Hollowtree

The specialist enrollment firm for DI and LTC

We design, launch, and run the benefits programs most firms won't touch.

Group disability insurance and guaranteed-issue long-term care for physicians, medical groups, and employers. We handle program design, enrollment, and ongoing support, working alongside your broker.

60-Second Overview

Modern Benefits. Deep Expertise.

Disability insurance and long-term care solutions — built with the technology and enrollment support your workforce needs.

Results from our published case studies

Group LTC

Benefits agency, 65 eligible employees

of eligible employees enrolled
32%
enrollment window
16 days
total HR time: census data and three emails
3 hrs
Read the LTC case study

1099 Disability Insurance

National anesthesiology MSO, 600 eligible 1099 clinicians

of eligible clinicians enrolled
21%
from kickoff to enrollment close
4 weeks
Read the DI case study

Results from individual programs. Participation, timing and HR involvement vary by group, product and carrier.

Start Where You Are

Whether you're growing a book, supporting a workforce, or serving a medical group, Hollowtree handles the operational burden behind the program.

For Brokers

Add DI & LTC revenue without getting pulled into enrollment.

Most brokers avoid DI and LTC because rollout turns into employee questions, chasing enrollments, and handholding. We help you offer the coverage while we run the enrollment and support behind it.

Broker-of-record protected. Carrier-agnostic.

Explore Broker Partnership

For Employers

Offer DI & LTC without creating internal lift.

We design, communicate, and support the program end-to-end so your team isn't managing questions, reminders, or follow-up. Employees get guidance at decision-time — not just access.

No internal build required. No ongoing management burden.

Explore Employer Solutions

For Medical Groups & MSOs

Bring high-value coverage to physicians and 1099 clinicians.

We support physician-led groups and MSOs with programs built for high-income, complex populations — including 1099 Disability Insurance aligned to how clinicians actually get paid.

Built for physician-led, high-income organizations.

Explore MSO Solutions

Where Most Programs Break Down, We Take Over.

Programs don't fail because of product. They fail when no one owns rollout, employees don't understand the decision, and enrollment gets dropped.

1

Design a Program That Will Actually Be Adopted

Most programs look fine on paper but never get adopted. We structure for real-world participation based on your population -- not off-the-shelf plans that sit unused.

2

Run Enrollment So Employees Actually Decide

Instead of employees ignoring emails or missing deadlines, we guide the decision in real time -- through reminders, education, video, and live support. Participation is driven, not hoped for.

3

Manage Everything After Launch

Instead of HR fielding questions about coverage or billing, employees contact us directly. We handle policy servicing, inquiries, and claims advocacy -- nothing circles back.

Solutions

Two financial risks most high earners carry uncovered.

Income protection

Disability Insurance

If income stops, everything else does too. We build group and 1099 disability programs for physicians, medical groups and other high earners that standard group plans under-cover, with specialty-appropriate definitions of disability and underwriting paths that work at group scale.

  • 1099 DI for MSO, PLLC and physician-owned structures
  • Traditional group DI for W-2 populations, coordinated with 1099 programs
  • Income-appropriate benefit levels for high earners

Asset protection

Long-Term Care

Extended care can erase savings, and state LTC mandates are making it harder to ignore. We design guaranteed-issue group long-term care programs and run the education, enrollment and servicing so the benefit is elected and kept. Eligibility and group-size requirements depend on the carrier and plan.

  • Program design across major LTC carriers, with no preferred-carrier agenda
  • Education and enrollment run by our team, not yours
  • Ongoing servicing: employees call us, not HR

Case Studies

Proof that enrollment can be simple.

Two published rollouts, one LTC and one DI, with the population, product and timeline behind each result.

How a benefits agency launched group LTC for its own team without an HR project

Long-Term Care Case Study

How a benefits agency launched group LTC for its own team without an HR project

A Long Island benefits agency with no LTC coverage and no in-house LTC expertise used Hollowtree to choose a group hybrid life/LTC product and run education and enrollment. HR's role was the census and three internal emails.

  • Group hybrid life/LTC
  • 65 eligible employees
  • 16-day enrollment window
Read the LTC case study
How a national anesthesiology MSO brought disability coverage to 1099 clinicians

Disability Insurance Case Study

How a national anesthesiology MSO brought disability coverage to 1099 clinicians

After a merger converted its clinicians to 1099 contractors, an MSO with no benefits infrastructure used Hollowtree to run communication, education, enrollment and payment setup for a physician-specific group DI program.

  • 1099 clinician DI
  • 600 eligible clinicians
  • Broker-introduced rollout
Read the DI case study

We work with leading DI and LTC carriers

Carrier names and logos identify insurers whose products we work with. They do not imply carrier endorsement of Hollowtree.

The Standard
Sun Life
Guardian
MassMutual Strategic Distributors
Ameritas
MGIS
Reliance Matrix
Trustmark
Chubb
Transamerica

Official Sun Life video

The three-party structure behind the program, explained by the carrier.

One program in practice

See how Sun Life, CCA and Hollowtree bring physician-specific disability coverage to 1099 clinicians.

Sun Life created this program overview to explain how the carrier, the Clinicians Care Association and Hollowtree work together. It is one example of how Hollowtree turns a specialized insurance product into a complete enrollment and support experience.

  • Sun Life provides the insurance and pays approved claims.
  • CCA provides the group policy and membership structure.
  • Hollowtree manages program access, enrollment, billing and member support.
Sun Life

Produced by Sun Life for Hollowtree's 1099 clinician disability program.

Subject to policy terms. This video describes Hollowtree's CCA/Sun Life 1099 disability program. Hollowtree also works with other carriers and program structures.

Frequently Asked Questions

Common questions about disability insurance, long-term care, and how our enrollment programs work.

Disability insurance replaces a portion of income if an individual is unable to work due to illness or injury. Long-term care insurance helps protect personal assets by covering the cost of extended care services — such as in-home care, assisted living, or nursing care — that are not typically covered by health insurance or Medicare.

Our approach is designed to minimize the administrative burden on HR. We support communication, enrollment, and ongoing employee questions, while keeping your team informed through reporting and coordination.

Timelines vary based on scope and census, but many programs can be implemented within approximately 30 days. We support the process from design through enrollment, helping streamline execution and reduce the need for internal project management.

No. We work alongside your existing broker or advisor. Broker-of-record relationships remain fully intact, and our role is to support program design, enrollment, and ongoing service in areas that may require additional specialization.

An enrollment firm focuses on the communication, education, and decision-support aspects of employee benefits programs. While brokers typically advise on plan selection and structure, an enrollment firm helps employees understand their options and navigate the enrollment process — particularly for more complex benefits such as disability and long-term care insurance. This includes coordinated communication, digital tools, and access to real-time support to help employees make informed decisions.

We serve as a primary point of contact for employee questions related to coverage, billing, and claims. This helps reduce the volume of inquiries directed to HR, while keeping your team informed as needed.

See How This Would Work for Your Organization

In a short call, we'll show you how the program would be structured, how enrollment would run, and exactly what your team would (and wouldn't) need to do. Not ready to talk? Build a one-page program outline in about a minute.