Email on Tap, Episode 1: Jen Capstraw, Director of Strategic Insights and Evangelism, Iterable

When you have an industry powerhouse on staff, what do you do? You tap that brain and pour out all the email knowledge. Add a dash of perspective from other influencers, marketers, and experts and you have yourself a delicious email cocktail. Yum.

That’s exactly what we’re doing in 250ok’s new video series, Email on Tap, featuring Anthony Chiulli, director of product marketing. He’ll travel the country to talk email, trends, predictions, and news to keep you in-the-know in 15 minutes or less.

To start, Anthony attended eTail West in resplendent Palm Springs, California, and he sat down with a stellar cast of characters we can’t wait to reveal. But first, we’ll start with one.

Meet Jen Capstraw, director of strategic insights and evangelism at Iterable, president and co-founder of Women of Email, and overall email boss. She sat with Anthony for a quick conversation about being an influencer, empowering women in the email community, and the email landscape today.

(Keep scrolling for key timestamps and even a full transcript. Plus, find links to our podcast version!)

Total Run Time: 13 minutes
00:30 – Finding a unique voice in thought leadership and content marketing
1:49 – Story behind the Women of Email organization
3:40 – More morality in email marketing prediction for 2019
8:25 – Deliverability and email marketing: How marketers can avoid issues and plan for the future
11:05 – Advice for aspiring email professionals in finding their voice and getting more involved

Listen and subscribe on your favorite platform:


Anthony Chiulli
0:05 Welcome everyone to Email on Tap, I’m your  host, Anthony Chiulli and we are at eTail West in Palm Springs, California. Today I am thrilled to have as my guest Jen Capstraw. She is the director of strategic insights and evangelism at Iterable and also the co-founder and president of Women of Email. Jen, thank you, so much for being on the program.

Jen Capstraw
0:27 My pleasure. I’m very impressed you got all my title correct.

0:30 I know, it was a lot but I got it. One of the things that I love the value is I followed you for a while now on social media and you tend to be such a powerful voice and an influencer on e-mail marketing. How did that come about and how do you find your unique voice when writing content or sharing social media?

0:52 It actually kind of goes back to my first career, this is a second or third, but I started out in radio and TV and, primarily as a broadcast journalist. And it was my job every day to be an expert on something and speak in an authoritative way. And so it comes kinda naturally to me, the thing that I am doing now, and I love and enjoy so much to position myself as someone who has something to say. I didn’t realize I had something to say for quite a while though. Before there were a lot of really powerful communities of email marketers, you know, I was just another marketer out there doing my thing. I’m reading the blogs and figuring out my own strategies and I didn’t actually realize until much later that I was doing some innovative things. And once I discovered that I found it pretty easy to, say, “Hey, I’ve got something say and I’m going to share it.” And that led to more job opportunities where that became a big part of the job.

1:50 Awesome. So I’d be remiss if we didn’t talk about Women of Email. What an amazing organization with over 3,000 members now. How did that organization come about, from an idea and translating into a powerful networking organization?

2:07 It actually started as a conversation about a lack of female representation at conferences and seeing a real imbalance of genders. If you are ever at an email event you, might notice that it seems to have a 50/50 split of men and women and we don’t necessarily see that represented on stage. So Kristin Bond, one of our co-founders, wrote an article about her observations of this problem and some potential solutions. It started the conversation in the space and that led me to connect with Kristin, with Laura Atkins, and with April Mullen, and we found we were all very like-minded, on the same page about this issue. The next day I was like, “Well let’s do something about this,” and we organized really quickly. Our growth, we did not expect the growth that we achieved in a very short period of time. We had 100 members within a couple of days and we created our speakers’ bureau, but it’s grown into so much more than that. It’s just a really enthusiastic and supportive community. We’ve got a mentoring program, we have scholarship opportunities for women to attend conferences who have financial situations or budgetary situations that aren’t gonna allow for them to go to these conferences, and it’s just a source of amazing advice and I love it. It’s awesome and it’s a great community be a part of. It is free to join so any woman or anyone who identifies as a woman who wants to join…

3:31 Come aboard. Yeah, what amazing organization. I’ve been so humbled by so many Women of Email here at this conference this week and it’s a pretty inspirational story, to be honest…

3:42 Thanks. I appreciate it.

3:44 You were on a recent webinar that I listened to that talks about a prediction for 2019 being more morality in marketing. Can you explain that? What do you mean by brands having more morality in marketing as a potential trend for this year?

4:01 It’s kind of a lot of ideas that are interconnected; one of them is that we’re seeing more brands step up and infuse their marketing messaging, that is, with concepts that are reflective of their values, sometimes their political or social. In those companies, those risks are taking off or they’re benefiting. It doesn’t matter where they fall, whether they lean more liberal or more conservative, if they take a strong stand on something and it’s a very strongly held belief of the founders and the leadership, it tends to pay off. It tends to produce more revenue, greater visibility. Most recently we saw it with Gillette, and there was a lot of negativity about that message because it was the first time that we saw a message about toxic masculinity in marketing. And a lot of people were very offended by it. But I expect to see a lot of success for Gillette as a result of this, because even when there’s controversy it doesn’t hurt. So, we saw a controversy, for instance, surrounding Chick-fil-a. We saw controversy surrounding Hobby Lobby, yet they continue to be very successful. So even when it’s controversial, it’s successful. But in addition to that, I’m seeing a trend toward greater respect and authenticity toward us prospects and customers. We’re seeing companies are wanting to treat people the way that they want to be treated, and I am seeing a connection between the rise of the Millennial generation assuming leadership roles and they have very powerful moral campuses and codes that they abide by, and it’s spilling into the type of messaging that they’re putting out there. I’m Generation X, but I am surrounded by Millennials. Most of the Women of Email are Millennials, most of the team that I work with at Iterable are Millennials, our co-founders are Millennials and so, once upon a time my point of view on marketing success was, hey if it, converts it’s working. And what I was observing is that the generation of marketers that are rising now are saying, “No, no that’s not enough. We need to treat people with respect, we need to honor their preferences, we need to be transparent about the messaging we’re sending to them, and so, it’s tied into who they are as people and it’s filling into our marketing. I think that’s tremendously valuable. It’s evolving my perspective quite a bit and it ties into this idea of a lifetime value as the ultimate KPI slowly brands are adopting LTV lifetime customer value as the biggest, the most important KPI. So that means you need to build a relationship that is long-lasting, you need loyalty and retention, and you can’t achieve that if you’re using cheap tricks to convert people. So all of these concepts are kind of interconnected and they’re leading to a fresh approach to marketing generally speaking, as well as email marketing specifically. I think it’s really fantastic, and I’m enjoying it quite a bit. I actually during that webinar created kind of a morality spectrum where you could score yourself or your brand on that spectrum, and we’re going to be putting out some more thought leadership that’s related to that concept.

7:24 You know, it’s interesting, in fact, I was sitting into a few of the sessions today and a lot of the keynote speakers are talking about not only building an emotional relationship with their customers and the importance of not just being surface level and the way that they market. but really truly being emotionally attached you’re creating that emotional relationship with their customers. And also trust. And I think that goes back to your response of more morality in marketing. There’s more at stake now with brands and the way that they identify and they interact with their customers than ever before. So I certainly agree with that prediction. And though I know it takes different levels for different folks of where they’re at, but, you know, we’re starting to see more brands stand up for social issues, take a stand or have a voice on whatever climate there in and whatever is going on. So, I certainly remember picking that up from your webinar and I thought it would be a relevant question to ask and have more information from you about that. Let’s shift gears and talk about deliverability for a moment. Email continues to be the highest generating channel, arguably the highest generating channel from social, from SMS, push. Why do you think not only is email still a part of the backbone or the workhorse for brands and their digital strategy, but more importantly with deliverability, where does that fall in your opinion on brands’ strategic roadmaps? Is it something that they only care about when something happens and the value goes up, or do you think more brands are starting to take into consideration deliverability as it relates to their email marketing?

9:12 I’m sure you know as well as I do that the only time people think about deliverability is when it’s a problem, which is unfortunate, but if you are practicing moral marketing and delivering relevant information, then the problem solves itself. It doesn’t become a problem. But often folks are thinking a little too late and those cheap tricks that I mentioned before, they do lead to deliverability challenges. So we’re not seeing it being a proactive thing. It’s reactive when it comes to deliverability, unfortunately, getting back to the idea of email being that ultimate ROI channel. I actually read a report that came out in December, it’s something like 82 percent of CFOs are predicting a recession by 2020, and we also have that article recently in the Wall Street Journal seeing like e-mail is the cool new channel. What’s old is new again. I think that we’re going to see more attention shifting back to email because it is so cost effective and so high ROI. We’ve had a tremendous decade. The last decade has been really phenomenal in terms of innovation and technology, and all these great things are happening but as our economic situation starts shifting and belts start tightening, CFOs are going to have to make some tough decisions. I think that we’re going to see them shifting back to email and giving it more marketing budget share and not investing in the riskier opportunities. So innovation might slow a little bit, but all of the innovation that we’ve had over the last decade has set us up for exceptional success going forward if we invest now and turn our attention now to the email channel.

11:04 You know, very well said. I want to close with this question: I’ve always respected your ability and your unique voice, and the way that you have perspectives and your research that you do on email marketing. What advice would you give someone aspiring to start their content marketing journey or tweeting or posting about relevant topics? What advice, tips, or tactics would you provide someone that’s really starting to get into that, being a veteran yourself in social media?

11:35 Well, first of all, thank you. I appreciate that. You know, the secret to success is authenticity. Be yourself. Throw a flag in the sand, have a point of view and express it and it doesn’t even have to be right all the time. My perspective is always evolving and shifting and changing as I take on new ideas and reflect on ideas in different ways. So don’t be afraid to take a stand and don’t be afraid to evolve away from it going forward. Don’t be afraid to fly a freak flag. Be authentic and true to who you are. I think like the weirder I am, the more people join my webinars, which encourages more bad behavior. But it’s really paying off for us at Iterable and people are really enjoying the sessions. So you just be you, and everybody has a story to tell. We’re all marketers as well as consumers, and just talking about your own experiences as the consumer through the lens of a marketer is always so interesting to other marketers, in a really easy way to connect and build your personal brand.

12:41 Jen, this has been great. Thank you so much for taking the time. I had a great time. Thank you all for tuning in and we hope to see you next time on another episode of Email on Tap.

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