Tumbleweed

AI-powered end-of-life planning platform embedded in life insurance products as a policyholder benefit

Customer Engagement Startup Seed (accelerator prizes and grants)

Overview

Tumbleweed is a customer engagement platform for life insurance carriers, focused on end-of-life planning, legacy preservation, and caregiver support. The company embeds its tools directly into carrier member portals as a value-added benefit for aging policyholders, with carriers accounting for over 90% of its revenue. It serves the estimated one in five Americans managing caregiving responsibilities for aging parents while also raising children.

The platform is delivered as a web-based SaaS application and includes a self-directed planning guide, encrypted document storage, and an AI care companion called CeCe. Carriers deploy Tumbleweed under their own brand or co-branded, with touchpoints built around quarterly check-ins and annual tax-season planning reviews. The company was founded in 2023 by Paul H. Richardson Jr. following a personal experience with legacy and caregiving challenges.

Tumbleweed launched Product 2.0 in October 2024 after extended user testing and has onboarded multiple carrier partners, including Wellabe, a Des Moines-based mutual insurer. The company completed the Global Insurance Accelerator (GIA) 2024 cohort and the NMotion accelerator powered by gener8tor, and received grant funding from the Iowa Economic Development Authority.

Products & Services

Tumbleweed Planning Platform

A web-based, self-directed guide that helps users organize critical documents, capture personal wishes, and record end-of-life preferences. Accessible on any device.

Key Features

Step-by-step guided planning workflows
Secure storage for legal documents, insurance policies, and medical directives
Consolidated family access point for key contacts and wishes

Target Users: Life insurance policyholders and their family caregivers

CeCe (Care Companion)

An AI-powered virtual assistant available 24/7 to provide guidance and resources during caregiving transitions and life planning challenges.

Key Features

Conversational AI for caregiving questions and next-step guidance
Available at any hour without scheduling
Integrated with planning platform for contextual support

Target Users: Caregivers supporting aging parents or managing a loved one's estate

Carrier Integration

White-label or co-branded deployment within carrier member portals, designed to increase policyholder engagement among aging members.

Key Features

Quarterly check-in touchpoints built into the carrier engagement calendar
Annual tax-season planning review as a structured benefit moment
Branded to carrier specifications

Target Users: Life insurance carriers, mutual insurers, and group benefits administrators

Resource Library

Curated educational content to support families navigating caregiving, estate logistics, and legacy planning.

Key Features

Guides on legal, financial, and emotional aspects of caregiving
Partner affiliate resources integrated into content
Regularly updated to reflect common planning questions

Target Users: Policyholders and their adult children

At a Glance

Founded: 2023
Headquarters: Des Moines, Iowa, USA
Employees: 1-10
Funding: Seed (accelerator prizes and grants)

Category & Focus

Category: Customer Engagement
Subcategories: Policyholder portals end-of-life planning digital member benefits caregiver support
Insurance Verticals: Life & Annuity Group Benefits
Target Customers: Carriers, Employers