About Jonathan Cherry

About Jonathan Cherry

Hi, I'm Jon - editor of Cherryflava since 2004.

I'm an experienced business strategist and keynote speaker.

I help brands solve their complex problems by facilitating great strategy, giving forward-orientated organisations the best platform from which to win.

Over the past 20 years, I've worked with a broad range of clients from a full-spectrum of different industries, that include: British American Tobacco, Dimension Data, Unilever, YPO, Back-a-Buddy, Woolworths, Yuppiechef, Santam and Sanlam.

I have an MPhil Futures Studies (Stellenbosch University) degree and am active member of the Association of Professional Futurists (APF).

What clients say about working with Jon
"Jon Cherry has played a critical role in the key milestones of our journey at Yuppiechef. Jon's ability to help teams understand futures better, bring new thinking and helping to drive innovative change within the business has been invaluable. Having worked extensively across the business over many years, Jon Cherry has provided insight and support to our teams and given them practical tools and key learnings on how to respond and make the most of emerging market opportunities."


- Shane Dryden | Co-Founder of Yuppiechef


‘Having your annual strategy session for your organisation is something the majority of us know is important but many times struggle to see the value post engagement. The Back-a-buddy team has used Jonathan from Cherryflava for three years in a row to assist us with the facilitation of our strategy workshop and the value of the session continues throughout the year.
I'll never forget in one of our sessions, Jonathan challenged the leadership team on what we thought had been a successful year. His words were "Do you want to stay pedestrian?", making us realise in an instant that the sky was the limit. We actually had so much more potential and could be creating so much more positive impact in the world than we were at that point. I think we quoted Jonathan's statement about 50 times that year!
What I love most about Jonathan's facilitation style is that you really feel heard while he at the same time challenges your thinking styles and encourages you to think towards the future and the generation of new ideas.’


- Catherine Du Plooy | Chief Operations Officer of Back-a-Buddy


"I worked with Jon when coordinating an event for YPO, focussing on the future of business. Jon brought a fresh, thought-provoking and unique perspective to the day’s events and I would highly recommend him for anyone contemplating tomorrow’s world, today”

- Chris Rolfe | Chairman of YPO [Malta Chapter]


“I first worked with Jon through my radio show in 2007. Since then, we have worked on live experiential marketing events, virtual treasure hunts and more. Jon has become a trusted thought-partner and invaluable business guide to me. His ability to cut through the noise and convey a clear message pushes me to dive deeper into what it is that I am trying to achieve. Our chats always leave me feeling hopeful and inspired. I believe Jon has the skills and knowledge to breathe life into any concept and set it up for a great future.
I would highly recommend Jonathan Cherry. “


- Sean Loots | Radio personality and producer


"Jon and I worked together while I was Head of Technology at Yuppiechef. While running a few departments it became apparent we needed fresh outlooks coupled with frameworks to drive change. Jon was exceptional in understanding the core problem(s) and then more importantly defining models to solve some very tricky operational issues.
I would gladly work with Jon again. In fact, I look forward to it."


- Steve Porter | Yuppiechef CTO


‘I have worked with Jonathan and recommend working with Jonathan many times! He’s gets an NPS of 10 from me. His strengths include: strategy development; brand and marketing development; futures thinking; scenario planning and facilitation. Also, be sure to check out his articles.’

- Rob Heyns | Founder of League of Beers


Not everyone has the ability to get a bunch of auditors thinking out-of-the-box in the highly regulated financial services industry. And, truth be told, there were a few skeptical glances when we decided to ask a futurist to assist us with the facilitation of our vision and strategy. But Jonathan won us all over with his relaxed style and the insight and fresh perspective he brought.
What I valued most from our workshop was not the tools, roadmaps and measurement indicators, but rather the questions he confronted us with. The one challenging question that stayed with me was, “What business are you in?
What?! We’re not in auditing? Blasphemy!
This got us back to our purpose, and away from an immediate inclination to list our activities as our strategy. Live the questions, right?!
Jonathan was key to getting us to construct our present with the future we want. Yes, we did end up with a spreadsheet, but it was an informed one. I highly recommend Jonathan to help you unlock your potential.

- Neil Slabbert | Senior manager Internal Audit at Santam

Hire Jon 

If you have a particular business, growth or strategy problem that you have been struggling with, please get in touch with us and let's have a chat to see if our unique brand of strategy facilitation is a good exercise for your organisation to consider as a step towards a resolution.