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4-day investment.

A lifetime of benefit

 When you...

...have trouble keeping up with continually changing technology and executive education

...struggle to live up to your strategic goals

...don't have a cybersecurity strategy aligned with your business


 then you need to come to the Cyber Strategy Retreat - Executive Offsite. 

Learn what it takes to get ahead, grow and keep all elements of your business aligned in this 4-day offsite event.  

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Not just another retreat...

Get access to world-class personal development courses, business coaching and cybersecurity strategic sessions all delivered in sunny and beautiful Bermuda. The 2022 offsite is not just another professional development or security training program, it will provide you with the expertise and clarity you need to succeed at work and beyond. 

In this program you will...

  • Create 6-month improvement plan aligning your cybersecurity, risk management, and strategic planning which you can implement right away
  • Learn skills to create & update detailed improvement plans and business growth roadmaps
  • Receive a cybersecurity certification – CCISO from EC-Council or CIPM from IAPP or even Both!
  • Improve decision-making in governance, objective-setting, and day-to-day operations for your internal communication, risk management, security and executive teams
  • Create strong long-term business relationships

Our Offsite 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"


Download the full itinerary guide here!

Day 1 - Arrive & Acquaint

April 08

Arrive in Bermuda. See your room & get acquainted with your new home for the next few days. 

Take a tour of the island. 

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

Join us for the welcome dinner & keynote presentation with the complete offsite family before turning in for your first night.

Day 2 - Develop & Drive

April 09

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.

Lunch and reflection time with a guided art tour of the grounds.

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

Have dinner on your own or with some offsite family members.

Attend a late-night group activity!

Day 3 - Live & Learn

April 10

Wake up to a beautiful island breakfast to get your day started.

Continue the classroom and boardroom sessions from the previous day. 

Engage with the offsite team with a  lunch and learn.

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 on a chartered yacht with the complete offsite family before getting some free time to explore the night time amenities. 

Day 4 - Reflect & Renew

April 11

Wake up to a stunning breakfast and start your last day.

Attend the final programming session.

Think about your experience here, lessons learned and your roadmap for once you get home.

Attend program graduation ceremony and say farewell to the offsite family.

Reflective luncheon with the family.

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 1 on 1 business and strategic development sessions with Keyaan Williams
  • Includes an ADDITIONAL day for private development sessions (offsite timeline for executive guests is April 08 - 12)
  •  Includes 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
  • Access to all special events and planned outings
  • Spousal/Partner accommodations 
  • Only 5 seats available!

Diamond Package

  • Private room
  • Full meal plan
  • Access to full Offsite program and Career & Professional development solutions presented by CLASS-LLC
  • Access to all special events and planned outings
  • Spousal/Partner accommodations
  • Only 20 seats available!

Gold Package

  • Retreat only (your own accommodation)
  • Access to full Offsite program and Career & Professional development solutions presented by CLASS-LLC
  • Only 5 seats available!
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Hear what people say about Cyber Strategy Retreat events!

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 30 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!

Why Bermuda? 

The decision to host the first offsite in Bermuda was fully intentional, we wanted somewhere that helped to drive home the goals of the program. Bermuda represents the best of balancing intensive, interactive workdays with relaxing evenings/time-off. This location enables attendees to be innovative, refreshed and ready to work again each day.

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