Why Joe Maddon and Theo Epstein would Hit a Home Run as CS Leaders

If only Joe Maddon and Theo Epstein were job searching – We’d hire them!


We’re considering extending offers to Joe Maddon and Theo Epstein (Cubs management) to head up our Customer Success team. I know they’ve got a lot going on – like fine tuning and conditioning the team for another World Series victory next year – but I just thought we should give it a try.


They have, after all, demonstrated the quintessential skills of customer success, haven’t they? If Customer Success leadership is about getting your team to facilitate your customer’s success, then isn’t that what Maddon and Epstein have done?


They DID get THEIR team to work together to enable Cubs’ customers (the loyal fans, if you will) to reach their goal of celebrating a world series victory.


Indulge me.


Here’s the arrangement:


Cubs fans enlisted (by virtue of their support) Maddon and Epstein (and the whole Cubs organization) to help them reach the elusive goal of celebrating a World Series victory.

The fans bought the Cubs platform   – tickets to the games, or just watching them on TV, the pre-games, the analyses, the stories behind the team and the players, the water-cooler strategizing, the swag, etc.


The Cubs fans bought the whole Cubs offering because they believed that their devoted fanship would somehow help enable a Cubs World Series victory.


Success for the Cubs’ customer was the world championship – nothing less.



Together, Joe Maddon and Theo Epstein took on the job of leading the Cubs Customer Success team to victory FOR their customer – the fans. Epstein spearheaded long-term strategy, while Maddon handled game to game execution.


As a Customer Success team, they employed several best practices:



Building the Right Team

The Cubs have “subject matter expertise”. Jake Arrieta knows how to throw strikes, while Aroldis Chapman knows how to throw heat.


Maddon could count on Ben Zobrist to get on base when he needed him to, and David Ross has the best Catcher’s ERA in the league (by far). The team that Maddon and Epstein have built is rock solid, and fully capable of facilitating successful attainment of outcomes (World Series victory) for their customer (the fans).


A Consistent Lifecycle Model

Working cooperatively with the sales organization, Epstein and the Cubs built a reliable and consistent CLM for their customer.


First, they sold them on the brand. While the Cubs had lots of long-time, loyal fans, their fan base has been growing for the past 3 seasons, with attendance going from 2.6 million in 2014 to 3.2 million this season. This doesn’t even include virtual fans. Indeed, the organization had a negative churn rate for the past 3 years.


After convincing their fans to buy tickets and/or watch games, the Cubs organization launched an effective campaign to solidify platform usage. Customers (fans) were provided schedule information for games and lineups, and had full access to statistics.


They also were able to hear Maddon discuss strategy and analyses of games. Keeping their fans in the loop earned the Cubs more confidence from their customers, and kept their loyalty high.


Once Launched, Fans were Onboarded Properly

Maddon and the Cubs organization continued to demonstrate the usefulness of their platform in helping their customers reach their outcomes. By playing well, making intelligent substitutions and rotations, and bringing home wins, the Cubs demonstrated their value to their customers from the start of the season.


As loyal fans, the Cubs customers continued to have positive experiences with the Cubs platform. They grew to expect quality performances, and reliability of the team.


In fact, many fans became advocates for the brand and brought along additional customers. They willingly shared their stories about their brand loyalty, and in doing so, inspired new users of the platform.


No surprises – the fans intend to renew their subscriptions with confidence that the Cubs will continue to deliver. Churn is NOT an issue.



Throughout the season, Maddon and Epstein continually analyzed the performance of their team, their opponents and their schedule to be able make priorities for the sole purpose of being able to help their customers reach their outcome. With the World Series as their target, Epstein made key hires, and Maddon prioritized certain games and players to be able to win what he needed to, and preserve talent for other significant innings or games.


Maddon knew how long he needed to rest his star relievers so they could throw most effectively when he needed them. This strategic prioritization is a key skill set for Customer Success, and not everyone can do it well.


Coordinating Resources

This is where Maddon demonstrated his genius. Almost like a college professor, he has a deep and thorough knowledge of baseball, his team and his opponents. He understands the data (how fast and consistent pitches are, where batters typically hit, how much recovery time players need, etc.).


Taking all of this into account, Maddon was able to coordinate his resources for the season, the week, the game, and the inning. He constantly made appropriate substitutions and field adjustments. And he did all this for his customer, the fans – keeping their goal of the world championship always in mind.



You can work as hard as you want, and analyze as much data as you want, but if your platform isn’t any good, your customer can’t use it to reach their outcomes. The Cubs (as formed by Epstein and led by Maddon) had a post-season Batting Average of .233 and their opponents’ was .232.


Cubs had an On-Base Percentage of .692, while their opponents’ average was .640. The Cubs scored 75 runs in post-season play, and their opponents scored 57. The Cubs were simply more effective.


So you can see why we’re scouting Maddon and Epstein for our CSM team lead, can’t you? They both clearly have the talents we’re looking for and the spirit for helping their customers attain their goals.  


Some say that winning isn’t everything, but if that’s your customers’ desired outcome, then I hope you have a CSM leader with the brains, decisiveness and perseverance that Theo Epstein and Joe Maddon have.

Tim is the Vice President of Customer Success at Bolstra, a customer engagement management platform. With over 9 years of experience in Customer Success, Tim has been a thought leader in the evolving Customer Success Management space. One of Tim’s notable achievements was the development of a customer success organization that he grew organically into a $7M/year add-on business for Indianapolis based Aprimo. Since that time, Tim has helped numerous B2B SaaS companies optimize their customer success environments. Tim holds a Bachelor of Science degree from Purdue University and is an avid sailor. He is an active member of the Indianapolis Sailing Club and sits on the board of directors.