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March 01, 2026 • read
A Day in the Life of an iCon 2026 Attendee
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Cassidy Downs PR Pro, Recreational Writer, Edvocate |
Cassidy Downs
Every year, iCon brings together Skyward users from across the country for three days of learning, hands on experiences, and community. At the 2026 conference, held February 25–27 at the Tradewinds Island Resort in St. Pete Beach, attendees enjoyed a packed agenda featuring more than 80 sessions, one on one support, and plenty of opportunities to unwind in between.
Wondering what it’s like to attend the conference? Read further for a “day in the life” of an iCon attendee, and plan on making the experience your own at iCon 2027.
Day one: Settle in, dive in
10:00 AM — registration opensYour first task of the day is checking in. A quick, smooth badge printing process gets you on your way, and your welcome tote bag is filled with goodies from exhibitors.
With badge in hand, your next mission is to secure one of the coveted one on one sessions with the Skyward team. Getting there early pays off — you manage to book a slot and look forward to sitting down with an expert who can address your district’s specific Qmlativ needs.
Enjoy the resort
With some time before sessions begin, you explore the beautiful Tradewinds property. You grab lunch at one of the on site restaurants and spend a few peaceful minutes enjoying the sand and sunshine.
1:00 PM — sessions begin
Your iCon 2026 journey officially begins! With choices ranging from roadmaps to roundtables to hands on guides, selecting just one session is tough. Thankfully, you’re reassured that all presentation slides will be available after the conference.
2:10 PM — session two
Next up: a professional development session on change management. You take plenty of notes, perfect for sharing with your district team once you’re back home.
3:00 PM — break time
A mid-afternoon pick-me-up keeps everyone energized. Conversations spill from hallways into snack areas as attendees compare notes from their first two sessions.
3:20-5:20 PM — more learning is occurring
The momentum continues through two additional time slots. With presentations from Skyward presenters, fellow district experts, or exhibitors, every session adds another piece to the puzzle and sparks new ideas. Marketing testimonial pit stop With a little time to spare between the last session of the day and the next event, you scheduled a quick meeting with someone from the marketing team to give your testimonial on your time with Skyward. Sharing your thoughts will contribute to future success stories and promotion, and you receive some Skyward swag to show off.
6:00-7:30 PM — Social Mixer: Meet the Skyward Staff
Day one ends with a relaxed networking mixer featuring drinks and appetizers. With the St. Pete beachfront within steps, conversations flow easily between new acquaintances and longtime iCon regulars. Attendees unwind, connect, and gear up for another full day ahead.
Day two: Full day, full heart
7:00 AM — breakfastThe Florida sunshine makes waking up easy. Breakfast in the resort lobby fuels the morning — and the coffee certainly helps. You revisit your tote bag and discover today’s challenge: an exhibitor BINGO card, complete with prizes for a full card and bonus entries for adding a testimonial on the back. You make a mental note to visit the exhibitors later.
8:00-9:00 AM — opening remarks
The day begins with inspiring updates from Skyward’s leadership, who highlight future plans and set the stage for a dynamic day of learning.
Breakout activities
With a little bit of time before sessions begin, you check out the bracelet making and photobooth breakout activities: keepsakes to jog your fond memories.
9:30-11:30 AM — popcorn and presentations
The morning is packed full with two more sessions and another yummy movie-inspired snack break to keep momentum up.
11:30 AM — lunch and Leaders in Excellence
Tradewinds provides a delicious buffet lunch, and you sit down to enjoy your meal. While you eat, you help celebrate the 2026 Leaders in Excellence with a special presentation honoring innovators who make a meaningful impact in their district with Skyward. You take note for on who you could nominate next year.
12:30-3:35 PM — sessions, snacks, and socialization
Three additional sessions help you refine your district’s next steps in Qmlativ. As the weather warms, an ice cream break hits the spot. You take time to visit exhibitors, completing your BINGO card and submitting it at the registration desk by the end of the day.
Conference day ends
You made it through the longest day of iCon! After a busy day, attendees are free to enjoy the beach, explore the resort, grab dinner, or sip something refreshing at the tiki bar. Luckily, St. Pete Beach makes it easy to shift into relaxation mode.
Day three: Last moments, lasting impact
7:00 AM — breakfast and closing remarksYou enjoy one more delicious breakfast while listening to final remarks and the announcement of game prize winners. Even if your name isn’t called, the excitement in the room is contagious.
8:00-11:10 AM — wrapping up and refreshing snacks
With just three conference sessions remaining, you can’t believe how much you’ve learned already. A BINGO session tests your knowledge and provides another opportunity for Skyward swag. In between sessions you enjoy one last break, this time with refreshing fruit, protein bars, and smoothies.
Departure, Reflection, Relaxation
Attendees head home inspired and informed — or extend their stay to enjoy the resort a little longer. With group rates available for extra days before and after the conference, many take advantage of the setting to relax and reflect.
As attendees make their way back to their districts, they leave with new connections, new strategies, and renewed confidence. iCon is more than training. The ideas shared transform school districts and impact real students and staff.
Thinking about edtech for your district? We'd love to help. Visit skyward.com/get-started to learn more.
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Cassidy Downs PR Pro, Recreational Writer, Edvocate |
Cassidy is the public relations specialist at Skyward, where she promotes a positive image in the K12 education software landscape through marketing tasks, success stories, and news monitoring. She also enjoys dabbling in writing, researching, and collaborating with her team of writers to explore and share edtech trends.
