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?
Replies