Customer Fit (or Know When to Fold 'Em)

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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.

Storytelling: How Customer Success Can Gain Influence Within Your Organization

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Guest blogger, Chad Horenfeldt, joins the Success League this week. Take a look at his post on how to demonstrate your CS team's credibility. Enjoy!

By Chad Horenfeldt

Losing a customer is one of the worst feelings for anyone in Customer Success (CS). You may feel numb or in a bit of shock depending on the circumstances and it can eat at you for days.  What’s worse is that you typically know why it happened and how it could have been avoided. You’ve explained the issues to your executive team or to your Sales team or to your Product team on several occasions. Your pleas for assistance, however, have fallen on deaf ears and your CS team’s spirits are in the gutter.

You may be be thinking: Why am I not able to get through to these people? What more do I need to do? How many more customers need to churn before there is some real action outside my team? Am I the problem?

Unfortunately, this is a reality for many Customer Success teams. You can bring data that clearly states why you are losing customers but still not get the resources and process changes you need to prevent customer churn. Does this situation or something similar sound familiar?

While you shouldn’t put all of the blame on your shoulders, you do need to look more closely at the approach you take in requesting assistance. While data and customer feedback can provide insight and justification for the changes you want to achieve, your message may not be getting through. When making requests at the executive level, you can’t just persuade the mind, you also have to also convince the heart. One way to do this is through the power of stories.

This post will detail how stories win people over and provide some practical tips on creating a culture of storytelling within your own organization.

Why are stories so impactful?

In the Heath brothers’ bestseller Made to Stick, we learn about a brave nurse who saved a baby’s life by ignoring what the instruments and those around her were telling her. The story begins with newborn suddenly turning a sickly black-blue color. The onsite medical team diagnoses the issue as a collapsed lung and prepares to operate. “It’s the heart” a desperate nurse cries out as she pushes away the other medical professionals and demands silence so she could check for a heartbeat with her stethoscope.

She immediately determines the baby’s heart had stopped even though the heart monitor reported no signs of trouble. The lungs were not the problem after all and the nurse provided the appropriate treatment. It was her experience and quick thinking that prevented a tragedy that day.

This true story was one of the many that psychologist Gary Klein collected as part of his research in this area. He demonstrated that stories like the one above are very persuasive as they illuminated a causal relationship that may have been ignored and highlighted people’s inventiveness in solving real problems.

This specific story teaches a few lessons. Besides the obvious approach to addressing a potential deadly condition for newborns, it provides a stern warning to medical professionals who may rely too heavily on machines and checklists. This nurse also serves as a reminder that hospitals need to have an adequate amount of trained and experienced professionals to make the right decisions when it matters. Finally, this story acts as a call to action that change is needed. As the Heath brothers point out, emotional stories like this one can provide the stimulation and inspiration to generate action. It’s a technique you can utilize for your own Customer Success teams.

From saving newborns to driving adoption

I experienced a similar situation to the story above although it was a little less dramatic. Ok, it was completely different but it’s still a good story so stay with me. Our Product team at Updater just launched a new feature but we were having difficulties in getting our largest customers to adopt it as it required a large number of customer administrators spread out across the US to make some configuration changes. Not an easy task - trust me - but not insurmountable.

One of our CSMs used our customer story Slack channel to document the approach she used to overcome this adoption challenge.  She described in detail how she coordinated with our client to launch educational email campaigns directly to the administrators who we needed to make these configurations and she specified how she creatively used one of our vendors, Intercom to do this. Another CSM who executed the campaign then provided the initial results. That’s when the magic happened.

The general manager of our division saw this amazing success story and shared it with our CEO and other relevant executive stakeholders including the Product, Engineering, Business Development and Data teams who all had a stake in making this feature a success. After several emoticons, virtual high fives and celebratory “reply alls” the message was clear: Customer Success was driving real outcomes for the organization. This specific example was going to impact our bottom line. Let’s now go into how you can easily replicate this at your organization.   

3 simple ways to create a culture of customer stories

We’ve proven that stories can make a difference and drive action. Now it comes down to creating habits within your Customer Success team to share these stories on a regular basis and to allow them to permeate throughout your organization. Let’s talk about a few ways that you can do this:

  • Customer story time. Do you remember when your parents read you bedtime stories growing up or reading stories to your kids? You can replicate this same type of situation in your own organization. Just schedule a monthly (recommended) or quarterly storytelling session where your CSMs can tell informal or formal stories about how they drove success with your product. Invite all the relevant departments: Sales, Marketing, Product, Engineering etc… They will eat these stories up.

    I was first exposed to this at Eloqua and then carried on the tradition at my subsequent start-ups. At Influitive we bribed other groups to come by serving beer. It was so popular there that the Sales team demanded us to record the sessions as they used the content in their sales conversations. CSMs learned from each other and improved their tactics. Marketing leveraged these stories to seek out full case studies. Product used the feedback to make changes to future features. We all had a better understanding of the needs of our customers.

    A variation of this is to present stories at your company offsites, internal churn reviews, new team member bootcamps and/or sales kick-offs. Keep this in mind: story time all the time.

  • Customer story Slack channel. I referenced this tip earlier. I wanted our team to share more of their stories so we can all learn from them. We started a Slack channel to capture customer stories - both good and bad. Our goal was to hear more of the challenges and successes that the CSMs were experiencing in their day to day and share those with each other and the rest of the company. Slack is a great mechanism for this as it’s easily accessible and the information is searchable for everyone (especially for team members that join later on) unlike email.

    To kick this off we set a team goal of 35 stories in one month. If we achieved this we would all go for a nice dinner and the top three submitters would be rewarded. The channel quickly grew in popularity as others became interested in the stories and the CSMs gained recognition and a sense of accomplishment for submitting them. Oh, and we did go for a nice Mexican dinner. This is win-win-win stuff (CSMs, your company, and your customers).

  • Customer awards. While the CSMs are typically the ones driving these stories, Eloqua devised a great way to extract these stories directly from clients by creating a more formal marketing award ceremony called “The Markies.” Even though Eloqua turned this into an Emmy-like production, the essence of this is very simple. Create award categories, have customers apply by providing a detailed justification on why they should win, hand out awards based on objective criteria, reap the rewards of some outstanding customer stories. Rinse and repeat on an annual basis (the Markies have been doled out to top marketers since 2007 and are going strong). I can tell you with 100% confidence that my finest moments as a CSM were when one of my customers got up to an accept a Markie award. There is nothing better than this. Nothing.

A major theme across these three examples is that shouldn’t wait for your budget discussions with your CFO and other executive stakeholders to gather customer stories. Proactively generate and share these stories on an ongoing basis so they naturally percolate throughout your organization. When other executives start citing them without you having said a word, you know you are making progress.

Customer stories = power: Where do you start?

Not having a strong voice at the executive level and not being able to get the resources you need can leave you and your Customer Success team demoralized. Particularly when you are doing everything you can to make your customers successful. You need to make the pain that you are experiencing come to life. You need others to feel the impact that your team is making. This is the power of a culture of storytelling.

When was the last time you had a CSM describe to your company how they helped one of your customers use a new feature in a way that no one expected? When was the last time that a CSM had a chance to outline the real reasons behind why you lost a customer beyond entering the reason code “not enough ROI?” It’s time to try some new approaches such as a Slack channel to tell the real stories behind the data.  Implementing these practices will change how your Customer Success team perceives itself but also how the company perceives you. You can hold your head up a little higher, get that resource that you desperately need and earn the respect that is rightfully yours. What are you waiting for?

If you’re looking for leadership guidance, The Success League is a customer success consulting firm that offers online training and workshops designed for success leaders. There are still spots open in our CS Leadership Training Program. For more information on this program and our other classes and workshops, please visit

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Chad Horenfeldt - Chad is a Customer Success executive with 15+ years experience building and developing high performing Customer Success teams. Currently, he is the Vice President of Client Success at Updater. Prior to Updater, Chad has held CS leadership positions at Bluecore, Influitive, and Oracle (Eloqua). Chad has been named to Mindtouch's top 25 Customer Success Influencer list in 2017 and 2018. He writes regularly on the topic of Customer Success on his blog The Enlightened Customer.

Strikedeck Radio - Episode 36


Tune in to this week's episode of Strikedeck Radio to hear our CEO, Kristen, speak with Vitor Lopes, a customer success professional based in Berlin, Germany. Vitor is currently advising early stage companies and is the former Head of Customer Success for EMnify. Hear Vitor and Kristen discuss ways that you can shape your customer success program to best fit the personality traits of individual team members. Enjoy!

Strikedeck Radio is a partnership between Strikedeck and The Success League. You can subscribe on Apple PodcastsGoogle Play, and anywhere else you get your podcasts or follow us on LinkedIn or Twitter to get updates on new episodes.

Goal Tracking 101 - Staying On Top Of Your Metrics

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By Amin Akbarpour

Goals. We all have them. As Customer Success professionals, they’re usually a combination of both quantitative and qualitative. Think things like customer advocacy (qualitative) and churn reduction (quantitative). The idea is obviously to hit these goals. Presuming you’ve done a good job of goal setting (check out Kristen's recent article on Annual Planning for Customer Success), then the next most important thing would be tracking towards these goals. There’s a number of ways to effectively do this depending on the goal in question.

Macro Meets Micro

Chances are your goals are set looking at the full year. You then take those calls and break them down into either quarterly or monthly time intervals. Why stop there? Take this one step further and break it down to daily goals. Here’s an example:

Goal: Close $100,000 in up-sells within your current book of business in the fiscal year.

First, figure out what $100,000 would look like in terms of your organization’s product or offering. In this example, let’s say this means selling 10 training packages. In cases where you offer multiple different paths towards this $100k goal, tailor it based on what you know about your book of business and what would be most beneficial to them.

Next, take the last time you or someone on your team (in cases where you haven’t before) successfully sold a training package. How many meetings did it take from initial conversation to close? Let’s say six and the entire sales cycle lasted three months. In order to get the first meeting in this series, how many emails or calls did it take? 15? Yes, 15.

From that information, we now know that it’ll take 150 outreaches to get the first meeting for ten successful deals. We also know that your average sales cycle is three months. If you’re in month 10 and haven’t gotten that first meeting then you’re most likely going to be out of luck in regard to hitting your target for the year.

Good Habits

Now that you’ve boiled down your annual goal to a daily routine, it’s important to stay on top of that. Everyone has their own way of doing this. Here are a few things I would suggest:

  • CRM Reminders: Whatever CRM or CS tool you use most likely has some sort of reminder system. Take Salesforce, for example. You can create recurring tasks associated with contacts and accounts. From there, every time you sign into Salesforce you can go to your personal dashboard and see what needs to be done for the day.

  • Calendar Blocks: It’s easy to get caught up in last minute madness or the daily chaos that comes with our jobs. Be organized and put a recurring block on your calendar for a couple hours when you shut your email off (I know, terrifying) and get stuff done. Focus on your daily outbound tasks that need to be done in order to hit your goals. If you work in an open office space, I find it helps sometimes to just reserve a conference room and lock myself in there. That way you can go uninterrupted and ensure you’re allowing time to knock out your tasks.

  • Prioritization & Resources: This is one I had an issue with when I transitioned from being a mid-market to an enterprise rep. Understanding that not every item raised by a client is a “raise the alarm, stop what you’re doing, all hands on deck” situation. It’s okay to take a day or two to knock out a client task if that means having balance in your days. Additionally, if you have resources around you that you can leverage (technical support team, sales engineer, project manager, etc) then leverage them! You’re one member of a team. Act like it.

Picking up these good habits and implementing them will help you make time in each day to hit your goals. Be diligent when you backtrack your annual goals into daily tasks. It’s important that you are formulated with this approach, and then be disciplined enough to consistently stick to the plan. Only then will you reap the benefits of your labor.

Need some extra help mapping and tracking your goals? The Success League is a customer success consulting firm that offers online training and workshops. Our upcoming CSM Training Program kicks off with classes like Customer Goals & Outcomes and Time Management for CSMs. For more information on these and our other classes and workshops, please visit

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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.

Classes Start NEXT WEEK - Sign Up NOW and Get a Discount!

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Our fall series of CS Leadership and CSM Training classes are starting next week. If you sign up now, you can receive 20% off our bundles! Hop on board soon though, as this flash deal ends this Friday, September 7th

Leadership classes start on Tuesday, September 11.
For the discounted bundle, please use code "FALL20LEADER" at checkout. 

CSM classes start on Thursday, September 13th.
For the discounted bundle, please use code "FALL20CSM" at checkout. 

Can't wait to see you in class!