For independent and smaller insurance agents, the mid-market space – employers with 51-150 employees represents a strong growth opportunity.  While it’s a competitive space, many of these employers still feel frustrated with generic solutions, reactive service and being treated like just another number in a large book of business.

Even if you haven’t sold to mid-market groups before, you can absolutely position yourself to succeed.  By leveraging your strengths – agility, service, local insights – and investing in the right tools and messaging, you can win over clients who are ready for a fresh alternative to big agencies and PEOs.

 

Why the Mid-Market Still Wants More

Not Underserved – But Often Underwhelmed

Mid-sized companies often get lumped into high-volume quoting cycles with little strategy behind the scenes.  They’re used to seeing recycled proposals, minimal follow-up and brokers who show up once a year at renewal.

This creates a perfect opening for agents who are committed to being proactive, strategic partners.  It’s not about years of experience in the segment – it’s about showing up differently and delivering better.

 

How to Position Yourself Without Mid- Market Case Studies

Leverage Transferable Experience

Maybe you’ve worked primarily with small groups, individuals or other lines of business.  That’s okay.  Focus on the strengths that carry over: responsiveness, education-first sales, compliance support or experience navigating complex family-run businesses.

Speak to the experience you have and bridge it to what you understand about mid-market needs:

“While I’ve worked more with smaller groups to date, the challenges around cost control, compliance and employee engagement are nearly identical – and my approach is designed to scale with you.”

Focus on Process Over Portfolio

When you don’t have big logos or case studies to drop, lean into your process.  Walk prospects through your onboarding steps, how you run plan analysis, how you manage renewals and how you stay involved throughout the year.  This reassures the buyer that you’re organized, strategic and committed to long-term success.

Be Transparent and Confident

You don’t have to pretend to have experience you don’t have. Just reframe it:

“I may be newer to groups of your size but that also means you won’t get a templated plan or a rushed approach.  You’ll get the attention and strategy that’s often missing from larger agencies who are just trying to push renewals through.”

 

Competing with PEOs and Large Agencies

Personalized > Packaged

PEOs and large firms often lead with bundled convenience.  But that can come with a lack of flexibility, generic plans, and limited transparency.  Your pitch: customized solutions, direct access and a strategic partner who’s invested in the business – not just the policy.

Availability as a Value Add

Mid-market clients are used to long hold times, service tickets and layers of bureaucracy.  You can win by simply being more available, responsive and proactive than their current broker.  Your service model is your selling point.

 

Technology: Your Investment in Professionalism

Modern Tools Signal Credibility

Whether or not you’ve worked with mid-market clients before, investing in good technology – quoting platforms, proposal tools, CRMS, HRIS access – shows that you’re serious, scalable and professional.  These tools level the playing field and allow you to match the experience larger agencies provide.

You Don’t Need a Tech Stack Overnight

Start lean.  Even one or two smart investments (a digital proposal tool and a clean CRM) can help you present like a pro.  The beauty of the mid-market is that just a few solid clients can easily pay for these tools and then some.

Local Expertise: The Differentiator You Already Have

Being based in Illinois gives you an edge – if you use it.  Mid-market employers want someone who understands their local workforce, the state’s regulatory quirks and how benefit decisions play out in their communities.

They don’t want someone in a national call center.  They want you.

 

Action Steps to Break into the Mid-Market

  • Build a Mid-Market Message: Write out how you help 51-150 life groups even if you haven’t yet. Focus on process, attention and problem-solving – not experience.
  1. Create a Clean, Professional Presentation: Use modern proposal tools, quote layouts, or visual plan comparisons to deliver a polished first impression.
  2. Start Networking Where They Are: Attend HR roundtables, local SHRM events and chamber groups.  Offer value – like free benefit audits or compliance checklists – to start conversations.
  3. Practice the Pitch: Prepare for objections like “How many groups this size have you worked with?” with honest, confident responses that redirect attention to your commitment and capabilities.

 

Final Thoughts

You don’t need a portfolio full of mid-market clients to start selling in the space.  You need the right mindset, the right message and a few smart tools to deliver like a pro.

Mid-sized employers aren’t just looking for experience – they’re looking for someone who will show up, listen and build a plan that actually works for their business.  That can absolutely be you.