Rise8 × Allaway

2025 Company Retreat

Hawks Cay Duck Key · Florida

The Client

Who is Rise8?

Rise8 modernizes software for the federal government — continuous delivery inside agencies where shipping slowly has consequences. Founded by Bryon Kroger, who co-founded Kessel Run, the Department of Defense’s first software factory, the company works with the VA, the Air Force and the Space Force from its headquarters in Tampa, Florida.

Their stated purpose is a future where fewer bad things happen because of bad software. That is not marketing language for Rise8 — Kroger started the company after watching outdated systems contribute to real operational failures. The teams embed inside the agencies they serve and work to a principle they call “I lead, we lead, you lead”: build the capability, hand it over, leave the client able to sustain it without them.

Which is a demanding way to work, and it happens on someone else’s site, on someone else’s clock, all year. The annual retreat is the week that belongs to Rise8 and nobody else — and their families came too.

Allaway hosted it. Five days at Hawks Cay Resort on Duck Key, in the Florida Keys, 15–19 June 2025. Leadership arrived first; everyone else followed from Miami the next day with partners and children in tow. We wrote the program end to end — airport shuttles through to staggered departures — and ran it on site: rooms, meals and every dietary requirement, vendors, AV, activities, the Kids Club, and a working space open from eight every morning for anyone who needed an hour on a client without missing the week.

Company: Software modernization & continuous delivery for government
Founded by: Bryon Kroger, co-founder of Kessel Run
Headquarters: Tampa, Florida
Works With: VA · U.S. Air Force · U.S. Space Force
Category: Company Retreat · Families Included
Allaway Partnership: 2025
2025 Program: Rise8 Company Retreat · June 15–19
Venue: Hawks Cay Resort, Duck Key, Florida
Allaway Scope: Program design · Hotel & F&B · Vendors · AV · Transfers · On-site management

01 Sun 15 June

3:30pShuttles from Miami for the leadership team
4:00pLeadership and families check in at Hawks Cay
6:30pSwag and packages arrive on site
7:00pLeadership team dinner at Angler & Ale

02 Mon 16 June

8:00aDedicated working space opens — available to Risers every day
9:30a – 5:00pLeadership meetings, and Kids Club for the children
12:00p – 9:00pShuttles from Miami, swag handed out at check-in
2:00pPool, beach, kayaks and paddle boards on the saltwater lagoon
7:00pWelcome dinner in the Dolphin Ballroom, and the Duck Scavenger Hunt begins
9:00pRisers Dance Party — kickoff remarks, palm trees and retro wave

03 Tue 17 June

7:30aEarly Riser run, and pilates on the Oasis Cay lawn
9:30aThe Risers Amazing Race — eight teams, bandanas and face paint
11:00aFree time: tennis and pickleball courts, kayaks, the rec room
1:00pThe Un-Conference
2:00pLeadership panel — get to know your Rise8 leaders
3:00pThe Core Practices Fair
7:30pRisers Game Night

04 Wed 18 June

7:15aBoxed breakfast for the fishing charter
7:30aEarly Riser morning walk and pilates
9:30aChoose your adventure: snorkeling, fishing charter, dolphin experience
10:00aPaint and sip on the Dolphin Deck
12:00pLunch and learn
1:00pThe engineering boat build — recyclable materials, one bucket of water
2:00pFamily laser tag and dart battle, all ages
6:00pDinner and the Risers Awards Night — duck hunt, walkathon, Amazing Race

05 Thu 19 June

7:30aA last Early Riser run, walk and stretch
8:00aBreakfast in the Dolphin Ballroom
9:00a – 2:00pShuttles back to Miami, staggered to flights
11:00aCheck-out

Two things run through every day of this program. A working space was open from eight each morning, so anyone who needed an hour on a client could take it without missing the week. And the children were there — Kids Club, family laser tag, a whole day built around them. Allaway wrote the program and ran it on site, with the rooms, the meals and every dietary requirement, the vendors, the AV and the Miami transfers confirmed before anyone arrived.

Hawks Cay Resort · Florida · 2025

Rise8 retreat session day, Hawks Cay, 17 June 2025

Rise8 retreat family day, Hawks Cay, 18 June 2025

Work & Play

Half of it was work. All of it was culture.

This was not a week off with a keynote bolted on. The strategy program ran at every level of the company and the leisure program ran alongside it, hour for hour, on purpose. Leadership met on their own before anyone else arrived. The Un-Conference put the whole company in the room and broke it into small groups. The Core Practices Fair gave each discipline its own table. A leadership panel opened the floor to anybody who wanted to ask. And a working space stayed open from eight every morning, because Risers are embedded in agencies where a deadline does not pause for a retreat.

Between those sessions: the Amazing Race in eight teams, a duck scavenger hunt running all week, a boat built from recyclable materials, game night, a dance party and an awards ceremony. Both halves were pointed at the same thing — a company whose people spend the year apart, on client sites, getting to know each other properly. Professionally in the sessions, personally in everything between them.

Leadership Meetings Un-Conference Core Practices Fair Leadership Panel Lunch & Learn Daily Working Space Amazing Race Game Night

The Venue

A boardroom and a marina. Same address.

Hawks Cay sits on its own island on Duck Key, an hour and a half down the Overseas Highway from Miami, and it was chosen because a week this varied needs a property that can absorb all of it. Two boardrooms for leadership and the daily working space. Three connected ballrooms that became an un-conference, a practices fair, a games night, a dance floor and an indoor laser tag arena on four different days. A ballroom and deck that fed the whole company every morning and hosted the awards night. A marina for the fishing charter and the snorkel trip, a saltwater lagoon for kayaks and paddle boards, tennis and pickleball courts, a lawn for sunrise pilates, and a kids club.

Nobody had to get on a bus to do any of it. That is the whole argument for a resort like this one: with families on site and sessions running between activities, every minute saved on transfers is a minute the week actually gets to use.

Island Resort Three Ballrooms Two Boardrooms Marina Saltwater Lagoon Tennis & Pickleball Kids Club

Hawks Cay Resort · Duck Key · Florida