Cold Calling

How To Prospect: Sales Leaders

14 Jan
min read

Learn about what leaders in the space are dealing with on a day to day basis, how to speak to their pain points and ways to overcome common objections with David Ashe, VP of Sales at Allego.

According to Nooks data, Sales leaders have the best connect rate and connect-to-meeting rate. Which makes sense, they're on their phone and always looking for ways to get closer to quota. But on the flip side, they receive the most calls and are often bombarded by sales people on multiple channels. We met with David Ashe, Director of Sales Development at Allego to learn how his team executes and capitalizes on dials to book meetings with Sales leadership. Here's a replay of our conversation and five takeaways: 

1. Show me you know me

When you're calling a Sales Leader, understand they spent many years doing what you're about to do. So they're likely to be as critical as they are empathic. To respect the process, it's important to have some kind of carrot and "show me you know me." 

David Ashe, who sometimes goes by "Dashe," suggests 'making digital deposits.' To do this, follow the company, like and comment on posts, start connecting with personalized messages, endorse them for their skills and build familiarity before you reach out.

2. Read the room

Tailor your outreach to the type of prospect you think you're trying to connect with. To do this, observe their social media. If they're an sharer with a large following, they might appreciate creativity and continued follow ups. If they're profile is short and sweet + accomplished based, they might appreciate succinct communication with data backed case study.

In other words, one size doesn't fit all. Spend the time to know your prospects, don't spray and pray and personalize.

3. Leave voicemails

If you spend time reading advice from Sales leaders on blogs and social media, you'll know that voicemails are somewhat controversial. Some Sales leaders preach against voicemails because it's an easy way to get blocked once they can identify your number as a Sales person. Some say that they waste time that could be spent on the next call while others agree that slow, targeted outreach via voicemail leads to meetings.

David Ashe teaches his team at Allego that it let's the prospect know who you are so you're more likely to get a "Yes" or a "No." And that answer leads to the results you really want - identifying who the potential buyer are. Everything is subjective, but if your goal is to set qualified meetings without spraying and praying, you might want to consider spending time on thoughtful voicemails.

4. Invest in strong mobile data

In the post-covid era of Sales, especially for B2B SaaS Sales Leaders, most are operating on their sell phone or through their cell phone with a software that connects to it. At the time of this writing, only 42% of Sales teams are back in the office full-time (HubSpot research). Invest in tools like Apollo, Zoominfo or something similar to arm your team with mobile data.

"But what if they get annoyed about calling their personal number?" - There are some negative externalities, but your connect rate and connect-to-meeting rate with sales leaders will speak for itself. Focus on conversation volume by calling the number they're most likely to answer.

5. Build your personal brand

More than any other vertical, Sales folks are on LinkedIn more than any other vertical. If you've logged in to LinkedIn today, that should come as no surprise. This presents a unique marketing/sales opportunity that teams who sell to other verticals just can't exploit.

By building your personal brand and posting consistently on LinkedIn about your expertise and product, you get an opportunity to build familiarity and show up in front of your prospects so they might actually listen when you get live on the phone.

Real estate agents and lawyers understand the power of advertising their personal brand - so should we.


If you sell to Sales Decision Makers, you're a part of an elite community of legendary cold callers that get the priveledge of having more conversations than any other vertical. Capitalize on your those conversations to increase conversions by doing your research and building familiarity. David Ashe's team at Allego uses Nooks to 5x their dial volume and have more conversations.

Follow Nooks for more Sales content and check out Allego's Revenue Enablement Platform.

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