It was a crisp morning on June 2025, and I found myself diving deep into a stack of documents that had landed on my desk late last week. The email chain and attached analysis from a colleague—let’s call him Chase Matthew—caught my eye immediately. He’d been juggling a complex portfolio of opportunities, and his latest update on the second-quarter numbers was both promising and a little daunting. I could sense the weight of responsibility in his words, and I knew I had a chance to step in and help steer things in the right direction.

Chase Matthew had laid out a detailed picture of his work: a pipeline brimming with potential, packed with 17 active deals that spanned a mix of early-stage ideas and near-closure wins. The total value was staggering—over $11 million in possible revenue, with a solid $5.9 million looking achievable if everything clicked. His focus was on a major client, one that dominated his efforts, alongside a handful of other promising prospects. But as I read through, I could see the cracks—he was leaning too heavily on that one big relationship, and some deals were stalling without clear direction.

I grabbed a coffee and settled in to think it through. The strengths were obvious: Chase Matthew had built strong ties with the key client, and a couple of high-value deals were on the verge of signing, one with an 85% chance of closing soon. That felt like a win we could build on. But the challenges? They were staring me in the face. Too much reliance on one source, a bunch of low-probability deals that needed a push, and some pricing pressure that could derail things if we weren’t careful. I could almost hear the clock ticking—Chase Matthew’s boss was expecting a consolidated update by tomorrow morning, and I didn’t want to let the team down.

I decided to jump in. First, I sketched out a plan to help Chase Matthew diversify his efforts. Those other prospects he’d mentioned? They were a goldmine waiting to be tapped. I suggested we lean on existing connections—folks he’d already met with—to set up workshops and pilots. My goal was to balance his workload, aiming for a 50-50 split between the big client and the new ones by the end of next year. It felt ambitious, but doable with the right focus.

Next, I zeroed in on the high-stakes deals. Two stood out: a massive project worth nearly $8 million and another smaller one at 85% probability. I proposed we prioritize those, nudging them toward closure by the end of the quarter. For the big one, I suggested looping in a senior contact—someone Chase Matthew had mentioned in passing—to keep the momentum going. The smaller deal? We could use it as a quick win to build credibility for more cross-selling down the line.

Pricing was another hurdle. I could tell Chase Matthew was feeling the heat from competitors undercutting us. So, I dug into our unique strengths—our innovative approach to automation and a track record of cutting costs by over 60% in similar projects. I encouraged him to weave those into his pitches, maybe even pull together a case study to show how we stood out. Compliance was another angle; with a 97% accuracy rate in our checks, we had something concrete to lean on.

As I flipped through the pages, I noticed a trend Chase Matthew had flagged: the industry was shifting toward digital solutions and stricter regulations. It was a perfect fit for what we offered—AI-driven tools and process optimization. I suggested we double down on that, embedding those capabilities into our proposals, especially for areas like loan processing and collections. It felt like we could ride that wave if we played it right.

But plans are only as good as their execution. I broke it down into actionable steps. For the stalled deals, I recommended Chase Matthew sync with a teammate to find sponsors and set clear next steps—deadlines like July 10th and 15th to keep things moving. The workshops he’d planned? I urged him to tailor them to the prospects’ pain points, using past successes as a blueprint. And for the big pitches, I suggested assigning a dedicated team to respond fast—within 48 hours—to keep the momentum alive.

Relationships were key, too. I advised Chase Matthew to follow up with a senior exec on one deal by July 1st and push for a high-level meeting with another prospect by mid-month. Little touches like personalized outreach—maybe a thoughtful invite or shared insights—could keep the conversation warm until those workshops kicked off.

By the afternoon, I’d drafted a response for Chase Matthew, outlining the strategy and tactics. I suggested a team training session by July 20th to sharpen their pitch on our tech edge and set up daily check-ins for the advanced deals to stay on track. As I hit send, I felt a surge of satisfaction. This wasn’t just about numbers—it was about helping Chase Matthew navigate a tricky landscape, turning potential into results. With a bit of focus and teamwork, I knew we could turn his pipeline into a success story by the end of the year.