We lost a $50M deal. Here’s why—and what I learned.

A few years ago, while working full-time with an IT services firm, we lost a $50M deal with a leading telco in the GCC.

We had built early rapport with the head of their technical team.

So much so, we deployed senior solutioning leaders into their office for over a year.

Our team helped:

• Shape the technical specs

• Co-create the pre-qual for the RFP

• And spent months deeply involved in the RFP process

By all traditional markers, we were in a strong position.

Then we lost the deal.

Not because the competitor had a better solution.

We were told the deciding factor was price.

But over time, we learned it wasn’t that simple.

We had been single-threading our engagement—relying on one champion to carry us through.

We never mapped the broader stakeholder ecosystem.

• No line into procurement

• No dialogue with the business transformation team

• No understanding of who the executive sponsor was—someone who wasn’t even based in the regional HQ where we had embedded ourselves

• No visibility into competitor positioning or how we were ranked in final evaluations

It was a wake-up call.

We all know enterprise deals are complex, non-linear, and influenced by buying committees.

But we still over-rely on the one person who gives us time and insight.

It feels efficient—but it limits your field of view.

And frontline sales teams operate under real constraints:

• Managing multiple in-flight accounts

• Prioritizing accounts showing early traction

• Avoiding “bypassing” their champion to maintain trust

• Waiting for the champion’s cue to reach out to others

That’s how even good sales teams get boxed in.

A well-intentioned, relationship-driven motion becomes a bottleneck.

This is why multi-threaded engagement isn’t a luxury—it’s a survival strategy in enterprise sales.

But here’s the thing: multi-threading doesn’t work if you treat it like a checkbox or fire off random emails to new contacts.

It requires structure:

• Knowing which accounts are worth deeper engagement

• Mapping key stakeholders and identifying gaps

• Defining clear reasons for reaching out to each person

• Crafting messages aligned to their role, timing, and context

What I learned the hard way?

Multi-threaded engagement must be designed in from day one.

Not added after deals start showing signs of trouble.

Curious to hear from others in B2B enterprise or SaaS:

• How are you structuring your multi-threading motion?

• What’s worked for you to avoid the “one champion” trap?