Episode Overview

Title: Email Marketing Automation That Moves People to Action
Host: Michael Stelzner (Social Media Examiner)
Guest: Jessica Best (Founder, Better Ave)
Date: October 16, 2025

This episode dives into the world of email marketing automation—how to move beyond basic newsletters into impactful automated communications that trigger the right behaviors at the right time. Jessica Best, a seasoned email strategist, shares frameworks, actionable examples, and her philosophy on building automations that genuinely drive leads, conversions, and long-term customer engagement.

Key Discussion Points and Insights

1. Jessica Best’s Journey into Email Marketing

• Jessica did not set out to be an email marketer; she has a background in journalism and content marketing. She learned the trade out of necessity and developed expertise by first managing newsletters, then becoming an email marketing educator and agency leader.
• Reflecting on her evolution:
  “I actually got scooped up by the email platform we were using to be their marketer … I went full meta. … I’ve gotten to work on some pretty big brands … and now I help more regional or growth mode brands bring email marketing to part of their strategy.” (03:56-05:53)

2. Why Email Automation? The Unique Power of Owned Audiences

• Email is the “owned” channel—subscribers have opted in, giving marketers a direct line, unlike social algorithms.
• The business case:
  “My two favorite letters: ROI. … We have permission to send, and then people read it and take the actions that we want.” (06:16)
• Automation multiplies effectiveness, timing, and personalization, going beyond sporadic newsletters:
  “When done well, email automation not only saves you time and sanity, it also puts something in somebody’s inbox at the exact right moment for them. There’s almost nothing more powerful than that.” (06:16-08:05)

3. Defining Broadcast vs. Automated Email

• Broadcast email: Sent to everyone at a scheduled time—marketer’s schedule.
• Automation: Triggered by recipient’s action or inaction, creating a nearly 1:1 relationship.
• Examples: welcome emails, re-engagement for inactive users, post-purchase sequences.
• “Broadcast … is sent on my schedule. Automation is that one-to-one send at the moment that means something to the recipient.” (08:22)

4. The Welcome Series—More Than “Thanks for Joining”

• Don’t settle for a generic thank-you; set the tone, show off your brand voice, and always include an ask.
• B2B and B2C nuances; if ecommerce, it’s usually fine to include an offer right away.
• “People will never be more engaged with your brand than the second after they just signed up to receive your emails. … We gotta ask them out again.” (13:38)
• Michael: “Should we also set expectations in the email as well?”
  Jessica: “Yes, and I want that on the signup form … Set expectations on what you’re going to receive and how often.” (16:22)

5. Sequencing and Timing of Welcome/Onboarding Emails

• Recommended: At least a 3-part welcome/email onboarding series.
• Timing:
  • Immediate send upon signup.
  • Second message a few days later (e.g., sample content, social ask).
  • Third message ~ one week from signup, ideally matching the day of week.
• “The first one has to go out immediately. … Then wait a couple days, send a plus-up. … I like to send [the third] on day eight.” (19:50)

6. Lead Nurture Automations

• Differentiate between those who opt in just for a resource vs. those requesting a demo/sales call.
• Automations can preempt sales calls: send confirmation, “what’s next,” or supportive information immediately.
• Jessica on supporting sales:
  “I want to figure out as a marketer, how I can best support my sales team by automating what they would send.” (21:42)
• For soft leads (e.g., PDF download), nurture with educational content, related topics, and light offers, not a hard sell.

7. Deep-Dive Example: Winnebago’s Automated Nurture Sequences

• Winnebago added automations for users requesting model brochures.
• Sequence highlights:
  • Immediate email: “Here’s the brochure you requested.”
  • Follow-up 1: Detailed specs content.
  • Follow-up 2: Behind-the-scenes/influencer video tours.
  • Follow-up 3: Brand storytelling—why Winnebago is unique.
  • Result: Expanded from a pilot to 9 models, a calculated ROI of 50:1.
• “We set this up for one vehicle and it made an immediate lift year over year in sales. … We matched back buyers, the warranty, registration, email address to the people that were on the nurture structure … a 50 to 1 ROI.” (26:16-29:12)

8. To Gate or Not to Gate Content

• Deciding whether to require a real email to access content depends on content value.
• For valuable, proprietary research, it’s fair to require a “real,” validated email; for lower-value content, offer both instant download and follow-up delivery.
• “If you have something on the flip side that’s more like primary research … You can gate that … But you don’t have to opt in for marketing automation.” (30:32)

9. Personalization Using Form Data and Behavior

• Use what you know: product choices, location (for dealer assignment), or even page of origin.
• Dynamic content or conditional paths greatly increase relevance.
• “Valuable personalization also makes sure that the content of that email matches what the person is shopping for.” (31:49)

10. Collecting the Right Data: Balancing Friction and Usefulness

• Don’t overload forms. Typically, four fields or fewer; ask only what you’ll use.
• Use progressive profiling (ask for more info on subsequent visits).
• “More than four fields on the first signup form is probably too many. … Progressive capture is actually a really sneaky way to keep friction really low, but still continually get to know that prospect better.” (34:59-36:51)

11. Handling Non-Business Email Addresses

• Many organizations filter by email domain for sales qualification but still nurture those leads until they qualify.
• Filtering is usually domain-based (e.g., block gmail.com/yahoo.com from sales queue).
• “It’s a blunt object, but it’s not actually a bad way to go about it… Most likely if you’re giving me a Yahoo address, you’re not the CEO of Coca Cola.” (39:42)

12. Post-Purchase Automations: Onboarding, Satisfaction, and Cross-Selling

• Don’t stop after the sale! Post-purchase onboarding, surveys, and “next ask” are crucial for loyalty and cross-sell.
• Use NPS (Net Promoter Score) to identify promoters and then prompt reviews/referrals.
• Mercedes-Benz example: only ask for a public review from customers who give a 10/10 on the satisfaction survey.
• “Right after that purchase there’s that moment where we’re really trying to both welcome them to the family … but we also gotta ask them how was your experience?” (40:29-42:41)

13. Cross-Selling and AI-Driven Product Suggestions

• “You bought this, you might also need that.” Beware of irrelevant suggestions (like more toilets after you buy a toilet).
• For large catalogs (thousands of SKUs), use AI/ML-based recommendation engines, e.g., Certona.
• “Frankly, they had 50,000 SKUs … If you have 50 SKUs, I don’t want to do that match up manually. … For Winnebago it was pretty straightforward … but once you get to at home … there’s not a great way to do that manually and I don’t recommend it.”* (45:22-46:43)

14. AI’s Evolving Role in Email Automation

• AI/ML have powered automations like product recommendations for years.
• Email platforms are advancing: flight risk prediction, engagement segmentation, and “next best message.”
• “Email marketing has been doing AI and machine learning led automation and triggers for a long time.” (47:06)
• Michael: “A lot of these email platforms … are almost like a big old database … Are you seeing [AI analysis] coming out from a lot of platforms?”
  Jessica: “Yeah, and actually again, it’s not even entirely new. … They are now progressing into flight risk, likely risk of no longer being engaged…”* (48:34)

Notable Quotes and Memorable Moments

• On most common mistake with welcome emails:
  “So many people are like, I did it. I set an oh, welcome email up. … You set it up in your email platform because it’s turned on by default … So I want to answer that in three ways.” (13:38, Jessica)
• On not stopping at the sale:
  “We’re really good at nurturing people by email until they buy something. And then we’re like, okay, thanks.” (40:29, Jessica)
• On automation’s key role:
  “Automation saves our sanity. … Once it’s on, it kind of makes you money till you turn it off.” (09:46, Jessica)
• Winnebago 50x ROI case:
  “Once we’d finished drinking champagne, we rolled it out for the rest of the models.” (29:12, Jessica)

Important Timestamps

| Timestamp | Segment | |-------------|-------------------------------------------------------------------------------------| | 03:56 | Jessica’s personal journey into email marketing | | 06:16 | The “ROI” of email and why automation is superior | | 08:22 | Broadcast vs automation defined | | 10:54 | Start with the welcome email/series, why it matters | | 13:38 | What makes a good welcome email—voice, next ask, and offers | | 16:22 | The importance of setting expectations up front | | 19:50 | Sequencing timing for welcome emails | | 21:42 | Lead nurturing—automation’s role in supporting sales | | 26:16 | Winnebago's nurture sequence and measurable ROI | | 29:38 | To gate or not gate downloadable content | | 31:49 | Personalization opportunities using captured data | | 34:59 | Form strategy: friction, progressive profiling | | 39:42 | Filtering/non-business emails in automation flows | | 40:29 | Post-purchase onboarding and survey automation | | 42:44 | Mercedes-Benz NPS and review automation | | 44:03 | Cross-sell and recommendation examples, automation at scale | | 47:06 | AI and ML’s long history in email marketing, future potential | | 49:44 | How to connect with Jessica Best |

Resources and How to Connect

• Jessica Best: LinkedIn, Jessica.Best
• Social Media Examiner: all show notes and links

Final Takeaway

Email automation presents a massive opportunity beyond sending newsletters: it’s about meeting users at their most engaged moments with just the right message, automated for scale, but crafted for personal relevance. Done well, as Jessica Best’s stories reveal, it drives formidable ROI, supports sales, increases customer loyalty, and expands possibilities for marketers in any industry.