The Summer I Learned Many Things about B2B SaaS from Softball

I think I finally understand the hype around American summers that the media has for so long presented to me: fleeting romances, coming-of-age summers, and escapist vacations (i.e. summer romances in Europe).

How unfortunate it is, then, that in our two-year professional break, this is the time of the year we chose to play-act at a nine-to-five. Doubly unfortunate for people like me who did not take the semester designations of “fall” and “winter” seriously (“where’s spring??”, I first asked the HBS administration, then the weather gods presiding over Boston). 

Initially, as a humor writer, I thought a little internship satire would hit the spot. However, after a terrible case of writer’s block, I am forced to conclude that Christie, the little rat in my brain, has been off for the summer, presumably writing romances inspired by all the New York Times Modern Love articles I read while bored on Zoom calls.

France, Christie? How cliche. 

With no easy quips on tap, I was forced to look within and ask myself: what was my summer truly about?

No prizes for guessing who didn’t get a return offer.

This summer, we joined a softball league on Mondays — a ragtag HBS team with 1) no steady bench of players; 2) 40% of the team new to the game; and 3) the spirit of underdog fire, American sportsmanship, and lost intramural games in our hearts. For six weeks, despite weekend hangovers, Monday blues, Excel models, and the kind of jetlag that can only be induced by a two-day round trip, we showed up to contest teams that had been playing together for years.

We were obviously fated for success (and romance, since I was assured that softball is popular in sports-based romance novels).

Go back to France, Christie. Other than using Tinder to recruit for a game with low showing, we disappointed on that front.

As I prepare to return to the recruitment arcade sans offer, I wonder if I can use my main focus this summer — i.e., softball — as a professional talking point. You’re witnessing the LinkedIn dry run, ladies and gentleman.

Point #1: You gotta know the rules of the game to play the game.

What does every Wall Street movie featuring impeccably creased suits, luxury yachts, and cocaine advocate? 

“You gotta think outside the box!” and “you gotta bend the rules!”

It turns out that rules play kind of an important role in both business and sport.

A former cricketer on the team, misled by the children’s game ring to “tagging”, tagged the baffled (and mildly terrified) runner with his bare hand.

“Use the glove!” he was told.

In his later career as first-baseman-running-to-home-base-because-I’m-an-inept-catcher, he learned from his mistakes and tagged with his gloved hand. However, no one accounted for the fact that he was holding the ball in the other hand.

“This has been good practice for if I ever become a coach. I didn’t know there were so many ways to get [the rules] wrong,” Tre, teammate, struggling optimist.

Point #2: Sometimes showing up is, in fact, not winning half the game.

You know what every inspirational video and your mom sending you to lose high school poetry recitation used to say? 

“Just start! Just show up on stage.” 

Well, I am here to tell you that sometimes showing up, far from being enough, is detrimental. Just stay home and be the hero.

That is exactly what we found out when 16 people came through to compete after we spent weeks barely meeting the required 10 players. With the batting lineup interminable and the fielding sit-outs decided by a spectre of complex math and gameplay mechanics…

If you win big enough in Encor, they just give you one to go.

… there was little hope for the outcome.

“I brought my brothers [visiting from Colombia] to the game, having thoroughly briefed them on how badly it could go. It somehow went even worse than that,” said Alejandro on our ~20 point loss that day (his brothers were unavailable for comment, having left right after).

Point #3: There IS a star player determining the outcome of the game.

On that note, I’ll say it: maybe it IS okay to admit that there are a few players who carry a game. Maybe it was our team captains, Ethan (the hard hitter and valiant pitcher) and Garrett (the able outfielder). Or perhaps it was Seth (our comprehensive shortstop), who regularly drew compliments that sounded borderline flirtatious from the opposition. Or it could be Nick, who took tagging the way it was intended: with the most fun back-and-forth running between bases I’ve seen.

Or maybe statistics don’t lie. The only game we won was when our boy showed up.

Point #4: It’s never too late to switch your career.

So what if we didn’t have a team of baseball/softball die-hards? We still recruited our team with the precision of George Clooney in Ocean’s Eleven. 

So what if our number three batsman didn’t smash the ball outfield? She did sprint between bases with the agility of a long-distance runner.

So what if the fielder kept taking catches bare-handed like you would in cricket? And so what if our batsman swung with a cricket flair and forgot to drop the bat while running?

A few injured fingers and a great deal of confusion later, we still had one win. So take that role even if you’re not qualified for it, submit that resignation letter today, and apply for your dream job. You’ll get… somewhere.

Point #5: Setting up a good incentive system is important.

When playing on a team with rookie overrepresentation, it’s very important to acknowledge the small wins…

Turns out that the tendency to not let go of the bat while running translates into a bit of a panicked fling, which may or may not be in the direction of the umpire or catcher.

…while also ensuring the team gets their just des(s)erts. 

We were promised soft-serve ice cream if we won. Despite pleas in our hungering and defeated eyes every Monday as we drove past McDonald’s, we only entered its hallowed grounds after our sole win.

Nothing stopped me from crushing my post-exercise burger weekly, though. Hundreds of calories as a reward for a game that involved, on average, two base runs, two swings and zero running on field makes for some well-aligned incentives.

Point #6: Judge your capex requirements correctly.

Capital allocation is an important skill that you are expected to know after business school, and it was one we found ourselves confronting one Sunday afternoon this summer. Specifically, what budget do you allocate to an activity that requires regular weekly commitment when you have a rotating crew of notorious optionality seekers with busy schedules?

If the answer is “minimal,” then you were right there with us. For most of the summer, that seemed to be the right answer as we scraped up enough gloves for the field and took in strays found on site. Until the semi-finals (haters say we only qualified because there were a mere four teams), we had been staring inevitable disaster in the eye. Or rather, Joseph (a first-time pitcher) did, for exactly two seconds as a ball hurtled towards his helmetless head.

As we’d said a few times that summer: “Ideally, the pitcher should wear a helmet.”

Whoops. 

Point #7: You gotta know when to quit.

Joseph collapsed like a heap of pins with a perfect strike, and the game froze to a standstill. What next?

We could a) stop the game immediately and rush Joseph to Urgent Care for a potential concussion; or b) leave Joseph draped out on the bench, continue playing the game we were already losing badly, and consult with a nurse on call because, for some reason, Harvard’s urgent care is not open 24 hours a day.

Perseverance is the mother of success. It’s not a good relationship. I think they’re estranged now.

Safe to say, with a good player down, we lost by an even larger margin than if we had retired injured. That being said, to Joseph’s large softball fan base, never fear: he made a full recovery from his concussion. Limited edition trading cards featuring our helmetless hero dropping soon!

Point #8: It’s all about positioning.

Never forget who’s controlling the narrative. 

Note: Don’t miss Christie’s debut novel, “Psspss I love you!”, about an ill-fated love affair between cat and rat!

Ramya Vijayram (MBA ‘26) is originally from Chennai, India. She graduated from the Indian Institute of Technology, Madras, with a Bachelor’s and Master’s in Biotechnology. Prior to the Harvard MBA, Ramya worked at Warburg Pincus in Mumbai, India, and McKinsey and Co. in India.