Sales Transformation Is Like October Baseball
I'll be honest—I'm not having the best August as a lifelong Cubs fan.
Here's my team: they had the most wins in baseball at the All-Star break, looking like the best squad we've fielded since that magical 2016 season. Fast forward six weeks, and we've managed to blow a commanding division lead, watching the Brewers surge past us while we've stumbled through one of the most disappointing stretches in recent memory.
With roughly six weeks left in the season, the division title feels like a pipe dream (just a 4.7% chance according to Baseball-Reference). But hey, we're still sitting pretty for a Wild Card spot at 98.7% odds. Could be worse, right?
Except then I looked at our World Series odds: a measly 6.3%.
That's when I did what any data-obsessed Cubs fan would do—I asked AI to break down the conditional probabilities. What are our odds of winning each individual round, assuming we make it that far? And that's when something clicked. Maybe we do have a chance. More importantly, maybe there's a lesson here about sales transformations that every CRO and RevOps leader needs to hear.
The Difference Between Cumulative and Conditional Odds (Or: Why Hope Springs Eternal)
Before we dive into transformation parallels, let's talk about why these numbers matter. There are two ways to look at playoff odds:
Cumulative odds are your chances from today's vantage point. The Cubs have a 6.3% chance of winning the World Series from where we sit right now. Brutal, but honest.
Conditional odds ask a different question: If you make it to a particular round, what are your chances of winning that specific series? And here's where it gets interesting:
Wild Card (98.7% chance we’ll be there, let’s F#&!king…go): 55% chance of advancing
NLDS (if we get there): 42% chance of advancing
NLCS (if we make it): 53% chance of advancing
World Series (if we reach it): 50% chance of winning it all
See what happened? Those conditional odds tell a different story. They say that while it's unlikely we'll run the table from here, if we can string together some wins and get hot at the right time, we're actually competitive in each individual matchup.
It's the difference between "this is impossible" and "this is improbable but achievable if we execute when it matters."
Sound familiar? Let me introduce you to the brutal mathematics of sales transformation.
Your Transformation Playoff Picture
Just like the Cubs' journey from 98.7% playoff odds down to 6.3% championship odds, every sales transformation faces increasingly difficult conditional probabilities at each stage. The difference? In business, there's no Cinderella story—just methodical execution through predictable pressure points.
Let me walk you through the rounds, using the Cubs' actual odds from Baseball-Reference as our guide.
The Wild Card: Recognition & Buy-In (98.7% → 55% conditional odds)
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The Cubs are almost certainly making the playoffs. In transformation terms, this is the Recognition Stage—your leadership team has acknowledged that the current sales approach isn't cutting it. Maybe you're losing deals to more consultative competitors, maybe your average deal size has stagnated, or maybe your best reps are succeeding despite your process, not because of it.
Getting to recognition feels like an achievement. Most companies never even make it this far, they're content to keep running the same plays, hoping next quarter will be different.
But here's where that 55% Wild Card win probability gets real: buy-in is exponentially harder than recognition. The Cubs might cruise into the playoffs, but actually winning that Wild Card series? That requires execution under pressure, perfect timing, and a little luck.
Same with transformations. It's one thing for a CEO to say "we need to change our sales approach." It's another thing entirely to get the board to approve a 12-month timeline, the CFO to free up budget for new tools and training, and the head of sales to admit that their current methodology needs a complete overhaul.
The Wild Card killers? Half-hearted commitment, unrealistic timelines, and the classic "let's try this new thing on top of everything else." Teams that survive understand that transformation isn't additive, it requires subtraction, focus, and genuine commitment to fewer things done better.
Division Series (NLDS): Design & Alignment (56.6% → 42% conditional odds)
Notice how the Cubs' conditional odds drop to 42% in the NLDS? That's because this round separates the pretenders from the contenders, we’ll probably meet the League Leading Brewers. Good regular-season teams with obvious flaws get exposed by scrappy Wild Card winners who've learned to win in pressure situations, I hope this happens:)
In transformation terms, this is Design & Alignment—where you figure out exactly what you're building and how the pieces fit together. Methodology selection, process design, tech stack alignment, compensation plan updates. The works.
That 42% success rate isn't an accident. This stage kills more transformations than any other, not from lack of resources, but from poor execution of fundamentals. It's like a playoff team that can't figure out its starting rotation or keeps making mental errors at crucial moments.
Common NLDS failures: methodology selection by committee (resulting in Frankenstein approaches), timeline compression ("we need to launch this quarter"), and death by customization where every stakeholder's pet requirement gets baked into an increasingly unwieldy system.
NLDS winners ruthlessly prioritize, pilot before they scale, and resist solving every edge case in version 1.0.
Championship Series (NLCS): Execution Under Pressure (23.8% → 53% conditional odds)
Here's where the Cubs' numbers get interesting. Notice how our conditional odds actually improve to 53% in the NLCS? That's because teams that make it this far have proven they can win when it matters. They've found their formula.
This is the Execution Under Pressure stage—the messy, grinding middle where your new methodology meets reality and reality punches back. Your top performers struggle with new approaches. Sales cycles temporarily lengthen. Pipeline coverage drops as reps become more selective.
And everyone—CEO, board, key customers—asks the same question: "When will we see results?"
This is transformation death valley. The pressure to revert is enormous. Your best salespeople threaten to quit. Your worst performers use the transition as an excuse. Wall Street asks uncomfortable questions.
But here's the paradox: companies that survive this stage often emerge stronger than before transformation started. They're like a team that figures out its playoff identity and goes on a tear.
NLCS winners have leadership teams that anticipated this dip, built cushion into timelines and forecasts, and doubled down on coaching during the rough patch.
World Series: Sustained Adoption (12.6% → 50% conditional odds)
If you reach the World Series, you're playing with house money. The Cubs' 50-50 odds here reflect something profound: teams that get this far have solved the fundamental problems that eliminate most competitors.
This is Sustained Adoption—where your methodology stops being "new" and becomes "how we sell." Reps naturally use qualification frameworks. Pipeline reviews focus on the right questions. Win rates improve and sales cycles become predictable.
But even here, half of all efforts fail. Why? Because sustaining change requires different muscles than implementing change. Different disciplines, different leadership skills.
World Series killers are often subtle: leadership attention drifting to the next initiative, gradual erosion of standards as new hires aren't properly onboarded, or success breeding complacency where teams stop reinforcing championship behaviors.
World Series winners treat transformation as continuous process, not a project. They build reinforcement mechanisms, measure leading indicators religiously, and understand that championship performance requires championship discipline, especially after you've won.
Wait Until Next Year (Or: There's Always a New CRO)
Of course, there's one more parallel between Cubs baseball and sales transformation that every leader needs to acknowledge: if this year doesn't work out, there's always next year. In baseball, that means new players, new coaches, maybe a new manager. In business? Well, that's usually a new CRO, a new strategy, and a fresh set of promises to the board.
The average CRO tenure is 25 months, yikes. That’s barely enough time to see a full transformation through, let alone weather the inevitable setbacks. By the time most transformation efforts hit their NLCS stage (execution under pressure), there's often new leadership who had no hand in designing the approach but gets judged on delivering results.
It's the business equivalent of a manager inheriting a playoff team mid-season and being expected to win the World Series with someone else's roster and game plan.
The Championship Mindset
But here's what gives me hope, both for the Cubs and for any organization brave enough to attempt real transformation: those conditional odds tell us that success is possible at every stage. A 55% chance isn't guaranteed, but it's better than a coin flip. A 42% chance means you're the underdog, but underdogs win all the time.
The teams and companies that make it all the way understand that each stage requires different tactics, different mindsets, and different success metrics. They don't just hope for the best, they study the specific game within each game and prepare accordingly.
So as we head into October baseball!….I remain cautiously optimistic about the Cubs' chances, conditional odds and all. Ask yourself: What stage is your transformation in? Are you trying to secure Wild Card buy-in, grinding through NLDS design challenges, battling through NLCS execution pressure, or fighting to sustain World Series-level performance?
And remember: even a 6.3% cumulative chance means someone wins it all every single year. The question isn't whether the odds are long, it's whether you're prepared to execute when your moment comes.
There's always next year. But why not this year?
What round are you in, and what's your conditional probability of success?
