In this episode of Mastering CS: Candid Leader Insights, Irina Cismas speaks with Oksana Aloshyna, Strategic Customer Success Manager at ShortPoint, about what she has learned from more than eight years of building customer-facing practices from the ground up.
Oksana shares how her role evolved from Support to Customer Experience and eventually strategic Customer Success, and why relationships remain at the center of how she works with customers.
She also breaks down the practical side of building CS infrastructure, from knowledge bases and customer journey mapping to health scores, personalized outreach, and AI. She explains why product usage data alone doesn’t tell the full story of account health and why a small CS team benefits from investing in self-service early.
What You’ll Learn
- How Oksana identifies and re-engages unhealthy accounts
- Where to start when building a knowledge base and customer journey
- How she combines product usage, engagement, and human context in health scoring
- How AI helps customer-facing teams become more independent
- Why personalized outreach works better for disengaged customers
- What Oksana would prioritize when building CS with only three people
- Why customer and internal relationships remain difficult to replace with technology
Key Insights & Takeaways
Personalization matters most when engagement is already low: Oksana invests time in researching individual accounts and referencing specific activity, problems, or past conversations instead of relying on batch outreach.
Start simple when building CS infrastructure: A knowledge base can begin with the 10–20 questions customers ask most. A customer journey can start with a whiteboard and the three biggest roadblocks customers face.
Health scores need human context: Product usage and communication data create a useful baseline, but they don’t capture every reason behind customer behavior.
AI works best as an enabler: Instead of replacing customer-facing teams, Oksana uses AI to help them handle technical requests independently and complete tasks that previously required engineering support.
Small teams need self-service: When resources are limited, documentation and tutorials reduce repetitive questions and create more time for proactive outreach, customer journey improvements, and strategic work.
Relationships remain a competitive advantage: Customers who trust their CSM share problems and future plans earlier, giving the team more time to respond.
Podcast transcript
From Support to Strategic Customer Success
Irina (0:06 – 0:51)
Welcome to Mastering CS Candid Leader Insights, the podcast where we dive into the world of customer success with industry leaders. I’m your host, Irina Cismas, and today I’m joined by Oksana Aloshyna, Strategic Customer Success Manager at ShortPoint, a platform that helps organizations build intranets on SharePoint and Microsoft. Oksana, I’m really happy to have you here.
You’ve been at ShortPoint for over eight years, moving from support into customer experience management, and now into a strategic CSM role. Help me understand where you are today.
What does your role actually look like right now?
Oksana (0:52 – 1:52)
Yeah, it looks like a combination of a lot of things, to be honest. I mainly focus on strategic accounts, big enterprise accounts, and accounts that have a lot of users. But I still have a huge customer base that I answer to daily, which also includes small and medium-sized business accounts.
We have been building those relationships for years, and I still guide those people with the questions they have for me and meet with them often. So it’s many hats, basically. It’s a lot of digging into usage statistics and the insights that can be given to me from the different tools that we have, like product monitoring and things like that.
But also, of course, the main thing is meeting with people, talking to people, learning their motivations, learning what drives them, what stops them, and going from there. So, mostly meetings.
Irina (1:52 – 2:07)
Okay, so most of your time is spent in customer-facing meetings or internal calibration meetings to understand the customer journey. Where would you say you spend most of your time?
Oksana (2:07 – 3:29)
I would say right now it would be bringing those accounts that are not super healthy, let’s say, back to us and back to being interested in the product. I would say this is my main focus now. I try to proactively determine who is not using the product very much, who is not very happy, and I reach out to them.
I would say what takes a lot of my time is trying to reach out in a very customized way. It would be much faster, of course, if I just sent them batch outreach emails, but I found that to be not very effective, especially with people who are already not very active in the product or not actively responding.
So that takes some manual digging and research for me to mention relevant things. “I know you built this page last month. How did that go?” Or, “I know you had this problem. How did that go?” I find that these reach-outs take the most time.
I also often try to record small video messages because we use Loom in our company a lot. We like that tool and use it on a daily basis. So reaching out with videos is also very effective.
And basically, that’s what I’m doing most of my time.
The Tools Behind Customer Research and Personalization
Irina (3:30 – 3:49)
That’s super interesting. So basically the personalization in your case works. The video is one type of content that your clients like to engage.
What other tools are you leveraging to help you extract the information to do the prep work?
Oksana (3:50 – 4:53)
We have several. We actively use Mixpanel for product information and to see how people use the product. We also always look at HubSpot and Freshdesk because all of our customer interactions are in Freshdesk, and all of our sales and Customer Success interactions, deals, and everything else are in HubSpot.
I sincerely wish it were one tool because there is a lot of integration between the two. But most of the insights I get come from these three tools.
And, of course, I find it very valuable just to talk with other team members. I’m very fortunate that both our Support and Sales teams, basically everybody customer-facing, usually stay with the company for a long time. Sometimes you can learn a lot from the technical tools, but it’s best to talk to somebody who knows the client well.
I think this is a great advantage, being able to talk to the team as well.
Building a Knowledge Base and Customer Journey From Scratch
Irina (4:54 – 5:30)
I know that you built the health scoring, knowledge base, and journey mapping practices from scratch. When you’re building something like that in an organization, where do you actually start? How did you start?
A lot of CSMs want to do this, but they feel overwhelmed because, as you mentioned earlier, there are a lot of tools, data points, and different ways of looking at the data. And in some cases, the data tells you the story you want to hear.
So how did you start?
Oksana (5:31 – 10:33)
I think one thing that made it easier to start in my case is that I joined so long ago, when there were fewer tickets and fewer customers. Everything was smaller back then. We didn’t have so many tools.
I definitely wasn’t overwhelmed, to be honest, so that’s a plus. But I think it always starts with mapping, seeing what people are asking and just putting it in front of you.
For example, with a knowledge base, you basically take the most common queries from people and answer them with an article or a video to deflect more questions like that in the future. So you start with the most pressing questions.
If you see that people are constantly asking about the same thing, this is what has to be put in front of you. Okay, we need to answer this question, we need to answer that question, and then you build it from there.
You basically create the 10 to 20 most important articles, and then you see if your Customer Support team is saving time by sending those articles instead of repeating themselves all the time.
It’s the same with the customer journey. Listen to what people are saying. If they run into the same roadblock all the time, if they want to install your product and they don’t have the permissions, for example, or if something else is going wrong.
You can use any tool. I’m not big on tools, especially expensive tools, because I think you can do it with pen and paper or on a whiteboard in a Zoom call with your colleagues. Just put it in front of them: “Guys, we have these three roadblocks in the customer journey. Here’s how we connect them, and here’s how many people are falling off or dropping off from installing or adopting our product because of these roadblocks.”
Then you already have the most basic version of a customer journey, right?
I’m also lucky at my company because we’re a relatively small team. We have 45 people in the company, so it’s cozy and easy to reach out to the Product team and decision-makers, bring these insights forward, discuss them, and actually see the impact.
It doesn’t take a lot of bureaucracy or time to get something adopted, so that definitely helps.
With health scoring, of course, it’s a little bit more challenging.
To be honest, when I started, I heavily based my health scoring system on product usage data because, in our case, a lot depends on that. We have a product that is quite sticky, meaning that if you start using it, most likely you will continue. But if you haven’t adopted it and we see low usage, then most likely people will abandon it because there’s a certain threshold of complexity that has to be passed.
When I moved into the Customer Success role, I based my health scoring first of all on Mixpanel data, which was a little bit underused before that. We collected a lot of data, but we didn’t analyze it.
To that, I’ve added statistics from both HubSpot and Freshdesk on how actively we communicate. Sometimes you can communicate about problems, and the customer might not be super satisfied with everything, but it’s much better than a silent account.
So it was very important for me to mark those silent accounts separately and also mark the accounts that we communicate with effectively.
And the third thing is that I really believe health scores are not perfect because, again, there’s this human factor where you cannot measure certain types of sentiment.
The health score can show you something really bad, but you know, “Okay, this person is just away on prolonged leave, and this is why the product is not being used.”
I always try to treat the health score as a baseline, so we know where we are. But then the context that I can get from my team members, Support, and Sales is always something additional that you can add to the health score. It’s not always about the numbers in the health score.
Using AI to Empower Customer-Facing Teams
Irina (10:35 – 10:59)
I want to address the AI part because it’s a topic that everybody speaks about it and in my interactions with customer success people I got different lenses on this topic. How do you leverage the AI in your day-to-day work? What are the use cases and how does it help you?
Oksana (11:00 – 13:21)
I think a very common way to think about AI in Customer Support and Customer Success is, “Let’s replace our support with AI and save a lot of money. We’ll never have to hire anybody. Let’s fire half of the team because now we have AI.” For me, that’s actually really terrible.
We have a very lean Support team and Success team, and we have no plans to replace people with AI whatsoever. What we do is try to enable them with AI tools.
In terms of replacement, we tried several tools on top of Freshdesk, for example, to write answers to people by sourcing knowledge from our knowledge base, videos, and other resources. It became a good draft for the Support agent to have in front of them, but it never became something that gets automatically sent to the customer.
I totally understand why. Especially with a more complex product, you need somebody to review it. You still need a human there.
What we use AI for is making customer-facing people more independent.
We often get requests like, “Give me custom CSS to make this element look better,” or, “Give me some JavaScript code to perform a certain function on the website.” Before, we would go to our engineers and say, “Hey, can you please help me? I have no technical knowledge about this, so could you please write that for me?”
It was challenging because developers are hired to develop, and engineers don’t always want to do Support.
We tried different systems. We tried rotating people, and we even tried hiring somebody who would be solely dedicated to answering Support questions. It doesn’t work really well. People with engineering knowledge want to be engineers.
Irina (13:21 – 14:34)
I totally understand that because, being on the Marketing side, there are parts of Marketing that require engineering. “Build me a landing page,” or, “Let me do this,” or, “Give me an SQL query that interrogates this for me and gives me the export.”
And it was always like, you know what, the engineering part of Marketing, let’s be honest, is usually boring and nobody wants to do it. So it always felt like, “You know what? I’m doing you a favor.”
It was always in between tasks, like, “If there are some story points remaining in the sprint, please also drag in this small ticket that basically enables the whole Marketing team.”
Indeed, now you don’t need that anymore because those quick and dirty things can be solved by people who don’t have an engineering background.
You basically become, as you said, more independent, stronger, and more self-reliant.
Oksana (14:35 – 15:50)
That’s amazing, and we just give engineers more time to work on complex things that can’t be replaced. It’s amazing to see how creatively people use AI on a daily basis to empower themselves to do tasks they couldn’t do before.
Another thing that I personally use, and I know a few of my team members also do, is AI for voice input. There are a few tools. I’ve tested things like SuperWhisper, and I’m now testing a free tool called Pipit, I think.
It’s a small tool that allows you to not type an email, but just use voice input. Before AI, it was pretty hard to use because some of the words were not transcribed well, there was weird punctuation, and other issues. But with AI, you can train it so that it transcribes your voice exactly as you want. You can create different styles, whether it’s an email or something for your colleague.
So I find myself using that a lot and just talking to my computer more because it’s much faster than typing things in.
What Oksana Would Do Differently After Eight Years
Irina (15:51 – 16:01)
Okay, that’s interesting. Okay, looking back at eight years of building, what’s something you do completely different from day one?
Oksana (16:04 – 18:25)
I think not much, but to be honest, what I would do even earlier is try to implement this more holistic view of customers within my team.
I think every company, in its evolution, starts with just answering tickets and responding to people’s requests after something has already happened. Then we start switching more and more toward giving people the right tools and asking them if everything is all right before they send a ticket.
So there was this big switch for me in my third year as a team leader, when I basically revamped the team from Customer Support to what we formally called Customer Experience. We included more of those things that we now know as Customer Success into our daily work.
I think I would want to do that even earlier if possible because I find that motivating for the team. When people see the logical chain of events with every customer, how they bring revenue, how they renew, what the sales cycles are, and everything else, they understand better what their impact is on the company. They see the results of their work versus just getting a thousand tickets every month, replying to them, and not knowing what’s going on.
I think that shift is very important. As soon as we made that shift, I think we became more motivated as people in customer-facing roles.
Another thing I would do earlier is those custom messages and video messages that I talked about before, being more personalized with people and giving a personal touch.
We always did a lot of that. We never used templates, which is what I love about the team. We never gave robotic responses, let’s say. But even more customization, even more attention to what’s happening in the company, and going from there would be what I would do if I could do it again.
Building Customer Success With a Three-Person Team
Irina (18:25 – 18:32)
And if you had to rebuild a CS work from scratch with only three people, what would you prioritize first?
Oksana (18:34 – 20:12)
I’ve built it with a very small team, so I think that’s actually how I built it.
What I would prioritize first is giving people time to not answer every question with a custom answer, but to create solutions that will help them save a little bit of time to do other things.
My mentor, our CEO Sami, always told me, even when I was a Support agent myself and had just started at the company, “Oksana, I don’t want you to just answer questions that you see for the first time. I want you to create articles. I want you to create tutorials immediately.”
At first, I was like, “Oh my God, this is just an incredible amount of tutorials to make,” and it seemed like a never-ending collection of questions. But when we created lots of them, we realized that people were answering questions super fast, and some of the questions were just never being asked because people were going to the knowledge base and serving themselves.
If I had three people, I would be very focused on that because it’s not a lot of resources. I would much rather involve them in other types of tasks, like proactive outreach, discussing the customer journey, reproducing more complex issues that people have, and suggesting new features for the roadmap.
That’s always the more interesting part than just mechanically answering questions. So I would definitely start by building a self-service system for the customer.
Why Relationships Still Matter More Than Tools
Irina (20:13 – 20:26)
You’ve built a dip in one place and kept finding new problems to solve. Is there a mindset or a piece of advice, something that you learned the hard way that still shapes how you approach the work today?
Oksana (20:28 – 22:01)
I talk a lot about people and relationships here, and I think I’ll talk about them again. It’s both relationships with customers and relationships with internal colleagues that are very valuable to me.
I think the priority is to have people around you who know a lot of context, who are ready to answer customers and support them.
Having all of this knowledge is very hard to replace. When a new person comes in, you can train them, of course, but there are several people in the company who still know the oldest bugs we had and the oldest cases we’ve handled. This gives them this irreplaceable experience and context. They can just hear about something and know what to do because they’ve already encountered it.
It’s the same with customers.
Again, as I said, health scores and all of those tools are very good, but if a person trusts you, they’re much more likely to tell you something is wrong beforehand, so you know how to prepare. They’re also much more likely to share their plans with you.
Relationships with people are the biggest advantage of this job. It’s also why I don’t think it’s going to be replaced by AI anytime soon, because people want to talk to people, buy from people, and renew with people.
So I think that’s the biggest thing I’ve learned.
Irina (22:03 – 22:29)
Oksana, this was a great conversation and I really enjoyed getting into the practical side of building the CS infrastructure, what it actually takes, where to start, and what you do differently. Thanks so much for joining me today.
And to everyone listening, thanks for tuning in. Until next time, stay curious, keep learning, and mastering customer success. Bye-bye.
