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Not just another retreat...

Get access to world-class personal development courses and coaching all delivered in sunny and beautiful Bermuda. Our executive offsite location and program is not just another professional development or security training program. The 2022 offsite is positioned to provide both you and your team with the expertise and clarity you need to succeed at work and beyond. 

The perfect atmosphere for professional development...

Now there is a renewed energy and excitement about the island as major renovations, new projects and legendary hospitality are paving the way for a next-generation destination to host meetings, conferences and incentive programmes. Set apart by its location out in the Atlantic, easy airlift access, the warmth of the people, its natural beauty, along with elegant and elevated style, make Bermuda an ideal destination for guaranteeing lasting memories.*

*Bermuda Tourism Authority

Our Leadership Team

Keyaan Williams

Founder & Managing Director



An MBA and JMT Certified Team Member, Keyaan followed a unique path to becoming a risk leader. After serving in the U.S. Army and spending more than a decade in various IT and security roles at the CDC in Atlanta, Keyaan founded CLASS-LLC. The vision was to help global customers benefit from strategy, governance, and program management lessons learned throughout his career. Beyond security, Keyaan is known for his service as the Past President of ISSA International, Chair of the risk committee for a global ministry, and Founding Member of the Private Directors Association Atlanta Chapter.

"Come to the Cyber Strategy Retreat to connect and develop new relationships and transform your organization's goals, vision and success"

Jared Kleinert 



Jared Kleinert is the co-founder/CEO of Offsite, a new startup offering end-to-end team retreat planning for remote-first organizations. Jared started his career as one of the first 10 employees at (now 250+ employees and 40,000+ customers strong) and later became known as USA Today's "Most Connected Millennial" for his research on the world's smartest and most talented Millennials, which became the basis for the award-winning book 2 Billion Under 20: How Millennials Are Breaking Down Age Barriers and Changing The World as well as his [email protected] keynote in 2015.

"Let’s work together to accelerate your growth, help you generate more predictable revenue, and create an Ideal Business that supports your goals and visions"


Learn tools and skills which apply to both cybersecurity and business development.



Experience a curated experience taking the best components from our Masterclass programs and integrating them with corporate development.



Gain the skills for you and your team to stay focused, motivated and excel in your workplace.



Day 1 - Arrive

Arrive to your room and get acquainted with your new home for the next few days. 

Have an informal sit-down with the offsite team and any staff that came with you to clarify your goals and aspirations for the next four days.

Attend the introduction session to get a more in-depth look at the schedule for the next few days and meet your cohort.

Have dinner with the complete offsite family before turning in for your first night.

Day 2 - Develop

Wake up and enjoy a tropical breakfast to get you fueled for the day.

Begin classroom and boardroom sessions in our fully stocked private meeting location.

Establish your practical, immediately executable strategy for your customer development, marketing, business development, sales, PR, networking and relationship-building, business operations, and/or any other priorities for your company.

Start combined CCISO and CIPM based Cyber Executive Masterclass sessions.

Enjoy some free time at the beach, spa or anywhere you feel comfortable to decompress and digest the earlier session. 

Have dinner with the complete offsite family.

Day 3 - Live & Learn

Continue the classroom and boardroom sessions from the previous day. 

Engage with the offsite team with a  lunch and learn.

Use your free time to explore the different hotel amenities. 

Close out the professional development work with understanding what next steps you need to take to succeed once you get back home.

Have a final dinner with the complete offsite family before getting some free time to explore the night time amenities. 

Day 4 - Explore

Take the day to explore beautiful Bermuda

  • See the city
  • Swim with dolphins
  • Relax at the beach
  • Enjoy a spa treatment
  • and much more!

Fly home and begin to put into practice what you learned over the past 4-days!

Schedule a conversation to learn more


Executive Package

  • Private room
  • Full meal plan
  • Includes complimentary access to CSR06 Recording community, Injecting Security and Cyber Career Lab Communities
  • Access to full Offsite program and Career + Professional development solutions presented by CLASS-LLC
  • Spousal/Partner accommodations 
  • Only 3 seats available!

Diamond Package

  • Private room
  • Full meal plan
  • Access to full Offsite program and Career + Professional development solutions presented by CLASS-LLC
  • Spousal/Partner accommodations
  • Only 10 seats available!

Gold Package

  • Retreat only (your own accommodation)
  • Access to full Offsite program and Career + Professional development solutions presented by CLASS-LLC
  • Only 3 seats available!
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Hear what people say about the Cyber Strategy Retreat!

Frequently Asked Questions

When is the offsite for 2022? 

The 2022 offsite is set for 08 - 11 April 2022.

How many spots are available? 

There area total of 15 seats available for this years offsite.

What about my spouse/business partner? 

You are in luck! Each offsite ticket comes with complementary accommodations for a +1. Your partner will be well taken care of while you learn and develop. It's a win-win!

How will course materials be delivered? 

Print materials will be handed out on the morning of the second day of the offsite, while digital materials will be emailed on the first day.

Don’t wait! Take yourself or your team leaders on a company changing experience today.

Learn more by scheduling a conversation below