How to Know If It’s the Right Time to Enter A Market.

In this episode of The Aibiliti Podcast, we explore one of the most overlooked but critical questions in go-to-market strategy: Is now the right time to enter this market? While companies often obsess over total addressable market (TAM) and execution capabilities, they frequently neglect timing — and yet, timing is often what separates success from slow, costly failure.

The episode breaks down what good timing actually looks like. It’s not about theoretical pain points or well-designed pitch decks; it’s about whether buyers are feeling the pain right now, whether urgency already exists, and whether shifting priorities in the market support the solution being offered. We also look at whether the market is “broken enough” to be ready for change — because comfortable markets rarely listen.

To illustrate the point, we share a real-world case where a large TAM and strong signals on paper turned out to mask a “stuck” market — one bogged down by long buying cycles, low accountability, and entrenched legacy vendors. The team ultimately paused and redirected toward a smaller but far more responsive market. The result? Faster conversations, quicker pilots, and actual momentum — all because the timing was right.

Listeners are encouraged to rethink how they assess market readiness. Ask whether budgets are expanding for the type of solution you offer. Whether buyers already acknowledge the problem. Whether existing alternatives are losing trust. And crucially — whether your team is ready to move fast when the window opens.

This episode is a reminder that winning isn’t just about building the best product — it’s about being ready when the door is cracked open and knowing when to walk through it.

Transcript

Welcome to the new episode of "The Aibiliti Podcast".   Today we’re diving into "How to Know If It’s the Right Time to Enter A Market." 

 There is a question I hear often.  But not always loud enough.  

"Is now the right time to enter this market?"

 “Is the TAM big enough?"

 "Can we execute there?"

 And that’s what I want to talk about today, because timing gets ignored more often than it should. And yet,  it’s often the difference between a deal won and a market that never quite opens up. Let me put it this way - A great product in the wrong market?  That’s hard. But a great product at the wrong time, that is a slow and expensive failure. 

So, what does good timing actually look like?

 Here’s what I look for.

 1. Are buyers feeling the pain right now?  Not last year, not in a slide deck,  I mean right now,  in the room, in the budget, in their day-to-day.

 2. You want urgency, but not the kind you had to create,  real urgency.   The kind that already exists before you show up.

 3.  Are their priorities shifting in your favor?

 Because if your solution relies on a budget line that's getting cut., or it replaces a process people are still emotionally attached to, you’re probably too early.

 4. And finally, Is something broken enough that it’s actually safe to sell the fix?

Because a market that’s too comfortable, that’s a market that isn’t listening.  I will give you an example. We once looked at a market where the TAM was massive.  Every slide said “go.” But when we spoke to a few people, informally,  what we found was inertia. The buying cycles were 18+ months. No one was really being held accountable for the problem. And there were legacy vendors in place with deeply entrenched relationships. It wasn’t a bad market.  But it was a stuck market. And it would’ve taken a disproportionate amount of time, energy, and trust-building to shift that.

So, we paused.

And a quarter later, another market opened up, smaller TAM, but high urgency, lean teams and nobody owning the space yet.

We were in conversations within 3 weeks, piloting within 60 days.

So, you see,  same team, same product, diffferent timing- but radically different outcomes.

So, here’s the takeaway. TAM is not timing.

Market size doesn't tell you if the market is open. If you’re considering entering a new space.   Ask yourself-

  •   Are budgets for this type of solution increasing or shrinking?

  •   Are we solving something buyers already admit is broken?

  •    Are the alternatives in place already being questioned, or are they still trusted?

 And most importantly-Do we have the capacity to move quickly if the timing is right?

 Because sometimes, the window is open but not for long. This isn’t about rushing market entry.  It’s about not mistaking potential for readiness.

 Sometimes, it is not about building the better product. It’s about showing up when the door is cracked open and walking through it before it closes.

Thanks for listening. Until next time.  Keep asking better questions.  

 

 

 

 

 

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