4 Ways To Prevent Sales From Overselling

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By Jeremy Gillespie

Sales is incentivized to close deals and customer success is incentivized to keep those customers. It’s pretty straightforward. But what happens when sales is closing the wrong type of deals? Deals that make it hard for customer success to do their job properly? Tension between the teams can arise and finger-pointing ensues. You may have experienced this yourself.

Growing a sales team is no easy task and being a sales rep isn’t either, but to prevent the sales team from over-selling takes practice. In this post, I’m going to cover four ways you can prevent this from happening.

Why This Needs to Be Solved

This is not a new problem, and it’s certainly not easy to solve, but the reality is - this is bad for the company. To start, it’s generally unprofitable. Of course you capture the initial revenue from the customer, but once sales commission is paid, the client is on-boarded, and time is spent on management you break even at best. However, the biggest cost is the opportunity cost to the company. Precious time and energy is spent focusing on customers who are going to quickly churn, while your best customers could have been getting the white glove treatment.

In addition, allowing this to go on reinforces bad habits. Sales reps who get by on misrepresenting the product, or continually using massive discounts to get sales on the board will continue to do so as long as it goes unnoticed or unchecked.

Lastly, it’s the customer who loses the most. They have purchased a solution and invested time and resources in it, when it ultimately won’t be a good fit for them. You lose the customer’s trust, eliminating any chance to expand the relationship. This can have ripple effect on your reputation in the market. So let’s discuss some ways you can prevent this.

4 Ways To Prevent Sales From Selling Bad Deals

Below are the four ways to prevent this. While there are other tactics you can use, I would suggest starting here.

1. Sales training

This is the number one way to prevent bad deals. Sales training is vitally important not only to get reps to meet quota, but to make sure they’re representing the product correctly. In addition to training, I would suggest you create an internal FAQ for reps to reference during their calls to drive accuracy and consistency.

2. Record & Review

There are a number of tools on the market, which let you record sales calls. Use them. Make it a habit to review calls on a monthly basis, especially while new reps are getting ramped up.  By recording calls you have a way to continually educate and coach reps so they can optimize their message and prevent mistakes.

3. Customer Success Approval

With larger sales opportunities, it’s a good idea to loop in customer success toward the end of the sales cycle. This allows sales and success can go over the requirements from the prospect to ensure your product can fulfill their needs. Some success teams even have veto power over deals (although they need to use it carefully!)

4. Clawbacks

Institute a commission clawback for customers who churn quickly. Clawbacks can be a little tricky, so do your best to make it as fair as possible and only apply it to deals where the customers has been misguided. Doing so will keep retention in the minds of your sales reps. If you prefer the carrot to the stick, try offering the sales team a bonus based on year one retention.

Just as the marketing and sales teams will always have some level of tension, so will sales and customer success. These tactics will align the teams on a common goal, which will help improve the relationship between the teams, as well as churn.

Need to learn more about how sales and customer success can work together better in your organization? The Success League is a customer success consulting firm that offers a CSM Certification Program that includes selling-focused classes like Uncovering Opportunities and Managing a Selling Cycle. For more information on these classes and workshops, please visit TheSuccessLeague.io

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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.

Success on the Road: Chicago & San Francisco

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By Kristen Hayer

Last week I was in Chicago training the fabulous team from 4C Insights, and then back in San Francisco working with a couple of different teams, including the Customer Success CAP class at University of San Francisco. Over the past several months I’ve worked with people who were totally excited about training, and others who felt forced into it by their boss or company. This has me thinking about learning a lot.

Two thoughts I wanted to share: First, I’ve used StrengthsFinder with a number of my own teams, and one of the strengths that almost always surfaces for top CSMs is Learner. I believe this is because Learners like to ask questions and listen (great skills in CS!) but also because our field is changing. Those who never stop learning naturally keep up with trends and rise to the top. Second, I think you can always learn new things, even when you’ve covered a subject in the past. Practical tips, new angles on a topic, fresh ways to practice a skill; these are part of the continual learning that is so critical in CS.

What are you doing to continue to learn about our field? How are you helping your team grow their careers in success? Always be learning!

You're Not on the Sales Team, but You've Got Some Selling To Do

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This is a previous post worthy of resharing. See Ashley’s take on how Customer Success and Sales are closely related and oftentimes interwoven.

By Ashley Hall

Across the SaaS industry the debate about success teams owning revenue metrics, whether recurring or expansion, is a hot one. You’ll find strong opinions all over the map. Some are from the school of thought that “trusted advisors” from a success team cannot truly be trustworthy if they are responsible for a sales goal. Others say that success team members know exactly what their client’s needs are, and therefore can sell to them most successfully. Regardless of where you land on this spectrum it is important to acknowledge that all members of a company have some selling to do as a representative of the brand.

I think that a success team can find amazing motivation in exceeding a steep sales goal. In my career as an account manager, I have been in roles where I’m responsible for both expansions and renewals, and in roles solely focused on renewals where expansions were handled by a salesperson. I’ve appreciated the need to sell in both roles. Whatever the structure of your team, here are some thoughts on approaching both expansions and renewals from the perspective of a customer success manager.


Of course we all hope for relationships that are thriving and renewals that are automatic, but unfortunately this is not always the case.  When approaching a renewal, always provide as much time as possible; busy business contacts do not love a surprise. 2-3 months prior to renewal, schedule a call with all key stakeholders. When requesting and scheduling this call be sure to provide an overview of renewal logistics, sharing important dates and tasks. Ideally, during the renewal call you will be able perform your usual business review, understand the goals of the client for the upcoming year, and develop an action plan.

It is not uncommon for clients to use the renewal period to renegotiate their contract or scope out your competitors. These scenarios require significant salesmanship. You and your team should be prepared to re-sell your product at the drop of a hat. Since you already have an established relationship with the client you have the huge advantage of being able to highlight key functionality and any roadmap items that will continue to serve the customer's needs. Industry knowledge and an intimate understanding of where your product sits in the competitive landscape is critical to this conversation.


There are a number of ways to approach selling new products or functionality to a current customer. Hopefully, with assistance of a product marketing team, your customers are frequently updated on new offerings via email.  If so, this can be a natural conversation starter for your and your team. If not, you should establish a regular cadence of contact with your clients to cover product and service updates. Tracking calls with each client to your roadmap will help you be sure you have discussed every new offering as it is made available. These calls are important - they establish you as the client’s product advisor – so make sure they are a high priority in your day-to-day work.

Staggered releases or beta programs are other low-pressure ways to begin a sales process with your client. Presenting them the unique opportunity to participate in a beta release, prior to a purchasing decision, is a relaxed way to ease the client into improved functionality. Your client has a chance to see the value of what is being offered, which leaves you with a bit less selling to do.

Staying in touch with your client’s needs allows you to successfully sell to them. You’ll be able to advise them on how to use their existing solution optimally, but you’ll also be able to weed out new functionality that truly is not necessary for their organization. Selling strategically based on your client’s needs, not just every new thing, will yield greater sales in the future.

Regardless of the metrics your success department owns, everyone in a start-up is an important extension of the brand. Awareness of the competitive landscape and your product will empower every member of your success team to sell in a professional, comfortable way. 

Need to learn to sell through your customer success organization? The Success League is a consulting firm that offers a CSM Certification Training Program that includes selling-focused classes like Uncovering Opportunities and Managing a Selling Cycle. For more information on these classes and workshops, please visit TheSuccessLeague.io

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Ashley Hall - Ashley loves to lead account management and success teams; from training newbies to building processes out of chaos. 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 is a senior account manager for Copper, and brings her work experiences to her articles and classes. Ashley holds a BA from the University of Colorado, lives in San Francisco, and and enjoys global travel.

Strikedeck Radio - Episode 52


This week's Strikedeck Radio podcast features Evan Rich, Director of Customer Success at NS1. Kristen consulted with Evan to build out NS1's first health scoring system. Episode 52 details that process and what it took to create, how managers and the team are organized, as well as what Rich would suggest to other leaders who are on the same path. Listen in and 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.

Leading Best With Zest (For Life)

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By Lauren Costella

If I’ve learned anything this quarter, it’s that keeping a positive attitude and building resilience is everything. I should know this by now, after all, I was an elite athlete for 17 years of my life. And, from my experience, if you can’t find optimism amidst the hard times, you’re in for a rough athletic career for sure. That said, and I suppose with anything in life, sometimes we lose faith; we lose perspective; and with it, we lose our positivity and optimism. The past month and a half has been that for me.

In our careers, it can be easy to be overwhelmed by the pressure. You have metrics to hit, deadlines to meet, projects to deliver and customers, investors, your team, and other departments relying on your performance. And everyone has an opinion on how things should work. When I think about my biggest “fear” it’s disappointing others. I don’t want to be the person to let folks down: I want to kick butt!

This quarter, I lost a bit of that perspective. A few things occurred: my team was behind on our priorities and metrics; we needed to restructure to better serve customers; and then I had various changes occur in my personal life. At times, all of these “issues” can be overwhelming. All I saw, at the time, were the problems, and it was disheartening. And once that emotional cycle kicked off, it kept going. I would carry the negativity, sadness, and frustration back into the meeting room and that spilled over into all of my interactions (business and personal), and it became very destructive. But one person really helped keep things in perspective for me, and he’s my brother Sean.

To provide some context, exactly two years ago, my brother was diagnosed with a cavernous malformation. It’s a rare disease that causes a large blood clot. This blood clot was located in his brainstem, and it started bleeding. My brother was rushed into the ER because he had lost feeling in everything below his neck. They did a brain scan and found the bleed, but the Reno hospitals told him it was inoperable. They said this clot could bleed again, and next time, it would likely kill him. He, from their perspective, was a “ticking time bomb” and could go off any moment. He was only 28 years only, newly married (a little over a year) with a six month old daughter.

The news couldn’t have been more devastating to me and my family, but then Stanford Hospital reached out, and said they could do the surgery. He was flown to California for the procedure. There were many, many risks, and the least of which being paralysis and the inability to talk, but it was also his only chance to live. He had the surgery, and miraculously, he survived. Within 3 days, he was home, within 8 weeks he was working full time, and within 2 years, he’s learned to adapt to his new reality. He still has residual effects like double vision, numbness, and his arms feel like they weigh thirty pounds; however, if you speak with him (despite these new challenges and believe me, they are challenges), he is happy, smiling and thankful to be alive. He’s living every day and every moment with zest, and thankful for the journey.

I share this story because sometimes we forget to have perspective; we forget how lucky we are to just be living each and every day healthy and alive, and instead, we get lost in the minutiae of everyday small dramas and setbacks. As I was going through some of these rough patches this past quarter, Sean reminded me, not only how lucky I am, but also to be thankful for the journey, even the tough parts. He reminded me to keep my optimism and redirect negativity to other outlets; ones that wouldn’t keep this cycle of destruction going. And I thought I would share how I go about doing those things with you today, because I get it; the world can feel like it’s on your shoulders, but the trick is not to let it squash you.

Redirecting Energy & Embracing the Chance to Build Resilience

Life is made up of moments. Each moment is a chance to be present, to listen, to learn, to feel and/or to act and have impact. And more importantly, any moment can change the course of your life in an instant (just like my brother). I recently listened to a podcast by Sheryl Sandberg and she talked about her life changing in a split second, when her husband died. If there’s one thing really stuck out to me when I listened, it was her perspective on resilience. And it’s something all of us need to continuously learn and practice.

Going through hard moments is just that, hard. It’s really easy to get caught up and wrapped up in sadness, anger and the emotion. It’s understandable, and it’s okay to feel. But you have to feel and deal. And the dealing is what leads us to resilience. It’s the dealing that builds our strength, our perspective, and our ability to move forward.

But dealing can be its own challenge. I personally need to talk about what I’m feeling. I try to direct that to people I trust, and I really try (though this is admittedly still a work in progress) to put a limit on the discussion. It’s easy for me to spin forever on a topic, but at some point, talking and reliving just breeds more emotion. So, I curb this by setting a time limit rule on myself. I let myself talk/grieve for a set time (sometimes it’s 30 min, sometimes a few hours, sometimes days), but I set a limit. I am not always perfect in meeting that limit, but saying to myself, “Okay, I’m done with that topic” empowers me to move forward.

I also channel my emotional energy into activity. I run, play tennis, do yoga, and get my blood moving. By doing these things, I find both my mind and body have the chance to “let go” and underneath the rocky spots is fresh soil. And with fresh soil, you can cultivate a new garden of life. It may not have the same plants as before, but it’s a new garden of opportunity. And that is exciting, which leads me to my next point.

Keeping My Optimism with Positive Affirmations, Smiles, and Laughter

Pity parties are just that, pity parties. Staying stuck in the negative is a real drag. And if I bring one superpower to the table it’s this: my energy and optimism is infectious. It can light up a room and breathe life into everyone. At the opposite end of the spectrum, I can also suck the life right back out. Optimism and positivity, then, is an essential ingredient for my person. Each and every day, I do two things: I give myself a positive affirmation, and I laugh and/or smile at least once.

I know it sounds a little cheesy, but it’s so important to remind yourself that you are doing great; you are powerful; you are worthy, and you are your own superhero. When I wake up in the morning, I read a daily positive affirmation, and I say it out loud. This starts me on the right track of reminding myself that I am me and that me is awesome! And today, not matter what it brings, will be the absolute best day of my life! It’s incredible how something so small can make such a big difference in your attitude and energy. I challenge you to do it right now! Give yourself a positive affirmation! Tell yourself you are incredible and amazing. Try writing it down! It works; I promise. And the more often you do it, the more you’ll believe it.

The other thing I do is smile. Even when I’m not feeling like it, I make a point to smile at one person each and every day. Just the act of smiling bring energy and life to me (and others). And when I have life and energy, I can solve problems. I can approach issues from a place of inspiration and hope, not helplessness and and despair.

We all can get caught up in the craziness that is our daily lives, but the attitude in which you approach the tough stuff matters. Ask yourself: how do you approach your own life? How do you approach your job? How do you approach your relationships? You can dwell in everything that went wrong or you can celebrate what went right! And you can look at every tough moment as a burden or you can view it as a journey. And each moment is one to be thankful for because whether it’s building resilience or creating joy, it can change in an instant. And given that, well, I don’t know about you, but I know I lead best with zest for life!

The Success League is a customer success consulting firm that offers both a Leadership Training Program and one-on-one coaching. Let us help you learn and grow as a success professional and leader. Please visit our website for more information. TheSuccessLeague.io

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Lauren Costella - Lauren is a change agent, communicator, leader and passionate champion for Customer Success. When she’s not working as the VP of Customer Success for Medrio, you can find her serving as an advisor for The Success League, a board member for the Customer Success Network, and blogging on the CS Playlist. Lauren has her MA and BA from Stanford University. She was a former USA National swim team member and enjoys staying active in the Bay Area.