How Bill Lost a Deal and Won it Back


This story is true. The names have been changed to protect the guilty.
Part one: Chasing the suspect

Bill sells data cataloging software. He had a named account list of 25 financial services accounts. He had a sense of the sorts of challenges these companies shared related to his product.

He identified 5-6 key contacts at each account and sent messages that highlighted the features he felt would be most interesting to someone in a given role. He got a whole lot of nothing for his trouble.

He followed up with messages which highlighted the pain those roles are likely facing around uncategorized data.

BOOM! – Response from a VP of Data Services at a large insurance company.

Call scheduled!

Part two: Discovery Call

Bill was excited and got his sales manager (SM) & sales engineer (SE) on the call. SM & SE introduced themselves to the prospect and started qualifying. They asked questions like this:

  • What do you do?
  • What are your data sources?
  • What does your tech stack look like?
  • Tell me about your application & data infrastructure
  • What is your pressing need?

By the time they reached the pressing need they were 20 minutes into a call that’d been scheduled for 45 minutes. The prospect then asked some fairly typical questions:

  • What does your platform do?
  • How do you compare against your competitors? (Prospect name dropped a few competitors)
  • Onboarding time etc.

SE answered most of the questions with general overview and promised to get back to the prospect with specific information. At that point the 45 minutes were up, and the call ended

Next steps: More info & time for demo via email

CRM status: Hot opportunity + SQL

What Bill didn’t know:

This insurance company had recently raised $150 million for M&A. At the time of the call the prospect was trying to integrate data from 12 acquisitions made over past 6 months. Clearly there was ample opportunity for Bill’s product; the company’s data environment was a train wreck. The prospect knew he had a problem and was evaluating 4 competing vendors.

Part three: Multiple follow up for next steps

Bill diligently followed up with no success, even with the SE/SM pitching in to help. Here’s what he sent:

  • Post call note (after 2 days) – with capability statement & financial services case study
  • 1st follow up asking for time (4 days later)
  • 2nd follow up asking for data needed for demo (3 days later)
  • 3rd follow up asking for time (7 days later)
  • 4th follow up with a white paper (4 days later)
  • 5th follow up with an analyst report (7 days later)
  • 6th follow up asking to confirm interest (7 days later)
Redemption stage one

Months later Bill looked at this account again and decided to see if he could make something happen. Here’s what he did:

  • Listened to and made notes about the discovery call
  • Looked at company’s current structure – saw the acquisition number had grown to 23 in the last 6 months.
  • Researched the acquired companies, understanding their business models, partnership structure and data infrastructure
  • Bill researched on LinkedIn for a couple of days to understand the different data roles present in the parent company and the acquired companies
  • Looked into the competitors whose names the prospect had mentioned and created a capabilities matrix matched with his offering
  • He found out what incumbent vendors they were using to address their data categorization challenges

After 3-4 days of effort, Bill had amassed a pretty good amount of sales intelligence:

  • Prospect company strategic priorities – current and future acquisition plan
  • Current and anticipated data infrastructure
  • Complete behind the firewall tech stack
  • How Bill’s company compared to competitors (not only the 3 names prospect mentioned but also 3 incumbent vendors)
  • Bill could not find a published case study that was a close match, so he went to the delivery team to find past clients with similar data categorization & integration challenges. He came up with 3 past clients with unique & complex requirements similar to the insurance company.
  • Bill spoke with his customer success & delivery team to understand the onboarding challenges they had with those existing clients and took notes on how his team overcame those challenges.
Redemption stage two: Contact

Bill sent a casual note asking how the prospect was doing and how his projects are going. He also slipped in 2 sentences about the onboarding challenges he’d picked up from his delivery team and asked if he was facing similar challenges with his latest acquisition.

BOOM! – Prospect responded within 3 hours and Bill shared some of the methods his team used to overcome the onboarding challenges

After 6 back & forth emails Bill was ready to ask if the prospect would like to spend 30 minutes on a call with his delivery head and get some feedback. The prospect agreed.

Redemption stage three: Discovery round II

The delivery head used the first 5 minutes of the call to reiterate the problems the prospect was facing. In the following 15 minutes the prospect gave a deep dive on where he was and the challenges they were struggling with. Bill’s team suggested some options and asked for sample data to show a demo with their data.

Prospect agreed and the demo was scheduled before they ended the call.

Redemption stage four: Demo, POC + Contract

The prospect invited 3 other team members for an exhaustive 2 hour demo. Bill’s delivery head answered every question they had, and they walked through the deployment scenarios in their live environment.

The prospect signed an SOW within 24 hours

LESSONS BILL LEARNED:
  • Earn the prospect’s attention by incorporating research about their situation and their challenges into our prospecting
  • Don’t expect the client to connect all the dots for us; if we solve these problems, we should lead, not follow
  • Reduce prospect’s anxiety and resistance by consistently demonstrating that we’ll make their life easier, not harder

One thought on “Rise & Fall of a Sales Opportunity”

  1. Great blog and so true. Too often, sales and business development people want to pick the low hanging fruit (which more often than not fails to establish a strategic relationship that converts the prospect into a long-term client, not just a customer).

    It’s more than walking a mile in the prospect’s shoes. It’s knowing where he’s going and what type of shoes he’s wearing.

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