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Ryan Sorley, Founder & CEO
Ryan Sorley, Founder & CEO Posted on June 30, 2021

Jeremey Donovan on Creating Successful Outbound Emails | Podcast

Every product marketer knows the feeling of repeatedly clicking refresh on an email campaign dashboard, hoping for an avalanche of new opens, and maybe—just maybe—some actual replies. Generating sales leads is not a job for the weak of heart. And it can be even more nerve-wracking if you aren’t totally confident about the emails you’re sending. 


Jeremey Donovan is someone who has earned the right to be very confident about the email campaigns he’s sending. As SVP of Sales Strategy at SalesLoft, he’s part of an organization that has analyzed more than three hundred million emails. The result: a formula and amazing set of tools that help take the guesswork out of creating effective outbound emails. 

In addition to his current role, Jeremey has held positions as an engineer, industry analyst, and worked in product marketing, operations, strategy, and sales strategy. In his spare time, he has written six books

Full disclosure—I’ve known (and admired) Jeremey for a while. We worked together at Gartner, and I count him as one of the smartest people I know. That’s why I was so pleased to have the chance to talk with him for the Blindspots Podcast. I knew that he’d have some great advice for product marketers who want to craft emails that help generate valuable leads for the sales team. Unsurprisingly, he delivered, and then some.

1. Remember —novelty is, by definition, short-lived

Humans are naturally drawn to novelty. This works out well for marketers with a knack for using the new and different to capture an audience’s attention and even motivate them to take action. But novelties have diminishing returns. Truth is, the unexpected is only unexpected the first time. After that, it immediately starts its journey from delightful to mundane. Worst case, if you use a novelty over and over again, you run the risk of creating disingenuous engagement that can cheapen the relationship and damage your brand. 

For example, Jeremey recalls posting a tip on LinkedIn about “Hey!” being the most effective greeting to use in marketing messages. Back when he posted this, using conversational language was refreshing, disarming, and a good way to break the ice. A year-and-a-half later, the “hey approach” has lost its shine. What used to be eye-catching and engaging is now something readers filter out.  

While it’s fine (and fun!) to use some novelty, Jeremey recommends a more reliable approach, “There are some tactics that are much more persistent because they’re less about novelty and more about things like minimizing human effort.” For example, very short subject lines (1 to 2 words) always outperform longer ones. And emails with brief body copy (50 to 100 words) tend to outperform emails that run longer than that. Doing the work to condense your message into as few words as possible may not be novel, but it delivers a tangible value to a busy reader. And, by keeping your email short, you increase the chances of the email being read, and—ultimately—generating a response.

2. Avoid "You love cats." It's a fool's errand.

There is no question that personalization can be powerful. Based on SalesLoft’s analysis of three hundred million emails, Jeremey has this to say, “If you personalize up to 20% of email content, you get a 2x increase in the reply rate. Beyond 20%, you’re wasting your time. In fact, above 20% it’s likely that you’ll decrease the effectiveness of your email because you’ve spent so much time tuning and A/B testing to get there.” 

In recent years, the personalization buzzword has been “relevance.” There are many ways to create relevance in your content. For example, an email that references content that the prospect either created themselves (“I read your piece” or “I heard your podcast”) or that features their insights (“I was really interested in what you said in that interview”) can be effective. However, because everyone is doing this, this strategy is starting to hit the novelty wall. As Jeremey points out, “Saying, ‘Hey, Ryan. I see you love cats. I love cats, too.’ isn’t going to work anymore.”

Instead of just trying to connect random dots in a highly personalized and labor-intensive email, Jeremey recommends leveling up with a more general email that delivers actual value—not just relevance—to the reader. As an example, he points to SalesLoft’s micro apps: emailgrader.com, subjectlinegrader.com, and cadencebuilder.com. “Being able to prospect a sales leader with valuable tools that their team can use right now is a lot better than being able to tell them I know they love cats,” Jeremey says. Definitely a lot better.

3. When you do personalize, be specific. 

Sometimes, 1:1 personalization is the best way forward. When you get to that stage, it pays to do your homework. “If you're including a researchable, discoverable detail, do your research,” Jeremey says. “Don’t say you’ll make a donation to a charity of the recipient’s choice. Find out which charity they care about, and name it. The likelihood that you’ll get a response will be much higher.”

4. Write like sales talks.

“What salespeople want most from marketing is good leads,” Jeremey says. “And I’ve adopted the belief that the only viable lead is a demo request, contact us, or pricing inquiry.” 

One of the biggest (and most often overlooked) obstacles to capturing good leads is a disconnect between how salespeople talk and how marketing talks. “Marketers use abstract and aspirational language,” Jeremey explains. “Salespeople want practical content they can use without being embarrassed.”

It’s the product marketer’s job to translate marketing copy into material the sales team can actually use. This means bringing the level of abstraction down and presenting the content using the terms and style that come naturally to a salesperson. It puts a whole new spin on “talk the talk.”

5. Embrace the value of qualitative work.

“You can get a lot of insights from just looking at operational data like customer usage data and so forth,” Jeremey says. “But that only tells half the story. There are certain insights that can only come through qualitative work.”

For example, Jeremey points out that win-loss analysis is not a big data sort of thing. It’s a qualitative exercise that encompasses not just what happened, but also why it happened. It factors in emotions and relationships, things that don’t typically show up in your data. 

The challenge is that most companies don’t have the internal resources to really dive into the qualitative exercises that complex questions require. “Fighting against confirmation bias, seeking disconfirming information, being patient and non-reactive—these are not easy skills,” Jeremey says. “This is why a lot of organizations turn to third parties to help with the qualitative side.” 

However a company uncovers qualitative insights, the important thing is getting that work done. Understanding all the dynamics at play in conversations and relationships is the only way to learn how to influence those interactions to drive positive outcomes.

Tune in for more great insights.  

Hopefully, you’ll be able to put these excellent tips to immediate use improving your ability to land your sales team some great new leads via highly effective email campaigns. Meanwhile, the info we’ve covered here only scratches the surface of the topics Jeremey and I covered over the course of our conversation. Tune in to hear the full episode (by clicking on the player above) and Jeremey’s thoughts about how to leverage primary research to fine-tune your sales process, when to introduce value plans, and more.

Want more episodes of Blindspots?

Join Ryan Sorley in thought-provoking conversations with subject matter experts to help product marketers address those nagging go-to-market Blindspots. Subscribe on Apple Podcasts, Spotify, Google, or listen on our website.  


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