Mastering email marketing with Dan Oshinsky

Join Michal Leszczynski from GetResponse and Dan Oshinsky, the mastermind behind Inbox Collective, in an illuminating webinar that dives deep into the art and science of email marketing. Discover the insider tricks and strategies that have propelled brands to new heights, grown audiences, and driven revenue through the power of newsletters.

Below you can read the edited version of the interview, for the unedited version, watch the recording above.


Michal Leszczynski (GetResponse): Good afternoon and good morning, everyone! It’s great to have you all here for our fourth hot seat event. Today, I’m thrilled to introduce a special guest, Dan Oshinsky, a respected expert in email marketing and newsletters. I’ve been an admirer of his work for quite some time. Welcome, Dan!

Please feel free to say hello in the chat and let us know where you’re joining us from. For those unfamiliar, today’s guest is Dan Oshinsky, who is joining us from New York.

Background and expertise

Michal: Dan has over 12 years of experience in email marketing and runs an email marketing consultancy called Inbox Collective, which helps brands grow their audience and revenue through newsletters. Before this, Dan led projects like the online briefing “Not a Newsletter,” which I personally recommend as a fantastic resource for email marketing news and tips. Dan has also managed email marketing teams at BuzzFeed and The New Yorker. Dan, is there anything else you’d like to add to your introduction?

Dan Oshinsky (Inbox Collective): You’ve covered it well, Michal. Thanks for having me. I’m excited to be here!

Michal: I’m honored to host you, Dan. Today’s session will be a live Q&A format. I have prepared a few questions, but we encourage everyone here to ask Dan anything about email marketing. This is a great opportunity to gain insights you might not easily find online.

Starting questions

Michal: To kick things off, Dan, could you share what led you to focus your career on email marketing?

Dan: Absolutely, Michal. Unlike many, I didn’t start out in email marketing. My background is in journalism—I studied at the University of Missouri and worked as a reporter before moving into what we at Condé Nast called ‘bridge roles.’ These roles connected me with various departments like marketing, product, and data teams, which is where I discovered the power of email as a versatile tool. It’s central to operations in any organization, affecting everything from subscriber engagement to revenue generation.

Over the last five years with Inbox Collective, I’ve enjoyed helping businesses maximize this tool. The continual learning and experimentation in email marketing make it a fascinating field that’s always presenting new challenges and opportunities.

Audience engagement

Michal: We have viewers from New Jersey, Arizona, Toronto, Texas, India, College Station, Myrtle Beach, and Vancouver. It’s a truly international group! Dan, before we proceed, was there any point when you considered shifting away from email marketing, perhaps toward newer platforms like social media?

Dan: Not really, Michal. While I was at BuzzFeed, I witnessed the rise and fall of platforms like Vine. Email, however, has remained a stable and effective medium. It’s great for testing and provides consistent value across various functions within an organization. I find the resilience and versatility of email far too compelling to consider a move to another platform.

The essence of email marketing

Michal: Since you’ve emphasized testing, we’ll dive into that later. For now, can you outline the key components of an effective email marketing campaign that subscribers genuinely look forward to?

Dan: The core of effective email marketing has always been about understanding your audience deeply. Often, I see newsletters attempting to appeal to ‘everyone,’ which ultimately appeals to no one. Successful emails have a very specific audience. For instance, The Skimm initially targeted millennial women who were incredibly busy, and Morning Brew focused on millennials working in finance. These newsletters began with narrow, niche audiences and expanded from there. Knowing who your audience is—what motivates them, what they care about—is crucial.

Providing value to subscribers

Dan: It’s also about what your email does for your subscribers, not just what it does for your website traffic. For example, a local news publisher might send out a daily list of stories primarily to drive website visits. However, from the subscriber’s perspective, the value might not be clear. Emails need to offer more than just links; they should provide genuine value, whether that’s entertainment, information, or opportunities for engagement.

Balancing content and promotion

Michal: That insight leads us to a common dilemma: how should brands and newsletter publishers balance content and promotion to genuinely provide value?

Dan: There’s no one-size-fits-all formula, much like there’s no perfect work-life balance. It’s more about chemistry—finding the right mix. I worked with a team in Florida, Poynter, which uses the concept of ‘work-life chemistry’ in their training. This analogy applies perfectly to email strategies. It’s not necessarily about a strict ratio of content to promotion but understanding how your audience reacts to different types of emails. Monitoring reactions, like unsubscribes or engagement levels, can guide how to balance informational and promotional content.

The role of A/B testing

Dan: This balance is where A/B testing becomes invaluable. For instance, if you’re promoting a new product, test different messages to see which resonates best with your audience. A/B testing helps refine your approach, ensuring that when you do promote something, it’s with the most effective message possible.

Michal: Speaking of testing, I recently read a comment from a seasoned professional who mentioned moving away from A/B testing subject lines, considering it less valuable now. What’s your take on A/B testing in general?

The dynamics of A/B testing in email marketing

Dan: The approach to A/B testing depends significantly on the maturity of your product or newsletter. For those just starting out, testing basic elements like the sender name, subject lines, and preheader text is crucial. These tests help establish best practices for your newsletter. Over time, you might focus on other aspects like conversion strategies or automation sequences before revisiting subject line tests.

For instance, I worked with a team that, after initially setting their email basics, began daily subject line testing due to their large audience. They noticed that a strong subject line could significantly affect their open rates. However, between initial tests and later optimizations, they focused on building their newsletter’s structure and subscriber engagement.

Testing should adapt to where you are in your product’s lifecycle. Start with foundational elements, and as your newsletter evolves, shift focus to fine-tuning and growth strategies. If time and resources are limited, prioritize your tests accordingly—some teams might not test every possible element, and that’s perfectly acceptable.

Frequency and focus of A/B testing

Michal: Understanding the need to prioritize, how often would you recommend A/B testing? Is there a ‘golden rule’ for how frequently one should engage in it?

Dan: There isn’t a strict rule, but it’s essential to develop a testing plan tailored to your goals and capacity. Your plan might be as simple as determining which types of emails convert best or which promotional messages resonate most on platforms like Facebook or Google. The scope of your testing can vary based on your team’s size and the sophistication of your email strategy.

Larger teams might manage multiple tests across different areas—growth, content, design—within a single quarter. Smaller teams or those new to A/B testing should start with a manageable list and expand as they gain confidence and observe what works. Always document your testing ideas and results to refine your strategy progressively.

Implementing learnings from external sources

Dan: It’s crucial to approach A/B testing with a mindset of experimentation. If you come across a strategy or tool, like the use of specific button colors that purportedly enhance conversion rates, don’t simply adopt it because it worked for someone else. Test it within your own context to see if it delivers similar benefits for your audience.

Michal: When testing elements like button color, how long would you recommend the test run?

Dan: The duration should depend on your audience size and the statistical significance of your results. If your list is large, you might quickly gather enough data to make informed decisions. For smaller lists or more critical tests, such as those affecting monetization or deliverability, consider a longer testing period to ensure reliability in your findings. Always use tools to calculate statistical significance to validate your results.

Exploring personalization in email marketing

Michal: Transitioning to personalization in emails, how do you approach it effectively without being intrusive?

Dan: Personalization should make emails feel relevant, but there’s a distinction between personalization and injecting personality into emails. Many brands could benefit from adding more personality—using personal stories or distinctive voices, for example, in their emails. For personalization itself, the strategy varies:

  • One-to-many: Simple personalization like using first names or adjusting messages based on geography to make the email feel slightly tailored.
  • One-to-some: Creating newsletters for specific interests like sports or business, allowing subscribers to choose topics they genuinely care about.
  • One-to-One: Advanced personalization, such as sending content based on very specific user preferences, like a newsletter tailored to New York Knicks fans.

Implementing personalization

Dan: Start with manageable steps in personalization. You don’t have to leap straight to one-to-one communication. Even minor personalization, like segmenting by interest or location, can significantly enhance engagement without extensive resources.

Michal: That’s insightful, especially considering that niche-targeted communications tend to have higher engagement, as we’ve seen with our own events.

Effective strategies for converting subscribers into paying customers

Michal: Let’s discuss strategies for converting email subscribers into paying customers or supporters. What approaches have you found effective?

Dan: The key is not relying on a single tactic. Successful strategies often include a mix of approaches:

  • Varied content placements: Utilizing different sections of your emails, such as the header or footer, to include calls to action.
  • Diverse messaging: Testing messages that highlight the benefits of subscribing or the unique value the organization brings.
  • Regular campaigns: Setting up a welcome series to introduce new subscribers to what you offer and encouraging them to take the next step, whether it’s subscribing, donating, or making a purchase.

Importance of consistent and varied asks

Dan: It’s crucial to ask frequently and through various formats. Many organizations fail by not asking enough. Remember, not everyone will see every email, so repeating your message in different ways ensures more visibility and higher chances of engagement.

Final thoughts on engagement and conversion

Dan: Often, people aren’t aware of offers or products simply because they missed the initial announcement. Regular communication, varied approaches, and consistent asks are essential to keep your audience informed and engaged, increasing the likelihood of conversion.

Overcoming the fear of overcommunication

Michal: It’s a common concern for marketers that frequent communication might lead to unsubscribes or disengagement. However, infrequent communication risks significant content being overlooked by most of the audience.

Audience engagement and personalization

Michal: Let’s now address questions from our audience about data-driven strategies and personalization in email marketing.

Understanding email marketing metrics

Dan: It’s challenging to pinpoint an average profit per email as it varies by industry and organization. However, understanding metrics like the average revenue per user or the lifetime value of a subscriber can guide your spending on audience growth and retention. Tools like Stripe can help calculate these figures, providing a clearer picture of what each subscriber brings to your organization.

Cost-effectiveness and ROI in email campaigns

Dan: For example, spending $10,000 to acquire 10,000 new subscribers at a dollar each, with 100 of them becoming paying supporters at $100 each, equates to breaking even—demonstrating a successful campaign through effective cost management and targeted acquisition strategies.

Tools for crafting optimal email titles

Michal: Regarding tools for optimizing email titles to maximize click rates, Phrasee is known but may be cost-prohibitive for smaller publishers. Alternatives like GetResponse offer subject line crafting and A/B testing capabilities.

Dan: AI tools, such as ChatGPT, can serve as brainstorming partners, helping generate initial ideas for subject lines which can then be refined and tested to better fit your audience’s preferences.

The role of AI in email marketing

Dan: While AI can assist in generating content ideas, it’s crucial not to let AI fully automate your email marketing. Newsletters should retain a personal touch and reflect the brand’s unique voice.

Importance of click-through rates

Michal: With the changes in how open rates are tracked, especially due to privacy updates like Apple’s Mail Privacy Protection, the relevance of open rates may have diminished, shifting focus towards metrics like click-through rates.

Dan: I advise teams to look at a variety of metrics including engagement, growth, and monetization. Understand what your email service provider measures and tailor your strategy to encompass diverse metrics to obtain a holistic view of your email campaign’s performance.

Comprehensive metric analysis

Dan: It’s important to not rely solely on one metric. Consider combining several to get a comprehensive view of your email performance. Metrics like time spent on site, Net Promoter Score, and audience feedback can give deeper insights into the effectiveness of your content and how it resonates with your audience.

Understanding and utilizing email metrics

Michal Leszczynski: Navigating click-through rates can be challenging, especially since they can vary greatly. How do you make decisions based on these metrics?

Dan Oshinsky: It’s crucial not to focus on just one metric like click-through rates. At BuzzFeed, I learned the importance of not relying on a “silver bullet” metric. If you optimize solely for opens, for example, you might resort to less desirable tactics just to boost those numbers.

The dangers of misleading tactics

Dan: Employing misleading tactics, like changing the sender name to something generic to increase curiosity and opens, can backfire. It might work in the short term, but it damages trust and brand reputation in the long run. Always strive for transparency in your email campaigns to maintain credibility.

Ethics in email marketing

Dan: Acting like a spammer by using deceptive subject lines or sending unexpected content makes you one, regardless of your business’s reputation. It’s vital to reflect on whether the tactics you’re considering could be perceived as spammy.

Non-profit email marketing strategies

Michal: Switching to non-profits, can you share some effective email marketing strategies for these organizations?

Dan: Non-profits need to focus on action-driven tactics, whether it’s encouraging donations or volunteer work. Start by understanding your audience’s interests through surveys to align your content and calls to action with their expectations.

Planning for major campaigns

Dan: For non-profits, major campaigns, especially end-of-year drives, are critical. Begin planning early, considering elements like matching funds, personal stories, and a cohesive theme across your emails. Don’t forget the power of a well-timed thank-you email, which can be highly effective in reaching campaign goals.

Continuous engagement

Michal: Many non-profits miss opportunities by not engaging their audience year-round, especially leading up to significant giving periods like tax season in Poland. Maintaining regular communication about your progress and activities keeps your cause top-of-mind, enhancing the impact of any call to action when the time comes.

Building relationships through email

Dan: Email is fundamentally a relationship-based communication channel. It’s about gradually building trust and providing value, so when you do make an ask, your audience is already primed to respond positively. This approach is core to my consulting work; my newsletter helps potential clients understand my thinking before we ever speak directly.

Focused engagement and trust-building

Dan: Effective organizations use newsletters to build relationships, establish trust, and familiarize audiences with their work. This foundation makes any subsequent asks much more likely to be successful. However, asking too much too soon can deter new subscribers, as we found with initial tactics at The New Yorker, leading us to limit communications from other Condé Nast parts in the first 30 days.

Best practices for resending emails

Michal: Shifting to the topic of resending emails, especially in light of inflated open rates due to technologies like Apple’s Mail Privacy Protection, what are your recommendations?

Dan: Resending emails should be done cautiously. While some ISPs may recommend always resending to non-openers, doing so can lead to diminished engagement and potentially flag your emails as spam due to erratic open rates. Reserve resends for critical communications, like major announcements or events, where the potential benefit outweighs the risks.

Handling increased email cadence

Michal: Let’s discuss transitioning from monthly to weekly newsletters. What advice would you give to someone considering this change?

Dan: It’s crucial to communicate clearly with your audience about any changes in email frequency. Ensure people can easily adjust their preferences and avoid automatically enrolling them in new cadences. Transparent communication about what to expect and how to opt in or out respects your audience and helps maintain trust.

Closing remarks and follow-up

Michal: As we wrap up, can you share where people can follow your work or get in touch?

Dan: Certainly! Visit InboxCollective to sign up for our weekly newsletter. I’m also active on LinkedIn. Feel free to connect with me there, and attaching a note to your connection request can help remind me how you found me.

Michal: Thank you, Dan, and thanks to everyone who joined us today. We’ll follow up with an email including the recording and additional resources mentioned today. Don’t hesitate to reach out if you have further questions.

Join the Online Marketing Certification Program
Get informed about all the latest resources and webinars. Join our newsletter!