The Top Email Prospecting Strategies of Boston Salespeople

Written by Kelly O'Halloran
Published on Oct. 20, 2020
The Top Email Prospecting Strategies of Boston Salespeople
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Drift Account Executive Sara Miller Blanc once conducted an A/B test to see if sales prospects opened her emails more when she included a photo of herself.

“With the same exact messaging, my open, click-through and response rates were two times higher simply by having a face with the name on the email,” Miller Blanc said. 

Meanwhile, Connor Ireland, a senior key account executive at SmartBear, has landed meetings from cold emails that include just the recipient’s name paired with a question mark in the subject line. 

“That’s it,” Ireland said. “You aren’t misleading them. You’re giving yourself a chance to have them read the meat and potatoes of your email.”

Definitive Healthcare’s Rachel Spadaro adds a bit more to her subject lines, tailoring them to include her prospects’ recent news updates.

“I use this information to personalize my message, which immediately captivates the reader and differentiates myself from other prospects,” Spadaro said.

Though their cold emailing strategies may differ in execution, one technique all the salespeople we spoke with agree on is the importance of personalization. Miller Blanc, Spadaro and Ireland walked us through their approaches to warming up their cold email outreach, below.

 

Drift
Drift
Sara Miller Blanc
Conversational Sales Advisor • Drift

What has been the most successful cold email subject line you’ve ever used? Why was it so successful?

I don’t have go-to subject lines. I personalize them based on an action the prospect took or something relevant to the recipient. I’ve found that subject lines about them — not me or my company — are more successful. For example, I’ve seen success with a subject line that includes competitors who are our customers to create intrigue and FOMO, and I’ve used the names of their colleagues to create familiarity and show that I’ve done my research. 

I also use a ton of Drift Videos in my cold outreach through email and LinkedIn. My subject line for these messages is typically “ 👀  made you a quick video.” I usually get a 50 percent watch rate and book at least one meeting out of every 10 that I send.

 


The first couple of sentences or even words can make or break the success of a cold email. What’s an effective strategy you use to hook the reader in once they’ve opened your email?

My first few sentences are short and sweet. I try to get to the point and tell them why this is relevant to them. I also use visuals like screenshots, GIFs of something relevant to their website or LinkedIn, or a personalized video I created through Drift Video. This enables me to actually speak to the specific value prop or problem we’ve solved for other companies like theirs.

To go along with the face-to-a-name idea, I also like to include a GIF of me waving at the bottom of the first cold email in a sequence that says something like “P.S. wanted to put a face to the name!”

 

Sara's TIP

Use visuals like screenshots, GIFs or videos that are relevant to your prospect's website or news updates.

 

What’s the most effective formula or approach you’ve used for writing cold emails? What were the results compared to other formulas/approaches you’ve tried?

The formulas are always changing. For a while, data showed better open rates when you used someone’s name in the subject line. Then, every company started including first names with marketing automation campaigns and open rates dropped. At the start of COVID-19, it made sense to use something pandemic-related in subject lines to show that they were contextually relevant and timely, but after a few weeks that felt inauthentic.

My best tip is to stay fresh, be creative and keep it personalized. That’s one of the main reasons I love Drift Video for cold outreach. I can record something ultra-personalized in 30 seconds, and it keeps things conversational and human.

 

 

Rachel Spadaro
Sales Executive • Definitive Healthcare

What has been the most successful cold email subject line you’ve ever used? 

There is no one successful cold email subject line. Each email I send out to a prospect is tailored to that company. I use articles and news about the organization to customize a subject that will attract the most attention. For example, if I see that a company just received FDA approval, I will write, “Congratulations on FDA Approval for…” If they offer a product relevant to healthcare I’ll write, “Product A’s relevance to the provider market.” These personalized touches  increase the probability of the prospect opening the email.

 

What’s an effective strategy you use to hook the reader in once they’ve opened your email in the first few words or sentences?

Before reaching out, I look up recent news articles and LinkedIn page posts. I use this information to personalize my message, which immediately captivates the reader and differentiates myself from other prospects. I then explain exactly how our solution can help their organization by providing customized examples. This strategy shows the prospect that I spent the time to understand their business. 

 

Rachel's tip

Tailor the message to the prospect’s title and job description to ensure the content is relevant to the prospect.

 

What’s the most effective formula or approach you've used for writing cold emails? 

The most effective formula is to be as specific and personalized as possible. I always mention information from the company’s LinkedIn or website to show I did prior research. I tailor my message to the prospect’s title and job description to ensure the content is relevant to the prospect. I’ve used standardized templates without any personalization in the past, and while it increased the quantity of emails I could send out, the response rates decreased significantly.

 

 

Connor Ireland
Senior Key Account Executive • SmartBear

What has been the most successful cold email subject line you’ve ever used? 

I have two that have generated a ton of interest that have led to meetings and opportunities.

“(First name)?” – just their first name with a question mark. 

That’s it. You aren’t misleading them. You’re giving yourself a chance to have them read the meat and potatoes of your email, which obviously has to resonate and highlight business problems they have, that you solve.

“(First name) - I noticed you head up the...” I have had great success with the subject line being a piece of the first sentence in your email. For example:

Subject: Noel, I noticed you head up the software testing indust…
Body: Noel, I noticed you head up the software testing industry relations and community engagement at SmartBear.

 

What’s an effective strategy you use to hook the reader in once they’ve opened your email in the first few words or sentences?

Getting them to say “yes” by saying “no.” I think it’s important on a cold email to not have an initial ask. Don’t ask to connect or to block off 10 minutes on their calendar. Instead, gauge interest by giving a value prop. For example: “Noel, would you be opposed to increasing SmartBear’s footprint in the software testing industry through more engagement with the testing community? Stuff like more exposure on well renowned podcasts, featured articles by industry thought leaders, etc.

Asking, because (competitor) or (another team within the organization) has implemented our engagement strategy and seen their customer base and engagement within the software testing industry increase by 235 percent.”

 

Conner's tip

Don’t ask to connect or to block off 10 minutes on their calendar. Instead, gauge interest by giving a value prop.

 

What’s the most effective formula or approach you've used for writing cold emails?

Fanatical prospecting; shout out to sales expert and author Jeb Blount. This means extreme personalization so that the recipient of the email knows the email could only be for them. You do this by researching your prospect’s name, company, industry and common business pains they have. You find out what motivates them, what tugs on their heart strings and what makes their heads hurt. 

I’ve written all types of emails. Mail merges that highlight how easy our tools are to use, and how we are the industry leader and all the biggest names use us. But my best-performing cold emails are personalized to that singular human.
 

 

Responses have been edited for clarity and length.

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