Sean MacPherson

1) Customer-facing expertise. The first one is what I like to call a customer-facing expertise. So what that means is: being the expert on the challenge you are solving is key. In the past several years, the buying cycles have really changed. It's all about educating your customers, not only why you understand their challenges today, but how you will solve them in the future. With so many products out there, the switching costs are really low. So if you are helping your customers think about their challenges in the future, or if you aren't rather, they're looking elsewhere because software is a commodity at the end of the day, especially in growing markets.

2) Customer-advocacy flywheels. Another way to look at this, even from a customer success angle, is customer-advocacy flywheels, as I like to call it. Advocacy in itself is such a key component to the success of everything: marketing, sales, and your customer efforts. Being able to tell those stories of success in the what, the how, and the why of their journey with your solution is such a powerful tool to leverage as any type of output. So whether it's like a traditional case study or more in a Slack group, like we've seen rising more and more today with the industry expert ones. So just being able to have more feet on the ground that aren't just your go-to-market folks.

3) Lead with telling your customer stories. I would say the last one is it really does lead in this kind of like dovetailing into this is lead with telling your customer stories themselves. Everyone loves a story. One company I always look up to, one leader I always look up to is Bob Iger, who was at the helm of Disney for a long time. So everything they do, they do it with a purpose, an experience, and that's all wrapped up in a story. That’s because people love stories, and if you can take your customers on a journey throughout your funnel, they're going to be your biggest advocates over time, in terms of just your biggest customers, your biggest champions, your biggest folks on social, you name it, that story is going to resonate. I think that's really inspirational and into turning that market, or that network effect, into revenue.

Two big ones, just because they're really big ones, and I think everyone runs into these.

1) Competitive markets. So we're in a newer space, in a newer market. So competitive markets, naturally they're challenging. It's so easy to build a product today. So as a market matures, you get so many competitors that are coming in that you have to really hone in on what you do and where are you going. We've had this struggle because companies come in with a fresh perspective of how to solve problems. You have to really focus on articulating why your vision, your product, and your experience, and what they should be investing in from the customer standpoint. And that's a big challenge as competitors are coming in fast and furious, especially challenging your sales, your sales narrative, or your market narrative, or even your customer narrative. Just being ahead of that, it's always a headwind.

2) Turnover and the great resignation. I think the other one is, and this is a big one, like everyone has it, especially in the past couple of years, is turnover and the “great resignation.” I think again, everyone's having this challenge. And not only during the pandemic, but post-pandemic world. Specifically in my realm with customer success, it's exploded. Investors and companies are starting to really understand how these investments in customer success have long-term payoff in terms of lifetime value. So naturally it's created a lot of challenges in retaining talent. So we've had to really focus on why our company and our organization is one where it becomes a launch pad for careers in customer success. So we think about how are we investing in the careers of folks and how are we ensuring they have paths at our company? Or, they are getting the skills and expertise to take that on at a new company and grow in their careers because that's really where a lot of the narrative has started to change, pandemic and post-pandemic world.

1) Growth at scale. Every company runs into this at different stages. So how are we continuing to scale without heavy investments, but still giving a world-class experience because that's at the core of our DNA? So it's a delicate balance of testing new methods, or appropriate experiences, to be able to help customers get value on their own or self-serve that value. So this takes time, especially in new markets like ours where we're flipping the script. So we are constantly testing and iterating on things. Some of these things will work. Others will fail, but it’s all in an effort to try and scale our business and put our customers in control versus us in control. So we want them to essentially get to value without us, and we want them to feel empowered to get there.

2) Ruthlessly prioritizing. At our company, we want to do everything. Being in a market that's traditionally working with agencies, we tend to think of ourselves trying to do everything. And that's a trap that you can fall into. We definitely fall into it. But the end of the day, we have to be thoughtful about what we do and what will lead to the most impact for our customers. So we are constantly reviewing, removing noise, to ensure we are focused on those right things for our customers that align to our vision.

3) The upsell flywheel. I've run into this roadblock at every company. It's what I like to call the upsell flywheel. We have an amazing customer success or value-led motion that leads to upsell. But we haven't necessarily codified that to understand, “What are the exact behaviors that lead to growth in our customers, specifically?” It's been a challenge at every company I’ve been with. The goal is, “How do you create an alert system that tells you when it's time to have an appropriate conversation about new features or upselling?” Not just kind of peppering them all the time. We're just embarking on that behavior-mapping journey right now to figure out, “What are those key moments?” So instead of going to our customers and saying, “This is a great new feature.” When are they ready for that feature? When does it make sense for them? To actually start educating them about that based off of what we're seeing them do.

1) Inverting. This is always my favorite one. So, inverting a problem. I really credit this to David Cancel, who really helped distill this thoughout the company at Drift when I was there. It's about looking at the outcome and finding all the places it could fail. So you, honestly, don't go there. It gives you less of a cloudy view of how to find the right critical path and avoid all of those failure points along the way.

2) Honestly, just being comfortable with failure. I think this is something that a lot of people struggle with, or aren't comfortable with, but it will help you learn and grow. So fail fast, test things, iterate. No one has a playbook for your business or the right framework. So it's all about testing it and finding the break points for improvement.

3) The scientific method. It kind of goes with being comfortable with failure. I'm a huge nerd. One of my favorite YouTubers is Mark Rober. I love embracing engineering in everything I do with planning. So when we're looking to make a change, we have to make sure it isn't drastic enough that when it either is successful or a failure, we know exactly what made it so. So, making one change, testing it, and quickly iterating it is a constant philosophy of my team and the priorities that we take on.

1) Listen to your customer stories. This is my favorite one. Every sale, lead, and customer has a slightly different perspective as to why they're buying. Understanding those stories and who the people are in those seats are so key to being successful in selling cycles today. People want to buy into a vision. They want to hear stories about how other people got there. I think long gone are the days of feature selling or tossing out random metrics to really wow an audience. If you can tell a compelling story about where a person started, their result, and then most importantly, how they got there, you're going to win that customer every single time.

2) Customer-led growth. What is becoming this more trending topic, which is called customer led growth, and credit to Chris Hicken over at NuffSaid for championing this philosophy, is focusing on the value customers receive versus the value the company thinks their customer should receive. So when we're making decisions about how to improve the experience with any part of our company, it's like, “How are you incorporating the customer data to make that decision, whether it's quantitative or qualitative?”

3) Focusing on where to market, sell, and service where you perform best, and segmenting off that. Some folks call it ICP. So meaning, where you address your customer's problems the most, service is lighter because there's a clear path, and that segment of the market clearly resonates best with your customers. So essentially, it’s easier for them to resonate with why they're buying this, how to get there, and how to be really successful with it. You're going to spend a lot less time and money selling those folks, marketing to those folks, and servicing them.

I'm going to cheat because I'm going to put one on my team.

1) Ethan Walfish. I learn from him every single day. I'm so, so thankful that he's actually on my team. Ethan Walfish is our support leader. He's amazing. He's not only built an organization from scratch, and the structure to support it, but he did it people first. This is generally challenging, especially in support, but we have scale across all time zones and we've introduced global support with ease. He's also a massive contributor to the support-driven community and gives back to a ton of folks there.

2) Howard Greene. A mentor of mine. He's a multi-time CFO with many scaling companies. Part of being a successful operator is understanding the business inside and out and the opportunities that presents. So he's my go-to person for advice when thinking, pressure testing new ideas, making sure we have the right barometers in place, thinking about how investments impact us three years out, et cetera, et cetera.

3) Kristi Faltorusso. Someone I don't know personally, but I feel like I know her personally because she gives so much back to the CS community through sharing her playbooks, is Kristi Faltorusso over at ClientSuccess. Her focus on showcasing how customer success is a revenue driver and how CS leaders can get to the level of other leaders in an organization is spot on. She's given back so much to the CS community and leveled up so many leaders in the last several years. And honestly, she's one of the top CS leaders in revenue operators out there!

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