Bottoms Up! A Sales Story from Madison Avenue

383 Madison Avenue - Bear Stearns Headquarters

Early in 2001, fresh in my role as Director of Sales for North America for a truly exceptional company, my CEO called me to the window of our Madison Avenue office. He pointed to a towering skyscraper under construction at 383 Madison Avenue. “Do you know who’s moving in there?” he asked.

Naturally, I didn’t. I was still learning the landscape of the Big Apple.

“Bear Stearns is moving its headquarters there,” he said. “And do you know how many users of our product we have in that building?”

I gave an apologetic head shake, my newcomer status on full display.

“Zero. We have never succeeded in winning Bear Stearns as a customer. I want you to focus on changing that.”

At the time, Bear Stearns was a titan of Wall Street—renowned for its intellectual rigor, high-caliber professionals, and a culture of modest, unassuming excellence. For me, this was the ultimate challenge: to prove my worth and finally break into a major Financial Institution, a step up from the legal firms I was currently handling.

Our SaaS solution was a perfect fit for the Latin America Fixed Income Research department, a team of 15-20 brilliant analysts, many from the region, led by a high-caliber pro I’ll call CR. The opportunity was clear, but the path to a "yes" was the real test. In direct sales, there are traditionally two paths to a "yes," but I discovered a powerful third.

1) The Top-Down Approach: Seeking the Rubber Stamp

This is the classic corporate raid. You aim for the decision-maker—the CTO, the department head, the person with the budget—and deliver your polished pitch. The goal is to get their approval, which theoretically trickles down as a mandate for their team to adopt.

• Expanded Advantages: This approach is fast and efficient. If you succeed, you can circumvent internal politics and lengthy evaluation cycles. A "yes" from the top can feel like a guaranteed win, as it comes with the authority to allocate budget and dictate policy.

• Expanded Challenges & Pitfalls: The major risk is the "ivory tower" disconnect. A decision-maker might love the concept, but if their team—the actual end-users—finds the tool clunky, irrelevant, or disruptive to their workflow, resistance will form. I’ve seen teams, unwilling to admit a new tool could make them more effective, subtly sabotage the adoption. The decision-maker, facing internal pushback, may be forced to rescind their approval, leaving you with a hollow "yes" that never converts into a successful implementation.

  
  

2) The Bottom-Up Approach: Cultivating the Grassroots

The more traditional, grind-it-out method. You start by winning over the end-users. You demonstrate how your solution makes their daily lives easier, hoping they become internal champions who lobby management on your behalf.

• Expanded Advantages: This builds a foundation of genuine support. When a purchase request comes from the team that does the actual work, it carries the weight of practical necessity. You have a group of invested users who are motivated to see the tool succeed because they directly benefit from it.

• Expanded Challenges & Pitfalls: This process is fragile, like a game of "Telephone." Your perfectly crafted value proposition can get distorted as it moves up each managerial layer. Your champion may lack the influence or persuasion skills to fight for the budget. Worse, they can face a skeptical manager who asks, “You’ve managed without it so far; why do you need it now?” Furthermore, end-users are often completely in the dark about budget constraints, so their passionate advocacy can hit an invisible financial wall.

  
  

3) The "Bottoms Up" Approach: The Strategic Alliance

This third way, which I named "Bottoms Up" for the celebratory success it can bring, is a deliberate amalgamation of the other two. It’s not a happy accident; it’s a coordinated strategy to create an unstoppable consensus.

My expanded approach at Bear Stearns looked like this:

• Phase 1: Forge a Genuine Champion (The "Bottom"). I was patient. I didn’t blast emails; I built my network. I finally connected with TW, the Latin America Strategist—a cultivated, open-minded analyst. He saw the immediate value and offered to champion the solution. His one condition: I had to get his entire 8-person team on board with a trial. A pure Bottom-Up advocate would have jumped at this, relying solely on TW's internal influence.

  
  

• Phase 2: Secure a Strategic Promise (The "Top"). But I knew CR, the department head, was a modern, confident leader who empowered his team. So, I did something different. I asked TW to help me schedule a meeting with CR himself. When I met CR, I didn’t pitch. I said, “Mr. R, I’m not here to sell you anything. I’m here to ask for a promise.” I had his attention. I outlined the trial for his entire team and said, “If I can get the majority of your analysts to sign their names endorsing our tool, I need you to promise me you will do everything in your power to find the budget. I just need your word.”

  
  

• The Ingenuity of the Move: This approach was powerful because it:

  • Showed Respect: I respected his time by not giving a full pitch.

  • Demonstrated Confidence: I was so confident in my product's value to his team that I was willing to let them be the judge.

  • Empowered His Leadership: I framed the decision not as a corporate purchase, but as an act of trust in his own team's judgment. For a leader like CR, this was affirming, not challenging.

The result was a powerful pincer movement. The bottom-up enthusiasm was now backed by a top-down promise. The team felt empowered, and CR was invested in the outcome.

Long story short, the department loved the solution. I returned to CR not with a plea, but with a signed list of endorsements and a draft contract. He told me no salesperson had ever approached him with such tact and ingenuity. He not only kept his promise but later offered me a job on his team—an offer I kindly declined.

Considering the fate that befell that magnificent bank during the 2008 financial crisis, I believe my decision was sound.

Oh, and as for TW? We became great friends and are in touch to this day.

Bottoms up!