Front Office

OTAs Explained: Its Roots and Evolution Through 20 Events

By LeagueApps
August 4, 2021
6 min

As an entrepreneur, I’m frequently asked if building and leading a business is the hardest thing I’ve ever done. I often reply that yes, it has its challenges, but given my previous career helping to lead Seeds of Peace, a non-profit that focuses on resolving conflict in the Middle East and South Asia, it pales in comparison.

My background in peacemaking has given me experiences that I’ve translated into a focus on leadership and culture at LeagueApps. It also offers up a model to our partners who confront many of the same challenges and opportunities that we do.

Encounters with Greatness

One of the formative experiences of my professional career was a trip to Silicon Valley. Given my unique background bridging cultures, I was one of two Americans invited to participate in a two-day retreat involving select Israeli and Jordanian entrepreneurs and venture capitalists where we engaged luminaries from the valley in private discussions. We heard the founding stories of Google, Facebook, LinkedIn, PayPal, EA Sports, and Zynga.

Over and over again, the explanation of how companies became great, and not just good, came down to a commitment to culture. The common advice that has always stuck with me was to define your culture and values early, hire and develop a team based on the clarity of who you are, and recognize that smart, aligned teams can solve the most difficult challenges. 

Culture at LeagueApps: Organized Team Activities (OTAs)

Inspired by that conversation, Brian Litvack and I were intentional about how we defined our value-centric culture (Sportsdog) from when we were a six-person team (including an intern), authentically surfacing the attributes that were already defining what made us successful and unique.

We recognized the importance of ritualizing those values—and stepping back out of the day to reflect on how we as a company could better live up to them. With founding team members in D.C. and New York City (and one colleague in Thailand!), we decided to formally bring the team together two times a year for a retreat.

Not wanting to simply accept the formula of a typical company offsite, we created our event that we called OTAs (Organized Team Activities, out of football parlance). To this day, 20 events in, our OTAs have followed a specific structure designed to leave us a more aligned, focused, and connected team after a few days. Months out from each OTAs, we’ll reflect back on where we are at, and where we want to go and then use OTAs to empower the team to meet the moment.

OTAs In a COVID World

In late January 2020, we were coming off a successful OTA with clear plans for the year. And then everything changed.

In July 2020, we ran a hybrid OTAs—with most of the content virtual, but hosting a few outdoor, small group in-person gatherings. It was the first time many of us had been together since COVID affected how we worked together.

In late January 2021, we ran entirely virtual OTAs. Drawing upon lessons learned from the more than 50 virtual events we hosted in 2020, we produced a tight event, capped off by a full-blown Sportsdog awards ceremony that honored our team members for exemplifying our values. 

But there is no replacement for in-person connection and relationship building. Beginning in March, we started to plan OTA20, with the belief that we could bring the company together this summer in a way that was safe, largely outdoors, and inclusive of those who would have to join virtually. These OTAs would be different, as people were craving connection, and we needed to integrate 44 new team members who had never met most of their teammates or been to OTAs in person.

Drawing upon my peacebuilding roots, I borrowed from a playbook I had seen perfected at Seeds of Peace as we designed an intentional experience that would be fun and effective. 

Seeds of Peace

My belief in the power of sports just doesn’t come from heroes such as Nelson Mandela, Jackie Robinson, Muhammad Ali, or Billie Jean King. It’s personal.

As part of their programs, Seeds of Peace runs a summer camp in Maine for teens from conflict regions. It is there that I got to know Arn Tellem, one of the top agents in all of sports and current vice-chairman of the Detroit Pistons, and Nancy Tellem, one of the top executives in Hollywood (they are now LeagueApps investors). They not only had a passion for bringing about peace in the Middle East, but a belief in sports, and in camp. 

Arn had coincidentally been a camper as a child at the very camp Seeds of Peace now operated and he had the idea of bringing NBA players, especially rookies he represented, to the camp each summer. Throughout the years, these visitors included Russell Westbrook, Derek Rose, the Lopez and Collins twins, Brent Barry, and the incomparable Brian Scalabrine. 

Seeds of Peace NBA Players

On those courts in Maine, it became so clear why Nelson Mandela said that sport “has the power to unite people in a way that little else does.” Seeing NBA players helped orchestrate a three-person weave with Israeli, Palestinian, and Egyptian campers was amazing and highlighted the common ground offered by sports.

A key facet of the camp was Color Games (war wouldn’t be appropriate) that shifted the identity of Israelis and Palestinians to the Blue and Green teams. Color Games left such an imprint on me that I borrowed its key elements for my wedding (which took place on the campgrounds) and in the planning for OTA20. 

The LeagueApps Olympics

Drawing upon the timing of the Olympics and the presence of Benita Fitzgerald-Mosley, an Olympic Gold Medalist who is on our leadership team, we embraced the Olympics—and the official motto of Faster, Higher, Stronger, Together—as the theme of OTA20. We examined the history of the Olympics—and Pierre de Coubertin’s famous Olympics manifesto of 1892 that birthed the modern games as inspiration for the keys to individual and collective achievement and a reminder of the critical platform of sport.

But it wouldn’t be the Olympics without, well, an Olympics. While we had done competition-like activities at previous OTAs, we took things to another level with this event. 

The Seeds of Peace Color Games model came in handy as we divided the company into two teams—Green and Gold.

We appointed team captains and dressed up in inflatable horses while marching with a bagpiper playing the Braveheart theme.

Jeremy Goldberg OTA Gold Team

We competed in a tug-of-war to get the competitive juices flowing.

We showcased the talents of the team in a competitive talent show that ranged from a comedic skit incorporating the Sportsdog values to lip-sync and dance battles and ending in original team songs (the team is not likely to be cast in Pitch Perfect 3).

We divided up into Green vs. Gold battles across a range of activities that spanned the athletic (volleyball and soccer), the intellectual (quiz bowl), and the in-between (cornhole and kan-jam).

And we ended with a team-wide relay race that would put a decathlon to shame, as a baton traversed nearly 30 different stations ranging from basketball knockout, sack race, balloon toss, reciting company values after eating peanut butter-covered crackers, and the exact memorization of a Jesse Owens quote.

But what was fun and games also was a chance for our team members to step outside of their typical identity tied to their role, and embrace an entirely new one. It invited new and veteran team members alike to step up and lead in new ways. It highlighted the need for everyone to contribute for their team to succeed. And as we learned through all of our sports experiences, when you’ve battled next to and across from people, you create memories and relationships that last. 

An Important Reminder about Sport

When I reflect back on OTA20, I start with a feeling of gratitude and appreciation. I took for granted what it meant to be in an office every day, or at a company retreat, with people you enjoy and respect.

I can see the positives of the new ways we work and collaborate, but nothing replaces the feelings you get when you are together via the structured time or through the informal moments that happen in the hallway or at a fire pit over s’mores. 

More than anything, I leave OTA20 with a greater appreciation of what youth and local sports leaders do every day. Running our own sports event wasn’t easy, particularly as you prioritize safety in all of its dimensions. But as I’ve seen through my work at Seeds of Peace and now LeagueApps, nothing brings people together or builds community like sport.