Stock Based Compensation Analysis
Turn Complexity into Clarity
Equity compensation can accelerate wealth—but also bring tax, timing, and concentration risks. At Monument, we help you manage Options, RSUs, and PSUs so you can make confident, tax-aware decisions.
This service is one part of your customized wealth strategy, designed to work together with everything else.
Why Stock Based Compensation Requires Planning
The choices you make around grants, vesting, and exercising options can have ripple effects across your entire financial strategy. We regularly help clients answer questions like:
- When should I exercise my options—and how will that affect my taxes?
- Should I sell shares after vesting or hold onto them?
- How do I manage concentrated stock positions without taking on too much concentration risk?
- How does my equity compensation impact my overall investment and cash flow strategy?
Stock based compensation is not one-size-fits-all. That’s why our planning is customized, scenario-based, and deeply integrated with your larger wealth strategy.
Stock based compensation is not one-size-fits-all. That’s why our planning is customized, scenario-based, and deeply integrated with your larger wealth strategy.
What Our Stock Compensation Planning Covers
Every equity plan is different, but our stock-based compensation analysis often includes:
Option Exercise Strategy
We evaluate timing, tax impact, and diversification goals to build a strategy for exercising incentive and non-qualified stock options (ISOs and NQSOs).
RSU, PSU and Stock Options Planning
We help you coordinate restricted stock units (RSUs), performance stock units (PSUs), and stock options along with your cash needs, tax planning, and investment strategy.
Concentrated Position Management
We assess your total equity exposure and develop strategies—such as staged selling, gifting, or charitable vehicles—to help reduce over concentration and improve tax outcomes.
Tax Projection Modeling
We project your potential tax liability based on various equity outcomes and work closely with your CPA or tax advisor to help prevent anything from falling through the cracks.
Scenario Analysis
We model multiple strategies for managing your equity—timing, diversification, tax implications—and help you evaluate the emotional and financial tradeoffs side-by-side.
Cash Flow Planning Integration
We map future vesting schedules, option exercises, and potential sale events into your broader cash flow picture—to help you anticipate what’s coming and how it supports your goals. We believe this can reduce reliance on mental accounting (e.g., “this grant will pay for college”) and build a more resilient, flexible financial plan.
Please see important disclosure information below.
Stock Compensation Planning That Moves With You
Your equity plan isn’t static. We develop a strategic approach that evolves as you:
Receive new grants or promotions
Change employers or move to a different equity structure
Consider a career pivot, liquidity event, or sabbatical
At each transition, we plan to revisit your strategy and update our analysis to reflect what’s changed.
Please see important disclosure information below.
Who Our Stock Based Compensation Planning Is Built For
Our planning is designed for professionals navigating meaningful equity decisions:
- Executives with complex compensation and income timing decisions
- Business owners planning for growth, exit, or succession
- Families looking to minimize taxes across generations
- Professionals who want to coordinate investments, giving, and taxes
Our team’s tax planning guidance is designed to support smart decision-making across the entire year.
Please see important disclosure information below.
The Monument Approach to Stock Based Compensation
We treat stock-based compensation as an integrated part of your wealth strategy—not a siloed decision. Our planning is designed to be:
Integrated
We consider tax planning, cash flow, risk, and timing together—not in isolation.
Personalized
Your plan is based on your unique vesting schedules, career plans, and life priorities.
Collaborative
We coordinate with your tax advisor or CPA.
Clear
You’ll leave each conversation with prioritized recommendations with clear rationale, supported by data.
What Will You Walk Away With?
Our stock-based compensation planning is designed to provide you with:
- A strategy for exercising options and managing vested shares
- A clearer understanding of tax implications and key deadlines
- Recommendations for managing concentration risk
- Ongoing updates as your career—and equity situation—evolve
Monument’s Leadership Team
mini HYPOTHETICAL Case study
Clearing the Path to CEO
Mark Chambers had a chance to leave an executive role at a large publicly traded company and join a startup as the CEO. It was an exciting opportunity that came with a slew of other interconnected decisions. It was really a complex life transition wrapped up in one key career decision: Can I take this new career opportunity and still accomplish our family’s goals for the future – or do I need to play it safe and stay in my current role?
A significant portion of their wealth was tied up in public company stock. Their oldest daughter was about to start college. They were planning a major home renovation requiring significant investment. And after years of building toward financial independence, they wanted to know whether taking this new position would put any of that at risk.
That’s where we came in.
We helped them get clear on their options by modeling out what a buyout package would need to look like to support the transition, complete the family’s planned home renovation, fund an additional year of education if their daughter chose to pursue her master’s degree, and maintain the cash flow needed to support their lifestyle.
As a result, they were able to see their chosen path clearly and have confidence it would work.
Mark went back to the negotiating table and secured a buyout that could support their vision.
As their oldest prepared for college, we helped them shift from saving to spending, developing a strategy for how to use their 529 assets.
At the same time, we coordinated with their CPA to manage the tax implications of Mark’s stock compensation and develop a strategy for exercising private company stock options as they vested.
We also revisited their estate plan, helping them evaluate whether documents drafted years earlier still reflected the realities of their family’s life today. With children entering adulthood, we identified planning opportunities and helped prepare them for more productive conversations with their estate attorney.
Instead of viewing each issue separately, they gained a clear understanding of how each decision affected the bigger picture. The result was confidence—not just in Mark’s career move, but in the family’s ability to pursue new opportunities without losing sight of the goals they had spent years working toward.
Understand Your Options
Monument helps you manage your equity compensation, freeing time and mental space to focus on what matters most.
Please Note: Limitations. The scope of any financial planning and consulting services to be provided depends upon the terms of the engagement, and the specific requests and needs of the client. Monument Capital Management, LLC does not serve as an attorney, accountant, or insurance agent. Monument Capital Management, LLC does not prepare legal documents or tax returns, nor does it sell insurance products. Please Also Note: Different types of investments involve varying degrees of risk. Therefore, it should not be assumed that future performance of any specific investment or investment strategy (including the investments and/or investment strategies recommended and/or undertaken by Monument Capital Management, LLC) or any planning or consulting services, will be profitable, equal any historical performance level(s), or prove successful. A copy of our current written disclosure Brochure discussing our advisory services and fees continues to remain available upon request or at monumentwealthmanagement.com.
