Services / Year-Round Partnership
Year-Round Tax Strategy PartnershipA Team That Doesn’t Disappear After April
Most firms file your return once a year and vanish until the next deadline. We work the other way. A dedicated team plans with you every quarter, watches your finances year-round, and catches opportunities before they expire.
The difference between a preparer and a strategist is timing. A preparer reacts to last year. A strategist shapes this one while there is still time to act.
12 months
Proactive planning all year, not just at filing time
Quarterly
Regular check-ins to adjust strategy as your year unfolds
Dedicated team
The same people who know your full financial picture
Proactive
We surface opportunities before deadlines close them off
Why Once-a-Year Tax Help Falls Short
By the time you sit down with a traditional preparer in the spring, the tax year is already over. Nearly every meaningful decision, entity structure, retirement contributions, timing of income and deductions, has already happened or is out of reach. The preparer can only report what took place. They cannot change it.
A year-round partnership flips that. Because we are engaged throughout the year, we can act while decisions are still in front of you. We meet quarterly, watch how your income and business evolve, and adjust the plan in real time. When an opportunity or a risk appears, we address it before the window closes, not after, when nothing can be done.
A preparer reacts to last year. A strategist shapes this one.
Services
What the Partnership Includes
Quarterly Strategy Meetings
We sit down with you throughout the year to review where things stand, adjust the plan, and make sure you are on track, rather than reconstructing the year after it ends.
Proactive Opportunity Spotting
We watch for deductions, elections, and timing moves that have deadlines, and we raise them while there is still time to act on them.
One Team, Full Picture
The same people handle your planning, your entities, and your filing. Nothing falls through the cracks between advisors who do not talk to each other.
Estimated Payments, Handled
We keep your quarterly estimates dialed in so the April surprise stops happening and your cash flow stays predictable.
A Plan That Evolves With You
A new business, a liquidity event, a move, a growing family, life changes your tax picture. Because we are always engaged, the plan changes with it.
Coordination Across Every Strategy
Entity structure, retirement, real estate, charitable giving, and filing are not separate silos. We coordinate them into one strategy that works together.
Who the Partnership Fits
The year-round model delivers the most for people whose finances keep moving:
High-income earners
Where proactive timing and planning meaningfully change the outcome
Business owners
Whose entity, payroll, and profit decisions happen all year long
People with equity compensation
Where vesting, exercise, and sale timing carry real tax weight
Real estate investors
With acquisitions, dispositions, and depreciation to coordinate
Anyone burned by the once-a-year model
People who want a strategist in their corner, not just a preparer
The best time to start a year-round relationship is early in the year, when the most decisions are still open, but there is value in starting whenever you are ready.
Process
How the Partnership Works
Onboarding & Deep Dive
We start by understanding your full picture, income, entities, investments, and goals, so the plan is built on reality, not assumptions.
Build the Strategy
We map out the year’s plan across every relevant area and identify the moves worth making and when to make them.
Quarterly Check-Ins
We meet through the year to review progress, adjust for changes, and act on time-sensitive opportunities before they expire.
Coordinated Filing
When filing season arrives, there is no scramble. The return is the natural result of the plan we have executed together.
Refine for Next Year
We carry forward what we learned to sharpen the following year’s strategy, so the plan compounds over time.
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?
Year-Round Partnership FAQ
How is this different from a regular CPA relationship?
A traditional CPA typically engages once a year to prepare your return, reporting on decisions that have already been made. A year-round partnership means we plan with you continuously, meet quarterly, and act on opportunities while they are still open. The goal is to shape the tax year as it happens, not just document it after the fact.
What actually happens in the quarterly meetings?
We review how your income and business are tracking, revisit the strategies we put in place, adjust for anything that has changed, and flag time-sensitive moves with upcoming deadlines. It is a working session focused on decisions you can still make, not a status report.
Is the year-round partnership worth it if my taxes feel manageable now?
Often the clients who feel "manageable" are the ones leaving the most on the table, because no one is looking proactively. The value of the partnership is in the opportunities caught early and the surprises prevented. A short conversation is the best way to gauge whether it makes sense for you.
Do you also handle my tax return, or just the planning?
Both. Planning and filing are handled by the same team, so your return reflects the strategy we have been executing all year. That continuity is a large part of what makes the model work.
When is the best time to start?
Earlier in the year is ideal, because more decisions are still open and there is more room to act. That said, meaningful planning can begin at any point, and getting started sooner is always better than waiting for the next filing season.
Trade the April Surprise for a Year-Round Plan
Stop working with a firm that disappears after filing. Let’s talk about what a proactive, year-round tax partnership looks like for you.