Offices
PayPortal

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?

$150K$3M
Do you own a business?

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

1

Discover

Tell us your situation. We will tell you if we can help.

2

Diagnose

We review your returns and find where money is being left on the table.

3

Strategize

You get a custom plan showing what you save and what happens next.

4

Execute

Entity setup, payroll, retirement vehicles, filings. We handle it.

5

Partner

Quarterly meetings. Proactive strategy. Year-round. Nothing slips.

Jesse Lipscomb, Founder & Enrolled Agent

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.

Enrolled AgentIRS-licensed tax specialist
Series 65 LicensedFinancial Advisor
Insurance ProfessionalLicensed and certified

The Team

Your tax advisors

A dedicated team of Enrolled Agents working with you year-round.

Sandy Kisner, EA — Tax Advisor

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 Advisor

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