Creating Estate Planning Documents with Vanilla

Key takeaways

• Vanilla built Document Builder to fix a process that’s traditionally transactional, reactive, and disconnected from a client’s broader plan, citing survey data that only 22% of clients get estate planning advice from their financial advisor at all.
• Existing client documents don’t need to be scrapped and redone: Vanilla can abstract documents that are still current and help surface planning opportunities.
• The self-guided, client-driven questionnaire model is considered a well-established, lower UPL-risk approach, though the risk profile shifts once advisors charge separately for the service or attorneys take on a more active drafting role.
• Once a client finalizes and notarizes documents, the plan flows automatically into the advisor’s view in Vanilla, turning document creation into an ongoing part of the estate profile rather than a one-time transaction.

The problem with traditional estate planning (0:00–4:41)

Historically, the estate planning process is transactional by nature, reactive rather than proactive, and disconnected from the rest of a client’s financial and tax planning. Advisors, attorneys, and accountants each work their own piece of a plan in a silo, and the only tool that scales across an entire client base today is really just Microsoft Word, PowerPoint, and Excel.

Based on the Spectrum survey named in the session, only 22% of clients get estate planning advice from their financial advisor at all, even though that kind of holistic guidance across a client’s full financial picture is what most clients say they actually want. Jim Sinai framed the alternative as an estate advisory approach: proactive, integrated with a client’s full financial picture, and powered by automation and AI rather than one-off transactions.

Where document creation fits into a broader estate advisory platform (4:41–9:43)

Sinai and Sam Trapkin, Vanilla’s cofounder, framed document creation as one piece of a broader estate advisory platform built around two core inputs: a client’s balance sheet and their estate planning documents. Rather than treating a signed revocable trust and pour-over will as the end of the process, Vanilla treats it as an input into what Trapkin calls a living representation of a client’s estate, one that updates automatically as assets change. That reframing, he said, is part of why customers use Vanilla to deepen an existing relationship rather than just check a box, since talking through a client’s full plan tends to be a more engaging conversation for both sides than reviewing investment performance alone.

Trapkin cited Vanilla’s own research, drawn from conversations with more than a thousand clients, finding that 23% of clients with more than a million dollars in household net worth did not have current estate planning documents in place at all, which left the remaining 77% as a large existing base that still needed their plan visualized and connected to real assets, not just filed away.

Inside the basic trust package (9:43–14:04)

Designed for mass-affluent clients with net worths under $5 million, Vanilla’s core document package centers around a revocable trust, a pour-over will, and key ancillary documents, including financial powers of attorney and healthcare directives. Clients move through a self-guided, client-driven questionnaire that an advisor invites them into, and Vanilla prints, ships, and includes state-specific notarization instructions once documents are finalized.

Trapkin said the documents were built from the ground up with a team of attorneys from top firms, with flexibility for more advanced planning built in from the start: a disclaimer trust structure, the option to leave assets to a surviving spouse outright or in a marital trust, perpetual pot trusts rather than outright distributions to children, corporate trustee appointments, and the ability to allocate GST exemption.

A look at the client and advisor experience (14:04–22:03)

Kendall Johnston-Legg, senior product manager, walked through the client-facing questionnaire using a sample couple, John and Mary. As clients answer questions about their family and assets, Vanilla’s visualizations translate concepts like outright distribution versus a marital trust into pictures rather than legal language, and the questionnaire adapts to prior answers, for example asking whether to plan for future children if none are listed yet.

Once a client finalizes and notarizes their documents, the plan flows automatically back into their advisor’s view in Vanilla, already populated with fiduciaries, beneficiaries, and the dispositive structure pulled straight from the questionnaire. From there, an advisor can pull up a waterfall projection under different death-year scenarios and generate a polished report for the client, turning the moment a client signs their documents into the start of an ongoing plan rather than a one-time transaction that ends up in a drawer.

What’s next: expanding complexity and integrating funding (31:04–35:53)

Panelists previewed where Document Builder was headed. On the simpler end, the team was considering a standalone will and a la carte documents like a financial power of attorney and HIPAA disclosure built specifically for clients’ adult children, a direction Vanilla later formalized through its expanded document creation offering. On the complex end, Trapkin said Vanilla was preparing to support more advanced structures like irrevocable trusts and SLATs ahead of an expected wave of planning activity as estate tax exemption changes approached.

Funding a trust after it is signed, meaning retitling real estate and other assets into it, remained a client-and-advisor-driven process at the time, though the panel described it as a roadmap priority built on the balance sheet data Vanilla already has for each client. On keeping that data current, Trapkin said the platform already integrated with portfolio management systems to reflect changing asset values automatically, rather than relying on a static export that goes stale the day it is pulled.

Q&A highlights

What options are available for clients with existing estate planning documents?
There are two primary entry points into a Vanilla: uploading and abstracting a client’s existing documents, or creating new ones through Document Builder. If a plan is more than five to seven years old or if a client’s personal or financial circumstances have changed, it is often more effective to build a current, integrated plan than to update outdated documents.

Who pays for the document package?
Clients pay directly through the Vanilla platform.

How does the self-guided questionnaire model address concerns regarding the unauthorized practice of law?
The self-guided model, where clients build their own documents through the questionnaire, is a well-established and lower-risk approach. 

Does Vanilla offer document services directly to consumers?
No. Vanilla is built exclusively for financial advisors and professional firms; we do not offer estate planning services directly to consumers.

How is client financial data integrated and maintained in Vanilla?
The platform integrates with major portfolio management systems (such as Orion and Black Diamond), which provides a dynamic, “living” representation of a client’s estate that updates automatically as asset values change. Advisors also have the ability to manually add assets to ensure a comprehensive view.

About the speakers

Jim Sinai, Chief Marketing Officer, Vanilla
Jim Sinai is the former Chief Marketing Officer at Vanilla, having led the company’s marketing and go-to-market strategy. He was previously at Procore and Salesforce.

Sam Trapkin, Cofounder, Vanilla
Sam Trapkin is a cofounder at Vanilla, where he has led the development of Document Builder and other core parts of the platform since the company’s earliest days.

Kendall Johnston-Legg, Senior Product Manager, Vanilla
Kendall Johnston-Legg is a former senior product manager at Vanilla, focused on the Document Builder product experience.

The information provided here does not constitute legal, financial, or tax advice. It is provided for general informational purposes only. This information may not be updated or reflect changes in law. Please consult with an estate attorney, financial advisor, or tax professional who can advise as to your particular situation.