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Economic Insider

How Tyler Rees and EnrollHere Are Improving the Medicare Enrollment Process

In an industry often filled with noise and hype, Tyler Rees is quietly making significant strides in transforming the Medicare sector. There is no media frenzy, no influencer-driven marketing campaigns, and no Zoom calls packed with buzzwords. Yet, behind the scenes, Rees is building something substantial—something that could change the way Medicare distribution works at scale.

His company, EnrollHere, is not just another tech platform. It is a comprehensive system designed to streamline the Medicare enrollment process, offering a vertically integrated approach that aims to improve efficiency and effectiveness. Rees’s strategy is not about gaining attention; it is about producing tangible results.

The Vision Behind EnrollHere

EnrollHere is designed with a focus on solving a common problem faced by insurance agents: navigating a fragmented system. Agents are often required to use multiple, disconnected platforms to quote, enroll, manage retention, and ensure compliance. This disjointed experience can lead to inefficiency and lost opportunities. Rees recognized this challenge and built EnrollHere to address it, providing agents with a platform that integrates all these functions into one seamless experience.

The platform is designed to help agents be more productive and profitable, allowing them to manage the full spectrum of the Medicare process—quote, enroll, manage renewals, and comply with regulations—without the need to juggle multiple tools. By centralizing these tasks, EnrollHere allows agents to focus more on their core work and less on administrative burdens.

The Infrastructure Approach

What sets Rees’s company apart from other tech platforms is the distinction he makes between software and infrastructure. While many startups focus solely on building software solutions, Rees’s vision for EnrollHere goes beyond that. He’s created an infrastructure engine that supports long-term scalability.

Rees has built EnrollHere not just to serve agents in the short term, but to grow with them over time. The platform is designed to scale without creating chaos, ensuring that agents can expand their operations smoothly and without unnecessary complications. Every component of the system is carefully structured to compound value over time. From onboarding to renewals, each step is designed to minimize friction and maximize efficiency, enabling agents to work more effectively without getting bogged down by administrative tasks.

This infrastructure-first approach sets EnrollHere apart from companies that prioritize short-term wins over long-term sustainability. Rees’s vision is not about achieving immediate, superficial success. Instead, it’s about creating a foundation that supports sustainable growth, both for the agents using the platform and for the company itself.

Agents Empowered for Success

EnrollHere’s model is not about simply keeping agents busy; it’s about enabling them to operate with greater efficiency. The platform’s design empowers agents to perform like business owners, rather than traditional sales representatives. This shift in mindset is an important aspect of Rees’s strategy.

By providing agents with the tools to manage their business more effectively, Rees gives them the freedom to focus on what matters most: growing their operations and serving their clients. Agents using EnrollHere are not just more efficient—they’re more empowered to take control of their business and maximize their profitability.

This approach has resonated with many agents in the Medicare space, who have found that the platform allows them to achieve better results without needing to increase their workload. By reducing the complexity of managing Medicare enrollments, EnrollHere creates an environment where agents can focus on what they do best—connecting with clients and closing sales.

Staying Behind the Scenes

Tyler Rees is not interested in being the loudest voice in the room. He doesn’t chase social media fame or industry recognition. In fact, he remains largely behind the scenes, focused on his work rather than on building a public profile. While others in the industry are competing for attention, Rees is quietly engineering outcomes that speak for themselves.

This approach might be seen as unconventional in an era of influencer-driven marketing and viral campaigns, but it is working. Rees’s focus on building a solid infrastructure, empowering agents, and delivering tangible results has not gone unnoticed. As the company continues to grow, more people in the industry are beginning to recognize what Rees is building: a model that prioritizes efficiency, ownership, and sustainability over short-term recognition.

The Bigger Picture

While others in the healthcare sector are often focused on revenue growth and external accolades, Rees’s priorities are different. He is building a system that is designed to last—not just for the current moment, but for years to come. EnrollHere is a platform built with permanence in mind. Rees’s approach is about creating long-term value, not just immediate returns.

As the Medicare sector becomes increasingly complex, systems like EnrollHere will become more important. Rees’s company is setting a new standard for how businesses in this space operate, focusing on streamlining processes and creating sustainable systems that work for everyone involved.

Tyler Rees may not be the loudest voice in the room, but he is definitely making an impact. And in an industry that often gets distracted by the noise, his quiet focus on infrastructure, efficiency, and profitability is gaining traction. His model could well serve as a blueprint for others looking to navigate the complexities of Medicare distribution—one built not on volume, but on strategic, long-term success.

 

Disclaimer: The information provided in this article is for general informational purposes only. It does not constitute business, financial, or legal advice. While the article discusses the strategies and practices of EnrollHere and its founder, Tyler Rees, individual results may vary. Readers are encouraged to conduct their own research and consult with professionals before making any decisions related to business or financial matters. 

How Allan Marshall & Associates Helps Canadians Begin Again—With Dignity, Not Judgment

By: Emily Rumball

Nobody expects to end up in debt. But life rarely works out exactly as we plan it. A job loss. A rent increase. A breakup or a medical issue. Even just trying to keep up in a changing world can leave people juggling bills and losing sleep.

Canadians currently carry a record-breaking $2.5 trillion in consumer debt—up 4.5% year-over-year at the close of Q4 2024—spread across mortgages, credit cards, lines of credit, personal loans, and more (Transunion, 2025).

This increase isn’t unique to a particular demographic, either. Over 32 million Canadians—nearly the entire credit-active adult population—have at least one open credit account (up 2.5% YoY). Millennial and Gen Z borrowers now hold over $1.1 trillion in outstanding credit, 10% more than the year before, and younger consumers, especially Gen Z, are leading the pack with 29–30% YoY growth in credit usage.

That’s the moment many Canadians realize they might need help. And that’s where the Licensed Insolvency Trustees (LITs) at Allan Marshall & Associates come in; specialists trained to guide people through financial distress with legal tools, accountability, and an empathetic approach.

The Little-Known Alternative to Bankruptcy

Most people have heard of Bankruptcy. Fewer know about something called a Consumer Proposal, a formal, legally binding agreement that allows someone to repay part of their debt, based on what they can realistically afford.

For many, a Consumer Proposal offers the structure and protection they need to get back on track, without the heavy stigma of Bankruptcy. But despite its benefits, it’s still widely misunderstood. The name itself, “proposal,” sounds more like legal fine print than a life-changing financial reset. It’s rarely talked about outside of trustee offices, and financial institutions don’t advertise it, because it doesn’t profit them. As a result, Canadians often struggle in silence, racking up more debt or turning to risky lenders, often unaware that something like this exists.

That lack of awareness can be costly, not just financially, but emotionally. A Consumer Proposal doesn’t erase the past, but it does offer a way forward. It impacts credit in the short term, yes, and it requires a stable income to qualify. But for many households, the trade-off may be worth it. Families go from borrowing just to survive to budgeting with confidence again. It means groceries paid with a debit card, not credit. A child’s birthday is celebrated without guilt. A full night’s sleep, uninterrupted by money worries. For thousands of Canadians every year, a Consumer Proposal isn’t just a financial tool; it’s the beginning of a very real, very human kind of recovery.

And yet, many Canadians may never have been informed that this option exists.

Not a Transaction. A Conversation.

Debt can be deeply personal. It’s not just numbers on a page; it’s the stress, shame, and difficult choices. That’s why the first conversation matters. The best LITs don’t just walk people through the paperwork. They listen. They explain things clearly. They help people understand what’s possible, not just what’s owed.

No pressure. No sales pitch. Just someone on the other side of the desk saying, “You’re not alone. Let’s figure this out.”

Why Language Matters

“Bankruptcy” carries stigma. It conjures images of failure, irresponsibility, or even personal ruin. But the reality is far more nuanced. Most people in debt didn’t get there from reckless spending. They got there because life happened: a layoff, a breakup, a medical crisis, or simply trying to make ends meet in an economy where expenses rise faster than wages.

In that realm, the language we use around debt and recovery matters. Terms like “insolvent” or “delinquent,” while technically accurate, carry a heavy weight that makes people feel judged, belittled, and beyond help. Allan Marshall & Associates takes a different approach, meeting clients where they are and using simplified, plain language and an empathetic strategy that helps people feel supported rather than judged.

The right kind of support isn’t just financial; it’s emotional. It offers clarity without condescension. It says: You’re still trustworthy. You’re still capable. And yes, you’re still allowed to hope for better. Shifting the language from blame to understanding is one of the most powerful tools in debt recovery—and one of the reasons people feel understood when they finally reach out for help.

What Comes Next

The goal isn’t just to erase debt. It’s to rebuild trust in systems, in support, in oneself. Some people go on to restore credit, save for a future they didn’t think they’d have, and even start businesses again.

But before any of that, there’s usually a quieter moment: when someone breathes a little easier and thinks, Maybe I’m on the path to recovery.

That’s where recovery really begins.

Help is here. Contact an LIT at Allan Marshall & Associates to explore your options.