Sarah Cunningham-Scharf, Head of Customer Success at Great Question, talks storytelling in CS, turning customers into champions, and the power of public speaking

In Vitally’s series, ‘17 Questions with the Future of Customer Success’, we’ll chat with Customer Success professionals, from Customer Success Managers to Chief Customer Officers, and everyone in between, to gain insight into both their individual roles and the ever-evolving Customer Success space. 

In this episode, we’re chatting with Sarah Cunningham-Scharf, Head of Customer Success at Great Question.

About Sarah

Meet Sarah—Customer Success leader, customer feedback fanatic, and storyteller. Sarah is based in Toronto, Canada, and has been working in Customer Success for two years. Prior to heading up Customer Success at Great Question, Sarah led Customer Success at Before working in Customer Success, Sarah held content and field marketing roles, and was operating as a freelance journalist.

One thing Sarah hopes exists in the future is Dog Halloween—where all the neighbourhood dogs get dressed up and go door to door asking for treats and scratches.

About Great Question

Great Question is democratizing customer research for product teams, designers, and marketers at leading organizations like LinkTree, O’Reilly, MainStreet, Vero, and beyond. Great Question empowers teams to make customer research a part of every sprint by enabling them to build a panel of customers to interview, survey, or get feedback on a prototype in one place. 

Q&A on the Future of Customer Success (Extended Cut)

Vitally Team: What’s your ‘before work’ ritual?

Sarah Cunningham-Scharf: So I am super fortunate to work for a remote first company with flexible hours because I am absolutely not a morning person. 

Normally I wake up and focus on getting myself into a state that's fit for other humans. So that's a positive headspace. A couple cups of coffee, some meditation, and stretching. And then with my second cup of coffee, I'll sit down and start by checking email for anything urgent from customers before putting my to do list for the day together and prep for the day's projects in meetings.

The Current State of Customer Success at Great Question

VT: What are the top 3 activities you spend most of your time on doing in your current role as Head of CS?

SC: So that's actually a super easy question to answer. So as the first person in customer success at a startup, you have three main pillars to hit. The first is customer relationship development, the second internal process optimization, and the third would be figuring out how you're going to scale over time. 

So my time is really split between interacting with customers through channels like zoom, intercom, Slack channels that we share with our customers, so that I can help them use our platform successfully. Then I spent a ton of time working internally cross-functionally to ensure our customer feedback is part of every product conversation and decision, and streamline how everyone engages with those customers from bug fixes to prioritization, etc. And then, in terms of figuring out how to scale, that's iterating on processes, finding ways to automate myself to scale, and figure out how we can do that going forward.

VT: What does Customer Success look like at Great Question right now?

SC: Today, customer success as a function is owned by me, but every single department is committed to and responsible for delivering on customer expectations. 

So let me explain that a little bit. So I report to our CEO who, prior to hiring me, was responsible for customer success. He also heads up our revenue function. I take care of things like day to day customer communications management of those accounts, and handle expansion revenue, like upsells, and renewals. 

I'm also responsible for customer advocacy.

And it's my absolute staunch belief that customer success loses when it's siloed. 

And so customer feedback and the customer voice is involved in everything from engineering sprints to product prioritization to marketing campaigns, and thinking about how it's going to roll out in the future. At its core, CS will only be as successful as our customers at any company today. So, I view my role and the CS function in general as bringing that customer lens to every business and product decision.

VT: If you could wave a magic wand and automate one part of your day-to-day work life, what would it be?

SC: That's a really easy answer. Absolutely follow-ups. 

As a solo CS person, I'm the face our customers know to get in touch with with questions and feedback. And at a growing startup, that means a ton of different conversations in a lot of different places. 

So, I'm excited to eventually get Vitally. We just implemented HubSpot to centralize all our customer relationship management, but we really want to get Vitally to centralize those conversations in one spot. And I'm hoping I can get reminders about who I need to follow up with, where I need to follow up with them, and tasks that need to happen before that. So like, basically, I just hope to one day not always have 23 tabs open in my browser, we'll see if it happens.

VT: One thing in your CS tech stack you can’t live without?

SC: Okay, today that is Mixpanel. So I need to know how our customers are behaving inside our product to identify indicators for both growth and churn. Eventually, I'll document those indicators. It'll be part of our playbook. But pinpointing those key moments is critical to figure out how successful customers are being successful so that that can be repeatable for the rest of our customers that come in. 

In the future, I'm super excited to sync Mixpanel with Vitally to automate those sequences and implement some playbooks and workflows for low touch CS as we scale, that'll be really helpful.

VT: Biggest workplace pet peeve?

SC: Okay, I think this is gonna be pretty relatable for a bunch of different people. But in today's world, and especially as a solo CS person, managing different customer time zones for chats and live calls can be challenging for a couple reasons. Like don't get me wrong, I love the flexible lifestyle and would way prefer that to a traditional nine to five, but sometimes when you're chatting with both New York and Australia on the same day, it can be a bit logistically challenging. Thankfully, we have team members all over the world who can step in while I'm sleeping.

But the other thing is, when you're trying to book meetings with people in different time zones, it confuses the daylights out of me. Like, what time is it tomorrow when it's 5 PM Today in Toronto, when you're talking to someone in Melbourne, I have no clue. And then like, don't even get me started on daylight savings time, it just throws a wrench into everything. It's an absolute nightmare.

Customer Research and Feedback as a Driver of Growth

VT: What’s one unique, yet critical, variable in your customer health score?

SC: We're a customer research platform. So when product designers, researchers, and customer marketers want to test new designs, get feedback from customers, they can do it really easily with our platform and democratize that research throughout their organization. 

So a really critical metric for us is how many participations our customers are getting from their customers per month. That means, for example, how many live interviews they're conducting, how many survey responses they're getting, so that they can include that feedback in every single product release. And that is literally our entire mandate. So it's really important to be able to track that over time.

VT: Advice on how to turn customers into product champions?


So I don't think there's a secret sauce here that I can spill the ingredients to, it's really about under-promising and over delivering on customer expectations. 

So something that I've studied at length is a customer's appropriate experience versus their desired outcome. An appropriate experience is simply meeting their expectations, you're delivering the product they expected, and they're getting the results they expected. A desired outcome is when you match that appropriate experience with something that makes their life better. And that's its basis, knowing what their goals are, what could make their life easier, what are their broad business objectives, and helping them get there through your product. And when you can deliver on that desired outcome, your customers will automatically become your champions.

Over the past week, I have actually learned how tight knit the UX research community is. And fortunately, we have a bunch of advocates in there, which is really exciting for me to see and to continue to grow through delivering on those desired outcomes.

VT: What’s one thing Great Question’s Customer Success team does that’s world-class?

SC: That's a great question. And pun absolutely intended. As cliche as it is, that would be customer research. So we have a fabulous product designer—sup, Sean?—who has a really close relationship with a bunch of our customers, and our early adopters. So through my check-ins, I'm able to figure out what our customers are doing today, what their goals are, etc., and match that up with our product roadmap, like, what features are we launching over the next quarter, and if I see something that might be enticing to a customer, I'll reach out to our product designer and say, ‘Hey, as you're building this out, it might be a really good idea to test it against this customer, this person from this company, so we can get their feedback and iterate on the design with that customer feedback involved in the product release’. So, again, that's like a great question, because it's what we do, but it's also what we’re world-class at and involves that process every single week.

VT: Best way to take a rest/decompress after a stressful customer call?

SC: Well, I live in Canada. So when it's not -1000 degrees outside, a nice walk, and some fresh air is really nice to decompress. 

But around this time of year, it starts to get fairly frigid outside, and not nearly as pretty and all the trees are brown, there's no leaves anymore. So I'll brew a nice cup of tea, and read a chapter of a novel. I find it really helpful to get outside of your own head for a minute and give your brain a chance to recover. And then of course, any great manager, if you let them know that you've had a kind of stressful experience, it's really helpful to have a one-on-one and talk it through, because brainstorming solutions and next steps is a lot better with other people, especially when they weren't there and didn't experience it firsthand. 

So doing something to relax, get outside of your head, and go head to head with one of your colleagues who can help you think through an appropriate solution.

The Power of Storytelling in Customer Success

VT: As a former journalist and SaaS content marketer, what role do you think storytelling plays in Customer Success?

SC: So customer success is storytelling. So in a past life, great journalism, and great content is all about educating an audience about an issue, articulating why they should give a heck about that issue, and how they can solve that issue, ideally, with your product or solution, right? So to do this well, you have to be empathetic, you have to be a problem solver, and truly, deeply understand the audience's experience. And that's exactly what stellar CSMs do. You dig to the root of why your customers have come to you, the problems they're looking to solve, and how you can help them get there. And through that, you want to be articulating in a really compelling way, what that ideal future state looks like and where your product will weave into that future state. And the best way to do that, and get empathy and connect with the customer, is by telling a story that they can relate to.

So, in terms of how it all interacts with each other, it's about valuable content.

And it's my belief that the most valuable content is educational. It's data driven. And it should teach your customers how to best use your product or solution, while relating to them on a really fundamental human level. And that's what I see great CSMs doing.

VT: What are 2 or 3 strategic CS initiatives you're hoping to carry out this year?

SC: Yeah, boiling this down to two or three is pretty hard. We’re a year old, so there's a lot that we want to be doing. But if I had to name two, the first would be creating a customer success playbook. As we grow this team, especially as a remote first company, we want to create repeatable processes so new folks can onboard quickly and help us scale. So that, to me, means documenting internal processes, identifying patterns so that you can really easily and seamlessly help customers grow and expand with you, and how to handle various scenarios that only come with time and learning from those customer interactions, so that eventually you can get to repeatable growth and that expansion revenue. 

The second one would be implementing Vitally. Automating so many of those little processes like follow-ups, trigger emails, objective customer health, rather than subjective customer scoring, like a green yellow, red, is not nearly as good as having an automated system that can eliminate bias from those customer health scores. That'll help us scale so much faster and likely grow our customers’ ACV.

VT: What is one concrete step a (more junior) CSM could take today to set themselves up for a Customer Success leadership position down the road?

SC: Okay, I'm going to say those really clearly: [clap] Practice [clap] Public [clap] Speaking.

As a CSM, you're the subject matter expert on your product for customers. Yes, that means knowing your product inside and out and being able to answer questions. But what a great CSM does is go beyond that kind of tactical step-by-step implementation, problem solving, question-answering into the strategic narrative. 

This goes back to how customer success really relates to storytelling. What I mean by that is, have the confidence to build a relationship with your customer. That's more like a strategic adviser relationship. Learn what keeps them up at night, what are their goals for the coming year? What issues are they looking to solve what will help them look like a superhero, so they know that you helped them get there. And that means having the guts to give them advice and guide them on stuff that might not even be related to your product. So, in terms of getting that confidence, being able to talk confidently in front of a crowd and speak confidently, even stand-up comedy, improv, just get that confidence because you are the subject matter expert, and your customer has to believe that too.

VT: One item on your desk (or in your home office) that you cannot live without?

SC: Okay, so sticky notes. So jumping between screens can look weird in our virtual life, like you don't want to be in a meeting going around like this. So, what I'll do is before a customer call, or if I need to remind myself to do something before the end of the day, I will literally take a sticky note and stick it on my monitor so that I have to drag my windows around it so that I literally have to pick it up and move it before I can see my screen perfectly. This will remind me what I need to ask about or what I need to do before the end of the day. It just gives you a jolt in this virtual world where everything can be pretty overwhelming from a notification perspective.

VT: What are the Customer Success trends you’re excited about/to see continue in 2022?

SC: So I think it's becoming increasingly well known how cross functional customer success is. Great companies around the world today succeed because the voice of the customer is involved in every single area of the business.

With that in mind, more focus on there being Chief Customer Officers is something I'm a huge fan of. No company has ever succeeded without their customers. What company doesn't have customers and has ever gone public or been acquired? You need to have your customers’ support if you're going to grow and continue to expand, and that voice needs to be heard at the highest levels, to drive company strategy.

VT: What advice do you have for CS leaders who are managing and scaling remote CS teams?

SC: So create a documented playbook. The remote world has opened up so many opportunities in terms of sourcing talent and growing a business, but it's incredibly draining for CSMs, for everybody, but especially for CSMs, who might find themselves in meetings for many hours a week. I remember, at my last company, there was one week where I was literally in Zoom for 30 hours in one week, and that is so exhausting. If you add team training on top of that, especially as someone's onboarding, your team is going to burn out. So document those processes, make it easy to onboard, and learn to give your team control over their own workflows. Also remember, there's no one there, like you can't turn around and ask your manager for advice on something, so being able to quickly check a document can help mitigate that instant response time.

VT: In your opinion, what is the biggest misconception around Customer Success? 

SC: Alright, so traditionally, there's been some conflation between customer success and customer support. Both are critical, both are so vital for success. I know that since I'm managing both today, and I've seen both managed really successfully at past companies. But customer support is tactical, while customer success is strategic. Customer support is about response time and answering questions, and solving problems instantly in an actionable way. Customer Success is about guiding customers along the strategic path over a longer period of time. And about advocating internally to make those journeys even more valuable so that they keep coming back for more and purchase more. Both roles are responsible for creating happy customers, but customer success is about the long game, while customer support is about short-term wins.

VT: If you were not working in Customer Success what kind of work would you be in?

SC: So when I was in high school, you know, when you take those personality quizzes to be matched up with a career, I got stunt double. So I like to think that I could still do that. But I don't have rubber bones anymore, I'm getting older. 

So more likely, I'd go back to my roots with storytelling and become a blogger or a novelist. Honestly though, I could also see myself becoming a gardener. In CS I'm used to talking to people all day, and I've heard that plants enjoy being talked to. So I grow some tall plants, let me tell you.

VT: What’s your best productivity tip for working remotely?

SC: Don't work a straight eight hours, take lots of breaks. The traditional nine to five is over, especially in the tech community. And that's great in a ton of ways. But it also means you don't have bookends to your day, you don't leave your office. And that puts someone at real risk of burning out. And I almost did at one point over the past couple years. 

So now, I've made a change so that I try to work for one or two hours at the max and then take a 30 minute break multiple times throughout the day to keep myself fresh and remind myself to pause and enjoy life. These kinds of tactics helped me prioritize work, not get overwhelmed, and actually do some other stuff as opposed to just sitting at my desk all day. And yeah, it's really important to remember that remote work doesn't have to be the only thing that you're doing.

“I think that anyone can be great at Customer Success, but what it really takes is a passion for helping people, and I'm so lucky that I stumbled into this career. Thank you so much for having me on guys. It's great to see this function growing over time and cheers to the future of Customer Success.”

You can find the rest of the ‘17 Questions with Customer Success’ series here. Interested in participating? Reach out to for more information.

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