How to not send the wrong emails at the wrong time

Founders and marketers suck at email.

Many of us still default to generic email sequences that we blast to everyone on our lists.

And email marketing, especially for SaaS, is just hard. We work around email automation tools, resort to ugly hacks, and even involve the dev team to send the right emails at the right time. But even then, things still break.

I've been a marketer for years, but I still mess up. A bug recently caused our system to send one of our old email broadcasts to everyone on our list. And it's not just me.




Now, it doesn't matter if it was an accident or not, sending the erroneous emails annoy the heck out of everyone.

That's why I built Encharge to help marketers do email marketing better.

In this post, I'll give you some practical tips to avoid sending the wrong emails at the wrong times. Like I did.

How to NOT send emails at the wrong time

Sending emails at the wrong time results in unsubscribes. I don't need a statistic here.

So before you hit that send button, follow these 8 tips to avoid those timing mistakes and maximize the impact of your onboarding emails.

Tip #1: Map out your customer journey — including all possible scenarios.

I'll start with the basics.

The customer journey is the path a customer takes when interacting with a brand or business. It usually involves multiple touchpoints and interactions from initial awareness to the final purchase and beyond.

It's not exact, but a simplified customer's journey usually looks like this:

customer's journey


However, what happens in real life is far more complex. Forrester has a good illustration that represents the average behavior of consumers.

Forrester illustration


Can you spot where the email is? It's scattered across the buying journey. They're in the Explore and Buy stages in this illustration, but if you ask me, they also play a huge part in the bottom-of-the-funnel stages, especially with conversions.

A customer journey map may seem unnecessary to some. But failing to understand your customer can result in messed up email timing.

Here's the ideal way to do this is:

  1. Study your customer's communication preferences. Take note of how they buy. Do they prefer to do their research on their own? Email and talk to a salesperson? Do they consume content? Every customer journey will be different — and it's your customers who decide this. So get to know them.
  2. Determine all the touchpoints where you want to reach out to customers. Decide which channel to use and assign appropriate communications to emails. You don't want to smother them with multiple messages!

Tip #2: Plan your segmentation and triggers early on.

You can throw social media content like spaghetti and you can get away with likes or new followers. But untargeted emails without a holistic game plan will lead to:

  • Disgruntled customers - "I just upgraded to a higher plan, why are you selling me this again?"
  • Confused subscribers - "Why are you still asking me to sign up, I already did."
  • Annoyed readers - "You sent me 4 emails in under an hour."

Segmenting by behavior is important because these emails have the highest likelihood of impacting the user. Of course, you can also segment by demographics and lead scores. And don't forget to consider:

  • Where they are in the funnel: Leads (further classified into the lead magnet they downloaded), free trials, expired trials, scheduled a demo, paying users, customers who canceled.
  • Their plan: Freemium, Free plan, Plus plan, Pro plan, Enterprise plan.
  • Their industry: SaaS, eCommerce, Educatio, Marketing, etc.

Your segmentation depends entirely on you and your email strategy. But you have to plan your architecture early on so you can readily use these segments and triggers to fire your email to the right person at the right time.

Tip: One easy way to segment your users during onboarding by asking them questions that can sort them into buckets — just like how we at Encharge personalize the customer experience.

segmenting at Encharge

Don't stop after segmenting the email list.

Consider your triggers. Here are some good examples:

  • Verified their email
  • Uploaded a list of contacts
  • Wrote an email
  • Set up a campaign
  • Sent an email

And track email metrics so you'll know how your email campaigns performed.

Lastly, for best results, do this:

  • When planning your segmentation, start with a few core criteria, like the ones we suggested above. Then further break it down based on more specific attributes like the user's behavior or engagement level with your product or service.
  • Opt for time-based AND trigger-based emails. Emails that are 'triggered' by actions or particular events are much more timely and effective so make sure to do those in addition to your time-based emails.!
  • It can be a bit overwhelming to plan the whole thing. There are always email experts you can hire or consult when you're ready to take email seriously. Best to do this early on when it's easier to implement.

Tip #3: Build your email onboarding flows

A comprehensive email onboarding plan includes a series of emails that are designed to take customers through the various stages of onboarding, from introduction to education to activation.

But what emails should you send? How long should they be? How frequent?

Every product is different, but here's a quick framework you can use.

More or less, there are 6 types of emails you should send during onboarding:

  1. Verification emails
    This email invites users to confirm their account info, sent right after signing up for your SaaS.

Verification email

  1. Welcome emails
    The most popular and most-read emails, welcome emails are usually the first marketing email sent to users. It introduces your SaaS and explains how your software is about to solve your users' problems.

Jira welcome email

You could play with layouts and graphics.

Spline welcome email

Or it could be in plain text.

Tome welcome email

  1. Nurture emails
    These are the series of emails sent after the welcome email. They show the value of your product, nudging users to continually use your software.

They can tell you what to do next.

Nurture email1

They can be resource emails with links to helpful guides and tutorials.

Nurture email2

Or maybe they can invite users to a chat session about your software.

Nurture email3

  1. Transactional emails
    Transactional emails are dynamic messages sent to confirm user activities or processes. They keep users informed about exciting events tied to their accounts.

They can include important notifications.

Transactional email1

Or invitations.

Transactional email2

Or a usage update email with a gentle hint to upgrade like this Todoist email.

Transactional email3

  1. "Trial is ending" reminders
    These emails are sent to give users a heads-up when the trial is expiring, or their cc is about to get charged. Send them 1 to 2 days before the free trial ends.

Trial is ending reminder

And another one on the day the trial expires (depending on whether you have a 7, 14, 21, or 30-day trial).

  1. "Trial expired" notification emails
    "Trial expired" notification emails are messages sent by companies to inform users that their free trial period has ended and they will need to subscribe or purchase the product/service to continue using it.

Trial expired

And don't forget about timing

Now that you know the types of emails, let's talk about the timing of when to send these emails.

In general, you send emails following the Fibonacci sequence — frequently at first, then gradually spaced out over time.

​​The Fibonacci sequence is a series of numbers where the next number is the result of adding the two numbers before it. For example: 0, 1, 1, 2, 3, 5, 8, 13…

So for example, you follow this flow for a 7-day SaaS free trial:

  • Verification email As soon as the user signed up
  • Welcome email: As soon as the user verified his/her email
  • Nurture email 1: Day 1
  • Nurture email 2: Day 2
  • Nurture email 3: Day 3
  • Nurture email 4: Day 5
  • "Trial is ending" emails: Day 7

That's it.

Transactional emails will be scattered between these emails. And since they depend on the user's behavior, that's where it could get a little tricky.

There may be branches of flows that you should set up depending on the user behavior. For example, you might send a different email depending on whether the user opened their welcome email. And not all email marketing platforms have this capacity — this is the very reason why I built Encharge—to support the sophisticated email flow smart marketers want for their customers.

And remember, crafting a winning email onboarding flow is about finding a middle ground between too many emails and just enough to lead to the AHA moment. Balance the time-based emails and behavior-triggered ones.

Tip #4 Pick an email marketing platform that lets you send emails at the right time

Choosing the right email marketing platform will make or break your email campaigns. Here are some helpful hints to help you pick the right platform:

  • Before choosing a platform, identify what you need it to do. Do you need it to support complex automation workflows? Or simply act as an email scheduler? You can choose a tool that best fits your needs if you know what your goals are.
  • Consider ease of use. You don't want a platform that's too complicated to use, as it will take up too much of your time. Look for a platform with an intuitive user interface and easy-to-use features.
  • Look for integrations. Your chosen platform should integrate with other tools you're using — particularly your CRM.
  • Consider your growing userbase and your budget. Email marketing platforms come in a range of prices that are dependent on your monthly active user.

Tip #5: Do QA to ensure timing and triggers are correct

Once you've finished your email campaign, it's time to go live with it.

But before you do, make sure to do a thorough QA (quality assurance) check to avoid any mistakes that could mess up the flow and timing.

Send drafts to yourself, your colleagues, and even a few test accounts to ensure your emails look attractive and work correctly. Check for things like broken links, typos, formatting, and compatibility issues across different devices and email clients.

You can also use A/B testing to test different copy versions to see what works best.

Few things to remember:

  • Always double-check the time zone: When you're sending an email that is time-bound, for example, a webinar registration link or a deadline reminder, you must ensure it's sent when your audience is available.
  • Test your email on different devices — desktops, smartphones, and tablets. In this way, you'll verify that your email looks and works the same way across different platforms.
  • Test if the triggers and flows are working correctly. If you have to create dummy accounts to test the flow, then do it.

If you don't do QA, you're gambling with your product. QA checks may take extra time, but they're well worth the effort.

Tip #6: Be on the lookout for feedback

Feedback, be it good or bad, is part of onboarding — and being open to it can help you improve your campaigns.

Always be on the lookout for the "Hey, I got too many emails!" or the "I got the wrong email. I already upgraded."

Yes, you planned it carefully. Yes, you have tested it. But in reality, you just don't know what could go wrong. Monitor it, especially during the first few days after launching your new onboarding sequence.

To find feedback, follow these tips:

  • Monitor your email metrics. Pay attention to your open rates, click-through rates, and conversion rates. Data like this can help you assess how your campaign is performing and where changes may be needed.
  • Encourage replies and engagement. You should include a call-to-action in your emails that encourages your audience to respond, especially during the early days of your new onboarding sequence.
  • Set up surveys or feedback forms. Use surveys or feedback forms to gather specific information from your audience.

Nimbus, a collaboration tool and organizer, uses feedback surveys to gather insights from its users.

feedback email

Tip #7: Do regular checks for bugs, broken flows, and the likes.

QA doesn't end after a campaign goes live. It's important to regularly check for bugs and broken flows in your email marketing campaigns.

To be on top of this, you can:

  • Sign up for your SaaS once in a while just to check everything's working as it should.
  • Designate who will be responsible for monitoring your onboarding flows. It's the most critical AND profitable flow so it's just worth it.
  • Document SOPs and your onboarding process for whoever is designated.

Tip #8: Prepare for future optimizations

Email onboarding flows are never truly finished. With constantly changing customer preferences and new features to introduce, you'll need to monitor that your email marketing remains effective—it's important to prepare for future optimizations and to get that email timing right!

Some key considerations to keep in mind:

  • Take the time to review and identify any outdated emails that need updating. You can also consider adding new or changing emails to your sequence to provide more value to your subscribers.
  • Keep your email marketing content fresh and relevant. This might mean assigning someone on your team to focus on content updates.
  • To keep your email onboarding flows performing at their best, it's important to regularly analyze and optimize them. Consider setting a regular schedule for reviewing and optimizing your emails — like quarterly or annually.

Tip: Have a fear of disrupting a well-performing sequence? To mitigate this risk, consider testing any changes on a small segment of your email list before rolling them out to your entire audience.

Never suck at onboarding emails again

Email onboarding depends greatly on timing. Sending the right message at the right time can make a great first impression. Failing to do so will lead to unsubscribes.

Here is a summary of my tips on how to NOT send emails at the wrong time:

  1. Map out your customer journey
  2. Plan your segmentation, triggers, and tracking early on
  3. Build your email onboarding flows
  4. Pick an email marketing platform that can support your plan
  5. Do a QA before hitting that live button
  6. Be on the lookout for feedback
  7. Do regular checks for bugs, broken flows, etc.
  8. Prepare for future optimizations

Have you implemented any of these tips? Let me know how it goes in the comments below!

  1. 2

    I spent a year building and nurturing an audience of 1000+ Shopify merchants and then the founder accidentally shot them a newsletter that wasn't even meant for the audience of that product. Definitely relate. (also thanks, mailchimp)

    But yeah, email is a tricky beast and the hard truth is even the best strategies are mostly ignored by audiences.

    It's an ungrateful job but we still have to do it.

    Great work with Encharge!

  2. 2

    The mistake I did early in my startup's early stage was to over-engineer my email strategy. I created all those smart customer segments, created integration with every tool my customers used, created smart drip campaign for each of those segments, added limit on numbers of email one would get in a week/day, and so on. Only finding myself wrangling with all the smart things I had done, investing too much time trying to understand and optimize my email campaign, ending up in a decision paralysis state where sending an email looked like a decision to choose a red pill vs blue pill.

    Years after that, here's what I learned

    • Stage 1. Keep it simple

    You don't need nurture email. You don't need those many onboarding emails, you don't need to respond to those many customer journey events, you don't need to automate that much. One email every month or 2 weeks is good enough.

    • Stage 2. If you directly jump into automation, segmentation, smart drips, etc. you invite the pain of dealing with data quality issues (duplicates, outdated info, etc.) and data integration issues., and of course the heat from the customers even when you feel you're doing all the right things helping out the customer.

    Solution: First work on getting all your customer events/data together in one warehouse which will be your source of truth. This can be done by using any Customer Data Platform such as RudderStack - https://github.com/rudderlabs/rudder-server

    • Stage 3. You can slowly start mapping customer journey and gradually start adding more onboarding emails, one at a time. If you see any negative response, back off.
    • Stage 4. Go for everything author mentions. You would feel more confident and have more trust in your email strategy now.
    1. 1

      @opensourcecolumbus What is your go-to stack for starting simple, when it comes to sending emails?

    2. 1

      Great tips. It’s always best to start simple and expand later.

  3. 2

    @kaloyankulov you mentioned using forms to get info from users during the signup process, then segmenting them with that data. Do you think that's worth the added friction during such an important moment? And do you have any tips on how to reduce the friction if you're going to do that?

    1. 1

      It really depends on the maturity of the tool and the volume of signups you get. If you are just getting a few signups a month and want to get as many people into the tool to test features and validate ideas, then yes, the friction would be bad. Conversely, if you get many unqualified signups and want to increase conversion rates, increasing the questions on the signup process will always be preferred. That's why you see big tools like intercom, hubspot with dozens of questions in the signup.

  4. 2

    Thanks for this thorough rundown! Yeah, I try to plan segmentation, triggers, etc. when I'm planning the features — that way they're baked in and not added later. Of course, I often have to add more on top, but this lays the groundwork and I think it's more efficient this way.

  5. 1

    Totally agree with you on the importance of mapping out the customer journey and planning segmentation and triggers upfront. It's all about understanding our audience and sending them the right messages at the right time. And creating killer email onboarding flows? That's the secret sauce to keeping users engaged and coming back for more!

    By the way, have you ever checked out ConveyThis? It's a pretty cool multilingual solution that can seriously boost your email marketing game. They seamlessly integrate language translation into email campaigns, so you can effortlessly connect with a global audience. It's like having a language wizard by your side. Definitely worth a look if you want to take your email marketing to the next level!

  6. 1

    Thanks for the thoughtful summary! Anyone knows how to collect the email open rate? When we send an email to customer without response, we want to know customer missed it or do nothing after reading it.

    1. 1

      I think mailchip can do it.

    2. 1

      Most esp tools provide open rates metrics :)

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