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Wynter Johnson

President & Co-Founder

With a career rooted in building systems that scale and brands that connect, Wynter leads with empathy, efficiency, and a deep belief in the power of meaningful support. It's this passion that led her to co-found Caily.

Caily was born from both professional insight and deeply personal experience. As a parent, a daughter, a granddaughter, and someone who has navigated the emotional and logistical weight of caregiving, Wynter recognized how fragmented — and overwhelming — care coordination can be. She created Caily to bridge those gaps, helping families feel more connected, more informed, and more supported in the moments that matter most.

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The Latest from

Wynter Johnson

What to Do When Your Loved One Has a Good Day

Good days in dementia are real — and knowing how to show up for them makes them count more. Here's what a good day actually looks like and how to be present when one arrives.

Your EHR Isn’t the Problem. The Gaps Around It Are.

Your EHR holds the clinical record, but resident communication may still be scattered. Learn how senior living leaders can reduce the workflow gaps around it.

When Caregiving Takes Over: How Dementia Caregivers Lose Themselves — and How to Find Their Way Back

Dementia caregivers often lose themselves in the role without realizing it's happening. Here's what role engulfment actually looks like, why it occurs, and what genuinely helps.

Your Emergency Plan Can’t Work If No One Gets The Message

An emergency plan can’t protect residents if staff and families don’t receive clear information. Use this six-question test to strengthen your senior living community’s emergency communication process.

The Grief That Comes With Loving Someone Who Has Dementia

The grief of loving someone with dementia starts long before any final loss — and it doesn't have a name most people recognize. This World Alzheimer's Day, we're making space for it.

The Employee Left. Did Their Access?

Shared logins and outdated permissions can leave former employees and unnecessary users with access to resident information. Here’s what senior living leaders should review.

What Families Should Know About Dementia Care in Senior Living

Memory care communities are built differently. Here's what families should know about dementia care in senior living — what to expect, what to ask, and how to stay close.

The Hidden Cost of Fragmented Communication in Senior Living

Fragmented communication is already costing senior living communities through staff time, repeated work, complaints, risk, and family frustration.

How to Be an Engaged Family Member at Your Loved One's Senior Living Community

The families who show up well in senior living aren't necessarily the ones who visit the most. Here's what engaged family membership actually looks like during Assisted Living Week and beyond.

How to Reset Your Caregiving Routine This Fall

September is a natural reset. Here's how to use it to reestablish visit habits, reconnect with the care team, and show up more consistently for your loved one this fall.

A Better Way to Think About Emergency Communication in Senior Living

What actually happens when an emergency communication plan is tested? A look at what CMS Appendix Z requires and where most plans quietly fail.

What It Actually Feels Like to Be in the Sandwich Generation

The sandwich generation — caring for aging parents while raising kids — is one of the most common and least supported caregiving experiences. Here's what it actually feels like, and what helps.