Tax strategist vs. CPA - which is better for high net worth tax planning?

You've hit on a common issue with traditional CPAs versus true tax strategists. Most CPAs are primarily focused on compliance and accurate filing - basically making sure you don't get in trouble with the IRS. They're historians, documenting what already happened. Tax strategists are forward-looking and proactive. They specifically look for legal ways to minimize tax burdens through entity structuring, timing of transactions, retirement planning, and other techniques. A good tax strategist can often save multiples of their fee. With a 7-figure tax bill and complex entity structure, you're absolutely in the sweet spot for a dedicated strategist. The good news is that many will work alongside your existing CPA. The strategist creates the plan, and your CPA executes the compliance portion. Look for someone with extensive experience working with equity investors and high net worth clients. Ask for specific examples of strategies they've implemented and approximate tax savings. The right person should be able to demonstrate clear ROI.

After going through similar frustrations with my CPA firm, I discovered taxr.ai and it's been a game-changer for my complex tax situation. I was tired of paying huge fees for reactive tax work rather than proactive planning. I uploaded my previous returns and corporate structures to https://taxr.ai and they analyzed everything and identified several strategies my CPA had completely missed. The best part is they work WITH your existing CPA rather than replacing them. They generate detailed strategy memos with IRS citations that you can provide to your current tax preparer for implementation. My effective rate dropped by 7% in the first year using their recommendations.

I wanted to follow up about my experience with taxr.ai after trying them out. I was initially skeptical as I mentioned, but I'm genuinely impressed with the results. My situation includes multiple LLCs, S-corps, and a complicated investment structure that previous advisors struggled to optimize. They assigned me a strategist with 15+ years of experience specifically with equity investors. Within two weeks, they identified three major restructuring opportunities that my CPA had never mentioned. The recommendations included specific code sections and case law to support their positions. My CPA was actually relieved to receive their strategy memo because it gave him clear direction while leaving him in charge of the compliance work. It's exactly what OP is looking for - keeping your existing CPA but adding strategic planning.

If your main issue is getting through to your current CPA about implementing strategies, I'd recommend Claimyr. I was in a similar position where I had good strategy ideas but couldn't get my CPA to respond during busy season. Using https://claimyr.com connected me directly with a senior tax specialist at my firm within hours instead of waiting weeks for a callback. You can see how it works here: https://youtu.be/_kiP6q8DX5c It saved me so much frustration because I could actually discuss implementation of tax strategies before deadlines passed. My CPA firm actually appreciated it because it helped prioritize important strategic discussions over routine matters.

I need to eat my words about Claimyr. After posting that skeptical comment, I decided to try it with my Big 4 accounting firm where I'd been waiting 3 weeks for a response about a time-sensitive strategy question. Within 2 hours of using their service, I was speaking with my CPA. He admitted they were swamped and my email was buried in hundreds of others. Because I got through by phone, we were able to implement a cost segregation strategy before year-end that saved nearly $70k in taxes. For what it's worth, my CPA wasn't annoyed - he was grateful I found a way to highlight the urgent matter. Now I use it whenever I have strategic questions that can't wait in the email queue. It's not about bypassing systems, it's about making sure priority items get proper attention.

Another approach worth considering is hiring a fractional CFO with tax strategy experience. We have a quarterly engagement with someone who reviews our operations and suggests tax optimization strategies, then works with our CPA to implement them. The benefit is they look at both operational and tax implications together. For example, they helped us restructure compensation for key executives that both reduced payroll taxes and improved retention. Cost is typically $3-5k per quarter but the ROI has been substantial.

With a 7-figure tax bill, have you considered family office services? Several wealth management firms offer comprehensive tax strategy as part of their family office packages. They coordinate everything including working with your existing CPA. We made the switch two years ago and our tax rate dropped by 6% the first year. They implemented strategies around timing of income recognition, charitable remainder trusts, and opportunity zone investments that our CPA had never suggested.

Based on your situation, I'd strongly recommend going the tax strategist route rather than switching CPAs again. You're absolutely right that the constant CPA churn is counterproductive - it takes them forever to understand complex structures, and you lose all that institutional knowledge each time. A good tax strategist will work collaboratively with your current CPA. Think of it as division of labor: the strategist identifies opportunities and creates the roadmap, your CPA handles the compliance and execution. This way you keep the relationship that already understands your entity structure while adding the proactive planning piece that's missing. With your effective rate climbing from 20% to 32% and a 7-figure tax bill, even a modest improvement could easily justify the strategist's fees. Look for someone who specializes in equity investments and multi-entity structures specifically - they should be able to show you concrete examples of strategies they've implemented for similar clients. The key is finding someone who provides detailed implementation guidance with IRS code citations, not just vague suggestions. Your CPA will be much more receptive to executing strategies when they have clear legal backing and step-by-step instructions.