How I Saved a Company from Losing Tens of Millions of Dollars

Studies say that retaining an existing customer costs five to 25 times less than selling to a new buyer. But they don’t tell you that even that approach can sometimes go wrong. You can spend years nurturing an account and still end up in danger of losing it! 

That’s precisely what happened in one of the organizations I used to work for before I was suddenly hired as the new sales manager. I felt very proud of this promotion—until I realized I was put on a ‘glass cliff.’ 

Several weeks ago, I wrote about my experience and this phenomenon, so here’s a little refresher. The ‘glass cliff’ is an unfair practice in which organizations deliberately hire female candidates and Women of Color for executive roles at times of extreme company crisis. 

In the organization I used to work for, I was that new Black female executive tasked to save what looked like irreparable business damage. On my first day at the new job, I got a challenging Fortune 100 company case just a step away from terminating their 10-million-dollar contract. Worse, our CEO told me that if I lost this account, he would have to lay off one-third of the company!

Initially, I froze. 

But then I worked my magic and successfully saved an at-risk client. 

During this long journey, I relied on the following two powerful tactics:

• Getting the right information and feedback

• Building deep client relationships

Cherilynn Castleman, CGI Managing Partner

It was my most challenging customer win and the one I’m most proud of. 

I’m revealing the entire process, so feel free to ‘steal’ it to implement deep sales into your customer relationships.


1. Schedule a discovery call

The first thing I did was arrange a meeting with the account’s senior VP. On that first call, I asked him three strategic questions:

• What did our team do well, and what could have been better?

• What is your most significant pain point?

• How do you envision your company’s success to look like?

The insight I received was critical. Also, I leveraged empathetic listening. I tried to listen without judgment and understand his perspective.

2. Immerse yourself in the client’s world

I asked my stakeholder to give me 90 days, during which I completely immersed myself in his company’s world. We had regular weekly calls during that time, and I used them to listen and learn as much as possible. They had our full attention, and they liked it.

In parallel, week after week, we were getting to know each other better and deepening our business relationship.

By immersing yourself in the customer’s or the executive’s world and understanding their perspective, you will learn to analyze and think like them.

TIP: Immerse yourself in your client’s world.  It’s all about insight. In the coming weeks, public companies will provide insight into how they’re adapting business strategies and navigating through the 2023 economic headwinds. Your clients 10-Q may be the best place to understand the initial financial impact of the changing economy on their business. Connecting with your clients and prospects only happens when you talk about something that matters to them.

Additionally, leverage LinkedIn’s newly introduced Deep Sales Platform – a technology tool that aims to shorten the buyer-seller gap -with high-quality data generating dynamic insights that empower sales teams to take the right actions and have better outcomes. 

3. Get the attention of relevant people

Talking to the senior VP was helpful, but we knew that to really move the needle, we must reach the president. So I worked with my marketing team to identify conferences he was attending. Finally, we picked one, so I got ready and found him on the exhibit floor.

5 Steps to Implement Deep Sales into Your Customer Relationships

I must admit I startled him a bit. I quickly introduced myself, asking for 15 minutes of his time to show him how he could realize an ROI with the investment he had with my firm. That got his attention – and my name on his calendar.

4. Ask the right questions

The following week, I was traveling to meet him in his town, carrying a 30-slide pitch made by my marketing team and clear instructions from my CEO on what to say. 

However, I used that time to ask those same discovery call qutions I asked his employee several months ago. What did we do well, and what could have been better? What is your biggest challenge? How do you envision your future? 

The response we got from him was invaluable. We learned that none of his 14 executives understood federal policies and guidelines that significantly impacted their organization. That discovery made all the difference.

5. Make the customer the hero of the story

I managed to book another meeting with the president, where I brought a subject matter expert on federal regulations. The goal was not just to educate them on the matter but to equip the president with key talking points to further resolve the company’s issues. Our mission was to help him become a knowledgeable executive and give him the power to save the day.

That move was a complete success. Then we did the same for his 14 executives, scattered around the country: the discovery interview and education on federal regulations for their regions. My team even tailored those approaches for each of the executives since each had a different strategy, so they were meeting other parts of our team.


After several months of working on this case, where we ended up helping them resolve their burning challenge, our customer case was saved. They renewed the contract, and the relationship between our companies was stronger than ever.

The moral of the story is that with deep sales tactics, you can get any business relationship going and thriving, even when it looks like a definite failure. Let’s recap:

  • We immersed in their world
  • We built relationships deep and wide
  • We helped the client meet their needs

Deep sales are about insights and relationships.

Use them both to level up your business relationships, and you’ll have a customer for life.

Are you ready to get the seat at the table of your dreams?

Join me LIVE this year at the Step Into the C-Suite Conference in New York, San Francisco, Washington, D.C., Chicago, and Atlanta.

The first 50 women to use the code LINKEDIN100 will receive $100 off their registration!

Register Here:


A Coaching engagement can help you get results.

Make yourself a priority and make coaching a critical component of your overall success strategy. Begin your sales coaching journey today. See if we’re a good fit to work together

Executive Coaching

Learn more about Executive and Professional Coaching with Cherilynn Castleman



Join Our Email List