We're having trouble filling our pipeline. Any suggestions?



Dear CEO,

Your sales pipeline can be your biggest asset, or your greatest liability. If you don't keep that pipeline healthy, you are going to wind up on a sales revenue roller coaster that will be hard to get off of.

What's the secret to filling your pipeline and keeping it healthy?

As you've probably seen, there are a lot of gurus out there with a lot of advice. Cold calling. Cold emailing. Social selling. Business development rep versus sales rep.

Even internally you're probably seeing a struggle.

If pipelines aren't full, sales is quick to point the finger at marketing. When quotas are missed, marketing is quick to point the finger at sales.

It's no wonder why most CEOs are at a loss of what to do.

Over the last 20 years I've either sold, or managed the selling of $1B in software. I've been around the block a time or two. Here's my honest advice on what works, and what doesn't.

1. How Many Prospects Do You Really Need?

Your numbers may differ ever so slightly, but on average, you need 40 leads to go into the top of your funnel to result in 1 closed deal at the bottom of your sales funnel.

Does that scare you? It should.

From the CEO-level down, you need to understand that prospecting is a full-time, all-the-time company effort.

It's not a one person, one team, or one department job.

Get your entire company focused at ways to get leads into the top of the funnel.

2. What's the Best Way to Prospect?

While prospecting is a numbers game, you will increase your odds of success (40:1) the more targeted you are in your approach.

Let me explain.

An executive with a general problem has no urgency to buy. But, an executive that has a very specific problem, will have both the urgency and the money to buy.

You want to find that person.

Invest in data profiling to find those prospects and get them into the top of your funnel -- quick. Don't be cheap here, you have to spend money to make money.

Once that person is in your funnel, keep every message and interaction focused on solving their very specific problem.

If you do, your prospecting results will go through the roof.

3. When is the Best Time to Prospect?


Long gone are the days where people are in their office 8:00 am - 5:00 pm. Some days they'll be in a conference room all day. Some days they'll be at a customer location. Some days they will be working from home.

It doesn't matter the time, device, or medium.

Deliver that targeted message, to that targeted executive any time, on any device using whatever channel is available to you.

4. Who Should Prospect?

Everyone in your organization should prospect. Even you. As a side benefit, it will keep you on your game for those investor presentations and questions that come out of left field.

5. Remember, Prospecting is Hard -- Give Your Team Kudos

I once had a senior sales leader tell me that prospecting was easy. That they could easily hit 100 prospecting calls all day every day. That anyone who couldn't do that was lazy.

So I challenged the executive: Put up or shut up. One day, 100 calls.

The executive made 3 calls.

Prospecting is hard. Recognize that, and recognize your teams for prospecting.

Your pipeline will make or break your company. Keep focused on getting leads in the top of your funnel, and then on delivering a targeted message to a very targeted executive.

Best of luck!