3 Lessons From my First 3 Years in Customer Success

In June 2018, I accepted my first official position in Customer Success. I had graduated from university just back in December and my first job out of college was, let’s just say, not what I expected it to be.

Hence why I was only there for 6 months.

I had moved my wife and I out to Arizona to start a new chapter with this job and was feeling pretty foolish at this point. I had just found out about this cool new space called “Customer Success” a month or two prior to getting this gig so I was hoping and praying it would work out.

3 years later, and I can say that choosing to persue a career in Customer Success is the second-best decision I’ve ever made (2nd only to marrying my wife).

My first gig was a Client Advocate position for a social media marketing company in Scottsdale. I was there for a year and have been working as a CSM for a global software company that creates Virtual Data Rooms for the past two years. It’s been an incredible journey and I’ve grown in ways I didn’t think was possible for the first few years of my professional career.

If I could give advice to any college graduate who is unsure about what they want to do career-wise, it would be to get a job in Customer Success. The skills you will learn and the community you will be a part of are unmatched.

So, with three years under my belt of working in the space, here are the top three lessons I’ve learned thus far:

The Customer may not Always be ‘Right’ but They are Always the Most Important

Sorry Sam Walton, but “The customer is always right” just isn’t correct anymore. As Customer Success Managers, we need to know our product and services better than our clients. This will help us provide them with the highest possible value when working with us.

And because of this, sometimes the client may request something that we can’t offer directly, have a misconception about what our product actually does, or even tell us what our product should be doing when in reality, it just doesn’t work that way. These kinds of conversations happen and sometimes we can’t deliver on specific requests exactly how the customer wants us to.

But because we are knowledgeable about our product or service and care about our customers, we can always offer some kind of workaround and alternate solution that can help our customers get where they want to go. A huge part of CS is delivering on customer’s desired outcomes. And sometimes we need to help them see how our product can do just that even if it may not be what they expect at times.

Working for a social media marketing company, I had to have these conversations nearly on a weekly basis.

Customer Success can only be Attained through Consistent Cross-Department Collaboration

Customer Success, when done right, isn’t just a department. It’s a company-wide mindset.

That means it’s up to Customer Success Managers and Leadership to ensure that other teams are doing what is best for the customer in the respective duties. Usually, this starts with teams like sales and product. Both of these teams are critical when it comes to company growth and customer satisfaction.

Breaking down internal silos is a key duty (often “unofficial”) of Customer Success. We, as CSM’s, are on the frontlines helping our customers succeed. But teams like product are working behind the scenes to ensure our customers are being successful with adopting the product. And teams like sales and marketing are helping to bring in new business to help the company grow and stay “afloat”.

So to ensure our customers have all the tools and training they need to succeed, it’s imperative to have conistent collaboration with these teams. This can be done in a variety of ways. This article isn’t meant to explain it all in detail but having open lines of communication through meetings, Slack channels, and informal conversations is a ‘must’ not only to help the company grow but to help the overall culture of the company actually be something to brag about.

My Job as a CSM is to Make the Lives of my Customers Easier

Simple as that. An organization can only be as successful as its customers. And the first thing you need to look at when assessing the success of your customers is how easy it is to use your product or service.

No matter how complex your product may be, it’s your job as the CSM to help your customer adopt and see value in it as quickly as possible. Value for your customer can be measured by how easy it is for them to achieve their desired outcomes.

So there you have it, folks. 3 simple lessons.

What have been your top lessons from your time in Customer Success?

So You’re the First Customer Success Hire at Your Company…

Congratulations! You’ve joined the exclusive club made up of individuals who are the first customer success hire for an organization.

What now?

Well, since Customer Success is still a new concept, every organization and every situation is different. We know that many organizations are finally starting to see the value in having a solid CSM team and are making the right moves to put it in place.

Take my experience for example. I was the second Customer Success Manager hired at my current company. It was me, another CSM that had been hired about 6 months previously, and the Head of Customer Success who was a woman who had been with the company for about 5 years working in various roles. When I was hired we had a cheap CRM and that’s about it. No playbooks, no CS Software, no real CS processes in place. I was still pretty new to my CS career so this was an exciting challenge to be a part of a CS department that was basically in “start-up” mode.

Now, a year and a half later, things are much different. We have HubSpot, Churn Zero, a Customer Journey Map in place, playbooks and processes so we know what’s expected for us to excel in our roles, and have a growing global team of rockstar CSM’s. It’s been a fun, bumpy ride up to this point and we’re still growing and evolving every day.

If I could sum up what I’ve learned being one of the first CSM’s at my company, it would be this: Collaborate with your fellow CSM’s on a daily basis and never be afraid to voice your ideas. As I said earlier, Customer Success is still new so many of your ideas on how to improve, streamline, and innovate things can be very valuable to the department’s and company’s growth.

So how about being the first Executive of VP-level Customer Success hire?

After doing some field research on the subject, I came across some great advice and best practices.

For starters, Gainsight wrote an article about this very subject and outlined the 7 most important things every new VP of Customer Success should prioritize:

1) Understand your customers
2) Understand your team
3) What is your segmentation strategy?
4) What is your engagement strategy?
5) What tools do you have at your disposal?
6) What are the boss’s expectations?
7) Make sure your CEO is all-in

Read the full article here: https://www.gainsight.com/blog/youre-the-new-vp-of-customer-success-now-what/

I also asked my fellow LinkedIn community about their experience being the first CS hire. I asked them to share the top 2 or 3 lessons they learned. And, as always, the advice did not disappoint.


1. Success teams are most reactive when they aren’t communicating or collaborating well with product, support and sales.

2. Digital engagement is key for Success teams, especially when there’s a large SMB customer base at play, but paradoxically, self-service strategies are useless if you don’t continue enough 1:1 conversations to know what your customers pain points are.

– Liz Stephany, Director of Customer Success at Close


Learn as much as you can about the sales process and do some support tickets to quickly learn what customers are regularly struggling with.

– Rav Dhaliwal


1. We know enough to listen and “love” on our clients, but are we doing this internally with our team? Continually improving new hire onboarding, and taking the time to understand each CSL’s superpower has been helpful in creating harmonious collaboration. Advocate and support your talent like you would your top client.

2. CS moves fast and information changes daily. Don’t assume that other key players across the organization know what’s going on. Take the time to pause and educate others on your process and share the “why” behind the decisions that you make to create buy-in. Trust can be ruined when decisions are made in vacuums. 

-Amanda Torrelli, Associate VP of Client Success at Mongoose


1. Be flexible. Customer Success is an integral part of any organization. With as much weight as CS holds, you can’t expect processes and procedures be 100% correct in their first iteration – fleaxability is key

2. The challenges you are facing are not specific to you/your organization. Leverage your network, connect with other CS professionals and don’t try to recreate the wheel for everything.

-Nashad Abass, Customer Success Manager


Lesson #1 – Infront of the customer, you are the CEO of the company and you got to own everything.

Lesson #2 – You got to set the expectations right at your customer’s end.

Lesson #3 – Its okay to question the processes at your organization and suggest changes which can expedite the delivery to your clien

-Amit Bhadu


1) Recognize that your CSMs will likely be more reactive to begin with and take that into consideration in your planning. There are probably a lot of quietly frustrated customers out there that no one is seeking out.

2) It’s already been said, but active listening in the first 30-60 days is critical to get a sense of what you need to prioritize. This applies to both customers and employees. Go on a relentless pursuit of learning WHY things are the way they are.

3) Don’t assume you’ve got the “playbook” from previous roles. Every company’s needs are different. Apply your best practices from the past, but don’t assume that they will all have a place.

-Parker Chase-Corwin


Make sure Executive Leadership is clear on why they are hiring YOU and why NOW. I’ve joined organizations where the leaders thought they understood CS or why they needed the function but clearly “didn’t get it”.

-Kristi Faltorusso


Progress over perfection, the program will constantly evolve. Be scrappy don’t get stuck over-engineering for scalability. Get started simple see what works and resonates then iterate. Build a foundation of every interaction adding value to the customer not a culture of “checking in” noise.

-Samantha Styles



Learn as much as you can about the sales process and do some support tickets to quickly learn what customers are regularly struggling with.

– Rav Dhaliwal


1. We know enough to listen and “love” on our clients, but are we doing this internally with our team? Continually improving new hire onboarding, and taking the time to understand each CSL’s superpower has been helpful in creating harmonious collaboration. Advocate and support your talent like you would your top client.

2. CS moves fast and information changes daily. Don’t assume that other key players across the organization know what’s going on. Take the time to pause and educate others on your process and share the “why” behind the decisions that you make to create buy-in. Trust can be ruined when decisions are made in vacuums. 

-Amanda Torrelli, Associate VP of Client Success at Mongoose


1. Be flexible. Customer Success is an integral part of any organization. With as much weight as CS holds, you can’t expect processes and procedures be 100% correct in their first iteration – fleaxability is key

2. The challenges you are facing are not specific to you/your organization. Leverage your network, connect with other CS professionals and don’t try to recreate the wheel for everything.

-Nashad Abass, Customer Success Manager


Lesson #1 – Infront of the customer, you are the CEO of the company and you got to own everything.

Lesson #2 – You got to set the expectations right at your customer’s end.

Lesson #3 – Its okay to question the processes at your organization and suggest changes which can expedite the delivery to your clien

-Amit Bhadu


1) Recognize that your CSMs will likely be more reactive to begin with and take that into consideration in your planning. There are probably a lot of quietly frustrated customers out there that no one is seeking out.

2) It’s already been said, but active listening in the first 30-60 days is critical to get a sense of what you need to prioritize. This applies to both customers and employees. Go on a relentless pursuit of learning WHY things are the way they are.

3) Don’t assume you’ve got the “playbook” from previous roles. Every company’s needs are different. Apply your best practices from the past, but don’t assume that they will all have a place.

-Parker Chase-Corwin


Make sure Executive Leadership is clear on why they are hiring YOU and why NOW. I’ve joined organizations where the leaders thought they understood CS or why they needed the function but clearly “didn’t get it”.

-Kristi Faltorusso


Progress over perfection, the program will constantly evolve. Be scrappy don’t get stuck over-engineering for scalability. Get started simple see what works and resonates then iterate. Build a foundation of every interaction adding value to the customer not a culture of “checking in” noise.

-Samantha Styles


To read my nearly 150 answers I got on my LinkedIn post, click Here

So friends, if you find yourself being the first CS hire for an organization, you’re in for a fun ride. There will be challenges along the way but make sure you have an open channel of collaboration with your team and the C-suite and a clear vision of what you want to accomplish for the organization.

Best of luck to you and, if you’re not only new to the org but new to Customer Success, welcome to the family!

Additional Resources

https://www.linkedin.com/pulse/one-step-time-lessons-learned-from-building-customer-success-steve/

https://360leaders.com/2020/10/09/customer-success/