Keep more of what you earn. Every year.
Year-round tax strategy for high-income earners tired of overpaying and under-planning.
How Much Could You Save?
Services
What We Do For You
Advanced Tax Strategies
Our clients routinely save six figures or more through strategies their previous CPA never mentioned. One conversation is all it takes to see what you have been missing. Book a call and we will show you the number.
Learn more →Entity Setup & Structuring
The wrong structure is costing you tens of thousands every year. We set up your S-Corp, optimize your payroll, and put you in a position to keep more from day one.
Learn more →Tax Preparation & Filing
As a subscriber, your returns are handled by a team that already knows your strategy, your entities, and your goals. No last minute scramble. No surprises. Just clean, accurate filing.
Learn more →Cost Segregation
Own commercial or investment property? You could be sitting on hundreds of thousands in accelerated depreciation. We run the study, find the savings, and put it to work immediately.
Learn more →Retirement Tax Planning
Maxing out your 401k is a starting point, not a strategy. We build retirement plans that let high earners shelter significantly more income every year.
Learn more →Year-Round Tax Strategy Partnership
A dedicated team. Quarterly planning. Proactive strategy 12 months a year. We do not file and disappear. We watch your finances, catch opportunities before they expire, and make sure you never overpay.
Learn more →Impact
What Our Clients Say
Advanced Tax Strategies
"I'd used the same CPA for over a decade and assumed I was doing everything right. In our first strategy session Roadmap found six figures in savings I'd been missing every single year. This wasn't tax prep. It was an actual plan, and my only regret is not making the switch sooner."
High-income professional
Concentrated Stock & RSU Diversification
"After years at a public tech company, most of my net worth had quietly ended up in one stock. Not because I chose it, just because the RSUs kept vesting. Roadmap built a multi-year plan to unwind the position on my terms without triggering a capital-gains disaster. For the first time I feel like I'm actually deciding instead of avoiding it."
Senior Director, Public Tech Company
RSU Withholding & the Surprise Tax Bill
"My company withheld the standard supplemental rate on my RSUs, so every April I got blindsided by a five-figure bill I never saw coming. Roadmap showed me exactly why it kept happening, got my estimates dialed in, and made the surprises stop. Now I keep more of what I actually earn."
Engineering Leader, Big Tech
Leaving California with Equity
"I was planning to move out of California with a large stack of unvested equity and had no idea the state could still tax a slice of it after I left. Roadmap timed my vesting and my residency the right way and saved me well into six figures. The planning paid for itself many times over."
VP, Technology
Entity Setup & Structuring
"Roadmap set up my S-Corp, cleaned up my payroll, and restructured how I pay myself. I now keep tens of thousands of dollars more every year, money that used to just disappear. I can't believe no one had walked me through this before."
Business owner
Retirement Tax Planning
"I thought maxing out my 401(k) was the ceiling. Roadmap paired a defined benefit plan with my entity, and now I shelter well over a hundred thousand dollars a year. Fifteen years of filing and nobody had ever mentioned it was even an option."
Physician
Cost Segregation
"I picked up a commercial property and my old accountant never said a word about cost segregation. Roadmap ran the study and accelerated hundreds of thousands in depreciation the very first year. One conversation put real money back in my pocket."
Real estate investor
Charitable Giving Strategy
"I wanted to give back but was doing it the least efficient way possible, just writing checks. Roadmap showed me how to donate appreciated shares instead. I gave more to the causes I care about, skipped the capital-gains hit, and lowered my tax bill doing it. My previous CPA never brought it up once."
Executive
Year-Round Strategy Partnership
"My old firm filed my return once a year and vanished until the next one. Roadmap meets with me every quarter, catches opportunities before deadlines close, and actually knows my full picture. In two years they've saved me more than my last CPA did in ten. That's the difference between a preparer and a strategist."
Chief Revenue Officer
A Funded Exit, Not Golden Handcuffs
"I'd hit the number where work was supposed to be optional, but the equity and the tax picture felt too tangled to walk away from. Roadmap turned a messy pile of vesting stock into a real exit plan with the tax bill accounted for. I finally know I can leave on my own terms."
Senior tech leader
Advanced Tax Strategies
"I'd used the same CPA for over a decade and assumed I was doing everything right. In our first strategy session Roadmap found six figures in savings I'd been missing every single year. This wasn't tax prep. It was an actual plan, and my only regret is not making the switch sooner."
High-income professional
Concentrated Stock & RSU Diversification
"After years at a public tech company, most of my net worth had quietly ended up in one stock. Not because I chose it, just because the RSUs kept vesting. Roadmap built a multi-year plan to unwind the position on my terms without triggering a capital-gains disaster. For the first time I feel like I'm actually deciding instead of avoiding it."
Senior Director, Public Tech Company
RSU Withholding & the Surprise Tax Bill
"My company withheld the standard supplemental rate on my RSUs, so every April I got blindsided by a five-figure bill I never saw coming. Roadmap showed me exactly why it kept happening, got my estimates dialed in, and made the surprises stop. Now I keep more of what I actually earn."
Engineering Leader, Big Tech
Leaving California with Equity
"I was planning to move out of California with a large stack of unvested equity and had no idea the state could still tax a slice of it after I left. Roadmap timed my vesting and my residency the right way and saved me well into six figures. The planning paid for itself many times over."
VP, Technology
Entity Setup & Structuring
"Roadmap set up my S-Corp, cleaned up my payroll, and restructured how I pay myself. I now keep tens of thousands of dollars more every year, money that used to just disappear. I can't believe no one had walked me through this before."
Business owner
Retirement Tax Planning
"I thought maxing out my 401(k) was the ceiling. Roadmap paired a defined benefit plan with my entity, and now I shelter well over a hundred thousand dollars a year. Fifteen years of filing and nobody had ever mentioned it was even an option."
Physician
Cost Segregation
"I picked up a commercial property and my old accountant never said a word about cost segregation. Roadmap ran the study and accelerated hundreds of thousands in depreciation the very first year. One conversation put real money back in my pocket."
Real estate investor
Charitable Giving Strategy
"I wanted to give back but was doing it the least efficient way possible, just writing checks. Roadmap showed me how to donate appreciated shares instead. I gave more to the causes I care about, skipped the capital-gains hit, and lowered my tax bill doing it. My previous CPA never brought it up once."
Executive
Year-Round Strategy Partnership
"My old firm filed my return once a year and vanished until the next one. Roadmap meets with me every quarter, catches opportunities before deadlines close, and actually knows my full picture. In two years they've saved me more than my last CPA did in ten. That's the difference between a preparer and a strategist."
Chief Revenue Officer
A Funded Exit, Not Golden Handcuffs
"I'd hit the number where work was supposed to be optional, but the equity and the tax picture felt too tangled to walk away from. Roadmap turned a messy pile of vesting stock into a real exit plan with the tax bill accounted for. I finally know I can leave on my own terms."
Senior tech leader
Process
How It Works
Discover
Tell us your situation. We will tell you if we can help.
Diagnose
We review your returns and find where money is being left on the table.
Strategize
You get a custom plan showing what you save and what happens next.
Execute
Entity setup, payroll, retirement vehicles, filings. We handle it.
Partner
Quarterly meetings. Proactive strategy. Year-round. Nothing slips.

Meet Jesse Lipscomb
Founder and CEO, Roadmap Tax Services
Enrolled Agent | Series 65 Financial Advisor
Most tax firms file your return and disappear. Jesse built Roadmap Tax to do the opposite. With dual expertise in tax strategy and financial advisory, Jesse works with high-income earners and business owners year-round to find savings their previous CPA never looked for. His clients do not wonder if they are overpaying. They know exactly where their money is going, what strategies are working, and what is coming next. That is what happens when your tax professional actually knows you.
The Team
Your tax advisors
A dedicated team of Enrolled Agents working with you year-round.

Sandy Kisner, EA
Tax Strategist
Sandy focuses on helping entrepreneurs and high-earning professionals reduce their tax burden and build long-term wealth. She works with small business owners, real estate professionals, physicians, investors, and brokers, delivering proactive tax planning tailored to each client. Clients rely on Sandy for clear guidance, creative problem-solving, and practical solutions that turn complex tax laws into real financial opportunities.

Alex Lazo, EA
Tax Strategist
Alex brings nearly five years of experience helping clients take control of their tax outcomes. A Point Loma Nazarene University accounting graduate, he specializes in proactive tax planning for real estate investors and self-employed business owners. Originally from San Diego, Alex is known for making complex tax concepts accessible and actionable, helping clients use the tax code as a tool for building wealth.
Questions?
Frequently Asked
Who is Roadmap Tax for?
High income earners and business owners making $300,000 or more per year. Doctors, executives, real estate professionals, and entrepreneurs who want proactive tax strategy, not just annual filing.
How is this different from my current CPA?
Most CPAs file your return once a year and move on. We work with you 12 months a year through quarterly planning, proactive strategy, and a team that knows your full financial picture. We find savings. We do not just report numbers.
How much can I actually save?
It depends on your income and situation, but our clients in the $300K to $1M range routinely save six figures or more per year through strategies their previous CPA never brought up.
Do I need to own a business to work with you?
No. Many of our clients are W-2 earners. High income employees often benefit the most because they have the fewest strategies in place and the most room for savings.
What does the subscription include?
Tax transcript analysis, personal and entity tax preparation, extensions, quarterly tax planning meetings, and year round access to your dedicated team. Add on services like advanced tax strategies, charitable giving, and cost segregation are available based on your needs.
I already filed this year. Is it too late?
No. Tax strategy is year round. The best time to start planning is now, not next April. We can review what was filed, identify missed opportunities, and build a strategy going forward so next year looks completely different.
Ready for Strategic Tax Planning?
Your financial goals deserve a strategic approach, not reactive tax preparation. Let's discuss what's possible for your situation.
Get in Touch
Our Offices
Serving clients from California, Texas, and Florida
California Office
4025 Camino Del Rio South, Suite 300
San Diego, CA 92108
(619) 280-2700
Texas Office
7460 Warren Parkway, Suite 100
Frisco, TX 75034
(619) 483-3982
Florida Office
14101 Panama City Beach Pkwy, 3rd Floor
Panama City Beach, FL 32413
(619) 280-2700
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How California Still Taxes Your RSUs After You Move
You moved to Texas, but California still wants a cut of your RSUs. Here's how state sourcing works, why the FTB sends letters, and how to plan ahead before you relocate.

When Your RSUs Vest, the Withholding Probably Isn't Enough
The 22% flat rate on RSUs leaves most tech executives underwithheld. Here's how the math works in a representative scenario and what to do about it before next April.

The Golden Handcuffs Exit: When Do You Leave $3 Million in Company Stock Behind?
A senior director wants to leave big tech with $3.2M in one stock. Here's how to plan an RSU exit, diversify without a tax hit, and coordinate the timing.