Services / Tax Preparation & Filing
Tax Preparation & FilingHandled by a Team That Knows Your Plan
For our subscribers, filing season is not a scramble. Your returns are prepared by the same team that built your tax strategy and set up your entities, so nothing gets missed and nothing catches you off guard.
Filing is where the year’s planning either shows up on the return or quietly disappears. We make sure it shows up.
One team
The people who plan your taxes are the people who file them
Year-round
We stay engaged after April, not just during it
Entity-aware
Personal, business, and pass-through returns coordinated together
No surprises
Estimates and liabilities reviewed before deadlines arrive
Filing That Reflects Your Strategy
Most tax preparation is transactional. You hand over documents in April, someone you have never spoken to enters them into software, and you hope the deductions you were promised actually made it onto the return. For high-income earners with entities, equity, and multiple income streams, that model leaves money on the table and creates risk.
Roadmap does it differently. Because we plan your taxes throughout the year, by the time filing season arrives we already know your structure, your goals, and the strategies we put in place. Preparation becomes the natural conclusion of a plan we have been executing together, not a rushed reconstruction of the prior year.
The people who plan your taxes should be the people who file them.
Services
What Subscribers Get at Filing Time
Continuity From Planning to Filing
The strategies we design during the year flow directly onto your return. There is no handoff to a preparer who was not part of the conversation and no risk of a deduction getting lost in translation.
Coordinated Personal & Entity Returns
Individual, S-Corp, partnership, and related filings are prepared together so they reconcile cleanly. When your entities interact, we make sure the returns tell one consistent story.
Accuracy You Can Defend
We prepare returns to be clean, complete, and well-documented. If a position needs support, the support is already in place, not assembled after a notice arrives.
No Last-Minute Scramble
Because we are engaged year-round, we are not chasing documents in April. Estimates are reviewed ahead of deadlines and your liability is understood well before anything is due.
A Return That Reflects the Whole Picture
W-2 income, business income, investments, real estate, and equity compensation are considered together. Nothing is filed in isolation, because your finances do not exist in isolation.
Who This Is For
Our filing service is built for people whose returns are no longer simple:
High-income W-2 earners
Especially those with equity compensation or supplemental income
Business owners and the self-employed
S-Corp, partnership, and sole-proprietor filers
Real estate investors
Rental income, depreciation, and multi-property portfolios
Households with multiple income streams
Where personal and business returns need to reconcile
Anyone tired of the April surprise
People who want the number known before the deadline, not after
Not sure whether your situation calls for this level of service? A short conversation is the fastest way to find out.
Process
How Filing Works as a Subscriber
Year-Round Groundwork
Throughout the year we track the decisions and strategies that affect your return, so the raw material is ready long before filing season.
Document Review
We gather and review your tax documents, flagging anything missing or inconsistent well ahead of deadlines.
Preparation & Coordination
Your personal and entity returns are prepared together, with the year’s strategies applied and everything reconciled to tell one consistent story.
Review With You
Before anything is filed, we walk through the return so you understand your liability, your deductions, and what drove the outcome.
File & Plan Ahead
We file, then immediately look forward, using what we learned this year to sharpen next year’s plan.
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?
Tax Preparation & Filing FAQ
Is tax preparation included with the Roadmap subscription?
Tax preparation and filing are part of the year-round relationship for our subscribers. Rather than being a separate transaction, filing is the natural conclusion of the planning we do together throughout the year. Reach out and we will walk you through exactly what your engagement includes.
Can you handle both my personal and business returns?
Yes. Coordinating personal, S-Corp, partnership, and related filings is a core part of what we do. When your entities interact, preparing the returns together is what keeps them consistent and defensible.
What if I have income in multiple states?
Multi-state filing is common for the clients we serve, particularly those with equity compensation, remote income, or a recent move. We handle state filings as part of a coordinated return. If your situation is complex, we will talk through it before filing so there are no surprises.
I already filed an extension. Can you still help?
Yes. An extension gives us time to prepare a complete, accurate return rather than a rushed one. If you are on extension and want the filing handled properly, the sooner we connect the better.
How is this different from using tax software or a seasonal preparer?
Software and seasonal preparers work from whatever you hand them in April, with no knowledge of your strategy. Because we plan with you year-round, we already know your structure and goals, so the return reflects a deliberate plan rather than a best guess made under deadline pressure.
Filing Season Without the Scramble
Let the team that plans your taxes handle filing them. Reach out to learn what a year-round tax relationship looks like for your situation.