Customer Relationships

10 Proven Emails To Increase Customer Lifetime Value

Mailbox Row Branded.png

By Jeremy Gillespie

Many companies are afraid to contact their customers because they think it’s going to awaken “hidden” churn. The reality is, communicating with your customers is a high-value activity that will prevent churn and increase your customer lifetime value. Below we’ve outlined 8 different emails you should be sending to build lasting customer relationships. In addition they are broken down by how they are sent:

  • Automated emails

  • Customer Marketing emails

  • Personal emails

Automated Emails

These are your high-leverage emails meant to get customers up to speed, make sure they’re on track and put a smile on their face.

Thank you emails

This email is often overlooked, but a nice email from the founder or CEO when someone starts using the product is a great way to start off the relationship. In this email, you’ll want to touch on the following topics:

  • Thank them for trying your product

  • Introduce them to your brand and core value of the product

  • Let them know you’re there to support them (and where they can get support)

Don’t overthink this email. Just make sure it’s sincere and has a nice friendly tone.

Onboarding Emails

This is an email that’s commonplace now. Onboarding emails come at the beginning of the lifecycle and their primary purpose is to educate the user. Use these emails to ensure they feel successful with your product. Typically, you’ll have a series of emails in your onboarding sequence, the goal of each one is to get the user to successfully complete the next logical step in the product. These emails are often the first introduction to your product and the foundation on which you build the relationship. The user should feel like they “know” how to use your product by the end of them. This is the “aha” moment for the user and can also be part of the onboarding sequence, but we separated it because it’s special.

Activation Emails

Once someone has taken the baby steps (onboarding) to get up and running in your product, you want the lightbulb to go off in their head as they understand why your product is an indispensable part of their workflow now. After someone has been “activated” they should be shown high-value features to deepen the relationship and become further integrated into their day-to-day.

Collection Emails

When a customer has a billing issue and goes into collections, you must communicate with them and the initial emails should be automated. For emails asking for money, make sure they are sent from your domain, have clear branding, and that customers have a way to respond. In addition, it’s recommended to have these transactional emails come from a different email service provider than your marketing emails to ensure high deliverability. You’ll want to keep a close eye on opens and click-through rates for these emails.

Cancellation Emails

Cancellation emails that improve retention and customer lifetime value?! Yes. There’s even a silver lining when someone has decided to cancel your product. Take this opportunity to learn from your customers. Give them an easy way to provide feedback on your product. If they are a high-value customer use this email to schedule an off-boarding call to gather verbal feedback and make sure they leave on good terms.

Product Progress Updates

Value, value, value….

Whether you like it or not, if you’re not showing customers the value you’re providing them, they can quickly forget. Use product progress updates to show them how they’re progressing with the product. One important point to remember is you should not only show them usage stats (i.e. number of emails sent, calls made, etc.), you must tie the activity to the benefit. For example, you may want to tell them how much time or money they saved by using a specific feature set. Generally, the progress updates will center around the core features customers have experienced during “activation.”

Customer Marketing Emails

These emails are sent as needed to further educate and inform customers about the product or company.

Educational Emails

Education is the name of the game. Customers are investing time and money to use your product and they want to know about every bell and whistle you have. Try to send monthly, or at least quarterly, emails to highlight valuable products or features of the product. Pair these emails with a webinar or live training, so all users to see best practices first hand and give them the opportunity to ask questions. One way to go deeper on specific features is to theme the quarters of the year, and hold an educational event each month to help them become power users on specific parts of the product.

Product Updates

The last thing a customer wants is to be surprised when they log into the product, only to find big changes. When you make updates to the product make sure you’re communicating them to the customers. For these emails, tell them what has changed, why you changed it, and how it’s going to make their experience better. These emails are a great compliment to the educational emails and show customers that you’re actively improving the product and using their feedback to make it better.

Personal Emails

Personal emails are typically sent by Account Managers to keep a pulse on the customer, make sure they’re reaching their milestones, and uncover up-sell/cross-sell opportunities.

Proactive Emails

It’s always nice for a customer to receive a friendly email asking them how everything is going and providing something of value. Better yet, point them in the direction of their next milestone in the product. These emails should solve problems before they happen and show customers you’re there to support them.

Business Reviews

Depending on the size of the businesses you work with, these may be more or less frequent, but sending an email to schedule a business review is a great way to partner with them on their growth with the product. Use these emails to find a time for review, provide them with highlights on the return on investment they have received, and areas you think they can focus on in the coming months.

All of these emails are the building blocks to effectively communicate with customers regularly and build a relationship. By no means is this an exhaustive list, but this is a great starting point. Each of these emails should be regularly measured and optimized to improve the customer experience. Remember, these emails are high-value and provide an opportunity to strengthen the relationship with your customers.

The Success League is a customer success consulting firm that offers a comprehensive CSM Certification Program which includes such classes as Managing Your Portfolio and Customer Advocacy. For more information on this program and our other classes and workshops, please visit

Jeremy Bio.png

Jeremy Gillespie - Jeremy is a growth marketing expert who loves using complex data to build creative retention solutions. He is a founding advisor to The Success League, and is also the founder of Built to Scale, a consulting firm focused developing customer acquisition and retention programs. He holds a BA from the University of Pittsburgh and MBA from Point Park University. He's a proud former Pittsburgher, currently living in San Francisco.

Murphy's Law in Customer Success

Bashful Puppy Small Branded.png

By Amin Akbarpour

We all know Murphy’s Law, right? It’s something along the lines of “if anything bad can happen, it will happen.” In customer success, a lot can go wrong very quickly even if you prepare to the utmost degree. I want to share a few of my more embarrassing misses as a customer success agent and – in hindsight – how I’d handle them if they happened again.

Technical Issues

This has to be at the top of the list for all of us, no? Whether it’s an in-person meeting where you can’t connect to a projector, or a phone call where no one can use the dial-in number, these are disasters that can derail any meeting. Some of the most common instances that have happened to me are:

  • Client is unable to join the screen-share solution

  • No means to properly project during an in-person client presentation

  • Internet lag times during a walkthrough of the product offering

  • R.I.P. PowerPoint

That last one is actually a fairly new one to me. So new, that the first and only times (three, to be precise!) it’s happened to me were all in one week. If you were to run into any one of these issues, it can completely derail your meeting and kill momentum. I’ve started to prepare for these mishaps in a few ways:

  • Ask the client ahead of time what web conferencing tool they use internally and adapt to them. This sometimes means having to download their software ahead of time and asking them to tack on credentials to the invite. Sounds like a tall ask but it also guarantees their ability to join seamlessly and the meeting to start without a hiccup.

  • Send a .pptx or .pdf version of the deck or material you were planning to cover ahead of time. That way if this comes up, you can quickly adjust. I tend to stick with sending it to just our main point of contact so that not everyone gets a look before the meeting. Definitely part of my inner thespian, but I enjoy the showmanship of presenting fresh material.

  • At some point, you start to pick up the parts of your app or product that take a while to load. I preload these pages in multiple tabs or windows just in case there’s a delay so I can still show them efficiently throughout the presentation.

  • Always. Always. Always. Make a .pdf version of your deck and have it open and in the ready in case PowerPoint crashes. Also, if PowerPoint crashed once, assume that it will crash again.

Human Error

Have you ever accidentally called a client by the wrong name? Or written it incorrectly in an email? Or even worse – referred to them as one of their direct competitors? If you have, then you’ve felt that catastrophic level of shame. There’s no cheat sheet for this one. If it happens, your best bet is to just own it in the moment and apologize. You can try to avoid this in the first place by double-checking everything written that goes out, and practicing before walking into any call or meeting. I personally have a habit of writing everyone’s name and the company name into my notebook a couple times before the meeting. It could just be a placebo, but muttering it, writing it, and then being able to look down and read it throughout the meeting might help to ensure that you don’t say anything contrary.

Ultimately, you will most likely run into one or more of the aforementioned scenarios throughout your tenure as a CS representative. Don’t beat yourself up if Murphy’s Law happens - it happens to everyone. You can’t prevent every bad outcome, but at the very least preparation can minimize the impact.

Want more practical tips on how to succeed as a CSM? The Success League is a customer success consulting firm that offers online training and workshops, including our popular CSM Training Program. For more information on this program and our other classes and workshops, please visit

Amin Bio Pic.png

Amin Akbarpour - Amin is a customer success coach and architect.  With relationship-building at the core of his practice, he molds teams by instilling the necessary principles to transform them into trusted advisors. Understanding what's needed for organizational change, he translates theory and ideology into practice and habit. Amin is one of the founding advisors to The Success League. In addition to his work with The League, Amin currently serves as an account manager for Persado. Originally from Southern California, Amin is a University of San Francisco alum who now calls New York City home.

Integrating Customer Experience Into Your Customer Journey

Basket Weave Branded.png

By Jeremy Gillespie

There’s been a hot debate between Customer Success and Customer Experience. Customer Success professionals believe customer experience is a subset of customer success. Customer Experience professionals believe customer success is a subset of customer experience.

We’re not going to solve this debate today. Instead, I’m going to lay out 3 simple steps to ensure that the customer experience is an integral part of your customer journey. But first, let’s make sure we’re on the same page about the difference between customer success and customer experience.

Customer Success vs. Customer Experience

The difference is can be a little confusing, so rather than trying to explain it in my own words, I’ll let industry leaders articulate the difference.

The Customer Success Association says Customer Success is about customer relationship, retention, and optimization, and the most effective way to keep your customers is to make them as successful as possible in using your products. Essentially, in their words, customer success is based around the value customers get from using your product.

On the other hand, Forrester defines Customer Experience as “every interaction, or touch point, your customer has with your brand. It not only includes the whats (the interactions), but also the hows (perceptions, feelings) of the customer experiences.” Rather than the value customers receive from your product, customer experience is about how customers interact with your brand, and ultimately how your brand makes them feel.

The interesting part here is both impact one another and are often intertwined.

So how do you make sure Customer Experience is at the core of Customer Success? Well… it starts with your customer journey.

Step 1 - Map your ideal customer journey

Mapping your customer journey is the first step to defining outcomes and experiences at each stage of their journey. Typically, the focus is to define the measurable outcome at each stage, which makes sense, but I’m going to go a step further.

I think it makes sense to use the think-feel-do framework here. This is a framework often used in marketing to develop persuasive messaging, but it translates well to customer success. As CS professionals, we are often concerned with “Do.” This is the change or action that you want a customer to take at a specific stage in their journey.

To incorporate the experience more, we need to also define what the customer should “Think” and “Feel” as well.

Step 2 - Define the experience at each stage

Just as you define plays and processes to work toward a desired outcome for the customer, you need to do the same for “Think” and “Feel.”

Think refers to how the customer perceives your product and how it will make them better at their job. Your goal is to have your customers think about your product in a specific way at each stage of their journey. Think of it as a new “lightbulb” that goes off about how your product supports their goals.

Feel is all about the emotions they feel at each stage. While this is tough to define, when you knock this out of the park, it’s virtually impossible for them not to take the desired action. At each stage you need to define how they should feel and what emotions they should have.

So just as you map your desired outcome for each stage of your customer journey, go back and also define what your customer should Think and Feel. I know it sounds a little fluffy, but having these defined will make sure everyone is on the same page about not only what success looks like, but also what experience they should have.

Step 3 - Gather feedback on the experience

So how do you know if you’re meeting the customer experiences you’ve laid out in step 2? The beauty here is you do not need to implement any new platforms or measurements; you can use the existing measurement techniques you’re already (or should be) using. Here are three ways to measure your Customer Experience across your customer journey:

  1. Net Promoter Score - the percentage of your customers who would—or wouldn’t—recommend your company to their friends, family, or colleagues.

  2. Customer Satisfaction (CSAT) - the average satisfaction score that customers rate a specific experience they had with your organization—such as getting an answer from customer support or returning a product.

  3. Churn - the percentage of customers who either don’t make a repeat purchase (for transaction-based businesses) or cancel their recurring service (for subscription-based businesses).

When you integrate Customer Experience as part of your customer success journey you should see all of these metrics improve. Most notably, you’ll see success at each stage improve, which will reduce churn and increase your customer lifetime value.

Need help weaving Customer Success with Customer Experience in your organization? The Success League is a customer success consulting firm that offers both customer journey mapping and process design engagements. Please visit for more information.

Jeremy Bio.png

Jeremy Gillespie - Jeremy is a growth marketing expert who loves using complex data to build creative retention solutions. By leveraging data and technology, he excels at creating innovative retention and expansion marketing programs for businesses of all shapes and sizes. Jeremy is a founding advisor to The Success League, and is also the founder of Built to Scale, a Bay Area consulting firm focused on helping businesses build scalable customer acquisition and retention programs. He holds a BA from the University of Pittsburgh and MBA from Point Park University. He's a proud former Pittsburgher, currently living in San Francisco.

Customer Fit (or Know When to Fold 'Em)

Poker Cards Chips Branded.png

By Steve Schwartz

I spent a few days last week at a conference in the desert oasis known as Las Vegas, but all too often referred to as Lost Wages. When I had a break, I found myself down in the poker room facing off against casino regulars, tourists, and other conference-goers. I’m a very patient player and have lots of time to think while folding awful hands. One thing I realized is that poker hands can be a lot like the three types of customers that I’m sure you all have experienced: perfect fit, good fit, and bad fit. You may not know what type of customer you have when they first sign up, but as more information is revealed about them, you need to act accordingly.

The shortest primer on Texas Hold’em I can offer is this: each player is dealt two cards that only they can see and a round of betting commences. Each player will use those cards and five community cards to attempt to make the best hand possible. There’s a round of betting and then three community cards (the flop) are revealed. There is another round of betting, then one more community card (the turn). Then another round of betting, and a final community card (the river). Finally, there is one more betting round before either one player remains or multiple players show down their cards to see who has the best hand.


You look down at two tens and raise the pot only to be re-raised by another player. You call and the flop brings two more tens and an ace. It doesn’t get much better than quads (four of a kind)! While you’ll have to invest some money for them to pay off, you’re confident you’ll be rewarded in the end.

Perfect fit customers don’t come along as often as you’d like, but when you find one, you want to maximize their value. That means that you’ll certainly want to invest heavily in their success in order to reap the profits of case studies, white papers, speaking engagements, and references.


This time you look down at an ace of spades and a king of hearts. It’s one of the better starting hands so you raise your opponents. You get a few callers and the flop comes king of spades, with the ten and 9 of diamonds. You’ve got a good hand, but there are still two cards to come and anything can happen. Someone could already have a straight or have a high likelihood of beating you with a flush. You’ll have to pay attention to the signals from the other players as the rest of the cards come to decide whether to keep going with your hand or to fold and give up.

Similarly, the most common customer you’ll find is a good fit. Their goals align well with your product offering, but things can change as their needs change or as they learn more about what your product can and can’t do for them. As you gain more information about your good fit customers, they may need significant investment in product enhancements to stay a good fit. At this point, you need to decide whether you’re willing to make those investments for the greater customer base, or let this particular good fit customer slip into the realm of a bad fit.


In our final hand of the night, you look down at two sixes (clubs and hearts) and call another player’s raise. The flop brings a jack, nine, and eight, all spades and there is a bet and raise before it gets to you. If another player has two spades, you’ve got a less than 3% chance of winning the hand. You could certainly invest more money and try to get lucky or bluff the other players, but most of the time you’ll cut your losses and fold the sixes.

We’ve all had bad fit customers, but sometimes we don’t realize it until we’ve invested far too much and can’t let them go. They ask for enhancements that aren’t worth investing in, their product usage doesn’t look healthy, and their expectations don’t align with what can be delivered. Just like our sixes, sometimes the best decision is a quick fold so you can focus on the next customer.

Whether with customer success or poker, it’s always difficult to make a decision when you’re heavily invested in a customer or a potentially good hand. My advice is to always use as much data as you can, whether it be product investment costs versus potential lifetime value or odds of catching the cards you need to win versus cost to see those cards. And remember, don’t believe the phrase “it’s better to be lucky than good.”

I’ll bet you didn’t think you’d learn all about poker reading a customer success blog! The Success League is a customer success consulting firm that offers training and coaching for customer success leaders (and those who want to be). Check out our Leadership page for more information on our programs, and learn when to hold ‘em and fold ‘em!


Steve Schwartz - Steve is a customer success leader who enjoys starting and building high-performance teams at early-stage startups. He has worked in startups for the past 14+ years in a variety of customer-facing roles. By engaging with customers during the sales cycle, he ensures customer expectations are fully understood and can be exceeded. When not writing for The Success League, Steve is co-leading Customer Success at Carrot Fertility. He holds a BS from Tufts University and an MS from Virginia Commonwealth University, and spends his free time with his wife and two kids exploring the Bay Area.

The Building Blocks of an Account Plan

Cobblestone Wall Branded.png

By Ashley Hall

Account Plans. They are just like going to gym: We should be doing more! Just like exercise, the more you schedule your account planning time and respect that time on your calendar the more successful you will be.

No single account plan can fit all clients across all industries, and compliment all platforms and services. Try as we might to have a standard approach to all our clients, at the end of the day they truly are all unique. Luckily, regardless of the variables, your team can define the basics of a comprehensive account planning approach.

Here are my non-negotiable requirements when it comes to building an impactful account plan.

Org Chart

My first step to building an account is always defining the team and their titles. Understanding your customer's internal organization is a huge part of your role. It’s your responsibility to be able to tell the story of the client and define their roles and goals. Think in terms of who is your main point of contact, your “champion,” their peers, and also two levels of leadership above them. The more contacts and touch points, the better.

Reasons for Purchase

Understanding their motivation for purchase helps set the tone of the relationship and gets you started on the right foot. That understanding sets you up to deliver upon their first success criteria. I love being able to look back on those original struggles or challenges months down the road and tout how we were able to solve for them. In other cases, if they are still struggling with those same challenges, you can highlight some red flags to tackle.

(Evolving) Success Criteria

In addition to the original reason for purchase I always like to highlight 2 or 3 other areas where they are trying to improve. This way our calls are impactful and goal-driven, not just “check in calls.” Again setting these criteria, and achieving them over time, fuels the content for future impact reviews and QBRs.

Red Flags

Highlighting red flags is another huge part of your role. You shouldn’t be solely responsible for solving them, but these are important to raise up to your management. Staffing changes, a high volume of feature requests, and escalated support issues are prime examples of red flags to monitor.

Initiatives & Next Steps

Next steps are such a huge help for me in my day-to-day. They are a reminder of what we are working on, and if I owe an action item or waiting for the client. Initiatives can be unique to our working relationship or their current team. Being able to recall and support a larger initiative of theirs will show the customer that you’re aligned with their current needs and supporting their bottom line.

Account plans provide your team and your clients continuity and structure. Account plans allow you to collaborate with your team internally, and are the basis of knowledge-sharing when it’s time to transition accounts from onboarding, to success, and at your next promotion. While they can sound daunting at first, this is an important initiative to begin. Start with the basics and you can always revisit and refine over time.

Looking for more tips on how to build account plans? The Success League is a customer success consulting firm that offers online training and workshops, including our upcoming classes on Customer Goals & Outcomes and Kicking off the Relationship, which are both a part of our popular CSM Training Program. For most information on this and our other classes and workshops, please visit

Ashley Bio Pic.png

Ashley Hall - Ashley loves to lead account management and success teams; from training newbies to building processes out of chaos to working directly with customers. She is passionate about helping customers achieve goals. With an eye on the future she is a powerhouse in building scaleable frameworks that support and drive growth. Ashley is one of the founding advisors to The Success League, and serves as a regular instructor for the company's CSM Training Program. She also serves as a customer success manager for ProsperWorks, and brings her work experiences to her articles and classes. Ashley holds a BA from the University of Colorado, Boulder and enjoys living in San Francisco while traveling all over the world.