Meet Hollowtree
How It Works
Enrollment execution without the administrative drag
Hollowtree builds the enrollment experience, runs the communication cadence, manages employee support and payment setup -- including payroll-compatible workflows plus ACH, card, and Apple Pay -- so HR stays informed without becoming the help desk.
Talk to a Benefit Expert- Branded enrollment microsites
- ACH, card, and Apple Pay support
- Structured employee education
- Ongoing servicing after launch
- Payroll deduction enrollment and reconciliation
- Enrollment analytics and stakeholder reporting
The Process
How rollout actually works
A controlled, five-step process — not a vague timeline. Every step has a clear owner and a measurable outcome.
Align on goals
Define audience, plan structure, and rollout timeline with your team and broker.
Build the experience
Create the branded microsite, enrollment flow, and education materials.
Launch communications
Roll out the structured communication cadence to introduce the program.
Open enrollment
Employees enroll and set up payments through a guided, mobile-friendly flow.
Report & support
Deliver results reporting and transition into ongoing program administration.
Ownership
What Hollowtree handles — and what your team does not have to
We take on the operational weight so your HR team can stay focused on the decisions that matter.
Hollowtree handles
- Branded microsite build and configuration
- Enrollment flow setup and testing
- Employee education content and video
- Structured communication cadence
- Live enrollment support for employees
- Payment setup, servicing, and reconciliation
- Results reporting and follow-up
Your team handles
- Program approval and internal sign-off
- Census file and basic setup inputs
- Communication review and feedback
- Internal stakeholder alignment
Comparison
Why Hollowtree is different
| Feature | Hollowtree | Carrier-Only | Generic Admin |
|---|---|---|---|
| Carrier-neutral guidance | |||
| Custom branded microsite | |||
| Structured communication cadence | |||
| Short educational video support | |||
| Direct employee support | |||
| Payroll + direct payment options | |||
| Ongoing servicing after enrollment | |||
| Broker-friendly execution model |
Payment Infrastructure
Modern Payment Infrastructure, Zero Payroll Friction.
We decouple benefits from your payroll. By using enterprise-grade payment rails, we ensure secure, direct-to-carrier billing that takes seconds for employees to set up.
Powered By Enterprise-Grade Rails
Secure Connection
Connect via Plaid for instant, encrypted bank verification without sharing credentials.
One-Tap Enrollment
Support for Apple Pay ensures a friction-less mobile experience.
Reliable Rails
Processing powered by Moov for institutional-grade ACH reliability.
Payment updates and ongoing support are managed directly through the employee's relationship with Hollowtree — not routed back to HR or payroll.
Employee Education
How employees get guided through the decision
Employees receive short, clear, mobile-friendly education paced across the enrollment window. Hollowtree handles the questions so HR does not get flooded.
The communication cadence
Employer introduction
The employer introduces the program to build internal credibility.
Hollowtree introduction
Hollowtree introduces itself as the enrollment resource.
Full overview
A short video walk-through that covers plans, pricing, and enrollment.
Reminder & re-engagement
Paced reminders reach unenrolled employees only — enrolled staff are removed from outreach.
Enrollment walkthrough
Live or asynchronous support to help employees complete the flow.
Deadline reinforcement
Final window communication that creates urgency without pressure.
The Technology
Technology that makes enrollment easier to complete
Mobile-first, guided flows with autosave, resume logic, and a clearer completion path — so more employees finish enrollment on their own.
Branded microsite
Each group gets a dedicated, branded landing page employees actually want to visit.
Plan selection
A guided, four-step flow that helps employees understand their options and choose with confidence.
Payment setup
Method-based rendering — employees see ACH, card, or Apple Pay based on what's enabled for their group.
Employee portal
Employees can review coverage, update payment methods, and access documents after enrollment closes.
Year Two & Beyond
What happens after enrollment closes
Hollowtree does not disappear after launch. Payment continuity, employee servicing, and structured access for newly eligible employees stay operational — so the long-tail admin stays off your plate.
Payment continuity
Billing continues seamlessly. Employees can update payment methods without involving HR.
Direct employee servicing
Hollowtree handles employee questions, changes, and support directly — year round.
Newly eligible access
New hires and newly eligible employees are onboarded through structured enrollment windows.
Billing & reconciliation
Ongoing payment reconciliation and billing updates managed operationally.
Governance & reopen windows
Deliberate reopen periods where appropriate, with controlled access and proper documentation.
Reporting & follow-through
Ongoing operational reporting so stakeholders stay informed without manual tracking.
See How This Could Work For Your Workforce
Whether you're exploring voluntary benefits for the first time or looking to improve an existing program, Hollowtree can show you exactly how rollout, payments, and ongoing servicing would work for your group.
Talk to a Benefit Expert