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A Tax Planning Update - and an Opportunity to Join the Casler Financial Team

Sep 28
4 min read

Tax planning has become an increasingly important part of the work we do at Casler Financial. Rather than simply preparing a tax return after the year is over, I want to help our clients look ahead—identifying opportunities, making thoughtful decisions throughout the year, and understanding how those decisions may affect their taxes before it’s too late to change them.


Earlier this year, we began developing our Tax Planning Memberships to provide more proactive, year-round planning for our clients. Jennifer Cherry was going to take the lead on much of the tax planning side of the practice, but she has recently decided to move on from Casler Financial.


As a result, our Tax Planning Memberships are currently full, and enrollment is temporarily on hold.


I know there are clients who have been interested in joining, and I don’t want to expand the program until I know we have the right person and the capacity to provide the level of service I want our members to receive.


And that brings me to an opportunity at Casler Financial.


We are looking for an experienced tax professional who genuinely enjoys tax planning—not just tax preparation.


Ideally, this person will be an Enrolled Agent or CPA, although I am open to someone with comparable tax education and significant relevant experience. More important than the letters after someone’s name is a strong understanding of the U.S. income tax system and a genuine desire to help individuals and small-business owners make smarter financial and tax decisions.


The right person should have a strong working knowledge of areas such as:

  • Individual and small-business taxation

  • S corporations, partnerships, LLCs, and entity structure

  • Retirement accounts and retirement tax planning

  • Business deductions and tax-saving opportunities

  • Accountable plans

  • The Augusta Rule

  • Estimated taxes and year-end planning

  • Compensation and owner tax strategies

  • Other legitimate, sometimes overlooked tax-planning opportunities available under the tax code


Experience with Holistiplan and Intuit Tax Advisor would be especially valuable. If you haven’t used one or both platforms but have strong tax-planning experience and are comfortable learning new technology, I’d still love to hear from you.


We’re looking for more than technical tax knowledge.


Casler Financial is a small firm, which means the person joining us won’t be stepping into a large corporate department with every process already mapped out.


We’re looking for a self-starter who sees something that needs to be built and is comfortable helping build it.


This person should be detail-oriented, organized, comfortable working independently, and experienced with—or interested in—developing systems, creating workflows, and documenting processes. I want someone who can eventually take real ownership of the tax-planning side of Casler Financial and help us continue improving it as we grow.


Most importantly, I want someone who cares about people.


Taxes can be confusing and intimidating. Our job isn’t simply to find strategies or produce calculations; it’s to help clients understand their options and make informed decisions about their businesses, retirement, investments, and financial lives.


What the position looks like


This will initially be a part-time contract position, with hours increasing as our tax-planning client base grows.


For someone who wants more, there is the potential for the position to develop into a full-time role over time.


Compensation will depend on experience, and for the right person and the right long-term relationship, profit sharing may also be a possibility.


I’m less interested in filling a seat quickly than I am in finding someone who is a genuinely good fit for our clients, our team, and where Casler Financial is headed.


Why I’m sharing this publicly


Something pretty exciting happened recently.


A tax professional reached out to me about working with Casler Financial after using ChatGPT to search for firms that matched the tax software they knew and the type of work they were interested in doing. Casler Financial came up in their search.


I loved that.


It reminded me that the right person for a small firm like ours may not necessarily find us through a traditional job posting. They may be searching Google, asking ChatGPT, reading tax blogs, or simply trying to find a firm whose philosophy and technology align with the way they want to work.


So I’m putting this out into the world.


If you’re an experienced tax professional who loves the strategy side of taxation, enjoys helping small-business owners and individuals find legitimate ways to reduce their tax burden, and would like the opportunity to help develop and eventually lead a growing tax-planning program, I’d love to hear from you.


And if you’re one of our clients reading this and you happen to know someone who sounds like the person I’ve described, please feel free to share this post with them.


To our clients waiting for tax planning


Thank you for your patience.


Pausing new memberships isn’t a decision I take lightly, but I’d rather temporarily limit the program than grow it faster than we can serve our clients well.


Tax planning remains an important part of where Casler Financial is headed. We’re simply taking the time to find the right person to help us build the next stage of it.


Interested in joining Casler Financial?


Please reach out and tell us a little about your tax background, credentials, tax-planning experience, the software you’ve worked with, and what you’re looking for in your next professional opportunity.



Casler Financial Tax Preparation • Tax Planning • Advisory • Representation

Serving individuals and small businesses throughout Oregon and beyond.

 
 
 

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