Undermountain Partners
Trusted, Practical Guidance After Loss
Like a compassionate project manager, Undermountain Partners helps sandwich-generation executors navigate the practical work of settling a loved one's affairs.
Always free for families • Secure & Confidential
Undermountain Partners Can Help When…
After the loss of a loved one, the responsibilities of settling their estate can be overwhelming.
You Don't Know Where to Begin
We help you make sense of what your loved one left behind by identifying accounts, benefits, and responsibilities you may not even know exist — giving you a clear, accurate picture of the estate and the confidence to take the first step.
You're Worried About Mistakes
We'll create a personalized estate-settlement plan tailored to your situation, your bandwidth, and the unique details of the estate — organizing everything in one place so nothing gets missed, duplicated, or left to guesswork.
You Need Ongoing Support
We work alongside you throughout the process, offering expert guidance, accountability, and reassurance — helping you move through estate settlement at your own pace and ensuring every task and decision is documented.
How We Support Clients
Whether you're planning ahead or navigating loss, we bring structure, clarity, and steadiness to work that can feel overwhelming.
Individuals Planning Ahead
- Identify the information your loved ones would need in an emergency or after your death
- Organize key documents, accounts, policies, and practical details in one place
- Clarify your wishes for personal, logistical, and legacy matters
- Prepare for conversations with attorneys, financial advisors, and other professionals
- Identify where outside professional support may be needed
- Create a plan to reduce confusion, delay, and unnecessary stress for your family
- Put systems in place so the people you love are not left scrambling later
Families & Executors After a Loss
- Identify assets, accounts, policies, and unanswered questions
- Organize information and create a clear picture of what needs attention
- Prepare for meetings with attorneys, financial institutions, and probate court
- Build a practical plan for the many steps involved in settling an estate
- Coordinate communication with heirs, relatives, and other stakeholders
- Help identify, research, and connect with outside professionals as needed
- Track progress, document decisions, and help keep the process moving forward
* Undermountain Partners does not provide legal, financial, or tax advice. Clients are encouraged to consult with their own legal, financial, or tax professionals for such matters.
Services
Practical, compassionate support tailored to your situation — whether you're planning ahead or navigating the responsibilities that follow a death.
After-Loss Support
Grounded support through estate settlement — understanding what needs to be done, organizing information, documenting progress, and keeping things moving without losing sight of the emotional reality.
Estate Organization
Getting organized before a crisis is one of the most practical gifts you can leave the people who love you. I help individuals create a clearer picture of the information, documents, decisions, and practical details their loved ones will need in an emergency or after a death.
Funeral Celebrant Services
I work with families in Litchfield County, Connecticut, and Berkshire County, Massachusetts to create memorial and funeral ceremonies that feel personal, thoughtful, and true to the person being remembered.
Meet Tracy Flynn
I founded Undermountain Partners to help people make space for healing amid the practical demands that follow a loss. After my father died in 2023, I saw how quickly grief can get crowded out by paperwork, logistics, and the pressure of everyday life. That experience changed how I think about what people need in the aftermath of a death.
With a 25-year career spanning sales, research, and leadership at organizations including Fidelity Investments, Coinbase, and Google, I bring organization, clarity, and a calm, steady approach to complex situations.
I hold the After Loss Professional credential through Professionals of After Loss Services, completed funeral celebrant training through InSight Books, and volunteer weekly with a hospice organization.
Undermountain Partners is especially focused on people in the sandwich generation: adults managing loss while also managing the rest of life. If you are planning ahead or navigating a loss, I'm here to help.
Better Together
Compassionate estate settlement support and AI-powered care estimates — a complete approach to supporting your family during life's most difficult transitions.
Estate Settlement Support
Undermountain Partners helps executors and families navigate estate settlement with compassionate, organized guidance — like having a project manager for one of life's hardest tasks.
AI-Powered Care Estimates
LTCareNav's free 60-second snapshot gives you a quick, broad-strokes look at potential care needs and costs — a helpful starting point for planning ahead.
Complete Family Support
Together, we cover the full spectrum — from estate settlement and after-loss guidance to AI-powered care planning that protects your family's future.
Your path to care planning and financial security.
Answer 8 questions and get a personalized snapshot of your care needs and financial runway, and the financial options and benefit programs most families never find — free, no credit card required.
Who needs help?
Tell us who you're planning care for.
The next questions will be about whoever you choose above — answer for them, not yourself (unless this is for you).
You Don't Have to Do This Alone
With compassionate estate settlement support from Undermountain Partners and AI-powered care planning from LTCareNav, your family has the guidance needed during life's most difficult moments.
Always free for families • No credit card required • Private and Secure
Undermountain Partners — Compassionate Estate Settlement Support
Tracy Flynn, founder of Undermountain Partners, provides practical, compassionate support for estate settlement and organization. Services include after-loss support, compassionate project management for estate settlement, estate organization for individuals planning ahead, funeral celebrant services in Litchfield County CT and Berkshire County MA, professional coordination, and legacy planning. Partnered with LTCareNav for free care cost estimates and personalized long-term care planning tools.
Tracy Flynn has a 25-year career spanning sales, research, and leadership at Fidelity Investments, Coinbase, and Google. She holds the After Loss Professional credential and completed funeral celebrant training through InSight Books.
Keywords: estate settlement, executor support, estate organization, after-loss support, grief-informed care, funeral celebrant, estate planning, settling an estate, sandwich generation, Undermountain Partners, Tracy Flynn