Kristi Herold of JAM: The Power of Flexibility; How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic

Karina Michel Feld
Authority Magazine
Published in
13 min readJan 4, 2021


Vision, Purpose & Values — your team cannot read your mind. Get clear with a vision of where you want your business to be going and share this with your team so you can all be rowing the boat in the same direction. Also be clear with the purpose and values so your team knows whether this is an organization they can truly invest themselves in. Having alignment in these areas will create a much stronger bond and empowerment amongst your team.

The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Kristi Herold — Founder & CEO — JAM / Founder & CEO — Sport & Social Group.

A born entrepreneur, Kristi Herold was looking to meet new people after moving to the big city of Toronto in 1996 and she took the opportunity to combine her passion for sport, business, and community and founded the Sport & Social Group (SSG) — one of the largest adult recreational sports league providers in the world, offering an incredible physical and mental health benefit to over 1.3 million participants since inception. When the 2020 pandemic hit, and the SSG operations were mandated to pause, Kristi led her team in the creation of JAM — a new service providing professionally hosted remote events helping corporate teams all over the world stay connected through play. Kristi has been recognized as a Top 100 Canada’s Most Powerful Women, a top 3 finalist in the Canadian Women Entrepreneur awards, Sport & Social Industry Association’s “Industry Impact Award” winner, has earned multiple Great Places to Work certifications and is a Governor General’s “Queen’s Diamond Jubilee” recipient.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in a small city called Sudbury, 4 hours north of Toronto and I was raised in an entrepreneurial household. My brothers, father and grandfather all had entrepreneurial instincts/backgrounds and we were raised to consider how we could work for what we wanted in life, as well as to consider the value and importance of our time/freedom to pursue a lifestyle that was important to us. My father was always home for breakfast and dinner and came to all our extracurricular events while managing his own business — leading by example what the true value of combining the importance of family first with what being an entrepreneur meant. I started my first real business — a lawn cutting service — with actual clients and employees at the age of 15 and never looked back.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favourite ‘life lesson quotes’ all came from my Mum — hard to pick just one — “Honesty is the best policy”, “if it sounds too good to be true then it probably is” and “I have to live with myself and so, I want to be fit for myself to know, that whatever I do and whatever I be, I will always be so proud of me.”

I have done my best to live by all of these quotes throughout my life. I’ve been told that I am honest to a fault — and anyone on my team knows where they stand with me, or where I stand on an issue, which overall has served me well. My gut instinct has been something I’ve relied on intensely throughout my business career and my Mum’s advice that “if it sounds too good to be true than it probably is” has served me well in that when I’ve had opportunities to invest my time or resources into something that seemed a little too promising — more often than not I have backed away and I’ve never regretted those decisions. Lastly, I don’t think anyone can go wrong in attempting to live by the last quote. It is always a good reminder to check in with oneself with any decision needing to be made whether it is something you can live by and be proud of.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I have always loved listening to and been inspired by Guy Raz’s NPR podcast “How I Built This”. I enjoy hearing the stories of incredibly successful entrepreneurs, the ups and downs they’ve experienced and the “never give up” attitude, resilience, creativity and determination to end up where they are today.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

In 1996, I founded the Sport & Social Group (SSG) — recreational sports leagues for adults — based in Toronto, Canada. Over 24 years I went from doing everything by myself on a shoestring budget, to building an amazing team, and with their help we have grown our organization to be one of the largest of its kind in the world. We were getting over 150,000 people playing a wide variety of team sports across 9 different cities in Canada and the USA. I was working on a couple of acquisitions prior to the pandemic that would have doubled the size of our organization by the spring — and then the pandemic hit bringing everything to a halt — effectively ‘benching’ all of our sports leagues for the last 10 months.

What did you do to pivot as a result of the Pandemic?

I spent about 6 to 8 weeks feeling sorry for myself and my team, struggling with both depression and the situation we found ourselves in. Businesses all seemed to be moving online — and I was blocked in thinking about how impossible it was to get our SSG members playing soccer, volleyball, softball etc., online. Many organizations in our industry inspired us to try offering hosted remote games and events online for our members. Things like Bingo, Trivia and speed-dating. We also created Team Trivia leagues, a podcast called “Ask an Athlete” and e-gaming leagues. We were open to trying anything to engage with our members and try to generate some revenues, however we found it challenging to earn enough money to cover our costs when only charging $5 to individuals to join us for one off events. By May we decided to branch out instead of focusing solely on our SSG members. We realized the world is a very big place with a huge number of corporations and organizations now working remotely, all who are missing out on the fun camaraderie and team building that naturally occurs in the day to day setting of an office. Seeing as our purpose had always been “connecting people through play” — we stayed true to our core purpose and started focusing on connecting corporate teams through remote games and events like Name-That-Tune, Bingo, Trivia, Escape Rooms, Scavenger Hunts and more. By August we had re-branded and launched JAM (Work + Play = JAM) as well as our new website;

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

We had our minds open to trying anything. In early spring I had a few discussions with others in our industry who had shared that they were having success with remote events at a corporate level. We had always dabbled in ‘in person’ corporate team-building events, so I figured we may as well reach out to some corporations to see if we could help them connect their teams playfully and help their cultures thrive in a remote working world. I hosted a few free events for friends’ companies and some entrepreneur organizations that I belong to in order to get feedback and test our offerings. By mid-summer it became clear that those we tested with were really loving their JAM experiences — they were booking packages for weekly and bi-weekly events for their teams. It also became clear that trying to sell our events as the Sport & Social Group was awkward, we needed a new brand in order to really ramp up this new opportunity. A good friend and amazing branding expert (Clay Hebert) as well as a few other friends, all offered some insights and by September, our newly branded remote events business “JAM” was born.

How are things going with this new initiative?

Play has been shown to stimulate creativity, improve brain functionality and increase energy. When teammates have the opportunity to ‘jam’ and connect through play, strong social bonds are created which help increase engagement and loyalty. Employees with positive work relationships are proven to be more dedicated, motivated and productive. Thus, JAM has really taken off, our services are clearly helping many organizational cultures and their employees thrive. Since May we have booked and produced over 500 events, positively impacting the lives of over 25,000 participants all around the world. Our NPS (net promoter score) is sitting at 83 which is an incredible accomplishment given that a 70 NPS is considered world class. Further — over 65% of our events have now been booked by repeat clients — many very well recognized large corporations — which makes me very proud of my team considering we’ve been operating for less than 8 months. We are on track to exceed 7 figures in revenue in our first year of operation which feels amazing, as a lot of hard effort and teamwork went into creating JAM from nothing during a very stressful and challenging time for our other organization the SSG.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There was not one particular person but rather a huge group of friends who I have leaned on for guidance in the last eight months. I am incredibly grateful to many folks from the Sport & Social Industry Association who took time to share their experiences around hosting remote events including Brooke & Sam Jresiat, Luke & Katy Wade and Robert Kinsler. Further, I am grateful to some friends and colleagues who were early adopters of our JAM services, like Jennifer Bouyoukos at Entertainment One, David Brady at Cream Productions, JJ Virgin with the Mindshare group, Andrea DiNorcia at IMCO, Ray Minato at Inertia Design and Barry Glassman of Glassman Wealth. They all provided great feedback, many signing on to packages for their organizations becoming repeat clients which boosted our confidence in our offerings. Friends like Scott Beffort, Shelli Baltman, Julie Mitchell and Clay Hebert all provided insight and guidance with our re-branding effort. Matt Bertulli of Pela Case and Erik Huberman of Hawke Media both shared their incredible wisdom teaching us how to implement effective digital marketing campaigns. I am also grateful to friends like Robert Glazer from Acceleration Partners who has helped generate awareness about JAM and the service we are providing by mentioning it a couple of times in his highly followed Friday Forward weekly business blog. My brother, Cameron Herold who is a world-renowned speaker, author and, business coach has been inspiring me, kicking my butt and challenging me to think differently and believe in our ability to grow JAM since the pandemic first hit back in March. Lastly, my entire team at the Sport & Social Group and now JAM, have been challenged to think differently and lean in to brand new roles in order to get JAM off the ground and growing. This has been one of the most challenging years our team has ever experienced with the mandated shutdown of our SSG operations — yet it has also been strangely exhilarating and rewarding to have been able to successfully pivot in our creation of JAM as a team.

Can you share the most interesting story that happened to you since you started in this new direction?

I think what has been most interesting for me was around the end of November, I was reviewing our list of clients and realized not only did we have many big-name, well-recognized corporate clients like Microsoft, Apple, Google, Entertainment One, Comcast, Pepsi, General Mills, Bank of Montreal (BMO), etc — but that all of these well-known clients had already become repeat clients, having used our JAM service for multiple events already and that there were many more lesser-known organizations on our repeat client list as well. When I dug into the numbers and saw the percentages of repeat clients after such a short stint of operating, it made me proud of the service our JAM team is providing and made me realize what a huge opportunity we have to help connect more corporate teams through play all over the world. We are impacting people’s work lives in a really positive way. I get excited about getting up out of bed every day knowing that the work I and my team are all doing is helping create smiles, laughter and connection for others.

What are your “5 things I wish someone told me before I started leading my organization” and why. Please share a story or example for each.

  1. Running your own business is a constant game of problem-solving — the people who succeed in business are those who embrace the problems as a game, seeking to solve the problems in the best way, with the best people possible in order to create the best result.
  2. Focus on driving revenue early — good word of mouth and repeat customers are gold — the earnings will come.
  3. It will be lonely — especially when you start — every decision and responsibility will fall on your shoulders. As you grow your business, be ready to give accolades to your hard-working teammates and don’t expect them in return. It is impossible for your team to truly understand the extent of work, time, energy, loss of sleep, financial resources etc that you invest in your business behind the scenes — accept it and keep working hard.
  4. Enjoy the journey — the road will be long, windy and bumpy with likely more downs than ups, it is important to find joy in all the little accomplishments along the way versus only focusing on the finish line.
  5. Vision, Purpose & Values — your team cannot read your mind. Get clear with a vision of where you want your business to be going and share this with your team so you can all be rowing the boat in the same direction. Also be clear with the purpose and values so your team knows whether this is an organization they can truly invest themselves in. Having alignment in these areas will create a much stronger bond and empowerment amongst your team.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

Since March trying to keep our 25 year old, 8 figure revenue organization, the Sport & Social Group afloat has been like riding one of the wildest roller coasters I’ve ever experienced. The news cycle combined with the variety of government mandates and programs intended to help small businesses, have affected me and my entire team and our customers greatly in creating fear, anger, confusion, resentment, stress, sadness etc. By early May, I finally leaned into acceptance of what I cannot control and work daily to remember the Serenity prayer “God grant me the serenity to accept the things I cannot change; courage to change the things I can; and wisdom to know the difference”. In addition to working to accept what is out of my control, and have the courage to make change where I can, I have been working hard to exercise daily, meditate and really lean on and stay connected with friends across North America in order to try to help others as well as not be afraid to ask for help from others when I need it.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

The movement that I would love to be an inspiration for, in order to do the most amount of good for the most amount of people would be encouraging people to always “Keep Playing”. George Bernard Shaw has been quoted as saying, “We don’t stop playing because we grow old — we grow old because we stop playing.” There is nothing I enjoy more than laughing and connecting with friends, family and colleagues, and what better way to do that than through play. Whether it be connecting and meeting new friends, or seeing old friends or work colleagues through the playing of team sports, or connecting and meeting with friends through play in community musical theatre, or connecting and laughing with family over a game of cards, a board game or charades or connecting with colleagues playing a silly game like “Name that Tune Bingo” or “Survey Says” or “Netflix themed trivia” online — continuing to connect with others through play is an important movement with massive benefits to our society. Playing team sports has been scientifically proven to be more beneficial for our physical health than simply going to the gym for a workout because of the mental health benefit that comes from connecting socially with others. Connecting with others through play in almost any form, helps to relieve stress, improve brain function, stimulate the mind, boost creativity, improve relationships and connections with others and keep people feeling young and energetic. No matter what our age the benefits for our entire society are massive, if we all make time in our lives to keep playing.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

I would love to have lunch with Guy Raz, host of NPR’s podcast “How I Built This”. I love his curiosity and approach in interviewing entrepreneurs and would love to hear more of the stories from him about all the incredibly inspirational people he has met. I truly love that he has been shining a bright light on entrepreneurs over the last number of years. Entrepreneurs often tend to be outcasts in the standard academic world, so it is wonderful to see entrepreneurs getting a well-deserved spotlight in the last decade, as they are innovators, creators, hard-working, driven and determined — they are the fuel of our society and deserve the bright light and attention that Guy Raz and his team have helped to get shone on them.

How can our readers follow you online?

LinkedIN — @Kristi Herold

Facebook — @Kristi Herold

Instagram — @kristiherold_

Twitter — @KristiHerold

Thank you so much for sharing these important insights. We wish you continued success and good health!

About The Interviewer: Karina Michel Feld is the Owner and Executive Producer of Tallulah Films. Karina has 20+ years of experience in TV, film, and print and is a respected member of The Producers Guild of America. The mission of Tallulah Films is to bring together directors, entrepreneurs, film investors, and screenwriters to produce award-winning TV and film projects. Tallulah Films continues to be drawn towards films that are meaningful, influential, and uplifting. Karina is also Co-Owner and CFO of Fresh Patch LLC (as seen on ABC’s “Shark Tank”).



Karina Michel Feld
Authority Magazine

Executive Producer of Tallulah Films