Hi, I’m Jason Phillips, a Commercial Insurance Agent with Midwest Select Insurance Group (MSIG). At MSIG, collaboration isn’t just a buzzword; it’s the foundation of how we operate. From strategizing quoting approaches with my Customer Service Representatives (CSRs) to mentoring fellow agents, I believe in a team-first mindset where we don’t just divide tasks, we multiply success.
Morning: Strategic Planning & Team Collaboration
My day starts early, usually with a cup of coffee and a focused review of my daily agenda. This is my time to prioritize, problem-solve, and prepare. I dig into quoting lists, evaluate cross-sell opportunities, and review key performance metrics with my team.
I also check in with my CSRs to provide coaching on complex renewals and brainstorm new ways to bring added value to our clients. With a health and life insurance background, I bring a holistic approach to commercial coverage, always seeking ways to layer protection and help clients see the bigger picture.
Midday: Out in the Field, Building Relationships
Late morning to early afternoon is when I hit the road, and honestly, it’s my favorite part of the day. Whether I’m meeting a contractor on-site, stopping by a client’s business for a renewal review, or grabbing coffee with a referral partner, this is where commercial insurance really happens.
Face-to-face connection is still a powerful currency in our industry. Being present helps build trust and gives me clearer insight into what my clients truly value and what I’m helping to protect.
I also use this time to keep my eyes open for new opportunities: recently opened businesses, in-progress real estate deals, or just a chance to speak with a business owner who isn’t getting the service they deserve from their current agent.
Afternoon: Client Support & Account Strategy
By late afternoon, I’m typically back at my desk or parked with my laptop following up on client calls and emails. These conversations often involve advising business owners on their policies, reviewing quotes, or explaining the difference between policy coverages like General Liability and Professional Liability.
One of my core strengths is simplifying complex concepts so clients feel confident in their decisions. Insurance shouldn’t feel overwhelming; it should feel empowering.
When I’m not speaking directly with clients, I’m working with the team on account strategy: identifying bundling opportunities, finding coverage gaps, and prepping for upcoming presentations. When we save a client money or win new business, it’s a collective achievement, and we celebrate it as a team.
Evening: Reflect, Reset, and Plan Ahead
I end each day by mapping out tomorrow: identifying top priorities, scheduling follow-ups, and reaching out to clients who are finally off the clock. Sometimes, that means sending an after-hours quote to a young family purchasing their first home or checking in with a small business owner juggling a dozen responsibilities.
Ultimately, this career is rooted in relationships with clients, teammates, and partners. I’ve found long-term success by showing up, listening intently, and doing what’s right even when it’s not easy. That’s what lasting trust is built on, and if you share that mindset, MSIG might be the right place for you.
About the Author
Jason Phillips is a commercial insurance agent at Midwest Select Insurance Group, serving clients across Wisconsin and Minnesota. With a background in health and life insurance, Jason focuses on helping clients obtain cost-effective coverage options across commercial, home, and auto insurance lines.
His approach prioritizes education, accessibility, and long-term relationships. Whether coaching fellow agents in the office or consulting with clients on-site, Jason leads with integrity, transparency, and a strong commitment to putting people first, because insurance is about people, not just policies.
