Marketing for Subscription Services

𝗪𝗲𝗹𝗹𝗻𝗲𝘀𝘀 𝗜𝘀 𝗮 𝗛𝗮𝗯𝗶𝘁. 𝗬𝗼𝘂𝗿 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗽𝘁𝗶𝗼𝗻 𝗦𝗵𝗼𝘂𝗹𝗱 𝗕𝗲 𝗧𝗼𝗼. If customers love your product but still cancel, the problem isn’t the product—it’s the experience. The best wellness brands don’t just sell products. They guide behaviours, reinforce habits, and remove friction. But too often, small moments of friction— a failed payment, a forgotten renewal, a skipped order— quietly push customers away before they even realize it. That’s why I put this table together. 7 high-impact automations that keep subscribers engaged, reduce churn, and make retention effortless. Each one removes a key retention blocker before it turns into lost revenue. 1️⃣ 𝗣𝗮𝘆𝗺𝗲𝗻𝘁 𝗙𝗮𝗶𝗹𝘂𝗿𝗲𝘀 → 𝗜𝗻𝘀𝘁𝗮𝗻𝘁 𝗥𝗲𝗰𝗼𝘃𝗲𝗿𝘆 ↳ Trigger: Payment fails (Recharge) ↳ Action: SMS + Email with urgency & FOMO ↳ Apps: SMSBump, Klaviyo → Catch failed payments before they cancel 2️⃣ 𝗨𝗽𝗰𝗼𝗺𝗶𝗻𝗴 𝗥𝗲𝗻𝗲𝘄𝗮𝗹𝘀 → 𝗕𝗲𝗻𝗲𝗳𝗶𝘁 𝗥𝗲𝗶𝗻𝗳𝗼𝗿𝗰𝗲𝗺𝗲𝗻𝘁 ↳ Trigger: Renewal approaching (Recharge) ↳ Action: Email & SMS reinforcing product value ↳ Apps: Klaviyo, PostPilot → Remind customers why they subscribed 3️⃣ 𝗟𝗼𝘄 𝗘𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁 → 𝗥𝗲-𝗲𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁 𝗙𝗹𝗼𝘄 ↳ Trigger: Skipped orders, no logins, inactivity (CustomerHub) ↳ Action: ‘Reignite Your Routine’ email series ↳ Apps: Klaviyo → Help them stay on track before they forget 4️⃣ 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 𝗔𝘁𝘁𝗲𝗺𝗽𝘁𝘀 → 𝗦𝗮𝘃𝗲 𝘁𝗵𝗲 𝗦𝗮𝗹𝗲 ↳ Trigger: Customer clicks “Cancel” (Recharge) ↳ Action: “Pause instead of cancel” + Exclusive offer ↳ Apps: Klaviyo, RetentionEngine → Give them a reason to stay 5️⃣ 𝗙𝗶𝗿𝘀𝘁 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗽𝘁𝗶𝗼𝗻 𝗢𝗿𝗱𝗲𝗿 → 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 & 𝗘𝗱𝘂𝗰𝗮𝘁𝗶𝗼𝗻 ↳ Trigger: First order shipped (Recharge) ↳ Action: Educational onboarding sequence ↳ Apps: Klaviyo, Postscript → Guide them to get the best results 6️⃣ 𝗠𝗶𝗹𝗲𝘀𝘁𝗼𝗻𝗲-𝗕𝗮𝘀𝗲𝗱 𝗥𝗲𝘄𝗮𝗿𝗱𝘀 → 𝗞𝗲𝗲𝗽 𝗧𝗵𝗲𝗺 𝗛𝗼𝗼𝗸𝗲𝗱 ↳ Trigger: 3rd, 6th, or 12th order milestone (LoyaltyLion) ↳ Action: Reward with a discount, gift, or VIP perks ↳ Apps: Smile.io, Klaviyo → Keep them engaged before they churn 7️⃣ 𝗛𝗶𝗴𝗵 𝗟𝗧𝗩 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀 → ‘𝗦𝘂𝗿𝗽𝗿𝗶𝘀𝗲 & 𝗗𝗲𝗹𝗶𝗴𝗵𝘁’ ↳ Trigger: Customer hits LTV threshold (Klaviyo) ↳ Action: Personalized gift or early access invite ↳ Apps: PostPilot, LoyaltyLion → Turn subscribers into superfans Subscriptions Should Feel Effortless. Your product builds habits. Your subscription model should too. Set up these workflows once, and let them do the work forever. If you need help with putting any of them together, reach out to me in DM 📥

Most cold emails don’t fail because of bad writing. They fail because they talk too much about the product… …and not enough about the problem. Here’s the cold email formula I’ve used in over 100,000 sends - including while helping scale Gong from $200K to $200M in ARR. It’s simple. It works. And it doesn’t require a single bullet point about features. The 4-part cold email formula: 1. Relevant intro Personalized and specific - not robotic. “Looks like you're hiring across your revenue org — congrats.” 2. Agitate the pain Make your prospect feel like you’ve read their internal Slack threads. “You either hit your headcount targets and sacrifice quality… Or you hire strong reps but miss your number.” 3. Paint the future state Share what you help others accomplish - not how your product works. “We’ve helped 100+ VPs reduce their miss-hire rate to single digits.” 4. The ‘Solve’ CTA End with a yes/no question - not a time request. “Is reducing sales mis-hires this quarter worth a quick chat?” You don’t need long emails. You need relevance, resonance, and a reason to reply. That’s how you build pipeline. P.S. Want to have actionable techniques, strategies, cheat sheets, & case studies to help you master your SaaS sales skills? Join 100,000+ other sellers who receive our newsletter every Tuesday: https://lnkd.in/egVNiFce

I’ve trained hundreds of sales reps over my career. Here’s the exact framework I use to write good cold emails from start to finish: 1. Lead with the pain not the pitch The goal of a cold email is to start a conversation, not close the deal. It’s to reflect back a real pain your buyer is already feeling often before they’ve articulated it themselves. No one cares about your product. Especially not in the first touch. They care about themselves and their problems. The biggest mistake I see reps make is trying to close too early. They shove value props, case studies, feature sets, and “we help companies like…” I always come back to this: “No pain, no gain, no demo train.” You’re not here to educate. You’re here to trigger recognition. To make them nod and go: “Yeah, we’re feeling that.” 1. Write like a human The best cold emails don’t have long intros. No “hope this finds you well.” Just a clear, honest attempt to connect over something they care about. Let’s say we’re targeting agencies running 10+ client accounts. Here’s how I’d start: “Hey — I saw you’re managing multiple clients. Curious if you’ve had to deal with deliverability issues lately, especially with the new Google/Microsoft changes. Is this on your radar?” That’s it. No pitch. No product. Just a relevant question that hits a live pain. You don’t need clever. You need to be clear. 1. Structure matters (but keep it stupid simple) I’m not into formulas. You don’t need a 7-step framework to write a good email. You need to understand the buyer and speak to them like a peer. Think about it like this: Line 1: Show you’ve done your homework. Line 2: Bring up a real, relevant pain. Line 3: Ask a question that invites a reply — not “yes.” If your email looks like a blog post, you’re doing it wrong. The goal isn’t to explain. The goal is to start a conversation. 1. Use follow-ups to build narrative (not nag) Most follow-ups sound like this: “Just bumping this to the top of your inbox.” “Not sure if you saw my last message.” Useless. Instead, think of your cold email sequence as a way to diagnose pain over time. Email 1 brings up the initial problem. Email 2 digs into what happens if it doesn’t get solved. Email 3 introduces that you might have a solution, if they’re open to it. Each message earns attention and adds value. Follow-ups shouldn’t be annoying. TAKEAWAY Conversations > conversions. Relevancy always wins.

Most hotels are missing a huge revenue channel by ignoring email marketing. Here's what we've learned building email strategies for hotels 👇🏻 While I've spent the last year showing you how to leverage social media, email marketing remains criminally underutilized in hospitality. Unlike social media followers, your email list is something you actually own. Email gives you direct access to potential guests, allowing you to: ✔️ Send targeted campaigns based on location ✔️ Retarget previous guests ✔️ Personalize messages ✔️ Drive bookings without constant ad spend But for hotels, email marketing has been a black box... Most industries have countless resources for email strategy. For hospitality? Almost non-existent. Even big brands are just running basic discount campaigns and bland promotional emails. Here's what's working in our email strategy: ✅ Building Our List There are two main drivers - previous guests and website sign-ups. For website sign-ups, we skipped the typical discount pop-ups that would cheapen our brand. We focused on value-driven offers like free stay giveaways to build our list while maintaining luxury positioning. ✅ Weekly Content Strategy Weekly emails strike the perfect balance–keeping guests engaged without overwhelming them. Unlike retail where customers buy monthly, hotel guests book a few times a year. We don’t need to flood guests with emails–we're playing the long game. Mix local activities, events, and property highlights. ✅ Personalization That Converts Targeted messaging helped our email strategy standout. We created campaigns for: ✔️ Local guests seeking quick getaways ✔️ Past guests reminiscing about their stays ✔️ Engaged subscribers ready to book All without paid ad costs. ✅ Email Flows That Drive Revenue This is where email marketing became a game-changer. We created automated sequences to: ✔️ Welcome new subscribers with our story ✔️ Re-engage guests who haven't booked in 9-12 months ✔️ Keep inactive subscribers engaged Here's exactly how to get started: 1. Choose Your Platform Klaviyo is our go-to. While there are many options, we've found it works best for hospitality and is easiest to use. 2. Build Your Foundation Start by compiling past guest emails from your PMS. Then create compelling sign-up offers and popup forms for new subscribers. 3. Set Up Your Flows Top priority: a welcome flow introducing your property's unique experience & story.  Then add: - Flows targeting previous guests - Re-engagement campaigns for inactive subs 4. Plan Weekly Content Map out a calendar mixing: - Local events and activity guides - Behind-the-scenes content - Strategic promotions (but keep them minimal) 5. Design Your Template Create a consistent look: - Clean header with logo and booking links - Mobile-optimized layout - Strategic CTA placement Every property's email list is unique. Test different approaches, analyze what resonates, and find what works best for your property.

Get a 51% Response Rate with the Right Email Structure If I had to start writing cold emails all over again, here’s how I'd do it—step by step, inspired by Steve Jobs' approach to communication. 1. Short & Straight to the Point Keep it brief. Emails under 125 words are more likely to get responses. Skip lengthy intros and get straight to the value you offer. ➔ “I noticed your team is focused on X. I think we can help with Y.” 2. Make It Crystal Clear Clarity is key. Avoid jargon, and let the benefit stand out immediately to build trust. ➔ “We can help boost your customer engagement by 20%.” 3. Add a Subtle Touch of Emotion Connect through shared values. When your message aligns with the recipient’s priorities, it resonates. ➔ Try: “We know transparency is a priority for you—our solution is built around that.” 4. Clear, Simple Call to Action (CTA) Direct, specific CTAs make it easy for the reader to respond. Keep it actionable and straightforward. ➔ Try: “Are you open to a quick 10-minute call next week?” 5. Use a Respectful, Human Tone Avoid robotic language; make your email sound personal. Think of how you’d talk to someone over coffee. ➔ Example subject: “Quick Question About [Topic]” ➔ Example body: “Hi [Name], I noticed that your team is focused on [relevant topic]. At [Your Company], we help businesses like yours achieve [benefit or result]. I’d love to discuss briefly how we might support your goals.” --- Want to enhance your cold emails or DMs? DM me for some tailored advice! #ColdEmail #EthicalMarketing #Communication #SalesTips

Here's my email/SMS signup optimization philosophy: Most brands treat email/SMS signup like a checkbox. Just slap on a popup, throw in a discount, and hope for the best. But your signup process is more than just a form, it's a funnel (okay, duh, but what does that actually mean in practice?). Here’s how I recommend our clients optimize their forms: 🧠 1. Signup is contextual Where someone comes from (ad, homepage, product page) should shape how and when the offer appears, especially on mobile. 🎯 2. Segmentation starts at signup Capture intent, interest, or preference right away. Zero-party data fuels better flows. You don’t need to ask everything at once, but just enough to personalize the next step. And here's the kicker: even in the absence of unique content in your flows, just ask a question. Collect data now, get higher form submission rates and leverage the info when you have the capacity to do so. 💬 3. Clarity beats cleverness “Get updates” won’t move the needle. Tell them exactly what they’re getting and why it’s worth handing over their info. Make the value obvious. ⚙️ 4. The welcome flow is part of the experience For some, the form is just the means for claiming a discount offer. A welcome flow hardly matters for the users that already have high intent to buy and convert right away. But the far majority of sign ups don't and the form is just the beginning of the process of selling. Tailor messaging based on what they signed up for. Prime them for that first conversion. 📊 5. Iterate like you mean it Test multi-step vs. single-step. SMS-first vs. email-first. 10% off vs. $10 off. Track by device. Measure dropoff. Then refine. Signup optimization isn’t just a growth hack, it’s foundational retention infrastructure. Bonus: When a brand is using Klaviyo for all of their messaging (and I am a strong believer in doing so), I almost always recommend using Klaviyo’s native forms. Too many third-party tools create unnecessary complexity, poor data syncs, and missed opportunities for segmentation. Klaviyo’s sign-up forms give you full control, faster testing, and direct data injection into flows. And based on some conversations I had this week with their product team responsible for improving forms, there are a bunch of exciting updates coming down the pipeline that will enable brands to do even more with them. If you’re only thinking about your list after someone joins, you’re already behind.

Clay use-case no one is talking about... AI Lifecycle Marketing So currently lifecycle marketing works as followed: - Users reach certain product milestones. - Those trigger sequences in software like ActiveCampaign or Customer.io. Great. This is always going to be around. But AI opens up a new way of doing this. What if you could use: - Every in-app action a user takes. - Answers from onboarding surveys. - Conversations from support chats. - Deep research done on the person + company. - Content consumption history before signing up. To create 1:1 personalized lifecycle emails. Which gives users product assistance, based on what they actually want/need. We just made it happen. Here's how: 1️⃣ Create CRM list for relevant user segments. 2️⃣ Auto-import that list into Clay. 3️⃣ Map all relevant properties as columns (e.g. Mixpanel/Amplitude data, Intercom history) 4️⃣ Enrich missing gaps in data. 5️⃣ Conduct AI research with Perplexity. 6️⃣ Feed all of this into a mega-prompt that contextualizes each input and has product docs uploaded into memory. 7️⃣ Send outputs to marketing automation tool, or to n8n/Zapier to send directly through Gmail. The hardest part of this was the prompt; One of the most difficult I've ever created. Claude Opus best handled the complexity - the outputs are seriously impressive. PHASE 1: These are going through Slack for an approval process. PHASE 2: Once everything is 100% refined they will be sent automatically. Game-changer.

It’s not that people aren’t using email marketing and automation. It’s that they aren’t using it well. Usecase: Onboarding Wrong way -> Nearly every B2B product has an onboarding flow. Sometimes from their marketing tool, sometimes from their CS tool, and nearly always it’s generic, unhuman, and not segmented. Better way -> Over the last decade, working with countless lifecycle teams, here is what I have found elevates an onboarding sequence and increases activation… - Stick to no more than 3-4 emails in the first 2 weeks - Audit your whole lifecycle flow to make sure they aren’t getting 4 standard onboarding emails, and another 2 triggered emails based on having not put in their CC yet and another 2 emails from sales. - Have your onboarding come from a person, not just the brand generically. name@domain.com will inbox better and get more engagement than team@, support@ etc. - Set expectations. In that first email let them know the core things that will help them be successful and to expect emails around those. Let them know the "when" - Don’t make them dig. What’s not helpful is the “If you have questions about setting up your first XYZ, here is the help doc” and they get linked to a 50 page monstrosity. Instead, link them to a specific video (that is up to date!) that walks them through step by step. Usecase: Newsletter Wrong way -> You send a newsletter that reshares your favorite blog article or social media post. You figure, if I have a good message, why not distribute it in more spots? Better way -> You want every channel to have a unique reason to go there. A better way is to have your social posts tease the value, and then the newsletter can expand on it. Or you take your great blog content and get a dozen experts to weigh in and make the newsletter send that. Other best practices…. - Use a personal name and company in the send-from name. “Casey at ActiveCampaign” for example. And have a unique tone of voice. All the top newsletters in B2B from Growth Unhinged, to Scaling SaaS to ProducTea come from an individual perspective, not the generic brand. - In terms of value of engagement, think opens < clicks < page views < replies. Replies are the gold standard that will get you into the primary folder and build relationships. - Have a clear purpose. Your customer newsletter is very likely different from your lead newsletter. Provide unique information and perspective. - Set expectations in a welcome email. The best newsletters do three things really well when you sign up… 1) Give you a recap of exactly when you will hear from them and what about “We message you on Fridays at 8AM PST about a usecase of a brand that scaled with SEO to their first $1m ARR”. 2) Give them content they can engage with immediately on your blog or elsewhere. 3) ask a targeted question to drive more engagement. What other applications of email marketing would you love to optimize in your business? I am happy to add insights in a future post.

I've worked in lifecycle marketing for 11 years, helping global brands drive customer retention. This took me 11 years to learn, I'll teach it to you in 5 minutes. → Frequency kills more campaigns than bad copy: Sending daily emails feels like engagement. It's actually training customers to ignore you. → Behavioral triggers beat scheduled sends by 300%: Stop sending emails based on calendar dates. Start sending them based on user actions. → The first 7 days determine the next 7 months: New customer onboarding predicts lifetime value better than any other metric. → Reactivation campaigns should feel like breakup letters: "We miss you" emails don't work. "Here's what you're missing" does. → Segmentation by value > segmentation by demographics: Group customers by how much they're worth, not where they live or how old they are. → Post-purchase is the new pre-purchase: The experience after someone buys determines if they'll buy again. Most brands get this backwards. Most companies focus on acquiring new customers when their biggest opportunity is sitting in their existing database. The brands with the highest retention rates don't have the best products. They have the best customer experience that makes customers want to come back. What would you add to this list? 👋 PS. I'm Anna. I'm the founder of SCHMACK and we help brands get more customers, that spends more and stay longer

Improving your B2B SaaS email footprint can drive growth. 5 tactics to consider (some might look like bad ideas): [1] 𝗖𝘂𝘁 𝗱𝗼𝘄𝗻 𝘆𝗼𝘂𝗿 𝗲𝗺𝗮𝗶𝗹 𝘃𝗼𝗹𝘂𝗺𝗲 - As new email triggers get added and user bases grow, the volume of emails ejected per day balloons exponentially. With Google's stricter spam policies, this can spell trouble. - I often see PMs build new notifications and keep them on by default. This should be done sparingly. - It's better for users to get fewer, more important emails than be swamped with an email upon every action. [2] 𝗧𝗵𝗶𝗻𝗸 𝗮𝗯𝗼𝘂𝘁 𝘀𝘁𝗮𝗻𝗱𝗶𝗻𝗴 𝗼𝘂𝘁 𝘄𝗶𝘁𝗵 𝘀𝘂𝗯𝗷𝗲𝗰𝘁 𝗹𝗶𝗻𝗲𝘀 - Here's a mistake I made - I once set the subject line of an automated email as: "[Alert] {First Name}, here are results matching your criteria". - Users were frustrated as they were lost in a sea of emails with the SAME subject line. - Using personalization isn't enough. Think about unique tokens in subject lines, especially for alerts and digests. - Using a solitary emoji for a few (not all) might be worth experimenting with. [3] 𝗘𝘅𝗽𝗲𝗿𝗶𝗺𝗲𝗻𝘁 𝘄𝗶𝘁𝗵 𝘀𝗲𝗻𝗱𝗶𝗻𝗴 𝗲𝗺𝗮𝗶𝗹𝘀 𝗮𝘁 𝗼𝗳𝗳-𝗽𝗲𝗮𝗸 𝗵𝗼𝘂𝗿𝘀 - Emails synced with a cron job (like a digest) are often set at optimal sending times. - The problem: every other platform is sending emails at that time too. - This might be counter-intuitive, but one should experiment with sending emails (with less time sensitivity like a digest) during downtimes. [4] 𝗥𝗲𝘀𝗼𝗿𝘁 𝘁𝗼 𝗽𝗹𝗮𝗶𝗻-𝘁𝗲𝘅𝘁 𝘄𝗵𝗲𝗻𝗲𝘃𝗲𝗿 𝘆𝗼𝘂 𝗰𝗮𝗻 - I've seen reset password emails with chunky, branded banners and flashy footers. - Adopt plain-text for system emails to avoid consuming real estate unnecessarily. - At max, plug in a logo + a single-line footer with the un-subscription link. - It also helps with avoiding the wrong inbox profile. [5] 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹𝗶𝘇𝗲 𝗯𝗲𝘆𝗼𝗻𝗱 𝗮 𝗻𝗮𝗺𝗲 - Most emails are "personalized" by referencing the name or company. - That's not personalization. That's just token insertion. - With LLMs on the rise, the best personalization will be contextualizing the copy based on the persona at hand. Let me explain the last point with an example. Assume the product is a Project Management tool like Asana or Clickup. Say they launch a new analytics dashboard view. A Marketing manager might get: "Our new Analytics Dashboard gives you a bird's-eye view of your marketing campaigns' progress. Track key performance indicators like campaign completion rates and team productivity, helping you optimize resource allocation and hit your marketing goals faster." But for the same feature, a software lead might get: "We've just launched our Analytics Dashboard, allowing you to visualize your development team's velocity and sprint progress. Monitor critical metrics like code commit frequency and bug resolution times to streamline your development cycles and boost overall productivity" -- What are your SaaS email tips?