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Email Tips to Increase Sales with Jay Schwedelson | Sell Smarter. Sell Faster. EP. 15

Email Tips to Increase Sales with Jay Schwedelson
Dani Buckley
Email Tips to Increase Sales with Jay Schwedelson


Email continues to be one of the most important and effective, but widely misused, tools we have in sales. If you or your sales team are still using email the same way they did 2 years ago, let alone 5 or 10 years ago, then an updated strategy is in order!

In this episode, we discuss how email continues to be a tried-and-true tool in the sales and marketing space while also continuing to evolve.

Dani is joined by Jay Schwedelson. Jay is the founder of SubjectLine.com, the leading free subject-line rating tool ranked in the top 1% of all websites worldwide. Having led SubjectLine.com through the testing of more than 12 million subject lines, Jay uses his knowledge to guide organizations across multiple industries on how to implement impactful email marketing.

Keep reading to see his thoughts, insight, and tips on this topic, and listen to or watch the full episode for a more in-depth explanation and conversation around this.

Email Plays A Critical Role In Sales Performance

First and foremost, when it comes to sales performance, email should play a critical role. Every email should not be thought of as “just another piece of marketing that can promote your brand or product.”

According to Jay, “It should be a fundamental way that you are driving leads and sales...I think the problem is that marketers often think of email as a ‘legacy channel.’ Not as a ‘leading channel.’ Because it doesn’t get all the sexy hype that social and search and display and all these others do.”

“Email done properly can become your primary avenue to drive interest, sales, and growth.”


One of the most challenging aspects when utilizing email, especially for B2B businesses, can be “getting that first appointment” or even just nabbing “that first point of engagement with a prospect.” For this, Jay has two tips to share:

1. Timing is Critical – The moment you get any contact’s information, get an email out to them as fast as possible. Hopefully, within a 3-hour window. “If you go beyond 24 hours from the time that you receive a contact, the value of that email address drops exponentially.”

2. Craft the Most “Openable” Subject Line – When sending the first email to a new contact, you, of course, want them to...open it! But you don’t want them to open “just to make a sale.” The goal is much bigger than that. “When you send an email that first time...if that recipient opens up that first email, the likelihood of staying in that person’s inbox for the entire future of your relationship with that person goes up massively...that one open on that one email is the trigger that keeps you in the inbox for the life of your relationship.”

When talking about the difference between One-to-One emails (typically sales - one person emailing a prospect) and One-to-Many (typically marketing – one person emailing several people a once), Jay emphasized the importance of having two radically different formats.

“You can’t live in the middle.”

“If you have a sales formant, it’s got to look like that dry, kind of, mostly text...it’s a One-to-One email. You don’t want the hybrid where it has some images in there and it’s kind of, ‘is this a marketing email or is this a personal email?’”

“Having radically different formats of thing spurs interest, spurs engagement. When everything kind of bleeds over, it’s all the same. It becomes wallpaper.”

Specific Trends in B2B Email Marketing 

Also, when asked about specific trends in the B2B space, Jay breaks down some practical tactics for crafting the most engaging subject lines:

“Too often people don’t spend enough time on the subject line. On the B2B side of things, in the last 12 months, there have been certain tactics, trends that have been a gamechanger.”

1. Put Your Target Audience in the Subject Line – “If you mention the job function or the title of the audience that you’re actually marketing to, the open rate goes up exponentially.”

2. Personalize – “Use the company name that you’re sending to...The closer you can bring it to that individual, whether it’s their career, company, or responsibility, put that in the subject line. That is the gamechanger that is generating opens right now on the B2B side specifically.”

Jay also makes sure to set the record straight around certain pieces of misinformation that have pervaded common knowledge around email for too long.

He says, “Another thing to think about...that if you use certain words in your subject line or body copy, or certain characters...that you’re going to get filtered. You’re going to go to the junk folder...Unfortunately, that’s legacy information from ten years ago.”

“It comes from where, ten years ago, if you sent out an email and you put the word ‘free’ in the subject line with an exclamation point, you would get filtered. Because filtering used to be based on the content of your words...Now, you get filtered because of the technical sending reputation of your IP address and your domain and the engagement that you have with your database.”

“You do not get filtered for the words or the symbols that you’re using...You can use the word ‘free,’ you can use brackets, you can use exclamation points, you can use capitalization, you can use emojis.”

“You can take the handcuffs off and it will work.”

In fact, “taking the handcuffs off” can work so well, that you might see an uptick in another metric as well: Unsubscribes. Surprisingly, Jay has a positively sunny view on the subject.

“You’re going to get better performance. Great. But you’re also going to get more unsubscribes...Those unsubscribes are actually sort of a good thing.”

“When you test a new tactic...what you are doing is, you’re letting your emails be seen...You're finally standing out! And these people that are unsubscribing are actually opening for the first time and they forgot that they were on your list!”

“They open it because you’ve tried something good. They’re unsubscribing at a higher clip not because you did something wrong, but actually because you did something right.”

Listen to the full episode and more on your preferred podcast platform.

2-Part On-Demand Webinar Series Why Your Website Isn't Generating Leads and Why Your Leads Aren't Converting Into Sales

About Author

Dani Buckley

Dani is the VP/General Manager at LeadG2. She has a diverse background in both advertising sales and marketing consulting that helps her address the varying needs of our diverse client base at LeadG2. She’s especially passionate about sales enablement and the many ways that marketing tactics can contribute to achieving sales goals. Dani is a writer, speaker, facilitator, camper van enthusiast, and personal development junkie. She currently lives in Northern California.

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