Takeaways from an 18-Month Sales Cycle

This post originally appeared in my weekly newsletter, BL&T (Borrowed, Learned, & Thought). Subscribe

Borrowed

"Long-term thinking levers our existing abilities and lets us do new things we couldn’t otherwise contemplate,” Jeff wrote. “Long-term orientation interacts well with customer obsession. If we can identify a customer need and if we can further develop conviction that that need is meaningful and durable, our approach permits us to work patiently for multiple years to deliver a solution.”

From "Working Backwards: Insights, Stories, and Secrets from Inside Amazon" by Colin Bryar and Bill Carr [Book]

Learned

This week, we signed a client after 18 months of conversations. The lead came to us through a former client stakeholder who had joined the company.

From the start, we saw we could add value, and our chances of winning felt strong because of the connection. But, the process was long: 12 months from the first call to presenting a proposal, four months from the proposal to sending an SOW, and another two to signing. Internally, it became a running joke as we guessed when—or if—it would finally happen.

Looking back, it’s easy to laugh at the lengthy sales process and move on. But I wanted to take some time to dig into what actually went down and pull out some takeaways.

Here’s a rough timeline, based on what I could gather from my notes, excluding the countless emails in between each event (more on that later):

2023

July: Met with key stakeholders for a meet-and-greet to identify if there was an opportunity to help and add value. There was.

2024

February: Regrouped to discuss budgets, timelines, and their challenges in more detail. We learned that our primary contact would not be the former stakeholder who recommended us. Funny enough, they moved on several months ago.
April: Received an invitation to participate in a formal RFP process. We had anticipated this step, but it seemed less like a project and more about several challenges/areas they needed help with.
May: Held a call to clarify questions and expectations for the RFP, followed by a proposal presentation a week later.
June: A key stakeholder informed us that we were one of two finalist agencies. They shared that our proposal was the strongest overall, but some team members felt the other agency had more depth in SEO/analytics. We hadn't caught this as a need (it isn't currently in the scope) but were lucky to have a chance to show what we could offer. The ask? Provide an SEO/analytics audit. We did.
Weeks later, we reviewed the audit insights with the full team, including folks we hadn't met yet.
Early July: Held a one-on-one call with the key stakeholder, who shared that the team was very impressed but still needed to gather alignment. We were told to expect a decision within a week.
Early August: A month later, we joined another call where the client shared, “Between us, the team is leaning toward you.” The next step was to review legal documents. This was promising, but we didn't get our hopes up.
Later that month, we received an email requesting a call to discuss the services they wanted to move forward with. We had no idea we’d won. During the call, we aligned on the scope and began drafting the SOW.
Early September: Within the following week, sent the SOW for review.
September-November: Several emails and a couple of calls to keep conversations going, address questions (mostly legal), and refine the scope.
Last week: Received final approval at the start of the week, closed on Friday.

What stood out most while recounting this journey was how we opted for persistence and patience over frustration. In situations like this, it’s easy to blame clients or even feel taken advantage of, but that mindset doesn’t serve anyone. The truth was that our key stakeholder was doing their best to move things along, navigating the bureaucracy that comes with a larger organization while also balancing other important initiatives.

All said, here are some takeaways I'll carry with me going forward:

Keep pacing aligned with reality.

Momentum matters, but it has to match the client’s readiness. Looking back, I’m grateful we didn’t go too far in scoping until we had enough information and could ensure our proposal would get the right attention. Jumping in too fast and over-investing can lead to frustration when things stall. At the same time, knowing when to go the extra mile can make all the difference—like providing the additional analytics and SEO audit when the decision came down to us and another agency.

It’s not a done deal until it’s a done deal.

Staffing: Over the last six months, there were plenty of moments when it felt like this deal could close any day. I’m glad we didn’t rush to allocate resources prematurely or put other projects at risk. Instead, we stayed focused on refining our plan for when it landed and ensuring we were ready to hit the ground running when it finally did.
New Business Goals: At one point, we kept saying, “If X client lands, we’ll hit our new business goal.” But as conversations dragged on, we adjusted our outlook, avoided over-relying on a win that might never happen, and stayed focused on bringing in other opportunities.

Find patience in understanding.

The client was managing a rebrand and a new site launch, all within the larger complexities of their organization. Delays had nothing to do with us, and their focus was elsewhere. By staying curious about their process and challenges, we avoided second-guessing ourselves and instead approached each interaction with empathy and persistence.

Keep showing up.

One thing I’m proud of is how consistent we stayed over the 18 months. We were in touch almost weekly, whether it was a strategic nudge like “we’re holding resources—what’s the timeline?” or a simple check-in to ask for an update. Props to Riley, Account Coordinator, for her persistence in keeping the conversation going over email. Each week, we focused on identifying whether the opportunity was still there, if we were doing enough to close it, and the best next action to take.

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It’s probably because I just ran a marathon, but closing this deal last week felt all too much like crossing the finish line. I'm just glad it wasn't 26.2 months. The win feels good, no doubt, but it’s just another milestone. A timely reminder that success comes from playing the long game—with patience, understanding, and focus.