| Apr 17, 2023 | | 7 min read

Jay Schwedelson’s 4 hot email outreach hacks


Crafting effective email outreach can be likened to the art of creating an enjoyable dining experience. Just as in fine dining, the presentation and quality of your email can make all the difference between leaving your audience craving more and prompting them to put it in the trash.

During Vendasta's Conquer Local Connect event, over 50 agency owners tuned in to watch Jay Schwedelson, CEO of Worldata and Founder of SubjectLine.com, share some new B2B email outreach best practices.

“When you send an email, you’re in a battle against all the other emails in that business owner’s inbox, so you need to think about what you’re going to do to stand out from the crowd,” he says.

Get more expert sales and marketing hacks straight to your inbox. Sign up for our newsletter.

In this blog post, we'll cover the four main takeaways from his session, and provide actionable tips that you can immediately incorporate into your agency's email outreach strategy.

Tip: Read Vendasta's VP of Growth, Joel Stevenson's golden rules for optimizing your overall sales outreach. By combining insights, you'll have a comprehensive understanding of how to best leverage emails in your sales outreach efforts.


#1. Stop with the webinars and ebooks!

Are you tired of using webinars and ebooks to engage your audience? According to Jay Schwedelson, those forms of content may not be the most effective way to reach local business owners with email marketing. Instead, Schwedelson recommends focusing on these three pieces of content:

  1. "Outlook" or "predictions" content
  2. Lists
  3. Recaps of your most engaging content

Schwedelson notes that these pieces of content have been the most engaging among recipients during the first three months of 2023, according to data from Outcome Media. He also emphasizes that creating lists is an easy and effective way to promote your brand.

By simply taking information from your website and turning it into a list, you can create engaging content that busy business owners can quickly digest.

“You always have something to promote. If you go to any page of your website, I guarantee that within 30 seconds, you’ll be able to create lists such as ‘7 things to know about ABC’ or ‘5 pitfalls when it comes to XYZ’,” he says.

“You take those things, slap it on a PDF with your logo and call it something exciting. We as recipients love digesting lists because, if you think about it, business owners are wearing 400 different hats. They have time for nothing, but they do have time for a quick hit list that can help them improve their business.”

Hot tip: When sending a list, Schwedelson recommends using the name of the content in your email and starting it with a number. For example, "5 biggest mistakes to avoid when responding to negative reviews."

#2. Use keywords that drive urgency

To improve the effectiveness of your email outreach, it's essential to pay close attention to the open rate—the proportion of recipients who opened the email compared to the number who received it. According to Schwedelson, the subject line is a key component in achieving a high open rate, yet too many sales reps and marketing professionals focus too much on the content of the email and too little on the subject line.

In fact, Schwedelson argues that if the subject line doesn't pique the recipient's interest enough to open the email, then the whole content of the email is wasted. Therefore, sales and marketing professionals need to shift their focus and spend more time crafting subject lines that entice recipients to open the email.

So which keywords should you try?

Outcome Media's analysis has shown that using words such as "tomorrow," "today," "last chance," and "now" can be effective in creating a sense of urgency and encouraging recipients to open the email.

As Schwedelson explains, "If it's just a generic promotion that's epically boring, nobody is going to look. In general, we as recipients want the thing that's not always there." So, remember to invest time and effort in crafting subject lines that are compelling and create a sense of urgency.

Hot tip: Next time you craft an email, spend more time and attention to the subject line than you previously would have. To ensure that your subject line is effective in driving urgency, consider seeking feedback from your colleagues and leveraging resources like subjectline.com. These tools can help you refine your messaging and maximize the impact of your email outreach.

#3. Add personalization to your subject line

Do you want to increase your email open rates by a whopping 38%? One easy way to do this is by segmenting and personalizing your emails based on the job titles of your recipients.

For instance, if you're targeting restaurant owners, you can craft subject lines that address their unique challenges, such as "5 must-try marketing tactics for restaurant owners.” Or for real estate professionals: "Realtors: Check out these social media channels to expand your reach.”

"If I'm a restaurant owner or realtor, seeing that personalization of my title in the subject line appeals to me and makes me think ‘hey, I  gotta check this out’,” he says.

“The faster you can tell somebody who they are in the subject line, that increases your open rate by 38% and it costs you nothing to do. Plus, you already have the data to do it."

Hot tip: For agency owners, the key is to use the data you already have on your audience to create personalized messaging that resonates with them. Segment your audience among the verticals you serve and then strategically target those segments based on the titles you want to target. The more specific you can be in your targeting, the better your results are likely to be.

#4. Use humor in your messages

In email outreach, it's important to try new things in order to engage your customers. According to Schwedelson, the key to effective email outreach is to experiment with different approaches.

"I may give you 10 ideas, and if four of those work, then you've found new ways to engage your customer, and that's a good thing. But you've got to keep trying new things," he says.

One approach that can work well is to inject some humor into your emails. B2B marketing emails that included GIFs had 34-percent higher click-through rates, for example. If you can find a GIF or a quirky picture that fits with your message, using it can help make your email stand out.

As an example, the team at Vendasta was impressed by a sales email that included a humorous GIF, which earned the sales rep a compliment. So don't be afraid to try new things and inject some personality into your email outreach efforts. The worst that can happen is you learn from it and try a different approach.

Check out more hot tips

Over 50 agency owners tuned into Schwedelson’s session for hot email outreach tips. Why not watch the full session for more great tips plus the Q&A session? He covers additional insights including:

  • The importance of optimizing the “from” field of your emails
  • Why specific call-to-action text boxes are more effective than generic ones, and examples that you can use
  • The importance of having a clickable logo in your email that goes to your homepage
  • Why NOT sending emails on the hour is an effective, contrarian strategy in email outreach
  • Why emojis are boosting open rates

Frequently asked questions

What is cold email outreach?

Cold email outreach is the practice of sending an unsolicited email to a potential client to introduce yourself and your product or service to establish the start of a business relationship.

How to write a good outreach email?

To write a good outreach email, focus on personalization, clarity, and relevance. Use a clear subject line, personalize the message to the recipient's needs or interests, and make sure your message is brief, clear, and actionable. Don’t forget to spend extra time on ensuring that the subject line drives urgency or achieves a connection with the audience that’s strong enough to get them to open the email.

About the Author

Vishal Teckchandani is a Content Marketing Specialist at Vendasta. A newcomer to Canada, he spent the last 14 years of his career in Australia as a financial services reporter and TV host. He has written extensively about how technology companies are transforming business processes and lives, and interviewed the CEOs of global banking, payments, SAAS, and cloud storage providers including Afterpay, ELMO Software, Macquarie Group, National Australia Bank, NextDC, and Zip Co. When he’s not creating content, Vishal loves to cook, explore Saskatchewan with his family, and volunteer for his community.

Share This