Tech compensation and career paths create a set of financial challenges that don’t show up in standard planning templates. Common issues we help clients think through include:

• Equity compensation (RSUs, ISOs, NSOs, ESPPs) and how it interacts with taxes, cash flow, and portfolio risk
• Concentrated stock exposure, often tied to both employment and net worth
• Irregular income from bonuses, refresh grants, or liquidity events
• Timing decisions around vesting, stock sales, diversification, and tax planning
• Career volatility, including role changes, layoffs, and compensation restructuring
• Balancing growth vs. risk when a large portion of future wealth is tied to a single company or sector

For clients who want to go deeper on portfolio construction, we also use clearly defined investment approaches—including our AI portfolios—alongside broader planning work to help manage risk, concentration, and long-term tradeoffs.

Rain Dog Financial is shaped by a deep background in software development and technical leadership. Before founding the firm, our work involved building software and working with large technology organizations.

This means:

• We understand how tech compensation actually works in practice, not just on paper
• We’re comfortable with complexity and conditional reasoning
• We speak plainly, not abstractly
• We expect—and welcome—detailed questions

You will never need to translate your world to us—we’ve lived it.

After the initial shock of a layoff, many people find the situation becomes less about immediate reaction and more about understanding what comes next. For senior tech professionals in the Bellevue and greater Eastside area, a layoff or severance package can be more about the start of a new chapter than the end of an old one.

After coming off a long career at Microsoft, Amazon, Google, or Meta, one question might be Do I need to keep working at all?  Is it time to:

• Take a break from working to see kids through high school?
• Join friends in a startup?
• Explore long-neglected interests such as music, art, nature or a totally different career?
• Give back through teaching or volunteer activities?
• Retire?

After years in tech, especially with significant equity compensation and accumulated assets, a layoff can be as much about opening doors as closing them. And a key question becomes how well your financial position supports those options.

At the same time, a severance package can raise a set of interrelated choices around:

• How severance payments are structured and taxed
• What happens to RSUs, stock options, and ESPP shares
• Whether and when to exercise options
• How to manage concentrated stock positions
• How long your assets can support time away from work or a full transition to retirement

Some of these decisions—particularly around equity and severance structure—can have large tax consequences and often cannot be undone later.

Rain Dog Financial works with tech professionals across Bellevue and the Eastside who are navigating these transitions—bringing structure to complex financial decisions while also helping you evaluate what those decisions mean for the next phase of your life. We can help find clarity on the immediate decisions, as well as moving forward confidently with a well-designed plan. For more on how to think through these decisions, see our guide to financial planning after a tech layoff.

If this sounds like a fit, the next step is a brief introductory call or meeting to determine whether working together would be useful.

During this conversation, we typically cover, at a high level:

• Your compensation structure
• Your investment assets
• Your near-term and long-term life goals
• Current specific decisions or tradeoffs you’re evaluating
• How we would approach those decisions, and where we would add value
• Whether our working style matches how you prefer to think and decide

This conversation is exploratory, not a commitment. Its purpose is to establish clarity—including whether it makes sense to continue.

Our approach is grounded in human engineering—bringing technical rigor and practical clarity to financial complexity so you can make decisions with confidence.

If it’s not a fit, you’ll know quickly.