Just as importantly, we committed to strengthening and retooling our culture so it could thrive in a remote environment, with greater intentionality around connection, collaboration, recognition, and shared purpose.

Today, the Alliance has team members across ten states who work together every day to support the insurance and risk management industry. While our workspaces may look different than they did before 2020, our commitment to our mission and to one another has never been stronger.

Remote Work Is Built on Trust

One of the biggest lessons we’ve learned is that successful remote work begins with trust. Trust at The Alliance is built on shared goals, level of output, taking genuine interest in others, and creating genuine connections, not the location of where they work.

While it’s easy to assume team members need to be seen to be productive, we’ve found the opposite to be true. When people have clear expectations, the right tools, and leaders who support them, they perform because they understand the purpose behind their work, not because someone is watching.

Trust doesn’t mean lowering expectations either; in fact, it requires greater clarity. Team members need to understand what success looks like, how their performance will be measured, and how their work contributes to the organization’s goals.

Communication Doesn’t Happen by Accident

In an office, communication often happens organically. A quick conversation by the water cooler or a question asked across a desk can solve problems before they grow. Remote work requires leaders to be much more intentional. At the Alliance, we’ve learned that regular one-on-one meetings, team check-ins, monthly All-Hands meetings, semi-annual organizational planning, and organization-wide communication are essential. Managers don’t wait until annual reviews to provide feedback. Rather, we encourage our leaders to have those conversations throughout the year. In fact, we have two Quack-Checks (formal check-ins) per year, so managers and team members have a dedicated platform to provide feedback to one another. Team members know where priorities stand, leadership shares organizational updates, and teams stay connected through purposeful communication. The goal isn’t to schedule more meetings, it’s to make every interaction meaningful.

Culture Can Thrive Without Four Walls

One of the biggest misconceptions about remote work is that company culture disappears when team members aren’t together every day. However, we found that culture isn’t created by a building, it’s created by shared values, strong relationships, hiring the right people (Ideal Team Players), and leaders who consistently invest in their people. We have a mascot, which is a duck, the thought behind this is to look calm on the surface, but paddle like hell under the water. We always paddle strong, together as one unit, one team.

We celebrate team members’ milestones, recognize accomplishments, encourage collaboration across departments, and intentionally create opportunities for team members to connect remotely and in-person.

We bring our entire team together twice a year for our in-person Value Day, which focuses on our core values and our mission. We also have four designated in-office interaction days, where our team can work from the office and know their colleagues will be there. We also have a few happy hours per year, a family event, and an awesome holiday party. These events give team members the opportunity to collaborate, learn, and strengthen relationships that carry over into their day-to-day work throughout the year. Those moments matter, but they’re successful because they’re supported by the culture we build every day.

We Focus on Team Members’ Well-Being

We have created an environment where psychological safety, inclusion, and well-being matter most. We have been told on numerous occasions by outsiders that our team members ask a lot of questions during live events and are not afraid to speak out, we absolutely never tire of hearing this. This is intentional, we encourage our team members to have those difficult conversations, to ask questions-no question is a dumb question, to admit their mistakes(they will not get into trouble for coming forward), and to speak up if they don’t agree with something, having no fear. We ensure that every team member has equal access to information, opportunities for advancement, access to the right meetings, and decision-making capabilities regardless of location or seniority. We encourage a healthy work-life balance with generous PTO offerings, mental health resources, a parental leave program, and sustainable workloads to prevent burnout.

Hiring the Best Person, Not the Closest Person

Remaining remote has also expanded our ability to recruit talented professionals throughout the United States. Instead of limiting ourselves to candidates within commuting distance of our headquarters in Austin, we can recruit skilled individuals from multiple states. That broader talent pool has strengthened our organization by bringing together team members with diverse experiences, perspectives, and expertise. As mentioned before, we have team members across ten different states.

Of course, hiring remotely also requires a thoughtful onboarding process. We try to conduct onboarding in person at headquarters in Austin, when we can. However, we have built a strong onboarding program to conduct them remotely as well. New team members don’t absorb culture simply by walking through an office. We intentionally introduce them to our mission, our people, and our expectations while providing the resources and support they need to succeed from day one.

Accountability Still Matters

Flexibility should never be confused with a lack of accountability. Successful remote organizations establish clear expectations around performance, responsiveness, collaboration, and results. At the Alliance, we focus on outcomes rather than physical presence. Team members are evaluated on the quality of their work, their contributions to the team, and their ability to fulfill our mission, not on whether they’re sitting in an office. That shift has encouraged ownership and empowered team members to manage their work while remaining accountable to their teams.

Leadership Looks Different in a Remote Environment

Leading remotely requires intentionality. Managers must build trust without relying on in-person interaction. They need to recognize accomplishments, identify challenges early, coach team members through difficult situations, and create opportunities for professional growth.

Those leadership skills partnered with the right tools have become even more important in a remote workplace. Strong communication, trust, empathy, transparency, functioning systems, monthly trainings, and consistency help team members stay engaged regardless of where they work.

Technology is Essential

Reliable hardware, secure systems, and collaboration platforms such as Microsoft Teams and Monday.com are essential to maintaining productivity and effective communication in a remote work environment. These tools support day-to-day collaboration and help employees remain connected with their teams while working from remote locations.

Consistent use of Company-approved technology promotes transparency, accountability, and efficient teamwork. Employees are expected to remain engaged, respond to communications within a reasonable timeframe, and use these tools as required to perform their job duties. Employees must also follow all Company security protocols to protect confidential information and ensure business operations continue efficiently.

Looking Back and Looking Ahead

If someone had asked us before 2020 whether we’d become a fully remote organization, we probably would have said no. Like many organizations, we adapted because we had to. What we discovered along the way was that flexibility, when paired with the right culture and leadership, can strengthen an organization rather than weaken it. Our experience has reinforced a simple but powerful truth: people don’t need to share an office to share a mission.

By investing in trust, communication, accountability, systems, and meaningful team member connections, we’ve built a workplace that supports our team members while continuing to serve the insurance industry with the same commitment and excellence we’ve upheld for more than 55 years.

The workplace will continue to evolve, and every organization’s journey will look different. Ours began with a global pandemic, but it continues today because we’ve seen firsthand that when you invest in your people, success isn’t defined by where they work, it’s defined by how they work together.

Topics Training Development