Ask the expert: Learning from our email marketing mistakes

An interview with Women of Email's Jen Capstraw

If you’re looking for a big email marketing “get”, you’d be hard pressed to find someone better than Jen Capstraw. With over 18 years of email marketing experience on the brand, agency, and vendor sides under her belt, Jen offers a level of knowledge and insight into email marketing paralleled by few in the game.

As Co-founder and President of Women of Email, Jen has played a key role in the ongoing effort to get the awesome women of email marketing the recognition they’ve long been due. At 5,000 members in more than 50 countries on six continents, Women of Email has grown to become the largest association in the email industry. The impact Women of Email has had on the amazing women who occupy the email space would be tough to overstate.

How does Women of Email support and advocate for women in the email marketing business? We’ll let Jen explain…

“We’ve filled 150+ speaker slots with emerging thought leaders. We’ve sent hundreds of women to conferences on scholarship passes who otherwise could not take advantage of those educational and networking opportunities. We solve problems, provide support, and create a forum for meaningful friendships to form in our online community and at our live events. And most importantly, we were the first to bring attention to diversity, inclusion, and equality in the email space.”  

So what’s next for email marketing in general and Women of Email specifically in the trying times ahead?



Here’s what Jen had to say…

Phrasee: How long have you been in the email marketing game? 

Jen: I sent my first email marketing campaign back in 2002. It was ATROCIOUS. This was back before CAN-SPAM so we didn’t even have an unsubscribe link. It didn’t even occur to us that someone might not want our messages.

Best of all, the CTA instructed the recipient to download a PDF form, print it, complete it by hand, then fax it back to us. Quality user experience!

Email was an increasingly bigger part of my job with each new role I took on from that point forward, and 18 years later, I’ve been on all sides: brand, agency, and vendor.

Phrasee: What’s your indispensable piece of advice that you give everyone to improve their email marketing? 

Jen: Too many folks are looking for easy answers. They want to be told what to do. And they’ll blindly follow what they think is “best practice” because they read it somewhere. The truth is there’s a lot of terrible advice out there! And a lot of it is being doled out by content teams with no actual experience with the channel.

If you want to succeed, apply some critical thinking. Are the decisions you’re making advancing your objectives and serving your audience? If the answer is no, step back and question the so-called best practices that are shaping your strategy.

There are really only two rules you need to follow: be legal and be relevant. Every best practice that truly matters will roll up under one of those two categories.

Phrasee: How do you think email is going to evolve over the next year? 

Jen: For starters, bad COVID-19 emails were so prevalent, they made headlines and memes. And brands learned a lot from those mistakes. They were also reminded of the power of the email channel, which doesn’t always get the respect it deserves.

The pandemic was something we all experienced together, worldwide, and some brands did a great job of emphasizing that “we’re all in it together” sentiment without coming across as trite. We’ve been talking for years about empathy in email, but the message really hit home in 2020, and the lessons will carry us forward.

I predict marketing budgets will be changing more dramatically in 2021 than in previous years, and that could be good news for email, bringing greater budget allocation to the channel with the highest ROI. Email is a reliable workhorse and an excellent channel of focus at all times, but especially during volatile times.


“There are really only two rules you need to follow: be legal and be relevant. Every best practice that truly matters will roll up under one of those two categories.”  

Jen Capstraw, Women of Email

Phrasee: What do you think are the biggest opportunities with AI in email? 

Jen: AI is largely in its infancy still. I am a big fan of Phrasee and do believe it is the most complex example of the power of AI in email to date, while most email-related AI is more rudimentary. But we have to start somewhere.

In the long term, I believe we’ll rely on AI to solve the problems our puny human brains struggle with most. Attribution is the area most ripe for AI. And that, in turn, will lead to AI mapping custom customer journeys in real time to maximize engagement, conversions, and customer lifetime value.

Phrasee: What do you think your biggest success has been as a marketer? 

Jen: I’d say my biggest success wasn’t as a marketer, but rather, for marketers. Catalyzing the founding of Women of Email has been the biggest mark I’ve made on this world.

At 5,000 members in more than 50 countries on six continents, we are the largest association in the email industry. We’ve helped countless women understand their worth and negotiate more effectively. Multiple members have told me they’ve been able to double their earnings since they joined our community, with at least one saying her income has tripled thanks to WoE. We’ve filled 150+ speaker slots with emerging thought leaders. We’ve sent hundreds of women to conferences on scholarship passes who otherwise could not take advantage of those educational and networking opportunities. We solve problems, provide support, and create a forum for meaningful friendships to form in our online community and at our live events. And most importantly, we were the first to bring attention to diversity, inclusion, and equality in the email space.

We’re making some important changes that will enable us to level up in 2021 – and do a much better job of reporting those wins! And anyone who’d like to help can make a donation at womenofemail.org or contact us to discuss our new corporate partnership program launching next year.


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