In our new episode of the Mastering CS, Candid Leader Insights podcast, Irina Cismas, Head of Marketing at Custify, discussed with Craig Taylor, Head of Customer Success at SimplePoll.
What You’ll Learn:
- How past experiences impact customer success
- How to implement a digital-first CS strategy
- The importance of technology in CS
- The right screening process for a CSP
Key insights and takeaways for CSMs based on the interview:
Learning & Development Background’s Influence on CS: Craig emphasized how his experience in learning and development shaped his approach to customer success. He highlighted the importance of focusing on desired outcomes and impact, rather than just inputs, a mindset he carried over from L&D into CS.
Defining and Aligning on Success Metrics: For Craig, a key factor in improving customer retention and satisfaction was understanding each customer’s unique definition of success, moving beyond usage metrics to align on customer-centric outcomes.
Digital-First Customer Success Strategy: At SimplePoll, Craig focuses on a highly digital approach to customer success due to the product’s extensive Slack user base. This involves data-driven, automated touchpoints designed to provide the right information at the right time, with minimal direct interaction.
Effective CS Team Building: Craig highlighted the pros and cons of building a CS team from scratch versus working with an existing team. He prefers building from scratch, allowing him to shape a team with the desired skills, attitudes, and culture.
Importance of Human Element in SaaS: Craig’s career advice from a former peer emphasized that while SaaS products often have similar technical capabilities, it’s the quality of human support and strategic guidance that truly differentiates them.
Podcast transcript
Irina 0:02
Welcome to Mastering CS Candid Leader Insights, the podcast where we deep dive into the world of customer success with industry leaders. I’m your host Irina Cismas and today’s guest is Craig Taylor, Head of Customer Success at SimplePoll. Craig, welcome and thanks for joining us today!
Craig 0:19
Thank you for the invite Irina, much appreciated!
How past experience influences the approach to Customer Success
Irina 0:22
Craig, you started out in learning and development. How do you think that experience has influenced the way you approach CS in general?
Craig 0:32
I’m so pleased that that’s one of the first questions that you’ve asked because for some time now I’ve been telling to people there’s a massive overlap between learning development and customer success and I think the longer I’m in customer success the bigger I see that overlap being. To answer your question, when I first started working in learning and development many years ago we were very much seen as order takers. An internal customer would come along and they’d ask for a course to be purchased or a piece of e-learning to be built or a video to be produced or a course to be paid for and back then we were very happy just to take that as an order.
We would say yes, no worries, let me make that happen and we made it happen. What we weren’t very good at all those years ago was better understanding what the outcome was that that internal customer was looking for so we just focused on the input. We never really focused on the output, the goal, what success looked like for that internal customer, what the number was they were looking to impact.
Learning and development has got much better at that over the years and now we always pay a great focus on why, what is the outcome you’re looking to achieve, what is the goal you’re trying to achieve. So when I moved across into customer success I found that was really helpful because although we clearly are interested in producing an input alongside that customer we’re probably more interested in finding out why, what impact are you trying to have, what goal are you trying to impact, what number are you trying to maintain or change in some way. So that focus on the big picture outcomes from my learning and development background has really influenced my approach with customer success.
Irina 2:27
I never thought if I would summarize what you said I remain with learning and development is 1.0 and CS was a natural evolution or transformation and it’s it builds on the learning and the development part but I think it was and I’ve run this series of discussions and interviews with dozens of head of CS people but I think you are the first one who had a strong background in learning and development and it was like hmm this man actually went through several learning and development roles until he actually ended up working in CS and now I have to ask you what was the moment or the milestone that actually convinced you to make the switch so what was the trigger?
Craig 3:21
It was completely accidental.
Irina 3:26
I would have thought you would say that it came as a natural transition. Why accidental?
Craig 3:36
Some years ago, I was working in a role that I wasn’t particularly happy in. It was a learning and development role, and I contacted a friend of mine, who was the CEO of his own startup, a fairly small business. I somewhat jokingly asked him—his name was Ben—”Ben, do you have any jobs going?” He messaged me back and said, “Actually, we possibly do.” So, after some conversations, I went to work at his startup as a solutions architect. It was a learning and development role because he had an online learning and development platform.
I’d been there several months, and we were having a few chats over time. The role never quite felt right. What I was doing felt right, but the role itself, on paper, didn’t quite feel like a perfect fit. Back in the autumn—probably the fall of 2015, so nine years ago now—he said to me, “Craig, would you like to head up our customer success function? Would you like to run the customer success team?”
I’ll be really, really honest with you, Irina: I thought it was a job title that he’d made up. I really did. I had never heard of customer success at that point. Now, when you think that this was almost ten years ago, it’s not that surprising because, although it existed back then, it wasn’t as well-known in SaaS businesses as it is now, in 2024, nearly 2025.
So, I did a little bit of googling and actually discovered, no, this is a genuine role, a genuine thing. And it sounded perfectly like what I was doing day-to-day anyway. So my job title changed, but what I was actually doing day-to-day hardly changed whatsoever. Completely true story—I stumbled into the world of customer success. It was not something that I went looking for.
Playbook for customer success
Irina 5:42
I somehow resonate with what you are saying because I was doing customer success without actually knowing that it was called customer success. I never thought about googling it, but at some point, I wanted to transform the support department—this is a true story from a former company I used to work for. I somehow found out about customer success, and at that point in time, I was under the impression that customer success was just a fancy term for support. So, I thought, okay, let’s transform support into customer success. I was actually doing customer success without knowing it.
Later on, I found out that this role wasn’t just invented; I was simply unaware of it back then. I had the impression that customer success was a buzzword, a fancy terminology for support. Of course, I was wrong, but in my defense, I was doing everything that customer success does: onboarding customers, making sure they were successful, and all of that.
I also resonate with what you mentioned about understanding the “why” behind what we do. While I don’t actively work in CS, in marketing, we also focus on the “why”—why you do what you do. This is what makes communication powerful, and it resonates with users. So, again, it’s something I completely understand, and I’m glad that it’s also emphasized in the CS space.
Now, I want to move on to the more challenging aspects and discuss business metrics. You basically moved the needle and impacted the business metrics that are most important for the C-suite—namely, NRR, time to value, and NPS. I have to ask, how did you manage to do that, and what is your playbook?
Craig 9:16
There wasn’t one playbook that governed everything; each aspect had its own playbook, sequence, and workflow. Sometimes, there were even multiple playbooks or sequences depending on the customer’s size—whether they were an enterprise or a small to medium business. There was no single magic solution; each playbook had its own unique elements. However, the common thread that connected them all was my strong belief in being data-driven—or, to be more accurate, data-informed. Every playbook I set up and ran used real, tangible data to inform its direction, rather than being triggered by something arbitrary.
Regarding the NRR you mentioned, the biggest factor in that playbook was understanding the “why” of the customer: why they were using our product, why they chose us, and what impact they were looking to achieve. I aimed to understand how they defined success in terms of using our product. Interestingly, it was never about the metrics we in CS often worry about, like usage, utilization, or logins per day—none of my customers cared about those. We worry about them, but the customers don’t. So, I focused on understanding the customer’s metric, their definition of success, and their idea of value. Once we understood and planned for that and adjusted our support accordingly, we saw the needle on net revenue retention begin to rise. With some exceptions, customers tend to leave when they don’t see value; if they do see it, they tend to stay, which, of course, impacts NRR.
I should add that sometimes it can take quite a while to see NRR improvements, especially when dealing with contracts that last 12 months or more. Changes can take time to become evident, but understanding the customer’s definition of success was the single biggest factor in that playbook.
You also mentioned time to value. We had a playbook of sorts when I started, but I split it into two parts. Originally, it was called the onboarding playbook, but I divided it into implementation and adoption, both of which used to be covered under “onboarding.” Once I split the phases into two separate playbooks, we could better focus on the delivery time of each, making the problem smaller and more manageable. I was quite cutthroat with that playbook because I’m very conscious that you only get one chance to make a first impression with a new customer—and that usually happens in the sales process. I couldn’t affect that part, but once they became a customer, it was all about the onboarding experience.
We were asking a lot of questions—too many questions, actually—right after the customer signed the contract. When I reviewed these questions with the team, we realized that some should have been asked during the sales process, while others were appropriately asked just after the contract was signed. But a large portion didn’t need to be asked right then; they were more relevant days, weeks, or even months down the line. We didn’t need those answers to deliver the first value. Once we stripped out unnecessary questions and asked the right ones at the right time, we significantly reduced the time to value for new customers coming on board.
In summary, I broke the problem into smaller pieces and was ruthless in evaluating each question and step, asking, “Do we need this at this stage?” If we didn’t, it was eliminated.
Irina 14:12
When it comes to questions, I think that’s one of the hardest parts—what to ask, when to ask, and how to phrase it. I’ve tried multiple times in my marketing role to uncover the story behind the customer and understand how we actually helped them. I realized that it can be challenging to get the right answers. To gather the necessary information, I often had to ask the same question in different ways and at different times, making sure that users or customers told me exactly what I needed to know or the information I would have to work with later.
In some cases, I noticed that customers might not even realize they’re just telling you what they think you want to hear. You have to overcome this barrier because, at least in our case, whenever we try to find out, “Okay, how can we help you? Why did you end up buying this CSP?” everyone tends to come up with generic CS challenges. I understand that part, but I want to go deeper.
So, I’m curious—how did you end up with the perfect questions? What was your process?
Craig 15:47
Knowing what the next person in line from an implementation perspective needed to know—and identifying the bare minimum they required for the next stage to be completed—was the filter I used. It wasn’t about what would be nice to know or what might be useful; it was about what was imperative for that next stage of implementation to occur. If it wasn’t imperative or mission-critical, then it was deferred to be asked later. It was as simple as that.
Once we applied this filter, we realized that a huge chunk—about 70 to 80 percent—of the questions we were asking still needed to be asked, but not immediately. They were important questions, but their timing was off; they would be better asked the following week or maybe the week after that. When we stopped asking these non-urgent questions upfront, we eliminated a significant source of delay.
For example, if we were asking a customer 30 questions, it was incredibly unlikely that the person filling out the form knew the answers to all of them. They’d have to go and find the answers, which took time and caused delays. We were on the clock as a business, having just signed a new customer, and by asking too many questions, we were essentially making our own lives more difficult and appearing inefficient in terms of time-to-value.
When we refined the questions to just five, six, or seven, the person completing the form usually knew all the answers right away. Sometimes, we’d get the form back the same day. Other times, if they needed to ask a few other people, we’d get it back the following day. By being more selective, we reduced the burden on the customer’s shoulders, received the data back more quickly, and could act on it faster.
What does a CS leader need to be successful
Irina 17:50
Awesome. I wanna ask you, because you’ve been in several—maybe you’ve had a lot of—leadership positions, and I know that you need a set of assets, or you need something unique, ammunition to work with whenever you are starting a new role.
What do you need in order to be successful in a new CS leadership role? What do you ask from the hiring manager, from the CEO, from the board of directors? It doesn’t matter—what do you need to be successful?
Craig 18:30
I think there are a number of things, but I would caveat them all by saying they’re probably the same things that anybody starting in any new role—possibly a leadership or management role—would need.
I’m looking for support from my leaders, support from my peers and my team, and support from the wider business. What does support look like? Well, it looks like people trusting what I say. It looks like healthy challenge. Challenging for the sake of being challenging is one thing, but healthy challenging is an incredibly valuable thing.
Support also looks like people willing to take a risk. When you’ve just parachuted a new head of customer success in to set up an entire new function, you’re probably doing that because you don’t have someone in the business capable of doing it already. Therefore, whatever they ask you to do is probably going to feel a little alien, a little strange. Maybe it even feels like there’s some friction with the way things have been done in the past.
That understanding and willingness to take a risk are things I would look for in anyone, from a leadership perspective. But again, I would say that those are things anyone starting in a new role—particularly in a change management role—would be looking for in terms of support and resources from within their business.
How to build a strong CS team
Irina 20:06
I want to speak about—you mentioned your peers, about the team—and we talked about the team that you are joining. I’m curious, speaking about the CS team that you are leading, what’s your process for building a strong CS team from the ground up?
Craig 20:24
I think there are two approaches. From the ground up would assume that there is nobody already in place within the business; there’s not already a team of CSMs, and I’ve been brought in to develop that. I think there are pros and cons to taking that approach.
One of the cons is that there’s nobody in place already—nobody is doing the work that you’re probably going to need done. So, from a time-scale perspective, creating and then building that forming, norming, performing, and storming team evolution all needs to be done from day one.
The positive of that is, yes, it might take some time, but in my experience, you can recruit for exactly the sort of person or people you’re looking for—with the right attitude, the right skill set, and the right experience. You’re not having to try and mold somebody who’s already in a role but perhaps isn’t performing the way you need. So, while there’s a time-scale perspective, the advantage is you can truly nurture and grow that team from scratch.
Of course, the flip side is if you’ve got an established team, great—a lot of the work is already being done. But it might not be done in the most optimal fashion; it might not be following best-practice methods. So, while you can carry on performing, there’s often a huge amount of change management that might be needed. People might need to be retrained, or, unfortunately, some might have to move on from roles if they’re not open to making those necessary changes.
So, I think there are pros and cons to building from scratch versus starting with an established team. If I had my choice every time (which I rarely do), I’d always love to build a team from scratch because, personally, I take a huge amount of pride in that. But it does come with the challenges of the time scale involved.
How much time does a CS leader need to make an impact on business metrics?
Irina 22:38
Now I want to ask you something that some of our listeners might find controversial, but I’ve recently seen some discussions on why VP of Sales roles have high turnover. Now, I want to ask you, how long do you think a CS leader needs to make a meaningful impact on business metrics? What’s the mandate, or what’s the minimal time frame, where you have a real chance to prove that you can impact the business KPIs?
Craig 23:16
So I’m going to be one of those annoying interviewees that comes up with the two-word answer. It depends.
Irina 23:24
Okay, it depends.
Craig 23:26
But let me caveat the “why it depends.” You used the phrase “business metrics” a few times during that question, and the “it depends” really depends on what that business metric is. What is it that the CS leader is expected to be able to change? Some business metrics can be affected comparatively quickly, while others take longer.
For example, if a CS leader is being asked to improve advocacy opportunities—such as increasing the number of champions, case studies, and advocacy opportunities—that might be relatively quick to do. Assuming you have good products, good support, and customers who enjoy using your product, you might already have a healthy base of advocates to work with. In that case, the hard work of being a good vendor is already done.
You just need to select those advocates and engage with them to create opportunities. That might take weeks or months, but it might not take very long. But that could still be a business metric: increase advocacy opportunities.
Now, compare that to improving renewal rates or increasing NRR. Those are things that may require some fundamental changes, either in the product itself or in the way you work with customers.
Even if you have a great product and great customers and are already doing good things, depending on your billing and renewal cycles, it might take you 12 months to start seeing the fruits of work that you begin today with new playbooks and processes. It might take 12 months before you can see the impact of those efforts on that particular cohort of customers. So, purely because of the passage of time, that may take longer than a metric like increasing advocacy opportunities.
And that’s why the answer is “it depends.” It depends on what the business metric is. It depends on what is fair and reasonable to give that CS leader to show the outputs of the work they’ve done and the effect they’ve had.
The role of technology in CS
Irina 25:53
Let’s bring technology into our discussion, and I want to know how you leverage it. I know that you—I saw it on your LinkedIn profile—implemented a CSP in three months, and now I have to ask, how did you manage to get budget approval for implementing the CSP? Because in some organizations, there are board members or CEOs who consider this not necessarily needed, and of course, there are workarounds that can be implemented.
What was your pitch?
Craig 26:31
This is going to sound surprisingly similar to the question you asked me earlier about how I got into customer success. It was really opportunistic. It was one of those moments when all the stars aligned perfectly.
The book just fell open at the right page. During the summer of 2022, I was interviewing for a new role. The interview process involved the CCO, Chief Commercial Officer, Chief Ops Officer, and Chief Executive Officer.
It became quite apparent from them that one of the challenges they were facing was that their customer data was spread across lots of different best-of-breed platforms—ticketing systems, product enablement systems, people’s inboxes, CRM, and so on. It was all over the place, which is somewhat understandable. Any mature business is probably going to use best-of-breed platforms to handle individual activities.
The problem was that, after 20-25 years in business, they had a lot of customer data but no single place to view it. They recognized this, acknowledging that sometimes decisions were being made without a full picture of the customer. They brought this up as a challenge multiple times during the calls, and when I mentioned CSPs, they hadn’t heard of them and didn’t know they existed.
They were familiar with CRMs but not with CSPs—the type of product that takes over after sales and marketing. Once I mentioned it to them, they seemed incredibly keen and wanted to know more about it. I did wonder, “Am I giving too much away during the interview here? Are they just going to go do this themselves?”
What I was really pleased about was that I got the job. I started in that role on the 1st of September, and one of the first things the CEO said to me was that they wanted to get up and running with this CSP.
He remembered it—I didn’t have to bring it up; he remembered. We signed a contract on the 1st of October, so I had four weeks to source a provider and complete the selection process. We did a soft internal launch in the first week of December and went live with real customers in the first week of January.
So, I didn’t have to go in there and sell the benefits of a CSP. They presented the challenges of not having one, and I just mentioned it, and the stars aligned. Things fell into place from that point onward. It was very opportunistic.
What is the screening process for a CSP?
Irina 29:22
Indeed, I think it was that rare chance when the CEO comes in, asks, and facilitates, and I think you were indeed lucky because you pitched it at the right time, and they listened to that part.
Now, you mentioned that you went through screening different CSP platforms. What did your process look like?
In that screening process, what were you looking for?
Craig 30:08
think anyone listening who has ever procured enterprise-level, business-wide software knows there’s a lot to go through, a lot of hoops to jump through. So I won’t list every single feature or functionality, but broadly speaking, I was looking for three things. I’d look for these three things in any type of software I was considering.
The first thing I’m looking for is: can it solve the problem we’ve got today? Today, okay? Not “it’s on the roadmap,” or “we’re thinking about it,” or “it’s in beta testing.” Can it solve the problem we have come to you with right now, out of the box? If it can, that’s great.
The next thing I’m looking for is: can it solve tomorrow’s problem that I don’t yet know I have? That may sound cryptic because we don’t know what the future holds. But what I mean is, if the product can solve today’s problem but has no extra features or functionality, I’m literally using every drop of the product’s power. What do I do tomorrow? What do I do in three or six months when we want to expand our CS thinking, and we’ve run out of engine power and features? So, I’m always looking for a product that does more than I need today, something I can grow into and mature with over time.
The third thing I’m looking for has nothing to do with the product itself. It’s about the company behind it. I want to work with a software partner who gets customer success. That’s different from a company that just understands its product. They should understand their product inside out, but I want them to understand the world in which their product lives—the customer success world.
During the selection process, I listened to how the sales development people spoke about customer success. I looked at how the pre-sales engineers spoke to me—were they just talking about features and functionality, or were they placing it in the bigger picture? We were fortunate that they brought in the CSM who would likely be working with us if we bought the product. That particular guy—also named Ben, a different Ben—really impressed me with how much extra value he could bring, beyond just telling me what buttons to press or levers to pull.
So, those are the things I looked for: Can it solve today’s problems? Is there room to grow with the product? Does the company understand customer success beyond just their product features? I found a provider that checked all these boxes, and as I mentioned, we signed within four weeks.
Short-term CS objectives
Irina 33:22
Thank you. Thank you very much for this, for sharing your three most important elements when you’re picking up new software. I also want to be mindful of the time, and I don’t want to end this conversation without actually asking you about SimplePoll and the company you’re with now.
What are your short-term objectives in terms of CS? What are you focusing on as we speak? What are the problems you’re trying to solve right now?
Craig 34:02
So, to wrap all of that up into one: SimplePoll is an app that lives in the Slack App Store. It’s a polling app that plugs into Slack. So, to use our product, you already need to be using Slack. I mention that context because there are a lot of Slack users out there—a lot—and many of them have our app installed.
I’m the only person on our CS team. I’m the Head of Customer Success, but I’m the only person within that CS team. So, unsurprisingly, the thing I’m focused on the most is adopting a digital customer success approach. 99.99% of the time, I have to rely on digital CS. I know “digital customer success” is a term that’s been used a lot over the past couple of years, but this role truly is a digital customer success role.
Very few of my customers do I ever talk to like we are now. I need to figure out, from a data perspective, a usage perspective, and other factors, when to communicate with them, what information to provide, and the best channel and timing for that communication. A huge amount—90%—of my time is spent focusing on digital-first customer success.
And while you used the word “challenge,” and it is a challenge, it’s also an amazing personal development opportunity. I’ve never worked anywhere with such a digital-first focus. So, yes, it’s a challenge, but within that challenge are some wonderful development opportunities for me to get to grips with an element of customer success I’ve never dealt with at this scale before.
Implementing a digital CS strategy
Irina 35:57
This probably requires a dedicated episode or maybe also a webinar theme. But I want to ask you, how did you with what did you start when you implemented the digital CS strategy?
Craig 36:20
Well, firstly, I didn’t implement it. They already had a CSP before I started, and the CEO was the previous Head of Customer Success, so I’ve taken over from a very capable hand. I took over digital success—digital customer success.
We are aiming to be able to tap the right person on the shoulder at the right time with the information they need in the right channel. We can’t rely on a monthly or quarterly success review or QBR to surface things, because they simply don’t exist. So, we’re constantly looking for ways to deliver the right information to the right person at the right time, in the right channel. It sounds simplistic, like something that just trips off the tongue, but there’s a lot involved in that.
In a nutshell, that’s what we’re trying to do with SimplePoll from a digital-first customer success perspective.
Irina 37:23
Greg, my last question before we wrap up, I want to know who has been the biggest influence on your career, and what’s the best piece of advice they gave you that still sticks with you today.
Craig 37:37
I’ve had lots of jobs over the years, from the military to learning and development to customer success. I’ve had lots of bosses, so it’s impossible to pinpoint one person who’s given me a single piece of advice. However, there is a person I worked with who wasn’t a boss of mine but a peer at HT2 Labs, during that first exposure to customer success I mentioned.
He’s a Scottish guy named Dave Tosh, currently based in Canada, and he said to me something that stuck. I’m going to do a terrible job paraphrasing what he said, but it was along these lines: Within a particular software space, there are various competitors, and they’re all pretty much doing the same thing. Some will have a feature that someone else doesn’t, and then the other will catch up and release a similar feature. It’s all pretty level-pegging; just like in the CSP world, they’re all quite similar.
The thing that sets them apart isn’t their code base; it’s their human base. It’s the people who talk to those customers, help them, support them, guide them, and help set a strategic direction for how they’re going to use that code base. Now, he didn’t put it as roughly as I just did. He had a wonderful way of summing it up, but I think that’s the best piece of advice I’ve ever been given from a SaaS/Customer Success perspective: the products are all pretty much on an even keel. It’s the humans alongside those products where the real differentiator happens.
Irina 39:12
Thank you so much, Craig for sharing your insights with us today and a big thank you to all our listeners until next time, stay safe and keep mastering customer success.
