The Family Behind Roopy
Roopy started with a question every parent knows all too well: “What are we doing today?”
For Jackie Dolan, a Winston-Salem native and mom to Charlie and Maggie, figuring out the answer was practically a weekly event of its own.
Between Facebook events, Eventbrite, parenting websites, local calendars, and word of mouth, finding something fun for the kids meant searching a dozen different places and somehow piecing together a plan that actually worked.
There had to be an easier way.
Jackie started wondering what it would look like if one tool could do all that searching, planning, and organizing for her. Something that knew what her kids liked, found great things happening nearby, and took the guesswork out of family time.
That idea became Roopy.
Together with her husband, Ruairi, and her brother-in-law, the first blueprints started taking shape.
What began as one family's frustration has grown into something much bigger, but the question behind every new feature remains the same:
How can we make a parent’s life easier?
Because parents have enough on their plates. Finding something fun to do shouldn’t feel like another full-time job.
A Little More Fun. A Little Less Work.
Finding a great family activity is only half the battle.
There are fantastic local businesses offering family deals, discounts, special experiences, and little extras. The problem is that they're scattered everywhere.
One offer arrives in a text. Another comes through the mail. Another gets mentioned on social media. And some of the best ones are the ones you only hear about from another parent.
We thought, why not bring them all together?
That’s where Roopy Perks comes in.
We want to make it easier for families to discover great local businesses, enjoy more experiences together, and get a little extra value along the way.
It’s better for parents, better for local businesses, and hopefully means a lot less searching and a lot more doing.
Meet the Rest of the Family
It takes a few extra hands to turn one family’s idea into something for families everywhere. Here’s the crew helping make it happen.
Kate
Chief Fun Spreader
Marketing & Social
Helping get the word out, share the good stuff, and make sure more families discover what Roopy can do.
Ruairi
Chief Connection Maker
Sales & Partnerships
Building relationships with local businesses and helping bring more great places, perks, and experiences into the Roopy family.
Brent
Chief of Keeping Things Moving
Operations
Helping keep everything running smoothly behind the scenes so families can focus on the fun stuff.
Eddy
Chief Idea Builder
Development
Turning big ideas into real features and helping Roopy grow into something that makes family life a little easier.
How Roopy Works
Roopy learns your family: your children's ages, what they love, your budget, and how far you're willing to drive. Then it builds a full day plan: a main adventure, a meal, a treat, and backup options, all chosen from real local venues and events. Save the plans you love, mark them done, and build a family adventure history.
The Roopy ecosystem
Personalized Family Adventures
AI-powered itineraries built around your family's interests, children's ages, budget and schedule.
Available
Family Perks
Exclusive benefits from participating local businesses: discounts, free items, and special offers for Roopy families. Starting in Winston-Salem, growing across North Carolina, then nationwide.
Available
Roopy Rangers
Children complete missions, challenges and adventures at destinations while collecting Ranger Badges.
Available
Roopy Plus
Roopy Plus unlocks the full Roopy experience: exclusive Family Perks from local businesses, Roopy Rangers interactive adventures for kids, and more as the platform grows. Core planning is free for everyone, and Plus adds the value-add benefits.
Learn About Roopy Plus