The “Why,” “When,” and “How” of Hiring Workers For Your Insurance Agency

We can’t talk about hiring remote talent for your insurance agency without at least some acknowledgement of the elephant in the room: Hiring a remote team can come with its fair share of challenges.

Even Chandler Hahn—longtime agent and extremely successful agency owner who interviewed both the experts whose advice we’re discussing today—expressed his hesitation at the idea of running a remote team. He had some difficulties keeping workers on task during the work-from-home pandemic years, and he was interested to hear how Austin O’Bryhim (State Farm agency owner and operator with a strong remote team) and Melanie Yeatts (CEO of Agency Resource Solutions) got around these issues.

Despite the challenges, building a remote team can work wonderfully if your agency is prepared and well-suited for distance work. In many cases, the benefits can outweigh the risks. Below, we’ll outline why hiring remote workers can be a great idea, pinpoint the right time to make the leap, and list some tips to help ensure the process goes smoothly.

As you read, acknowledge any innate reservations you feel. If you anticipate the challenges, you can use them to build a proactive plan for success.

One of the best reasons to hire remote employees is to facilitate growth. Sign up here to get fresh, new leads from EverQuote to keep your new team members busy.

Why, When, and How To Hire Remote Team Members In Your Insurance Agency

Why Hiring Remote Employees Is A Good Idea

Remote workers open the door to many possibilities you simply can’t replicate with an in-person team.

1. Remote producers — with proper structure, office culture and management — often have better productivity and focus than their in-office counterparts.

Often, the biggest reservation agency owners have toward operating a remote team is the fear that work-from-home employees won’t stay focused on their work.

However, Melanie points out all the distractions in a typical in-office environment: Coworkers chit-chat nearby, phones ring across the room, interested customers walk through the doors, the smell of somebody’s lunch emanates from the break room microwave…

Remote workers don’t have someone popping into their office to talk about what they did last weekend. They can sit at their desk at home in peace and get down to business with the day’s tasks.

“Employees have increased productivity when they can work on their own terms,” Melanie says.

2. By hiring remote workers, you’ll have access to a huge talent pool with high-quality applicants.

Hiring locally severely restricts your candidate pool. “If you’re trying to hire someone right there in your town who can drive to the office, you’re really limiting yourself from accessing some good talent,” Melanie says.

Austin agrees: “Why not open yourself to the entire country (or the boundary where you’re allowed to hire)? Make sure you’re maximizing that. You’d be surprised, the talent across the country is pretty incredible.” He adds, “My girl in Texas, she's my top producer every month.”

3. You’ll boost employee retention and your workers’ quality of life.

Austin says, “There’s more to life than work.” For employees to be happy, their work lives have to leave enough room for their personal lives to flourish.

Offering work flexibility is a great motivator for many job candidates. Melanie recalls of her past job searches, “If you offered me the flexibility to take care of things for my family, that was huge for me.” She emphasizes that the ability to do remote work while also weaving in personal responsibilities throughout the day can be a make-or-break factor for parents and people in caregiver roles.

When To Start Hiring Remote Team Members

If you strike at the right time, you can use remote team members to fill in gaps and accelerate your agency’s growth.

1. Is your talent pool feeling a bit empty?

Austin’s agency is based in Jackson Hole, Wyoming, a famous tourist town with a notoriously high cost of living. Many companies in his town struggle to pay livable wages while dealing with higher than average business expenses. “The joke is that if you live in Jackson, you don’t work in Jackson. And if you work in Jackson, you don’t live in Jackson.”

Due to the local economy, Austin found it necessary to hire a remote team to keep his agency in the green. If you live in a similarly expensive area—or a sparsely populated town with few good candidates—broadening your search can only help your prospects.

2. Do you need coverage for extended hours?

Austin deliberately hired remote workers spanning multiple time zones. This strategy allows him to open the office earlier and stay open later, which provides broader availability for clients.

If you serve clients across the country, operating a similarly distributed network of remote producers can help you meet your clients’ needs during their local business hours.

3. Are you scaling operations?

As your agency grows, you can prevent understaffing by hiring offsite workers to fill in the gaps. You’ll be able to scale up the volume of clients you help without overwhelming your in-office staff.

If you want, you can even specialize the tasks your remote workers and in-person employees handle. For instance, Melanie’s team continuously assesses whether remote workers could take on more customer service tasks, allowing her core team members to focus on making more sales.

4. Do you need redundancy?

Austin says maintaining a “bench” of remote workers provides a buffer against unexpected absences of key team members. “None of us are truly prepared for that happening, losing a key team member for a significant amount of time,” he says. “You need to make sure you have a bench going.”

How To Build A Great Remote Team

Successfully integrating remote staff will require putting some strategies into place before you hire.

1. Build a culture that encourages accountability and communication.

Chandler asks about one of the top concerns employers have with running a remote team: How do you know if your team members are actually working when they say they are?

Austin says, “The easiest way to combat that feeling of, ‘Is my team being productive?’ is to instill in them good communication. We have an office Microsoft group chat going at all times, and they can put into the chat, ‘Going to pick up my kid,’ or whatever they’re doing at the moment. Then if someone calls in asking for that person, we can say, ‘They just ducked out for a minute, they’ll be right back.’ This policy has led to my team communicating consistently. They’re open and honest with me.”

2. Establish clear expectations.

Melanie’s team provides offsite staff with a daily checklist of things to accomplish. She says, “Remote workers have to understand that, while this is a great job, it is still a job.”

Outlining your expectations clearly and giving employees a defined list of items to work on will help keep everyone on track.

3. Emphasize autonomy and trust.

Both Melanie and Austin emphasize that micromanaging doesn’t work. You can provide encouragement, expectations, and guidelines to stay within, but at the end of the day you have to trust that your remote producers are going to get the job done.

Austin says, “I give my team full autonomy. The boundaries haven’t been tested by anybody, because I have checks and balances in place.”

4. Use tried-and-true hiring principles.

Rather than posting a job description and hoping for the best, approach hiring as a methodical process with strict best practices. Since this is such a deep topic in and of itself, we recommend checking out these resources if you’re ready to start actively looking for candidates:

• The 16+ Secrets To Hiring Insurance Agents Who Will Actually Produce (+ 5 Mistakes To Avoid)
• 15 Tips For Recruiting Insurance Agents (From Industry Experts)
• How to Recruit Gen Z Employees into the Insurance Industry
• Hiring Insurance Producers During Trying Times
• 20 Best Insurance Agent Interview Questions for 2025

Austin also recommends involving your existing team in the hiring process. If your current staff has the opportunity to meet each new prospect, you’ll have a great idea of the cultural fit before you ever extend an offer.

5. Prioritize team-building and connection.

Regular optional video chats can help your workers get to know each other and feel like a cohesive team. Austin’s team begins Mondays by discussing the weekend, and ends Thursdays with a chat about upcoming plans. Melanie’s team meets for coffee chats and cocktail hour on Zoom so everyone can catch up.

If your team isn’t too far distributed, occasional in-person meetups can also foster a sense of connection. Austin flies his whole remote staff to Jackson Hole for a four-day annual retreat. He says, “It’s one day of work, and three days to go do what you want.”

He also makes the effort to send gift cards for movies, massages, or other fun treats to his remote staff members who can’t always participate in local team outings.

6. Offer competitive compensation, benefits, and professional development opportunities.

Remote staff should be on the same pay scale as your in-office team, Austin insists. “They should have access to the same commissions, the same benefits, all of that.” This prevents remote workers from resenting the core office group, and vice versa.

Austin aims to pay his employees between five to ten percent above the traditional going rate in their local area. “Invest in them! Compensate them appropriately. You know they’re not going to be looking for a job elsewhere if you treat them right.”

Additionally, make sure your remote employees have a dedicated working space equipped with everything they need to do the job effectively. Austin gives out a laptop, a printer, and multiple monitors so nobody feels constrained if they can’t afford to put together a high-tech setup on their own.

Finally, offering continuous training encourages employees to stick with you for the long haul. If possible, develop your training regimens to accommodate a variety of learning styles. Include videos, self-study, and other options so employees can stay up to date in a way that suits their needs.

Since licensing in most locations is required after 90 days on the job, you’ll have the opportunity early on to see how your employees prefer to learn and work.

7. Monitor performance.

Though Austin emphasizes that there’s no need to police your workers as long as they’re consistently hitting goals, it’s still a good idea to track metrics such as call logs, outbound calls, quotes created, conversation pivots, and Google reviews.

If a team member isn’t meeting expectations, try to address the problem early, directly, and fairly. Treat remote workers the same way you’d treat in-office staff. “If they’re violating your code of conduct,” Austin says, “They don’t get any extra leeway just because they’re remote.”

8. Look up legal regulations.

Before you make a job offer to a candidate across state lines, research the state-specific requirements for non-resident producer licenses, business entities, and tax withholding. When in doubt, Austin recommends finding a “really, really good accountant.”

9. Consider outsourcing.

If you’re interested in reaping the benefits of having a remote team but it sounds like too much hassle to hire and manage that team, Melanie suggests outsourcing some labor.

Quality outsourcing companies can help you hire US-based team members – both those who are already licensed in their home states and those who are not, so you don’t have to worry about handling the legal aspects, the training, or the day-to-day operations for a team that isn’t sitting next door to your office.

Give your remote team a boost with high-quality leads from EverQuote.

As the industry continues to evolve, we expect remote work to keep getting more popular. If you keep an open mind and embrace the trend, you’ll be well-positioned to grow your agency whenever the opportunity arises—no more combing through local job candidates and panic-hiring the first person who comes along just to meet increased demand.

Better still, you can grow your agency whenever you want by signing up for high-quality leads or calls from EverQuote. Filling your pipeline with EverQuote leads means you can drum up more business whenever you want to or fill in the gaps during slow seasons.

Contact EverQuote today to start receiving leads or calls.