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Mastering CS – Candid Leader Insights – Ep 9 – Sadie Shepard

January 9, 2024 25 minutes read

Summary points:

In our new episode of the Mastering CS – Candid Leader Insights podcast, Irina Cismas, Custify’s Head of Marketing discusses with Sadie Shepard, Advisor and Owner at SADESHEP.

Let’s discover Sadie’s journey in marketing, sales, and customer success.

What you’ll learn:

  • Ways to enhance customer experience
  • Key elements of a successful business
  • How to handle difficult customers
  • The challenges of improving CS processes
  • How to choose the right tools for CS
  • How to build a case for a customer success platform
  • How to handle unexpected career challenges

Key insights and takeaways for CSMs based on the interview:

Successful business: The primary focus is on creating a personalized and efficient infrastructure, leveraging their experience in customer-facing roles and team collaborations. This includes strategically integrating technology, automating tasks, and developing standard operating procedures (SOPs) tailored to their needs. The goal is to build a self-sustaining business model that allows for focusing on enjoyable work rather than daily operational tasks.

Having the right tech stack: Effective customer success in today’s business environment relies heavily on a specialized tech stack, tailored specifically for customer success teams. This approach is vital for navigating and managing the complexities of the customer journey. Utilizing a dedicated customer success platform, as opposed to general CRM systems, enables these teams to handle intricate customer data and interactions with greater precision and efficiency.

Advocating for a CSP: The cornerstone of progress lies in enhancing data quality and meticulously evaluating the existing tools across various departments. Such an approach allows Customer Success teams to align closely with the customer journey, ensuring a seamless and efficient experience. By analyzing the capabilities and limitations of current tools and identifying gaps, Sadie effectively advocates for the implementation of a dedicated customer success platform.

Handling career challenges: Resilience in the face of adversity is a crucial aspect of professional growth, as illustrated by the speaker’s experience of being laid off in February 2020 despite stellar performance. This event, while devastating, highlighted the business-centric nature of employment and the reality of being perceived as a resource. However, the speaker leveraged this challenging period as an opportunity to apply their skills in a different industry, demonstrating the versatility and transferability of their expertise beyond the tech world.

Podcast transcript


Irina 00:04
Reflecting on the challenging year of 2023, in the field of customer success, if you could choose a movie title to describe your lessons learned this year, what would it be?

Sadie 00:16
Yeah, if I could choose the movie title, it’s a little bit heavy. But I think that I would choose ‘Revival Through Resilience.’ The reason for that is because this year has been a difficult one, I’d say, for SaaS in general, but especially for customer success managers. We’ve seen just a significant number of organizations not really knowing what to do with the function, ultimately.

And what that’s done is it’s just required the customer success managers to navigate all kinds of changes, and really meet these demands around retention and navigating customer relationships, in spite of the fact that at a more macro level, a lot of these organizations are struggling to keep up with some of the boom that we saw around the pandemic time.

So I think it’s just really been mission-critical for customer success managers to be especially resilient and adaptable over the last year or so, navigating a lot of ambiguity and variables. And ultimately, though, I think the revival is on the horizon, whether or not that’s directly in 2024. We’ll see. But yeah, that’s what I would call it.

Irina 01:39
And if there’s one thing you could have done differently from a sales perspective this year, what would that be?

Sadie 01:45
Ah, yeah, I think that I’ve reflected on this actually quite a bit. The thing that I would have done differently this year is just to evangelize the role more, up, down, and across the business. So what I mean by that is highlighting wins, separate from the metrics that we look at in a vacuum. To say, you know, here’s the contribution of CES, of course, we always want to be able to associate the function with revenue, whether that’s protecting it or growing it.

But ultimately, I think there’s so much that goes on behind the scenes with customer success managers. To just really brag on the role and the value that is being delivered outside of some of those metrics, I have some regret about not doing that, to the extent that the function deserves.

Practical ways to enhance customer experience

Irina 02:44
You’ve transitioned from corporate roles to business adviser focusing on blending different functions for better customer outcomes. Can you share some practical ways you’ve combined strategy, operations, and infrastructure to enhance and support customer experiences?

Sadie 03:01
Yeah, absolutely. Thanks for asking that. So, I think that one of the fundamental beliefs that I have is that customer success truly is business success. You know, in order for a business to deliver on what their goals are, which ultimately is growing and maintaining their revenue, there have to be intentional processes in place. And as companies grow, the way a $5 million company functions versus a $50 million company, versus a billion-dollar company, there are going to be a lot of different stages.

I think that what we’ve found is, more often than not, especially in SaaS these last few years, as these companies have grown, the infrastructure behind the company can’t necessarily keep up with the growth that’s happening. So, what does that do? It creates friction, ultimately, with the customer experience. So we have, you know, I really have a passion for auditing, if you will, where there are gaps today. What are some of the challenges that I’m seeing internally that are keeping customer success managers from being most effective?

And, you know, understanding from both a customer level as well as a customer success manager level, where are some of those disconnects? What needs to be solved for internally? More often than not, it ultimately comes back to maybe the operations, and just the way the day-to-day is designed, doesn’t actually support the overarching strategy. So I’m passionate about just understanding those things, creating things so that ultimately we’re measuring the right things. We’re creating repeatable outcomes for customers, so that customer success managers are enabled, and ultimately, both business and customers thrive.

Key elements for a successful business

Irina 05:06
You are currently focused on developing the business strategy and the foundation for your own business. What are the key elements you are incorporating into this, especially with your patient for operational design?

Sadie 05:20
Yeah, thanks for asking that. It’s been a journey, having spent over 10 years in corporate roles and now kind of being a glorified corporate dropout at this point. Part of why I’m doing this is because I have a passion for, you know, so much of what I’ve learned in being customer-facing, but also working for multiple different teams and organizations through journeys of growth. So, ultimately, the focus that I have right now, as I work towards launching my own advisory, is to get a framework in place. Understanding the strategy is one thing, the brand is another; there are all these sexy, exciting things that come with creating your own business. But for me, what I really want to design is an infrastructure that works for me, so my day-to-day is humming along.

And ultimately, in doing that, it will allow me to create a framework that I can take to other organizations that are similarly struggling with the foundational elements. Right now, I’m really focused on designing my singular tech stack as an individual. Questions like, where can I leverage AI in my day-to-day, what tasks can I automate, what will my SOPs look like? It all sounds fluffy and like a lot of work for a one-woman show. And of course, this will iterate as time goes on. But I think that it is so mission-critical, based on what I’ve observed in businesses in the past, that infrastructure is often lacking, or it’s not intentional.

So right now, I’m super focused on designing my version 1 of the infrastructure for my business, so it can run itself. And I’m getting to do the work that I enjoy, versus being in the weeds every day, with the business running me.

Go-to tools

Irina 07:22
And in terms of infrastructure, can you go a bit into details? I’m curious, what did you set up? What are your go-to tools that make you efficient, in what you do?

Sadie 07:41
It’s been a journey trying to figure that out. I’ve spent a lot of time, I would say, over the last three months or so, before I fully stopped in my full-time role that I had prior to this, doing a lot of research and ultimately trialing several different software. For me, Trello is something that I have been using for over a decade now. I think it’s super intuitive and easy. And that has helped me just take everything that’s going on inside of my brain and dump it into a singular space, and really start to be intentional about prioritizing. You know, what needs to happen and in what order, so Trello is something I’ve been leveraging, but I’ve also been looking at Zoho. I’ve had Dubsado, which is kind of an entrepreneurial CRM system, that I’m currently exploring as well. And, I can’t say enough good things about it.

But it’s actually really funny what I’ve learned through this process. There are so many tools out there, and a lot of folks in organizations ultimately have all these different tools in their tech stack. But many of these could be sunsetting one another. You know, there are ways to leverage Google Workspace, for instance, that can totally negate the need for something like Calendly. I didn’t realize that until I started to really get into the meat and potatoes and see what I need in my day-to-day versus what are the products I think I need. It’s been a really interesting journey, and I think ultimately, it will help me a lot with my consulting around businesses being able to get certain tools off their plate and really double down on leveraging what they have today.

But yeah, in the immediate, I’m trying to just focus on my CRM, and I’ve also really been liking Scribe, which is an AI that helps to create SOPs. So again, even though I’m a one-woman show, I would like to think that in the future I won’t be, and so I want to be really intentional about creating processes, even if it’s just for myself in the immediate. And I’ve really been enjoying Scribe. So that’s what I got.

Must-have processes

Irina 10:13
We’ll come back to talk about the processes, even if you are, as you mentioned, a one-man show and you are definitely wearing different hats, what are the processes that you consider are a must-have, even in a company of one?

Sadie 10:37
Absolutely, I think the most important thing is, or let me take a step back, the two most important processes in my mind are very intentional website design that supports the lead generation processes, which I can delve into a bit deeper. But I would say the first one is just having your digital presence designed and really integrated with your sales process. So that would be the first one.

And then the second one, I would say, is the onboarding experience. What I mean by that is, if I think about where my super focus is, what’s the first process that I need to plan? Where do I start with that, rather than just diving right into, you know, whipping up a website, and marketing myself this, that, and the other? I really think it’s important to be intentional about creating that repeatable kind of journey. So what does that mean? It means how do leads contact me? What’s the first step that I want them to take? Is it submitting a form? What are those 10 must-have things that I need to know because I need to capture that data for auditing what my business looks like, over the long term. You know, is it a video call or an in-person appointment? These things that seem so rudimentary, I think, are really important to get your hands around early on, so that you can start to understand what people are coming to me for. A business of this size, that’s $10 million, is frequently running into issues around this particular situation, maybe enablement for their CS team, or where are the quality leads coming from? Is it through my LinkedIn posts, or is it just organic SEO, or search, or whatever that may be?

I think that having a super well-thought-out contact qualification, proposal, and acceptance process, all of that, is what I’m focused on right now. And I’ll be honest with you, it’s a headache. It’s made me realize how much I’ve just taken for granted in the past, having worked with wonderful departments who set these things up for me. But ultimately, having grown and scaled teams, it is one thing that I hear over and over again. And I think brands have an incredible opportunity in the marketplace to differentiate themselves as a vendor if they can create that really repeatable, cohesive, predictable experience for customers. And that starts with when said customer is just a prospect. So I could nerd out about that one all day, I’ll spare you.

But yeah, that’s what I’m focused on. And then ultimately, onboarding. That sets the stage for anything and everything. I am so passionate about that, having been in the Customer Success arena before. You know, a poor onboarding experience can really be hard to come back from. So that’s phase two for me, is just creating a really repeatable, frictionless, high-touch, but low-effort on my end, onboarding experience.

How different roles shared the approach to customer success

Irina 14:14
I think you’ve managed to create those almost picture-perfect processes because you’ve also filled in various roles in your professional journey from being an account executive to being a digital marketer. So when you mentioned the source of opposition for leads, I was thinking of your digital marketer hat. Now, how do you think those different roles have shaped your approach to customer success? What helped you? What did you pick from those roles? And how did those skills helped you become a better customer success person?

Sadie 14:54
Yeah, thanks for that. It’s a great question, and I’ve done a lot of reflection lately around, you know, just the fact that I’ve had all these different roles as I’ve tried to narrow down what my services look like for my business. It’s been a fun game of combining all these different things that I’ve done and figuring out how they play well together. It’s interesting you bring up the digital marketing experience that I have because what I’ve really started to realize is that with customer success, once upon a time when I was first in marketing, the industry knew that marketing was important, but it struggled to define the value of marketing in terms of dollars. What I mean by that is, you can throw all these tactics out there, like blogging, SEO, user groups, and conferences you’re attending. Those are tactics, but what’s really going to drive the business forward and create the most deal? Where do we need to double down our efforts because it’s going to create the most revenue and opportunity for us in the marketplace?

So, with that, things like qualifying leads, ranking them as hot versus not hot, and whatever those underlying factors are, were once pretty subjective, I’d say. A lot of what we’ve learned about marketing over the past 10 years, I think, will similarly influence customer success. Right now, it’s a bit nuanced. There’s this need for customer success, but how do we actually measure the impact and the value outside of just retention or expansion metrics, or NPS, or whatever it is that we want to throw out there? I think the efforts of marketing once upon a time, which we’ve seen evolve over the last 10 years, have been an interesting observation for me, having been a marketer and now a customer success professional. Understanding that marketing, too, was once confusing for a lot of people, but super valuable. I think that will translate to customer success. We’re starting to see that. I’ve had a lot of conversations with marketing folks about exactly this. I think they should be some of our best friends in the industry because so much of what marketing is putting out there and measuring, both the data and the qualitative component, is very relevant and similar to customer success.

That’s my monologue about that. Having been a sales professional prior to getting into customer success, it’s funny, one of my longtime mentors had a bit of a reckoning with me where he said, ‘You’re great at sales, but you don’t like this, do you?’ And I said, ‘No, like, thank you for telling me that. I don’t, but I’m good at it. So I’m supposed to do it right, and you make good money, supposedly.’ It’s funny, I’m so appreciative of that conversation, because from there, that’s really where I pivoted and got back into customer success. I’d been in customer success, moved to account management, moved to new business, and then I went back into customer success after this conversation with someone I very much admire. He saw me and said, ‘You like the prescriptive side of the house, which is really what I think customer success is. It’s not just helping people. Yes, that’s a component, but it’s also being very prescriptive in, you know, what’s the problem? How do we critically think through that?’ I’m so grateful for him being transparent and just seeing me. Truthfully, I’m super passionate about customer success. As I said, I think that at the end of the day, it is so critical. With subscription models, you’re continuously having to sell and retain customers. And with that, it requires that you have super strong people on the client base inside and CS. Did I answer your question?

Working in sales

Irina 19:27
Yes, you did. I want to do a bit of a follow-up on this because you said that you were very good at sales, and you really hated it. And I want to ask you, first of all, why did you hate the sales part? What was that thing that made you run away from that function? What’s the part that actually helped you become a better salesperson?

Sadie 19:59
Yeah, I love this question. And I can just think of the folks that I’ve worked with in the past, and the clients as well, who are going to laugh if they ever hear this. But ultimately, I think that I didn’t hate sales. What I didn’t like about sales was that it felt like there was an ‘icky’ factor to it. And I’ll be honest, just the stress that comes with never getting a break. It’s like, ‘Oh, you’ve crushed it. And now we’re going to elevate things further.’ And you’re kind of like, ‘Wait, I’m looking for a quick exhale.’ That was something that, after having been in it for five years, just exhausted me. I was looking for a break, but I still wanted to be able to help people and really leverage the commercial side of what sales was.

So for me, one thing I really struggled with in sales, that I would say is ultimately the biggest deterrent for me, was that once I closed a deal, I didn’t want to let go of that customer relationship. At that point, I knew that Shawn was coaching his daughter’s hockey team, and they had just started fostering a puppy. And we were working through this long journey together of really partnering with one another to solve for a problem he was dealing with day in and day out in his business. And then it was ‘Sayonara, Shawn, here’s your team now,’ and I didn’t talk to Shawn again. It’s interesting, I think that I learned a lot about myself and just the working style of being solid in the relationships, digging into the pain, and coming up with what’s the root problem we’re trying to solve for. Who all can I bring on my side of the house and get on the customer side of the house to really quarterback getting things over the line and meeting those expectations and ensuring that the customer is going to be taken care of, but letting them go was tough for me.

So it’s actually funny when I moved over to customer success originally from sales, I ended up having a lot of the clients that I had originally been the salesperson for as an account executive, and re-inherited them as a customer success manager. And that was just so gratifying, to be able to really help ensure that the outcomes we’d agreed to were being met. But yeah, at the end of the day, I think the biggest thing that separates a good CSM from a great CSM has a lot to do with understanding the fundamentals of sales. I really can’t stress enough how much I think that’s going to continue to be important in the years ahead. The commercial skills, the negotiation, the ability to ask uncomfortable questions, to deal with objections, all those things. Ultimately, I can thank sales for having given me a lot of background that I think some folks may not have.

Deadline with difficult customers

Irina 23:24
I want to ask you a question about the sales skills that you were forced to develop that basically helped you in the CS roles. How do you deal with uncomfortable conversations in CS or how do you deal with difficult customers? What’s your recipe of dealing with those customers?

Sadie 23:49

Anyone who has worked with me, be it a customer or a colleague, will say that I am transparent. I’m as transparent as they come. And I think that when I’m dealing with customers who are frustrated, or past the point of frustration, the way that I approach that is with radical curiosity. Let them talk, take their responsibility. Whatever shortcoming has been there, just take it as your own. It’s not personal, it’s business. And I will say that the approach in handling things where a lot of times people just want to be heard. They want to know that their message is landing. I think about my experience when I’m a customer, whether I’m at a restaurant or I’ve purchased something and it shows up broken, and I have to call the customer service.

You know, I really try to be very intentional in how I handle those conversations and not make it about the delivery. Customers can be tough, but instead, I try to focus on the solution. We’re going at this together, I’m your partner in this, I’m in the trenches with you. Dump it all on me. I might not have the corrective action right this very moment, but we’ll work together. I’m here for you to get on the other side of this.

And it’s interesting that you bring that up because I have found that some of the strongest relationships that I’ve built with customers, and accounts that I’ve been able to grow and really get meaty insights into, have been a result of starting with reactive, really conflict-filled situations. It’s just interesting that once you get on the other side of that, you’ve really established some rapport and some trust, and ultimately an understanding that might not have existed prior.

But yeah, I shoot straight. At the end of the day, it’s business, but we’re all people. And I think that it’s just important. That’s important.

Challenges in improving CS processes

Irina 26:41
So you’ve mentioned that many companies struggle to synergize strategy, operations, and infrastructure to improve their CS processes. What are some common challenges that you’ve observed in this area? Why can they manage to do this? And what would be your recommended solution?

Sadie 27:03
Yeah, I think that it’s a good, it’s a great question. So, I think ultimately, what happens a lot of times is similar to what I was speaking about earlier, around crafting my own business and trying to be really intentional with setting the stage for success before just letting the business run wild. I think often, businesses, once they’re rolling, don’t pause to reflect on whether what they’re doing is working, or whether it’s actually getting them closer to where they’re trying to go. Especially in an industry like tech, we find we’re moving at lightspeed, things are changing very quickly. You’ve got to be agile, you might be under-resourced, significantly overworked, whatever it is, there’s not always a pause for reflection to say, ‘Where do we maybe need to restructure this?’ Or, ‘Is this process one that can be automated, or maybe even nixed altogether? Why are we doing it? Is it just because we’ve always done it, or is it because it’s legitimately necessary?’

In my observation, that sort of quiet reflection, if you will, an inventory of what’s going on, just simply doesn’t happen sometimes. And so, when you bring fresh perspectives, or folks like myself, who have experience working in silos outside of their particular function at that moment, you start to recognize things. Like, this part of our process, why are we taking a renewal conversation that starts with a customer success manager, but at a certain threshold, punch over to a sales executive? Is that really the best thing from a customer perspective? Is it a good experience? I’m in the weeds of their use case, but wait, I don’t have the commercial acumen maybe that the sales executive does to manage this conversation.

I think that some of those things that sound maybe a little bit rudimentary, we just forget, and it starts with leadership at the top. Understanding, you know, ‘Is what we’re doing really effective?’ Always being willing to innovate is important. But in order to innovate successfully, you have to prioritize, you have to take inventory, which requires intentionally taking some time out to just have that thoughtfulness. And then ultimately, you have to manage the change. I think that’s where organizations struggle as well. Sometimes they throw tactics or solutions at things, but if the change isn’t actually being managed, then it doesn’t go anywhere.

Choosing the right tools for CS

Irina 30:18
I mentioned that I want to go back to the idea of tools. And I want to ask you, how crucial is choosing the right tools and technology for CS success. Because I understand their perspective. I understand that, depending on where you are in a company journey, or in the lifetime of a team, the technology stack changes. I want to understand how important is it from your perspective, in the lifetime of a CS department.

Sadie 30:57
Yeah, this is a question that can really get me riled up. So, I think that the tech stack for customer success is, unfortunately, often overlooked. Frequently, I’ve experienced organizations that haven’t had a customer success platform in place, for instance. So, customer success has been reliant primarily on a Salesforce or a HubSpot, which ultimately are CRM systems. Whereas the sales side of the house or the marketing side of the house, support, finance, whoever else, they have their special tools, but customer success is expected to just kind of roll with bits and pieces of everyone else’s.

Going from that situation to adopting and implementing a customer success platform, as we did with that organization, was a huge game changer. It empowered the customer success team, but also garnered some internal recognition and respect. It showed that, yes, we have a seat at the table, and we’re a true strategic team. With that, it’s required to fundamentally understand what’s happening in the customer journey, where and when. Without a customer success platform, if you’re taking something like Salesforce, for instance, and trying to use that to manage your day-to-day, it’s not going to work the way that you want it to at a certain level of the organization. When there are several complexities, whether it’s with regard to use cases, or the industries and the way that you’ve segmented how you look at your customers, you can only go so far with something like Salesforce.

I think that companies need to be very intentional about what’s the purpose of customer success? How are they set up for success or friction in their day-to-day? More often than not, what we find is that it’s a lot of work to implement any of these tools. And there’s so much customer data all over the place that a lot of times, customer success managers end up using things like Excel, or their own personal wheelhouse, and there’s not that overall infrastructure and tech stack in place that allows them to really be efficient in their day-to-day. I think that anyone who is a customer success manager and regularly hears feedback from their team about feeling like they’re spinning their wheels or can’t get enough done, should consider what the tech stack in place is today and how the team’s working, and advocate where you can to try and streamline it. Because I know that has been a huge challenge of mine in the past, and ultimately, a solid customer success platform is something that empowers the rest of the business as well. I think that that’s a case worth making. So, does that answer your question?

Building a case for a Customer Success platform

Irina 34:32
Yes, it does. And I want to follow up, how did you build the case for a CSP in the past? How did you get it funded? Because I know a lot of CSMs are forced to work, as you said, in tools that are dedicated for other teams. And they have a hard time proving the value. How did you do it in the past?

Sadie 34:57
I have failed and I have been successful. So I want to start with that. It’s actually pretty funny, I was super bullish on ChurnZero. I’ve worked for an organization that was eight companies glued together over two years. And with that, you can imagine the systems, the processes, the data, all just kind of disparate and all over the place, which was extremely challenging. One of the things that I really wanted to get in place was a customer success platform. And I knew that if we were to get a customer success platform, the first thing I had to do was get a lot of the data in significantly better shape. I also spent a lot of time auditing some of the tools that we had in place today that belonged to those other departments, understanding how in-depth I can get within a Freshdesk to analyze this customer and what they are complaining about, or great, they’re super engaged, regularly reaching out to support to get little tips and tricks here and there.

I spent a lot of time trying to understand all these different tools that we were leveraging outside of any sort of customer success platform. And ultimately, that’s how I built my case – there were deficits here, here, here, and here. We were trying to do this, this, this, and that, but we’re spending x hours. Getting super granular takes time and focus, but that was a huge initiative that I wanted to be able to reach. So, quantifying that, getting direct feedback from the team, that was something I was super intentional about. Thinking, you know, trying to advocate for something because it’s what you want, and it makes your life easier as a leader, is one thing. But knowing what my team is running into day-to-day, those were all things that I brought up and presented in my case for it.

Then ultimately, I spoke quite a bit to other departments to understand what disconnects they’re feeling with customers. Because at the end of the day, to be really solid in your role as a customer success manager, there is so much reliance on understanding what other things are happening behind the scenes, separate from conversations that you’re having as a customer success manager. A lot of that focus was on not wanting to look uninformed. But we look sloppy to the customer when Sadie’s reaching out, and meanwhile, I had no idea that Irina had just had a conversation yesterday, and something’s up in flames.

So I think that those are things that are just going to become more and more critical, I would say, as businesses look at the CS function – like, how do we actually support this team to be effective? At the end of the day, we’ve got to have a cohesive story. We can’t have all these different bits and pieces. It’s not the best use of time for CS to try to put a story together.

Learning from mistakes

Irina 38:22
I want to ask you about mistakes because I think mistakes are the biggest source of learning. So what was your latest one? Or the ones that you remember you’ve made in your CS role that actually turned into a valuable learning experience?

Sadie 38:45
Yeah, that’s a great question. I think one of the biggest mistakes, maybe one of the biggest mistakes, I’d say, is waiting for others to take action on things that I could. I realize that’s a little bit vague. But what I mean by that is, with customer success, the demands from customers never slow down. So, one thing that you can control is creating content, creating templates, and being intentional about how you’re spending your time and creating a strategy that works for you. I’ve spent time in the past trying to be everything all at once to everyone and ultimately, failing to plan is planning to fail. Having just the intention to ask ‘Is what I’m doing moving the needle? Is this purposeful?’ That’s something I’ve struggled with in the past.

Most recently, I’d say one of my biggest mistakes and learnings was not taking the responsibility to advocate for customer success and all the work that was being done for the team, beyond those metrics we spoke about earlier. That’s something that I recently came up against. After some reflection, I was like, ‘Where did I fall short?’ And it’s like, I should have been more proactive internally, with sharing some of the things the department was doing, instead of assuming that because these other departments or leadership has access to see what we’re doing, I should be bragging on this stuff more. So, that was a recent learning.

I think one other thing that I just want to highlight, while I’m here on my soapbox, is communication. Over-communicating is just, that’s a mistake that I see made so frequently in business, and especially for customer success, like, over-communication is critical. As is understanding how your counterparts and your customers like to communicate. Don’t assume everyone is like you and wants to go back and forth over Teams. Maybe they want to pick up the phone, maybe they want to have a 10-minute touch base once a month. Maybe they’re happy for you to just send them a Vidyard video every now and then to check in. I think that’s another mistake that I frequently see made – people are frustrated with not being able to get responses from their customers or teammates, and it’s like, take a step back and consider: Are you communicating in a way that works for you, or a way that works for them? So, I’ll step off my soapbox now.

Navigating unexpected career challenges

Irina 42:00
You’ve been very open about being laid off in 2020. Despite your high performance, can you walk us through how you navigated this unexpected career challenge? And what kept you motivated during that time?

Sadie 42:13
Yeah. So, in February of 2020, I was laid off. The quarter before, I’d had stellar performance. I was so proud, I felt like I was at the peak of my career at that time, and it was extremely devastating, which is probably the right word to use. I felt very much like a resource for the first time in my career, where, despite the work and the care that my manager at the time had for me, and the love that I had for my team and what I was doing, at the end of the day, this is business, and I didn’t have a job there anymore. That was a significantly challenging time for me.

But what I took from that experience was all that I had learned in my professional role up to that point, and I was able to apply it to a different industry for a little while. I do not like to sit around and twiddle my thumbs. So during 2020, I pivoted to a different industry and was ultimately very successful in that, using the skills that I thought were so specific to the tech world.

So, I think that anyone who is going through a layoff, you know, there’s such like an identity crisis at the time, and you’re questioning a hundred things. There’s so much to say, but number one, just process for a minute. It’s okay to be devastated over it. Just because it happens with any sort of frequency these days doesn’t mean that your experience should be minimized. And ultimately, know that the situation gets better, and everything that you’ve done up to that point is going to take you places. You still have the stuff to take you elsewhere.

For me, I pivoted during 2020, and then I got back into SaaS, and it’s not true that leaving tech means you can’t get back into tech. I hear people say that sometimes, and that’s bogus. At the end of the day, I just can’t stress enough: give yourself some grace, process, and ultimately, just keep moving forward.

I don’t know if I answered that question in full, but that’s my piece on that. But is there anything else that I can add to that for you?

Moving to a different industry

Irina 44:50
I want to ask you, what do you think were the key factors that helped you succeed in a different industry and then make you successfully return to it?

Sadie 44:59
Yeah, it’s so funny, what helped me do well in another industry was having a lot of those soft skills, which I thought at the time were great, but also some of those hard skills that I learned from being tech-savvy. You know, we work in tools and different systems, and we love to leverage automation. Those were things that I was able to apply to real estate for a while, where I worked with transaction and operations for these teams. I was able to take a lot of the streamlined automation components, if you will, and apply that to this powerhouse of a real estate team that was just so inundated but didn’t even know where to put it all.

The other thing that was great was, you know, I knew how to read contracts, how to negotiate, and had the leverage. One thing that I thought about with real estate is the experience of having been in uncomfortable situations and hearing ‘no’ frequently from a sales perspective. It really helped me develop some thick skin. I think you have to have that; real estate is a super competitive industry. There’s an emotional toll that is often involved with buyers, there are tons of financial hoops, there’s just a million things that could go wrong. I’m appreciative for having had that opportunity.

Because I think that, ultimately, what led me back to Tech was that I knew it was a temporary thing. I kind of treated it like what it was. But what led me back to Tech was that I missed the level-headedness, if you will, of working in the B2B space. And that was one thing that served me and differentiated me, if you will, when I was spending time in another industry – just the acumen for business that not everyone necessarily has outside.

Advice for CSMs

Irina 47:28
Reflecting on your journey, especially the resilience you’ve shown through career ups and downs, what advice would you offer to CSMs to stay inspired and effective in their roles, especially in challenging times? If you wrap it up in one piece of advice?

Sadie 47:46
Yeah, I want to be thoughtful about my response to this. I think the biggest advice I would give customer success managers is just to slow down to speed up. I think that goes beyond customer success, but it is a role that has a lot thrown at it all the time. And ultimately, there’s still ambiguity and nuance from one organization to the next. As CSMs, it can be really easy to get sucked into your world and your role and think, ‘I’m not doing enough,’ or ‘Why am I burnt out?’ or ‘Why can’t I solve this problem independent of a peer or a counterpart having to get involved?’ At the end of the day, I think it’s so important to just exhale.

Just remember that everything has its highs and lows, and I think this year, especially, has been really tough for customer success managers with just burnout in general. There’s tons of evidence out there that would support me in saying that. But at the end of the day, customer success managers are more often than not in the role because they’re in the business of helping people, and they don’t give themselves enough credit.

So I would just say, slow down to speed up, enjoy the end of the year, and be optimistic about what’s to come because it’s easy to get into a negative headspace and spiral, but that doesn’t do anything for anyone. So just, yeah, that’s my advice.

Predictions for customer success in 2024

Irina 49:42
As we wrap things up, I love to hear your thoughts on the future. What are your predictions for the customer success industry in 2024? Are there any trends or changes you foresee that we should all be keeping an eye on?

Sadie 49:55
Yeah, I think that for 2024, we’re going to see tons of hype around AI. And that in itself is a whole separate saga. But ultimately, in 2024, I think Customer Success (CS) will be impacted by AI, which is great in a lot of ways, especially if you can leverage it to make your day-to-day more efficient. I think that we’ll also continue to see more specialization and needs for specialization in Customer Success.

The last thing that I would add to that is just the emphasis on commercial ability and overall sales aptitude. I think that’s something we’re really going to see customer success managers needing to develop. It’s not just about being buddies with the customer and having those soft skills, but we’re going to see organizations really start to invest in customer success managers being commercially equipped. So, that’s what I would say about the outlook for 2024 in the Customer Success field.

Irina 51:05
Thank you very much for that! It was a pleasure to have you with us today.

Sadie 51:13
I appreciate it.

Nicoleta Niculescu

Written by Nicoleta Niculescu

Nicoleta Niculescu is the Content Marketing Specialist at Custify. With over 6 years of experience, she likes to write about innovative tech products and B2B marketing. Besides writing, Nicoleta enjoys painting and reading thrillers.

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