Caily: Building the Future of Family Health, Rethinking Coordinated Caregiving

Summary
We partnered with Caily to build a cross-generational caregiving platform from the ground up, combining healthcare-grade security with family-friendly UX. Together, we delivered a subscription-based, cross-platform product integrated with EHR systems. The solution empowers care receivers, supports seamless family coordination, and lays the technical foundation for future B2B expansion.


Setting the scene
Wynter Johnson, President of Caily, knew something had to change when her family struggled to coordinate her grandmother's care. Phone calls between siblings, missed medication schedules, scattered medical records, and the constant worry about whether everyone was on the same page—it was exhausting for a family that just wanted to provide the best care possible.
Wynter discovered what 53.4 million American family caregivers already know: the tools to manage caregiving simply don't exist. You're either drowning in spreadsheets and group texts, or you're using clinical software designed for hospitals, not families.
That's why Wynter founded Caily, a platform where care receivers can maintain their independence while families coordinate seamlessly around them. Unlike other caregiving apps that treat patients like passive data points, Caily recognizes that the person at the center of care should have a voice in their own coordination.
But building a platform that handles the most personal aspects of healthcare while serving users from tech-savvy millennials to elderly grandparents? That requires serious technical expertise. Wynter needed partners who understood both the emotional complexity of family caregiving and the technical demands of healthcare technology.
That’s where Momentum came in. With our deep expertise in regulated healthcare environments and human-centered digital products, we were uniquely equipped to translate Caily’s emotionally complex mission into a secure, scalable, and intuitive cross-platform experience. From the very first conversations, it was clear we weren’t just building an app, we were helping build a new model for caregiving.
What we were up against
Caily faced challenges that most HealthTech startups never encounter. This wasn't about connecting doctors with patients, it was about building technology that strengthens family relationships during some of life's most stressful moments.
To meet those demands, Wynter needed a product partner who could not only write secure, compliant code, but also design with empathy, plan for scale, and build trust through every interaction.
Making Complex Systems Work Together
"The thing that keeps me up at night is connecting everything," Wynter told us early in our partnership. "I know we're going to have this app and this website, but then we've got like 50 other systems that need to talk to each other."
Caily needed to integrate with EHR systems for medical records, subscription platforms for billing, communication tools for family coordination, and analytics platforms for business insights. Without an internal IT team, they needed a development partner who could navigate these integrations while serving as strategic technology advisors.
Designing for All Ages and Abilities
Most apps target a specific demographic. Caily needed to work equally well for a 30-year-old managing their parent's care from their iPhone and an 80-year-old care receiver checking in on an iPad. The interface had to be powerful enough for complex care coordination yet simple enough that technological barriers never prevented someone from participating in their own care.
Including the Person at the Center of Care
Here's what makes Caily different: most caregiving solutions exclude the care receiver entirely. Family members coordinate "around" them rather than "with" them. Caily's core innovation, giving care receivers meaningful control over their own care coordination, introduced permission complexities that traditional patient portals don't face. How do you build a system where someone can choose to share their mood with their daughter but not their son? Where they can participate in care discussions without feeling surveilled?
Designing for Future Compliance from Day One
From the start, Caily’s infrastructure was developed with future readiness in mind. If the platform ever expands into more regulated environments or involves clinical professionals, it’s already on a path that could support higher standards. This early attention to compliance reflects Momentum’s approach to building systems with long-term responsibility in mind.

Four things that had to work perfectly
To bring Caily’s vision to life, we focused on four mission-critical goals, each designed to prove product-market fit, reduce complexity, and set the stage for long-term growth.
Create a Platform That Honors Dignity
Build technology where care receivers maintain meaningful autonomy while enabling seamless family coordination around their needs and preferences.
Eliminate the Integration Nightmare
Connect with existing healthcare systems, communication tools, and business platforms so families aren't forced to manage data across dozens of disconnected applications.
Prove the B2C Model
Validate market demand through individual family subscriptions before expanding into the massive employer-sponsored benefits market.
Establish Technical Foundation for Scale
Build architecture that supports current family needs while positioning for rapid expansion into enterprise clients and new geographic markets.

"The way Momentum presented their proposal was incredibly clear and comprehensive. I could walk into a meeting with our investors, show them the detailed breakdown of resources, timelines, and deliverables, and feel confident that we were making the right decision for Caily's development."

Building the strategy
We approached Caily as more than a development project. This was about understanding the emotional dynamics of family caregiving and translating them into technology that actually works.
Discovery Workshops That Set the Direction
We began with intensive workshops to map the complex dynamics of family caregiving, trying to understand why families struggle with care coordination. We learned that care receivers often feel excluded from their own care management, leading to resistance and frustration. That shaped our strategy, making participation optional, flexible, and respectful of autonomy.
Building a Thoughtful, Empowering MVP
With our roadmap established, we focused on building the five core modules that would make Caily indispensable for caregiving families while pioneering a new approach to care receiver autonomy.
Laying the Groundwork for B2B Growth
Recognizing the massive opportunity in employer-sponsored caregiving benefits, we built B2B infrastructure that would allow companies to offer Caily as part of comprehensive employee wellness programs.

How we got it done
From day one, we knew this was more than a HealthTech build. It was a human problem with technical implications. We applied our product thinking, agile delivery, and healthcare experience to create something intuitive, secure, and deeply respectful of user needs.
Co-Creating the Vision with Stakeholders
We started with stakeholder sessions that went beyond typical requirements gathering. We mapped family caregiving workflows, identified emotional pain points, and established technical requirements that balanced Caily's ambitious vision with practical implementation realities.
Testing Ideas with Real Families
Our design process involved actual caregiving families from the beginning. We created wireframes and prototypes that were tested with both tech-comfortable adult children and elderly care receivers, iterating based on real feedback from people managing real care situations.
Agile Development with Healthcare Focus
We implemented two-week sprint cycles with continuous stakeholder feedback, but added healthcare-specific considerations like security reviews, accessibility testing, and EHR integration planning to every iteration.
Testing for Trust, Accessibility, and Security
Our testing process included not just standard QA but also accessibility validation for users with varying technical comfort levels and security audits for healthcare data protection.
Full-Scale Launch and Marketing Coordination
The launch wasn’t just technical, it was strategic. Momentum and the Caily team worked together on timing, go-to-market messaging, and platform readiness, with a fully scoped marketing campaign led by Caily’s team.

The tech behind the magic
Caily needed to be fast, flexible, and future-proof. We chose technologies that balanced startup speed with healthcare-grade reliability, enabling seamless mobile and web access, secure data handling, and plug-and-play scalability for future enterprise use.
Backend: Ruby on Rails + PostgreSQL
We chose Rails for its rapid development capabilities and PostgreSQL for complex relationship modeling between care receivers, caregivers, and the intricate permission systems that make Caily's approach possible.
Mobile: Flutter for iOS and Android
Flutter enabled us to deliver consistent experiences across both platforms while reducing development complexity, which was critical for a startup that needed to prove market demand quickly.
Web Application: React.js
A responsive web interface ensures full platform access from any device, particularly important for users who prefer desktop interactions or need larger screens for easier navigation.
Security: HIPAA-Ready Infrastructure
End-to-end encryption, granular access controls, and comprehensive audit logging protect sensitive family health information while preparing for future regulatory requirements.
Healthcare Integration: EHR Connectivity at Scale
We integrated with leading EHR systems used by tens of thousands of healthcare organizations, including Nextgen, Veradigm, AllScripts, Altera, AthenaHealth, Cerner, and Epic. This allows care recipients to pull in existing health data securely and efficiently—without needing to switch systems or enter it manually.
Payments: RevenueCat + Stripe
Unified subscription management supporting both individual family plans and future enterprise offerings, with seamless billing across mobile and web platforms.
Infrastructure: AWS with Auto-Scaling
Cloud hosting with automated scaling ensures platform reliability during peak usage while maintaining cost efficiency for a growing startup.

Bringing it all together
We translated Caily’s core principles: dignity, autonomy, and simplicity into product features that feel personal and practical. Every interaction was designed to reduce friction, honor privacy, and make caregiving coordination feel human again.
Simple Onboarding for Complex Family Dynamics
We built onboarding workflows that help families establish care circles without feeling like they're setting up a medical device. Care receivers can choose their participation level—from full involvement to selective sharing—while ensuring caregivers have the information they need.
Check-Ins That Empower, Not Monitor
Rather than clinical assessments, we created mood tracking and health monitoring that care receivers complete independently, sharing insights with their support network without feeling like they're being monitored or judged.
Secure Storage with Granular Control
Secure storage for medical records, insurance information, and care instructions that families can access when needed, with clear permissions so care receivers control who sees what.
Circle Chat That Includes Everyone
Communication tools that keep all caregivers informed while allowing care receivers to participate in conversations about their own care, fostering collaboration rather than exclusion.
Scheduling That Actually Works
A shared calendar combining medical appointments, medication reminders, and daily habits tracking that care receivers can manage independently or collaboratively, depending on their preferences.
EHR Integration for Complete Picture
Direct connections with major healthcare systems so families can access medical information within Caily's platform rather than logging into separate portals or calling doctor's offices.
Flexible Plans for B2C and B2B Scale
Cross-platform billing that supports both individual family validation and future B2B expansion, with seamless user experience regardless of how they subscribe.

The complexities beneath the surface
Behind the clean interface were real technical hurdles. From handling multi-platform sync to designing invisible-yet-powerful permission logic, we solved for scale, trust, and clarity without compromising the emotional tone that defines Caily’s experience.
Unifying Disconnected Healthcare Tools
Wynter's biggest worry was systems integration, and for good reason—caregiving families typically juggle dozens of disconnected tools. We solved this by building APIs that connect Caily with EHR systems, communication platforms, and business tools, creating a unified experience that eliminates the data silos that make caregiving coordination so frustrating.
Invisible Protection, Visible Trust
Healthcare applications often feel clinical because of security requirements. We implemented enterprise-grade protection—encryption, access controls, audit logging—that operates invisibly, maintaining the warm, family-focused experience that makes Caily effective while preparing for future HIPAA compliance.
One Platform, Three Generations
Our cross-platform architecture ensures that whether someone checks care updates on their smartphone during lunch, reviews schedules on a laptop, or completes daily check-ins on a tablet, everyone accesses the same real-time information through interfaces optimized for their comfort level and device preferences.
Care Receiver Autonomy Without Chaos
The biggest technical challenge was building permission systems that give care receivers meaningful control without creating coordination chaos. We developed sophisticated but invisible access controls that let care receivers choose what to share with whom, while ensuring family members have the information they need to provide effective support.

What we achieved together
Caily’s launch wasn’t just a product milestone, it was a strategic foundation for market traction and long-term growth. From day one, families across generations have been using the platform to simplify caregiving and strengthen support systems.
Technical Success
Caily launched on schedule in July 2025 across iOS, Android, and web platforms with zero downtime and seamless cross-platform synchronization. All five MVP modules: onboarding, document vault, daily check-ins, circle chat, and scheduling were delivered within timeline and budget.
User Experience Victory
The platform successfully serves users across three generations, from tech-savvy millennials managing parent care to elderly care receivers maintaining independence through technology. Feedback consistently highlights the platform's intuitive design and respectful approach to care receiver autonomy.
Market Validation
Individual family subscriptions are validating market demand and user engagement, providing the proof of concept needed for B2B expansion into employer-sponsored caregiving benefits.
Foundation for Scale
The technical infrastructure we built supports Caily's current family-focused operations while enabling rapid expansion into enterprise clients and new markets without architectural constraints.
Business Impact
Caily is positioned to transform the $470 billion family caregiving market by proving that technology can strengthen family relationships rather than replace them. The B2B opportunity alone represents massive growth potential as employers recognize caregiving support as essential employee benefits.
"What I value most about our partnership with Momentum is their willingness to challenge our assumptions when necessary. They don't just build what we ask for—they help us build what our caregivers actually need, bringing their healthcare expertise to every conversation."

Momentum partnered with Caily to transform a deeply personal caregiving vision into a market-ready platform that empowers both care receivers and their families. By building technology that honors care receiver autonomy while enabling seamless family coordination, we created a solution that strengthens relationships while improving care outcomes, positioning Caily to reshape how America approaches family caregiving challenges.
If you're curious how this vision comes to life in practice, explore the Caily app—now available on Google Play, the App Store, and at caily.com. It’s already helping families coordinate care with more clarity, ease, and peace of mind.

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