An Ally in Every Deal: What Separated the Win from the Losses

Over my career, I've been part of many large institutional pursuits at previous firms, before my current role. Three stand out, not because they were my only big ones, but because each taught me something different about working with an ally on the inside. All three were household names, nationally recognized organizations, and any one of them would have been a significant win for the firm I was with at the time. None involved my current employer.

I won one and lost two. In each, I had a different ally on the inside. What differed was how much attention we gave to what that ally knew, what they hoped, and what they could actually influence, and how well we acted on it.

Deal 1: The ally who was rooting for us (Loss)

This was a large, nationally known public company. We had a true inside track. A key decision maker was fully engaged, and our entire deal team got on a call with them to ask every question, learn who was in the room, and understand each person's motivations. We built a presentation strategy and executed it nearly flawlessly.

We lost. A decision maker a level above our ally had a relationship and a compelling business interest in selecting a competitor, one with a meaningful financial stake in the company. Our ally likely knew it was a tough haul. But they liked our team, and they believed the company would get a solution built around its needs and that we would grow together. They were rooting for us, and they were honest with us about what they knew. Their support just wasn't the deciding vote. We likely lost before we walked in the door.

Lesson: an ally's enthusiasm and an ally's influence are different things. Ask how they see the odds, and who else has a stake in the outcome.

Deal 2: The ally we didn't listen to (Loss)

This was at a previous firm, not my current employer, and the client was a large public-sector entity with national visibility. We spent years cultivating the relationship. We met with decision influencers, current and former, studied how the previous bid played out and why the incumbent won, and reached the highest levels of the organization to earn recognition. We also learned exactly what price it would take to win.

Then leadership at that firm, focused on margin, decided we would price higher and win on presentation. The deal team knew better: public-sector buyers look at price first and nuance second. The firm chose a different strategy.

We never reached the finals. The incumbent, priced lower, secured a renewal and the bid process closed before we ever presented.

Lesson: the intelligence was right, and we had it. The gap was internal. Information is worthless if the organization won't act on it.

Deal 3: Listen, influence, execute (Win)

This was a very large national not-for-profit, and it went very differently.

We listened. We identified the right decision maker and spent years strengthening the relationship. We met with the team that would use the solution and listened for pain points. We learned what purchasing needed, what operations needed, and what the lead decision maker would value most.

We influenced. We shaped our message around those needs and brought in people who could speak directly to each pain point. We showed how our organization's reach could help extend the impact of their mission, something no price sheet could say.

We executed. We understood the incumbent's likely pricing, bid competitively, and delivered the presentation flawlessly.

Our ally delivered, our organization acted on what we learned, and we won.

Lesson: the win wasn't luck or a better pitch. It was a real relationship, an understanding of each stakeholder, a competitive price, and an organization that trusted its deal team.

What these pursuits taught me

• Test your ally's reach. Enthusiasm isn't influence. Ask who else decides and who sits above the committee.

• Separate hope from influence. A friendly ally may be rooting for you while knowing the odds are long. Ask directly how they see your chances and who else has a stake.

• Listen to every stakeholder. Buyers, users, and decision makers each want something different. Win all three conversations.

• Act on what you learn. If your ally tells you the price, the criteria, or the risk, your internal process has to be willing to hear it.

• Price to the buyer, not the P&L. A bid that wins nothing earns no margin.

• Align internally first. Sometimes the hardest sale isn't to the client. It's to your own organization.

The takeaway

Across many pursuits, the pattern held. An ally can tell you how to win. Whether you do depends on seeing the full picture, giving every stakeholder a reason to say yes, and having the discipline to act on what you've learned.

These experiences are from earlier in my career, with previous employers, and do not involve my current employer. The views are my own.

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