Fill Your Sales Pipeline by Finding “The Entry Point” (Interview with Craig Rosenberg)

When Craig Rosenberg conducted training for sales reps at an enterprise software company, he pushed them to consider alternate points of contact to fill their sales pipeline.

Part way through, a salesman interrupted his presentation and said, “Craig, I just want you to know that I only go high. I only go to the C-level.”

In response, Craig asked, “That's great. Tell me about your pipeline.”

The salesman’s response? “Well, I have zero deals right now and I really need marketing’s help.”


If you can do cold outreach to executives only and keep a full pipeline, more power to you. But if you’re reading this article, you can understand why going high isn’t Craig’s only strategy.

Craig co-founded TOPO, a research and advisory firm that helps companies grow faster. TOPO analysts help companies build strategies to help salespeople fill their sales pipeline without relying on ‘straight to the top’ methods.

Instead, Craig recommends finding the “entry point.”

The ideal entry is often someone who owns the process you’re selling to—a reliable stakeholder more involved in your niche than, say, the VP of Marketing or whatever part of the organization you’re selling into. This is often your ideal customer profile in Salesforce.

Once you establish a foothold with the entry point, then you make your play to the top. And since an entry point is easier to get access to than an SVP, you’re more likely to have more opportunities to keep your pipeline full.

In our conversation, Craig described how to find the entry point, then how to follow through with specific sales plays his clients use to frequently close deals.

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How to Keep Your Sales Pipeline Full by Finding the Entry Point

To begin, Craig used Marketo as an example of finding the entry point.

“Marketo is the hero of the B2B martech stack,” Craig began, “but they are rarely engaging with the CMO early in the process. They sell to the Director of Demand Gen and the Director of Marketing Ops. Everything they do pivots around that person.”

In other words, Marketo doesn’t start by going straight to the top. Instead, they identify roles like Director of Demand Gen and market to those people first, then work their way onto the CMO’s radar.

Marketo identifies roles like Director of Demand Gen and markets to those people first, then works their way onto the CMO’s radar.

Who’s Your Product Built For? That’s Probably Your Entry Point

To find your own entry point, start with the role your tool is built around.

Whose problems does your solution solve? Your entry point may be that person (or likely, one level up from that person). Craig also recommends looking at who’s showing up to conferences.

Who Comes to the Second Sales Meeting?

Once you’ve started getting in the door, Craig recommends observing major players in the second sales meeting with a company. Who gets brought into the room? Who gets in the way? Whose absence makes things harder?

“Those are things that don't show up in marketing data,” he said. “Those are the things we need to capture from true engagement and you can make adjustments based on that information, even though it's relatively qualitative.”

If you guessed wrong about the entry point, keep moving.

“We have to go after someone else in the organization, that ‘other purse.’ What we don't want to do is just grovel,” Craig said. “Maybe we have the wrong entry point. Maybe the entry point isn't who we thought it was and maybe we need to cultivate a different entry point. That's totally part of a go-to-market pivot.”

Maybe the entry point isn't who we thought it was and maybe we need to cultivate a different entry point.

There May Be More Than One Entry Point

In the process, you may even find that there’s more than one entry point.

“I just met with a company the other day and their entry point is still technically the Director of Marketing Ops, but they realized that these big companies now have data scientists, right? Analytics is not horizontal, it's vertical. And they realized that those people were actually a fantastic secondary entry point,” he recalled.

So while their primary focus is still the directors, they also connect with their secondary entry point: analytics guys whose job is to bring ideas to the table.

In summary:

  • Start by assuming your entry point is the person your tool was built to help (or one level higher).
  • Revise based on who you observe at the second sales meeting.
  • Adjust and pivot as needed until you consistently find the right entry point.

3 Sales Plays to Use After Connecting with the Entry Point

Once you’ve identified and made contact with the entry point, it’s time to make a play. Craig described three that he has seen be highly successful:

  • The "High/Low" Approach
  • The "Educational" Approach
  • The "Hero" Approach

Sales Play #1: The “High/Low” Approach

The high/low sales play is perfect for when your entry point is a relatively low-ranking person in the organization.

By cultivating a relationship with the entry point, you learn everything you can about the challenges and roadblocks their company faces. Then, you take that information and write a detailed letter to the C-level role you’re targeting. This is the “high” phase of the play.

“Once you get in and understand what's happening, now you can actually write a note to someone and say, ‘I know what's going on. Here are three roadblocks you face. I have an idea on how you can fix them.’”

That makes ‘going high’ significantly more likely to succeed than if you were just writing a blind sales letter to that C-level player.

Now you can actually write a note to someone and say, ‘I know what's going on. Here are three roadblocks you face. I have an idea on how you can fix them.

Sales Play #2: The Educational Approach

The educational play is about putting together an educational offer that gets your product or service in front of multiple stakeholders.

For example, Craig works with a B2B company in the adtech space. They know it’s a hard sell and they have to go through twenty-something people to get buy-in. They can’t pitch the C-level right away, so instead, they find the entry point.

Then, they’ll say something like, “We have a story about what the next wave of ad tech is going to look like and how you will track/manage/measure this and that. We'd love to come in and tell the team about it.”

That incentivizes the entry point to tell everyone else about it. “That person would help them spread the message throughout the rest of the organization. They would organize a virtual webinar with like 15 people, or they'd say, ‘You’ve got to come in and show that to my boss,’” he added.

Alternatively, they might put together a presentation on how to get a sales team to 70% daily customer engagement (one that features their tool as a part of the solution, of course).

It’s a play that wins friends quickly and makes it easier for you to get in front of the roles with buying power.

Sales Play #3: The “Hero” Approach (Arming the Champion)

The hero sales play is a little more hands-off. In the “hero” play, you find an entry point that will champion your tool to their company. Then, you give them everything they need to make the case for your sale.

“We often just send them the deck and the data sheet and let them see what they can do,” Craig told us.

For this play to work, you have to think about what your buyers typically do after you engage the entry point, then arm that person with everything they need to keep things moving along.

Remember the ‘Why’

In most cases, you’re not making the sale with the entry point alone. Instead, you’re talking to someone who can introduce you to the person with buying power. You don’t want to aim too low, but you also don’t want to go so high that you miss out on sales.

“It's really an efficiency thing,” Craig emphasized. “You should always be multithreaded. You should always see what you can get. The focus of everything is to embrace that way in the door.”

“I think the reality of the new stakeholder map is that your skip levels (or whatever you want to call them) are extremely powerful and empowered. Their purchase power is different than in the past,” he reflected.

Pitching an entry point is a way to accommodate that reality in your sales process. And by doing so, you’re much more likely to keep a full sales pipeline.

Note: At Troops, we’re building solutions that help salespeople close more deals as a team. Want to know more about how it works? Sign up for a free trial.


Written by Scott

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