Email Marketing And Nurture

Email Marketing & Nurture

Overview

This skill covers B2B email marketing strategy and execution: writing and formatting emails, building nurture sequences, managing lists and deliverability, measuring performance, and producing newsletters. All practices are sourced exclusively from Exit Five podcast guests across 33 episodes. Do not supplement with general marketing knowledge not represented here.

Email as a Channel: Strategic Framing

Treat the inbox as an invited personal space. When someone receives your email, they have invited you into their personal communication space. Write as if you're respecting that invitation — use conversational tone, avoid corporate jargon, and treat the recipient as a real person. (Source: Alyssa, Episode #312)

Position email as a relationship-building channel, not a conversion-centric channel. In B2B, recognize that 95% of your audience is not in-market at any given time. Use email to introduce your brand, educate prospects, and nurture them until they enter the buying window. Integrate email with other channels (social, paid, events) to reinforce your message. (Source: Jaina Mistry, Episode #241)

Define the specific job each email campaign is meant to do, then measure it accordingly. Not all emails should be measured by the same metrics. A nurture email might be measured by engagement; a closing email by demo bookings. Opens and clicks are supporting metrics, not leading KPIs, unless they directly contribute to the campaign's stated goal. (Source: Joe, Episode #312)

Establish a principle that every email must serve one of two purposes: (1) share an idea or insight worth your audience's time, or (2) promote a product feature, event, or initiative that drives business results. Never send an email simply because it's been a while or to hit a sending target. (Source: Amanda Natividad, Episode #205)

Decide deliberately whether email is the right primary channel for your audience. (Note: this is contested — see Where Experts Disagree.)

Email Copywriting Fundamentals

Apply three core rules to every email: one person, one message, one CTA type. Write to one specific person or persona; have one core message or theme; have all links lead to the same destination. These constraints force clarity and prevent the cognitive overload that kills engagement. (Source: Samar Owais, Episode #247)

Treat every email as a one-to-one conversation, not a broadcast. Write as if you're having a conversation with one person. Avoid marketing jargon, corporate announcements, and generic language. Recipients can sense whether you're talking to them or at them. (Source: Samar Owais, Episode #247)

Write marketing emails as if writing to a friend. Open Gmail, put in a friend's or customer's name, and write the email as you would to them one-on-one. This naturally creates more human, personalized copy. (Source: Pierce Uijainwalla, Episode #167)

Replace "we/I" language with "you/your" in email copy. Rewrite copy to focus on the recipient's needs. Replace "We are excited to announce" with "You can now do this." This pronoun shift dramatically improves engagement because recipients care about their own problems, not your announcements. (Source: Sheri Otto, Episode #247)

Replace generic industry buzzwords with specific, niche language. Avoid vague phrases like "advanced workflow," "emerging technologies," or "best-in-class solutions." These could apply to any company and signal lazy or AI-generated copy. Use specific language that speaks to the unique pain points and terminology of your target industry. (Source: Sheri Otto, Episode #247)

Lead with compelling hooks in email copy. Start with a hook that creates curiosity or addresses a pain point. The hook should make recipients want to continue reading and understand why the email matters to them. (Source: Pierce Uijainwalla, Episode #167)

Add "so you can" clauses to bullet points. Don't just list features or benefits in isolation. Add a "so you can" or "so that" clause to each bullet to explain what the recipient will accomplish. For example: "Enhanced patient member safety and quality so you can reduce liability and improve outcomes." (Source: Sheri Otto, Episode #247)

Provide clear context in email copy to reduce cognitive load. Ensure copy clearly explains what the email is about and why the recipient should care. High cognitive load causes recipients to ignore or delete the email. (Source: Pierce Uijainwalla, Episode #167)

Add a "What You'll Learn" section at the top of long, content-heavy emails. If you're sending a longer email repurposing dense content (e.g., from a webinar or report), add a brief section at the top that tells the reader what they'll learn and why it matters. (Source: Samar Owais, Episode #247)

Subject Lines

Optimize email as a chain: from name → subject line → preview text → headline → body. Think of email engagement as a chain where each element must pull the reader forward to the next. Any break in the chain loses the reader. Optimize in sequence: (1) from name/alias, (2) subject line, (3) preview text, (4) email headline, (5) body content. (Source: Jay Schwedelson, Episode #329)

Use sentence case in email subject lines instead of title case. Avoid title case or all-caps capitalization. Write subject lines in sentence case (capitalize only the first word and proper nouns). Title case reads as corporate jargon and reduces open rates. Subject lines should be conversational. (Source: Samar Owais, Episode #247)

Ensure the subject line matches the email body and recipient context. The subject line should accurately reflect what's in the email and align with the recipient's stage in the buyer journey. If the subject line promises one thing but the email delivers another, open rates will suffer. (Source: Samar Owais, Episode #247)

Personalize subject lines with company name to lift open rates. Include the recipient's company name in the subject line (e.g., "Is Acme at risk?"). This increases open rates by approximately 41% because it immediately signals relevance. (Source: Jay Schwedelson, Episode #167)

Personalize subject lines with job function. Include the recipient's job function (e.g., "just for B2B marketers" or "just for HR Pros") to increase open rates by approximately 38%. This signals the email is relevant to their specific role. (Source: Jay Schwedelson, Episode #167)

Use industry or company name in subject lines instead of first name. Replace generic first-name personalization with industry or company-specific personalization (e.g., "For retail professionals" or "Litmus needs to know this"). This signals relevance and drives higher open rates. (Source: Jay Schewedelson, Episode #241)

Personalize subject lines with industry vertical. Include the recipient's industry (e.g., "This is trending in the retail sector") to increase relevance and open rates. (Source: Jay Schwedelson, Episode #167)

Segment subject lines by customer longevity. Tailor subject lines based on how long a customer has been with you (e.g., "This is just for our new customers" or "This is for customers that have been with us for five years"). (Source: Jay Schwedelson, Episode #167)

Use competitive positioning in subject lines. Include your company name versus a competitor's name (e.g., "Acme vs. Competitor X") to create intrigue and signal a comparison recipients want to see. (Source: Jay Schwedelson, Episode #167)

Use a colon in subject lines to boost open rates. Include a colon after the first word or first few words (e.g., "Invited: AI is going to take your job"). This punctuation creates a natural pause and helps structure the subject line. (Source: Jay Schwedelson, Episode #167)

Avoid using "webinar" in subject lines. The word "webinar" depresses open rates. Focus on the topic or benefit instead (e.g., "How to implement a change management office" rather than "New webinar: How to implement a change management office"). The same applies to "ebook" and other generic delivery terms. (Source: Jay Schwedelson, Episode #167)

Avoid edition numbers in newsletter subject lines. Do not include edition numbers (e.g., "June Edition," "Issue #27"). These become outdated quickly and don't convey value. Focus on the actual topic, key stat, or benefit. (Source: Jay Schewedelson, Episode #167)

Optimize the first email to new subscribers with a compelling subject line. The first email is the most important email you will ever send a subscriber. Use a compelling subject line instead of generic ones like "Welcome." The first email teaches email clients and the recipient whether you belong in their inbox. (Source: Jay Schwedelson, Episode #167)

Analyze your own email-opening behavior to inform subject line and send strategy. Observe what makes you personally open emails — it's typically one of three things: the sender, the subject line itself, or the time of day. Use this self-awareness to inform your strategy across all three levers, not just subject lines. (Source: Alyssa, Episode #312)

Prioritize building reader trust in the sender name and consistent delivery schedule over optimizing subject lines. When readers recognize and trust the sender, they will open emails regardless of subject line quality. This trust is built through consistent, valuable content delivered on a predictable schedule over time. (Source: Dave Gerhardt, Episode #166)

Preview Text and From Name

Start email preview text with "and," "but," or "plus" to increase open rates. (Note: this is contested — see Where Experts Disagree.) These continuation words create a psychological chain that makes readers continue from the subject line to the preview text. (Source: Jay Schwedelson, Episode #329)

Alternatively, remove preview text entirely and use short subject lines (3 words or fewer) to create white space. (Note: this is contested — see Where Experts Disagree.) Since 98% of emails include preview text, the absence of it makes your email stand out. Use hidden code or images to suppress preview text from displaying. (Source: Jay Schwedelson, Episode #329)

Send emails from a person's name rather than company name. Send from a named individual (e.g., "Jen from Gong" or "Dave from Exit Five") rather than just the company name. The email address doesn't change; only the friendly from name includes the person's name. The email body must also feel one-to-one to maintain this connection. (Source: Jay Schwedelson, Episode #167; Joe, Episode #312)

Treat the friendly from name as an extension of your subject line. Change the from name with each send to reflect the email's content or offer (e.g., "Acme Events," "Acme Demo," "Acme Special Guide"). This increases open rates by approximately 31%. (Source: Jay Schwedelson, Episode #167)

Prioritize friendly from names as iOS 18 removes pre-header text. With iOS 18's mail app update, the pre-header text is removed from email previews. The from name and subject line will be the only visible elements to capture attention. Invest in strategic friendly from names accordingly. (Source: Jay Schwedelson, Episode #167)

Use multiple friendly from names to justify higher email send frequency. (Note: this is contested — see Where Experts Disagree.) Create sub-brands within your email sending by using different friendly from names for different content types (e.g., "Acme Events," "Acme Content," "Acme Software Updates"). This allows you to send more emails to the same audience without annoying them because recipients perceive them as coming from different senders. (Source: Jay Schwedelson, Episode #167)

Email Formatting and Design

Break email content into short blocks (3-4 lines max) to increase click-through rates. Avoid large text blocks. Large blocks (5+ lines) trigger subconscious avoidance — readers immediately tune out, similar to how they react to large text blocks in text messages. This applies even if your overall newsletter is long; visual formatting matters more than total length. (Source: Jay Schwedelson, Episode #329)

Limit paragraph length to 3-4 lines maximum. Longer paragraphs (6+ lines) appear visually overwhelming and cause recipients to skip the content entirely, regardless of how compelling the message is. (Source: Jay Schwedelson, Episode #167)

For prospects new to your brand, keep emails tight (under 75 words). They barely opened the email and won't read long blocks of text. For existing customers or highly engaged subscribers, you can be more verbose. Regardless of length, always break content into short paragraphs and use visual hierarchy (bullet points, colors, blocks) to maintain readability, especially on mobile. (Source: Jay Schewedelson, Episode #241)

Add read-time estimates ("2 min read," "3 min read") to content blocks. Include explicit time estimates for content blocks in newsletters and emails. This helps readers make quick decisions about whether they have time to consume the content and increases click-through rates. (Source: Jay Schwedelson, Episode #329)

Write call-to-action buttons in first person to increase click rates. Use "I want to see the secrets" or "Show me the full trends report" instead of "Read the case study" or "Register now." First-person CTAs increase click-through rates by over 20% because they make the recipient feel invested in the action. CTAs can be full sentences, not just 2-3 words. (Source: Jay Schwedelson, Episode #167)

Avoid "Register Now" as a call-to-action button. This phrase is generic and uninspiring. Instead, use first-person, benefit-driven CTAs like "I want in," "Save my spot," or "I can't wait." (Source: Jay Schwedelson, Episode #167)

Use a single call-to-action as the default email strategy. Default to one CTA in emails to maximize focus and click-through rates. Multiple CTAs dilute the message and confuse recipients. Only use multiple CTAs in specific scenarios where they are highly relevant to each other (e.g., a calendar of five separate events). (Source: Pierce Uijainwalla, Episode #167; Samar Owais, Episode #247)

Angle email subheads toward reader benefit, not feature description. Subheads should answer "why should I care?" rather than just describing what something is. For example, instead of "Building a high ARR per employee business," write "How to build a high ARR per employee business." (Source: Samar Owais, Episode #247)

Ensure visual and message harmony between email and landing page. When an email promotes a specific offer or topic, the landing page the recipient clicks to must match the email's message and design. This consistency ensures recipients understand they clicked the right link and increases conversion rates. (Source: Pierce Uijainwalla, Episode #167)

Use animated GIFs strategically to elevate emails — with caution. Some email clients only display the first frame of an animated GIF, so test to ensure the first frame is meaningful and doesn't create a confusing visual. (Source: Pierce Uijainwalla, Episode #167)

Use creative design transitions to elevate email visual appeal. Incorporate subtle design transitions (curved lines, flowing elements) in HTML emails to break up monotonous straight-line layouts. This elevates the email design and makes it stand out from typical corporate emails. (Source: Pierce Uijainwalla, Episode #167)

Send Timing and Frequency

Send B2B webinar promotions and long-form emails on Fridays and Sundays for higher engagement. Fridays see higher registration and show rates because professionals take fewer calls and consume more content. Sundays around 11 AM see 60% higher click-through rates year-over-year for business emails because professionals have time to focus on email without Slack interruptions. Test these days if you haven't already. (Source: Jay Schwedelson, Episode #329)

Resend emails to non-openers with a modified subject line indicating the resend. Send a follow-up email to non-openers 2 days after the initial send with a subject line that signals the resend (e.g., "Oops, you missed it" or "This one's really important"). This approach can generate an additional 25% of unique opens. Be transparent about the resend rather than disguising it. (Source: Jay Schewedelson, Episode #241)

On email send frequency: this is genuinely contested. (See Where Experts Disagree for the full breakdown.)

Segmentation and Personalization

Start segmentation with exclusion rules rather than inclusion. When planning an email send, begin by identifying who should be excluded: people who just had a good conversation with sales, those who recently contacted support with a product issue, etc. This approach reduces over-inclusion and improves relevance without requiring complex inclusion logic. (Source: Beth O'Malley, Episode #241)

Use "read the room" segmentation based on recipient action and journey stage. Segment email messaging based on what action the recipient just took. If someone downloaded a white paper, they're likely in early research — don't immediately push them toward a sales call. Collect strategic data about where people are in their journey and send appropriate messaging for that stage. (Source: Beth O'Malley, Episode #241)

Use website behavior tracking to personalize email with transparency about what you know. When a recipient visits a specific page on your website (e.g., pricing page), send a follow-up email that explicitly acknowledges this in the subject line and headline (e.g., "We saw you were looking at this"). Testing shows this transparent approach outperforms stealth tracking. (Source: Jay Schewedelson, Episode #241)

Track structured clicks by content topic to build micro-segments, not just maximize click rate. Intentionally design emails with distinct content sections and tag everyone who clicks on each section. Use these structured clicks to build micro-segments for future targeted campaigns. This prioritizes intent-based segmentation over vanity metrics. (Source: Jay Schewedelson, Episode #241)

Use dynamic content blocks in email to serve multiple personas. Instead of sending separate emails to different personas, use email platform dynamic content features (like HubSpot's conditional content) to show different sections of the same email based on the recipient's persona or role. (Source: Matt Carnevale, Episode #155)

Collect persona and role information during onboarding. Capture the prospect's role and persona classification early in your onboarding or data collection process (e.g., signup forms, welcome surveys). This data enables you to segment future communications and avoid sending irrelevant messages. (Source: Dave Gerhardt, Episode #155)

Segment email performance metrics by initiative type, not just by "email" as a whole. Differentiate between top-of-funnel content (e.g., checklist signup), mid-funnel content (e.g., case study download), and bottom-funnel content (e.g., demo request). Each has different benchmarks and success criteria. Reporting on "email" as a single channel masks actual performance. (Source: Jay Schewedelson, Episode #241)

Segment event attendees by ICP tier and deploy targeted nurture campaigns. After capturing leads at an event, avoid sending all attendees into a generic company nurture. Segment the lead list by job function, deal size, and ICP tier, then deploy targeted nurture campaigns tailored to each segment's specific interests and buying stage. (Source: Kristina DeBrito, Episode #227)

Select email, SMS, or in-app messaging based on user journey stage and device context. Use email for users who are inactive or not logging into your product (to pull them back in). Use in-app messaging and push notifications for active users already in your product. Use SMS for time-sensitive, transactional, or urgent communications. Match the channel to the action you're asking for and where the user is most likely to be. (Source: Gabby, Episode #312)

Prioritize relevance over volume when deciding what to include in emails. When stakeholders request multiple product updates in a single email, push back with data: research shows recipients won't engage with emails longer than 10 seconds. Segment your audience and send only the most relevant message to each segment. (Source: Gabby, Episode #312)

Deliverability and List Health

Avoid no-reply email addresses to enable reply tracking. Use a real, monitored email address so you can track and respond to replies from engaged subscribers. Replies are a key engagement signal for deliverability and represent your most valuable audience segment. (Source: Sara McNamara, Episode #256; Beth O'Malley, Episode #241)

Use the "reply with GUIDE" tactic to increase response rates and improve inbox placement. Instead of sending email with a link to a landing page to download a guide, send a short letter-format email asking recipients to reply with the word "GUIDE" to receive it. This increases response rates by approximately 300% compared to traditional form-based downloads. When someone replies to your email, it signals to email providers that they're engaged with your sender, which improves inbox placement. (Source: Jay Schwedelson, Episode #329)

Track and monitor email replies as a high-value engagement metric. Replies are a strong indicator of genuine engagement and signal positive brand sentiment to inbox providers like Gmail. Monitor reply rates and consider replying to replies yourself — this can change recipient perception of your brand and build stronger relationships. (Source: Jaina Mistry, Episode #241)

Include a whitelist prompt in your welcome sequence to reduce spam folder risk. In your welcome email or early in a welcome sequence, ask subscribers to whitelist your email address or add you to their contacts. Provide clear instructions on how to do this in their email client. (Source: Sara McNamara, Episode #256)

Diagnose deliverability issues before optimizing email copy. If an email has zero or near-zero opens, the first step is to investigate whether it's a deliverability or technical issue, not a copy problem. Check if the email landed in spam, if there's a list quality issue, or if there's a technical error in the send. Only after ruling out deliverability problems should you focus on optimizing subject lines and copy. (Source: Sheri Otto, Episode #247)

Implement a re-engagement campaign before removing inactive contacts. Before implementing a sunset policy to remove inactive subscribers, run a targeted re-engagement campaign. Invite inactive users to opt back in or confirm their interest. Only after this attempt should you remove truly unresponsive contacts. A sunset policy should be the final step, not the first. (Source: Joe, Episode #312)

Run quarterly reengagement campaigns to remove cold subscribers and reduce email costs. Every three months, send a reengagement email to subscribers who haven't opened an email in the past month or couple of weeks. Ask them to confirm they want to continue receiving emails. Remove those who don't respond. This reduces email platform costs and improves deliverability metrics. (Source: Amanda Natividad, Episode #205)

Monitor inactive and lurker engagement cohorts to identify hidden value and prevent unintended churn. Track users who read emails consistently but don't click or take obvious actions ("lurkers"). Use a 90-day engagement window to identify healthy segments. When you stop sending to a segment, measure whether usage or conversions drop afterward. Sometimes a "low-performing" email is actually driving behavior you're not attributing to it. (Source: Alyssa, Episode #312)

Avoid misleading subject lines and fake reply/forward formatting. Do not use clickbait subject lines that don't match email content, and never use fake "Re:" or "Fwd:" formatting to trick recipients into opening. These tactics trigger spam complaints, violate anti-spam regulations, damage brand reputation, and can result in fines. (Source: Jaina Mistry, Episode #241)

Nurture Sequences

Establish a strong content strategy before building nurture email sequences. Before designing nurture email flows, first establish a foundational content strategy across owned channels (newsletter, podcast, social media, blog). A consistent content machine that delivers value across multiple channels does much of the nurturing work automatically. Only after this foundation is in place should you layer in targeted nurture emails. (Source: Matt Carnevale, Episode #129)

Layer multiple touchpoints into nurture strategy beyond email alone. Nurture sequences should not rely solely on email. Incorporate multiple channels and signals: website retargeting, paid ads, podcast listening, video consumption, and other owned properties. Track when prospects return to your website or engage with other content properties as signals of engagement, not just email opens and clicks. (Source: Dave Gerhardt, Episode #129)

On nurture sequence cadence: this is contested. (See Where Experts Disagree for the full breakdown.)

Build nurture sequences around whitepaper content, not additional downloads. When someone downloads a whitepaper, don't ask them to download another asset in the follow-up nurture sequence. Instead, break down the whitepaper's key insights across multiple emails and deliver them in digestible pieces. Reference the whitepaper they already downloaded and remind them why they downloaded it. (Source: Samar Owais, Episode #247)

Add context to follow-up emails by referencing the recipient's prior action. When sending a follow-up email after a significant action (e.g., whitepaper download), reference that action in the email body to remind the recipient why they're receiving it and what problem they were trying to solve. Don't assume they remember downloading something weeks ago. (Source: Sofia Silva, Episode #247)

Diagnose nurture email performance by separating open-rate issues from conversion issues. When nurture emails have high open rates but low conversion, the problem is not the subject line — it's the message or offer mismatch. For enterprise/long-cycle deals, recognize that nurture emails may not drive direct conversion; instead, they build trust and authority to keep you top-of-mind until the buyer is ready. Adjust success metrics accordingly. (Source: Eli Rubel, Episode #120)

Match intent data quality to outreach strategy. If your intent data is weak or unproven, place those accounts into a nurture flow and track engagement with your own communications until they score higher. Only use direct outreach when you have high-confidence intent signals. (Source: Chris Rack, Episode #140)

Use interactive demos in email campaigns and PLG onboarding sequences. Embed or link to interactive product demos in email campaigns, particularly for PLG onboarding sequences. This helps re-engage users who haven't logged in after day one by educating them without requiring them to be in the product. (Source: Natalie Marcotullio, Episodes #176 and #122)

SaaS Onboarding Emails

Define and optimize for micro-conversions in SaaS onboarding email sequences. Each email should drive a single micro-conversion (a small, specific action that moves the user toward the "aha moment"). Identify your primary activation metric through customer research (e.g., "creating a first workspace") and make that the sole focus of the first onboarding email. (Source: Samar Owais, Episode #247)

Prioritize time-to-value in the first onboarding email; mention setup speed. Focus on the fastest path to the user experiencing value. If some users want to complete onboarding in one sitting, include a postscript or secondary CTA that acknowledges this and links to a guided walkthrough or checklist that can be completed in a specific timeframe (e.g., "30 minutes or less"). (Source: Samar Owais, Episode #247)

Spread onboarding content across multiple emails instead of one long email. Do not try to cram an entire onboarding flow into a single email. Break it into a sequence of focused emails, each with one micro-conversion. This reduces cognitive load, improves click-through rates, and allows you to measure engagement at each step. (Source: Sofia Silva, Episode #247)

Move product demos to in-app onboarding, not email. In SaaS onboarding emails, do not include product demos or lengthy feature walkthroughs. These belong in your in-app onboarding experience. Email should focus on driving the user to take the first micro-conversion action. (Source: Samar Owais, Episode #247)

Re-engagement Emails

Use a dedicated re-engagement email framework before pitching features. When reaching out to cold or dormant leads, do not lead with product features or benefits. Acknowledge the previous relationship, give them a reason why now is a good time to reconnect (new updates, relevant case studies, exclusive incentives), and ask for their input on what's changed. Send as a plain-text email from a specific person, not a branded template. Include an easy opt-out option. (Source: Sheri Otto, Episode #247)

Lead re-engagement emails with social proof instead of product pitches. When re-engaging cold leads, use customer case studies and social proof from similar companies or industries as the primary hook. Show them how a comparable company solved a problem they likely still have. Follow social proof with a soft ask for reconnection rather than a feature-focused CTA. (Source: Sofia Silva, Episode #247)

Always provide an easy opt-out option in cold/re-engagement segments. Include a clear, easy way for recipients to opt out or indicate they're no longer interested. Frame the opt-out positively: "If this is no longer of interest, click here and you won't hear from us again." (Source: Samar Owais, Episode #247)

Welcome Sequences

Build welcome sequences based on available content, not arbitrary email count. Do not create a welcome sequence with a predetermined number of emails. Instead, determine how much valuable content you can create, then build the sequence around that. Start with one email and expand as you create more content. Sending low-value emails to meet a quota will increase unsubscribes and harm deliverability. (Source: Sara McNamara, Episode #256)

Develop a distinct persona for your role in the recipient's inbox. Define who you are as a sender and what role you play in your audience's inbox. Assign a specific team member as the consistent sender and build a narrative around their voice and perspective. This creates continuity and gives recipients a reason to opt in — they're subscribing to a person and their perspective, not just a company. (Source: Alyssa, Episode #312)

Newsletter Strategy and Production

Build newsletters with 50% evergreen content and 50% ephemeral content to reduce production burden and increase reusability. Structure newsletters so that half the content is evergreen (timeless, high-quality pieces that can be reused indefinitely) and half is ephemeral (current events, timely value). Send evergreen content on a fixed schedule (e.g., Wednesdays) and ephemeral content on another (e.g., Sundays). Evergreen emails can be resent to new subscribers without filters or concerns about repetition. (Source: Brendan Hufford, Episode #242)

Build newsletter consistency through repeatable content structure, not just topic novelty. Create a stable, repeating newsletter structure (e.g., workplace trends section, AI section, thought leadership topic, water cooler chatter, fun fact, cartoon) that stays consistent week-to-week. This reduces the cognitive load of deciding what to include and allows the writer to focus on quality content within each section. (Source: Arielle Gordis, Episode #166)

Add a personality section to newsletters to increase time-on-page and reader retention. Include a recurring section (e.g., "Since You Didn't Ask") where you share personal, non-marketing content — random observations, pop culture takes, office anecdotes, or anything unrelated to your core topic. This humanizes the sender and makes the newsletter feel like it's from a real person, not a brand. (Source: Jay Schwedelson, Episode #329)

Establish a weekly newsletter creation timeline: research early week, draft mid-week, review and polish before send. Spend the first few days researching trends and gathering information, write the draft mid-week, then review and refine multiple times (e.g., 7+ passes) before sending. (Source: Arielle Gordis, Episode #166)

Test multiple content formats in recurring channels to find what resonates. In a recurring channel like a newsletter, intentionally vary the format and content type across issues (personal notes, listicles, thought pieces, webinar recaps, how-to guides, etc.). Track which formats generate the most engagement and responses, then deliberately increase the frequency of high-performing formats. (Source: Dave Gerhardt, Episode #314)

Build newsletter content by curating and storytelling around existing podcast episodes. Instead of creating original newsletter content from scratch, listen to high-performing podcast episodes and extract key frameworks or insights. Wrap these in a personal story or hook, then present the guest's framework or takeaway. The overlap in audience is minimal — less than 5% of LinkedIn followers see any given post, so repurposing is not redundant. (Source: Dave Gerhardt, Episode #169)

Invest in a dedicated newsletter writer to build an engaged audience. (Note: this is contested — see Where Experts Disagree.) If you decide to invest in email newsletters, hire a dedicated writer (not a contractor juggling multiple projects) to focus exclusively on creating high-quality, non-promotional content. The newsletter should provide genuine value (e.g., trends, insights, analysis) rather than promoting your product or company. (Source: Dave Gerhardt, Episode #183)

Use a weekly newsletter as a copywriting practice vehicle with built-in feedback metrics. Each week provides a natural deadline and feedback loop through open rates, click rates, and direct responses. Over the course of a year, a weekly writing practice generates 52 opportunities to test, learn, and improve copywriting skills in a real-world context. (Source: Dave Gerhardt, Episode #129)

Replay successful content multiple times across different audiences and channels. Once you identify content that works, don't publish it once and move on. Replay that content multiple times to different segments of your audience and across different channels. Most of your audience won't see a single post, so repeating successful content ensures it reaches more people. (Source: Dave Gerhardt, Episode #200)

Boost newsletter promotion posts to retargeting audiences. Create a post promoting your newsletter with a link, then boost it specifically to your retargeting audience (warm traffic). Your retargeting audience already knows your brand and is more likely to convert. Track email signups in your CRM to measure impact, as engagement metrics on the post itself may not reflect actual conversions. (Source: Anthony Blatner, Episodes #228 and #152)

Bridge long sales cycles with subscribable media subscriptions. For B2B products with 6-12 month sales cycles, split campaigns into direct-offer campaigns and long-term nurture campaigns. Implement a middle step: get interested prospects to subscribe to your owned media (LinkedIn page, thought leader accounts, YouTube channel, podcast, newsletter). Once subscribed, they receive ongoing content for free during the long consideration period. (Source: Anthony Blatner, Episodes #228 and #152)

Webinar Email Strategy

Run ungated webinars focused on delivering value rather than lead capture, with personalized follow-up based on engagement signals. Remove gating from webinars to maximize attendance and audience reach. Measure success through engagement metrics and longer-term pipeline influence (30-90 day lag to demo booked or closed deal). Use personalized follow-up emails based on three data points: (1) how many webinars the person has attended, (2) what you know about them from website behavior and previous interactions, and (3) questions they asked during the webinar. (Source: Eoin Clancy, Episode #326)

Use "attend to receive" model for webinar registrations. Increase live webinar attendance by offering exclusive content or benefits only to live attendees (e.g., a special tip sheet, Q&A session, or exclusive content that won't be available in the on-demand recording). This incentivizes people to attend live rather than wait for the recording. (Source: Jay Schwedelson, Episode #167)

Measurement and Analytics

Move beyond opens and clicks to measure email's actual business impact. Stop relying solely on opens and clicks as success metrics. Instead, measure email's impact on business outcomes: Did it drive pipeline? Did it influence a deal? Did it increase brand awareness or search volume? Track email's contribution across the full customer journey. (Source: Beth O'Malley, Episode #241)

Use email holdout groups to measure incremental impact of email campaigns. When sending email campaigns, create a holdout group by excluding 10% of your target audience from the send. Track conversions in your CRM for both the sent group and the holdout group over the same period. Compare conversion rates between groups to quantify the true incremental impact of the email, removing self-reported attribution bias. Customer.io has this built natively into their platform. (Source: Pranav Piyush, Episode #191)

Monitor multiple metrics holistically, not single metrics in isolation. When making changes to email campaigns, monitor multiple metrics (unsubscribe rate, bounce rate, reply rate, engagement) rather than optimizing for a single metric like open rate. A change that improves one metric might harm another. (Source: Sara McNamara, Episode #256)

Move beyond vanity metrics and focus on engagement narratives and contact frequency. Dig into deeper questions: How many contacts did this person receive before they converted? What's the engagement narrative over time? How many emails are they actually receiving, and when? Look at unsubscribe patterns to understand if you're sending too frequently or at the wrong times. (Source: Alyssa, Episode #312)

Measure newsletter success beyond open rate: track reopen rate and content repurposing as engagement signals. In addition to unique open rate, track total open rate (which includes people reopening the email) and monitor how often readers return to old newsletters. Also measure downstream engagement by repurposing newsletter content into video, LinkedIn posts, or blog content and tracking shares, comments, and reach. (Source: Arielle Gordis, Episode #166)

Require a minimum of 500-1,000 recipients for statistically valid subject line A/B tests. Do not run A/B tests on subject lines with fewer than 500 recipients (preferably 1,000+). Smaller sample sizes produce unreliable results due to outliers and personal preference bias. Always have a clear hypothesis and action plan for how you'll use the test results before running the test. (Source: Sara McNamara, Episode #256)

Only A/B test subject lines with a clear hypothesis and action plan. Before running a subject line A/B test, define why you're testing, what you expect to learn, and what action you'll take based on the results. Testing without a plan wastes time and resources. If you're testing poor subject lines, you're exposing part of your audience to ba

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