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Employee Spotlight: Debbie Gallegos

Meet Debbie Gallegos, a Senior Associate on our Resolutions Team! Although she’s been with Tax Guard for five months, Debbie brings nearly two decades of tax resolution experience, helping taxpayers navigate complex IRS matters with expertise and compassion.

A few fun facts:

  • Has worked in the tax resolution industry since 2008
  • Proud mom of three kids
  • Loves to travel and explore new places
  • Dog mom to two adorable Yorkshire Terriers

One of Debbie’s most memorable cases involved helping a client receive Innocent Spouse Relief, eliminating more than $20 million in tax liabilities and giving her the opportunity to move forward after years of hardship. It’s a powerful reminder of the life-changing impact financial advocacy can have.

Debbie’s advice for business owners? Stay current with your ongoing tax obligations — even if you owe back taxes. Many business owners focus on resolving past-due balances while unintentionally falling behind on current compliance.

We’re grateful to have Debbie’s experience, dedication, and compassion on the Tax Guard team. Welcome aboard, Debbie!

Employee Spotlight: Sean Diller

Meet Sean Diller, an Associate on our Resolutions Team who helps businesses navigate IRS challenges and maintain critical funding relationships. Sean has been with Tax Guard since January of 2025 and works with businesses to resolve liabilities and keep operations moving forward. 

A few fun facts:

  • Loves gardening, especially finding hardy perennials that can survive Colorado’s tough climate
  • Previously taught 7th-grade math and science in New Orleans
  • Used to have recurring nightmares about alligators (a Louisiana souvenir!)
  • Has a soft spot for lilacs

Sean’s advice for small business owners? Set yourself up for success with the IRS — know your filing and deposit requirements and keep access to your EFTPS account handy.

What motivates him every day is knowing these challenges have solutions and helping businesses come out stronger on the other side.

We’re excited to have you on the team, Sean!

Employee Spotlight: Megan Harless

Tax Guard’s Resolution Team is specialized in resolving issues for businesses that owe money to the IRS that are also working with a bank, asset-based lender, or factoring company.

Meet Megan Harless, an Associate on our Resolutions Team who plays a critical role in helping clients and lenders navigate complex tax challenges. In her role, Megan works to prevent enforced collection actions, negotiate affordable payment plans for tax liabilities, and support strong funding relationships between clients and lenders.

Megan is celebrating 7 years at Tax Guard this February, 2026 and her expertise and dedication continue to make a meaningful impact across the team.

A few fun facts about Megan:

  • A huge fantasy book fan (think Robert Jordan and Brandon Sanderson)
  • Devoted dog mom to Grizzly and Panda
  • An outdoor enthusiast who thrives in summer — kayaking, biking, river rafting, and hiking
  • Loves color in all forms (her home has all of the colors of the rainbow, depending on where you’re standing)

Megan is passionate about correcting a common misconception in tax resolution: that it can be done in a day or without documentation. She knows that real progress takes time, detail, and collaboration — and that thoughtful, well-supported work is what leads to successful outcomes.

What motivates her every day? Being part of a supportive team that collaborates to help taxpayers navigate challenging situations. We’re grateful for your dedication and expertise, Megan! 

Employee Spotlight: Charmagne Castillo

Tax Guard’s Resolution Team is specialized in resolving issues for businesses that owe money to the IRS that are also working with a bank, asset-based lender, or factoring company.

One of the defining members of the Resolutions team is Charmagne Castillo!

  • Resolving tax issues since 2010
  • Proud mother of three collegiate daughters
  • Skilled wakesurfer
  • Travel enthusiast

“At Tax Guard, I’m committed to helping businesses stay open and funded — making a lasting impact every day.” – Charmagne

Thank you for all your dedicated work, Charmagne!

Employee Spotlight: Rachel Paine

Meet Rachel Paine, the Senior Tax Advisor in our Resolutions department. You may have seen her in our regular webinar series. To ensure Tax Guard provides customers with the information they need to make more informed decisions, she helps lenders evaluate funding risks and works with taxpayers to resolve IRS liabilities with the goal of preserving the funding relationship. Learn more about Rachel and her work at Tax Guard below.

How did you get involved with the small business lending and due diligence space?

Honestly, I fell into it. I have always been in finance-related roles, mainly focusing on risk management and helping people. I love my role at Tax Guard because I have the opportunity to tap into my education in psychology and my background in finance to better understand people, advise lenders, and work with stressed taxpayers — it’s essentially win-win-win.

What motivates you to come to work each day?

It’s rewarding to help businesses understand that an IRS liability isn’t a death sentence. It’s the best feeling when a taxpayer tells me they feel lighter or relieved when we finish our introductory call — one taxpayer even referred to the meeting as “tax therapy.” It’s very special to know you’re easing people’s stress by working through problems together, and I’m lucky to feel like I’m making a real difference.

What might people misunderstand about Tax Guard or your role?

Tax resolution gets a bad reputation for being complicated and stressful, but Tax Guard’s team and approach are different. We are specialists in the tax resolution space — all we do is work with businesses who owe money to the IRS that are also working with an asset-based lender, bank, or factor. Since our monitoring system identifies issues earlier in the process, i.e. when a business has cashflow problems, we can be proactive in our resolution by addressing problems before they snowball.

When faced with a tax problem, the process to resolve the issue can feel overwhelming. My role is to educate taxpayers about their options for resolution because there are a lot of misconceptions about how the process works. Similarly, I help lenders understand their risk and exposure when funding, with the goal of preserving funding relationships.

What area of your job excites you most and why? What do you find most rewarding about your job?

I cherish the relationships I have built. Working together feels like a true partnership, which makes addressing complex and stressful problems significantly easier and more enjoyable.

As someone who has worked in the industry for several years, I understand how daunting tax resolution can be. So when a taxpayer tells me they’ll sleep better that night seeing the light at the end of the tunnel with IRS issues, or having a lender thank our team for saving a funding relationship, I find it extremely rewarding.

What are your passions outside of work?

Anyone who knows me knows that I am a crazy dog lady! My fiancé and I have 3 dogs and a cat. Prior to us having a zoo of our own, I fostered 75 dogs and helped them find their forever homes. Besides spending time with my fur babies, I love taking advantage of living in beautiful Colorado and getting outside — especially camping, off-roading, mountain biking, and swimming.

When I’m not outdoors, I love to spend time with my friends and travel. Italy is my favorite place in the world and I’m always ready to go back and visit!

What is your favorite dessert?

I have SUCH a sweet tooth—gummy candy, sour candy, chocolate candy. Ice cream is mandatory in our house, especially mint chocolate chip, black raspberry chocolate chip, and graham cracker (not super common, but I highly recommend trying!).

If you could have your own TV show, what would it be about?

I have a couple of ideas if any TV producers are listening:

First off, my own sports show. My fiancé and I are really good sports commentators (or so we think). We typically beat the commentators to the punch for both the NHL and Formula 1, so I think we could hold our own.

I also love to cook and bake, but my show would have a twist: it would be a specialty show about cooking and cleaning at the same time. I always make it my goal to have a clean kitchen by the time the food is ready, even though it drives my fiancé mad.

What’s your favorite part about Colorado?

Colorado summers are extremely underrated. Like many people, I moved to Colorado to ski, but I stayed for the summers. The mountains in warm weather are unmatched, and my fiancé and I like to spend our time off the beaten path, camping with our dogs and enjoying the outdoors with no one else around.