00:00.00
Niraj Ranjan Rout
Hello everyone, welcome to the Experience Matters podcast. Today we have Christian with us. Christian Sokolowski is the Vice President of Customer Support at Rebuy Engine, a company that helps e-commerce brands personalize the shopping experience using AI. Christian brings over 14 years of experience in IT operations and customer support.
00:20.26
Niraj Ranjan Rout
Before Rebuy, he worked across multiple industries — from managing tech support in the hospitality space to leading support operations in logistics and e-commerce.
Quite clearly, Christian, you have a very diverse experience, having worn multiple hats through the years. I’m really looking forward to this conversation and your insights.
Let’s start by getting a sense of what you do in your current role. It’d be great to understand exactly what you do at Rebuy.
00:38.99
Christian Sokolowski
Likewise. Thanks for having me.
00:56.53
Niraj Ranjan Rout
I see that you’ve been there for more than three years. Could you help us understand how your role has evolved during that time?
01:05.14
Christian Sokolowski
Sure. Like you said, I currently hold the role of VP of Customer Support. Originally, I joined around three years ago when it was still a very small startup — probably around employee number 25.
01:19.09
Christian Sokolowski
I had worked with some of the people here before, and they knew I had a knack for building operational teams and structure. So, initially, my goal was to come in and build everything from scratch. There was a small team doing some level of support, but there wasn’t any real framework around how things should work or how we could grow.
01:36.45
Christian Sokolowski
The company itself was growing so fast that we needed to evolve and build from the ground up — but do it responsibly. It was a startup when I joined, so funding was a big factor.
02:00.22
Christian Sokolowski
Building everything from scratch, my role has since transitioned into having a larger presence within the company. Initially, I was focused purely on support; now I act more as a liaison between the product and go-to-market teams.
02:16.99
Christian Sokolowski
That’s really what support should be, in my opinion — bridging the gap between both sides of the house, because both impact us.
02:26.15
Niraj Ranjan Rout
Yeah.
02:29.28
Niraj Ranjan Rout
Makes sense. How has the team evolved over the last three years? How big is it now, and as it’s grown, have there been any new skills you’ve hired for or mentored your team toward?
02:49.59
Christian Sokolowski
Yeah, we’ve grown from a very small team — probably three or four people including myself — to about 20 people now.
02:58.44
Niraj Ranjan Rout
Wow.
02:58.92
Christian Sokolowski
Tremendous growth from both the team and company perspective. We’re now well over 100 people company-wide, so we’ve seen great results all around.
03:11.25
Christian Sokolowski
From an overall perspective, our team is unique because we’re customer support — but not the typical “frontline” people might imagine.
03:23.73
Christian Sokolowski
Everyone on our team has gone through at least a bootcamp to become a junior full-stack developer. So when customers talk to us, they’re essentially speaking with a level-two support engineer from the start.
03:33.29
Niraj Ranjan Rout
Wow.
03:37.71
Christian Sokolowski
What we really teach people here is emotional intelligence. They already have the technical background to get started, but learning how to handle customers and grow within their roles — often into senior developer positions — is key.
03:57.34
Christian Sokolowski
And most recently, of course, AI has been the big topic. So, training people on how to use AI effectively to increase efficiency has been a major focus.
04:08.30
Niraj Ranjan Rout
That’s very interesting. You mentioned that the entire support team essentially has an engineering background, and you work with them to help them get started in support — then later they can move deeper into engineering if they’re interested.
That’s quite unique — hiring engineers for a support team. How do you find the right skill set and attitude in people who may not have been trained for customer-facing work?
04:43.48
Christian Sokolowski
Yeah, that’s a good question. I’ve found a lot of value in partnering with bootcamps that genuinely care about their students and focus on helping them evolve.
04:59.01
Christian Sokolowski
One of them is a program called V School, which I’ve partnered with. We help mold their curriculum to align with what we’re looking for.
05:09.62
Christian Sokolowski
Whenever I need new talent, I reach out and ask for the best candidates. A lot of our hires have come from there, so we know exactly what foundation they have when joining.
We also rely heavily on referrals — if someone on the team recommends a candidate, I’ll prioritize them, because good people tend to know other good people.
05:34.49
Christian Sokolowski
Maybe their resume doesn’t look like “Harvard graduate,” but I believe real-world experience often matters more than what’s on paper.
05:44.03
Niraj Ranjan Rout
Makes sense. You mentioned V School — could you share a bit more about what that is, for the audience?
05:52.64
Christian Sokolowski
Yes. V School is based out of Utah — fully remote now — and they offer several programs, mostly focused on software development.
06:11.25
Christian Sokolowski
They teach everything from front-end to back-end development. For us, it’s more front-end heavy.
But what they don’t teach is how to interact with people — that’s where we step in.
06:22.10
Christian Sokolowski
I focus a lot on emotional intelligence — how to handle conversations, manage people, and become a trusted advisor.
Support isn’t just about fixing things; it’s about partnership and retention.
06:47.76
Christian Sokolowski
In my opinion, the biggest goal in support is becoming a trusted advisor and partner to our customers — because retention is everything. The more you retain, the stronger your business becomes.
06:58.71
Christian Sokolowski
We encourage our customers to reach out to us frequently. Interestingly, a third-party analysis showed that the more someone interacts with support, the more likely they are to stay — as long as the experience is good.
07:24.83
Christian Sokolowski
So we really focus on creating those strong one-on-one interactions.
07:35.05
Niraj Ranjan Rout
Makes sense, that aligns with what we’ve seen at our company too. Good engagement with support is generally an excellent indicator of customer health.
07:45.68
Christian Sokolowski
Yes, absolutely.
07:46.56
Niraj Ranjan Rout
I understand you scaled from a handful of people to 20, and your customer base has expanded. How has your tooling evolved over these three and a half years? Are you bringing in new tools or phasing some out? What areas are you exploring?
08:13.93
Christian Sokolowski
We use an omni-channel solution, Intercom, as our main ticketing and chat system. It’s evolved significantly from just basic chat to now handling conversations from multiple sources like email and social channels.
08:29.35
Christian Sokolowski
With e-commerce, social media has become a major channel, so being able to interact across platforms is crucial.
We’ve also integrated AI tools like Cursor, which helps with coding — since we do a lot of that daily.
08:58.39
Christian Sokolowski
Our team customizes things for customers since our app sits on top of their e-commerce stores. Making our product look and feel native helps retain customers and drives upsells.
09:25.59
Christian Sokolowski
We also use AI internally for queries and quality assurance. We’ve built internal AI bots — one for team questions and another for QA on tickets.
09:50.36
Christian Sokolowski
We also use sentiment analysis to evaluate conversations objectively and see what we’re doing well or not.
As you probably know, CSAT is great but often biased — with under 10% response rates that capture only the extremes.
10:17.50
Christian Sokolowski
So sentiment analysis helps us fill those gaps and improve efficiency.
10:26.40
Niraj Ranjan Rout
Very interesting. How important are autonomous bots in your setup? Do customers interact with AI first before being routed to a human?
10:41.07
Christian Sokolowski
Yes. Our level-one support is AI-driven, and we’ve seen resolution rates between 35–45% when customers engage with it.
11:01.55
Christian Sokolowski
Customers can always choose to talk to a human, but recently we’ve seen some AI fatigue — people asking directly for human support.
The challenge now is keeping customers engaged with AI so it continues to reduce handle times and save resources efficiently.
11:42.27
Christian Sokolowski
We review content daily — updating scripts, adding guidance, and refining interactions.
It’s a huge area that’s exploding across the industry.
12:11.75
Christian Sokolowski
AI isn’t taking jobs away — it’s creating new ones. So we’re focusing on upskilling our teams to use it effectively.
12:25.52
Niraj Ranjan Rout
Makes sense. You mentioned sentiment analysis earlier — are there other ways you’re using AI to extract insights?
12:51.69
Christian Sokolowski
Yes. We use AI for content suggestions — identifying repetitive questions we aren’t addressing well, then creating documentation for them.
13:13.15
Christian Sokolowski
We also tag tickets automatically to detect product-related issues. This helps us identify which features drive the most satisfaction or friction, and we share that data with the product team to guide priorities.
13:51.65
Niraj Ranjan Rout
That’s a great segue into the second part — your role as a bridge between GTM and product/engineering.
How did you transition from managing support to this cross-functional role?
14:14.83
Christian Sokolowski
It was a natural progression. As a support leader, when something goes wrong, it impacts us directly. So I started getting more involved in decisions that affect both product and GTM.
14:33.51
Christian Sokolowski
Now I act as that bridge — weighing priorities between what GTM teams push for and what’s feasible for product to deliver.
15:13.46
Christian Sokolowski
It helps to be the “voice of reason” between the two sides, ensuring alignment instead of tension.
15:22.39
Niraj Ranjan Rout
Makes sense. How do you manage that operationally? Through reports, cadences?
15:35.03
Christian Sokolowski
I’m technically part of the GTM org, so I join weekly leadership meetings covering pipeline, retention, and expansion.
We share data from support to help inform decisions and prioritize improvements. I also meet regularly with product leadership to relay customer insights and pain points.
16:35.12
Christian Sokolowski
I’ve always had strong relationships with product teams in past roles, and that’s been key — if support and product are at odds, nothing gets done.
16:51.16
Niraj Ranjan Rout
Absolutely. You’ve also worked in other sectors like logistics. How does customer support differ across industries compared to e-commerce?
17:19.41
Christian Sokolowski
There are similarities, but e-commerce is definitely different — and honestly, more fun. In telecom or enterprise support, you’re dealing with big corporations where uptime and metrics rule. In e-commerce, you’re working with passionate entrepreneurs — often bootstrapped — who depend on you directly.
18:27.40
Christian Sokolowski
Urgency is higher. A small bug for a big brand might be minor, but for a small seller, it’s critical. So we treat every issue with the same level of importance.
19:06.78
Christian Sokolowski
We also deal with a wide range of users — from non-technical shop owners to advanced developers — so being both educator and advisor is essential.
19:34.87
Christian Sokolowski
Seasonality plays a huge role too — Black Friday and Cyber Monday are make-or-break moments.
19:40.19
Niraj Ranjan Rout
Totally. Given how AI is shaping support today, do you see it helping you strengthen customer trust — or making it harder?
20:05.88
Christian Sokolowski
I think it’s helping. For customers who embrace it, AI provides instant answers — which today’s users expect. We’ve also seen that faster response times directly correlate with higher CSAT, with or without AI.
20:45.27
Christian Sokolowski
When people escalate past AI, we focus on giving them personalized attention. AI handles repetitive queries, freeing our team to deliver more thoughtful human interactions — which has boosted CSAT to 96% this year, up from 95% last year.
21:34.84
Niraj Ranjan Rout
That’s impressive. Last question — how do you manage and maintain your help center in such a fast-changing environment?
21:57.34
Christian Sokolowski
Documentation is tough to stay on top of. Many companies write docs and never revisit them. We track which articles are being used, how often, and whether they actually resolve issues. If not, we review and improve them.
22:36.49
Christian Sokolowski
We also use AI content suggestions to identify missing or outdated topics. Writing for both humans and AI now is key — because AI models need clarity too.
23:16.13
Christian Sokolowski
Having someone dedicated to content accuracy will soon become essential for every company using AI.
23:31.67
Niraj Ranjan Rout
Makes sense. Does your support team own documentation, or is it handled by product or marketing?
23:39.60
Christian Sokolowski
We own the knowledge base 100%. I even write about half of our documentation myself — it keeps me close to the product.
23:53.41
Christian Sokolowski
When a new product or feature is released, the product opens a JIRA request tied to their epic so we can follow along. They provide specs and videos, and we write content that’s more customer-friendly and instructional.
24:30.28
Christian Sokolowski
Support teams use the product more than anyone else — so they’re best suited to explain it clearly and engagingly, not just technically.
24:49.34
Niraj Ranjan Rout
Makes sense. That’s very useful. This was a great conversation, Christian — thank you for your time.
25:02.18
Christian Sokolowski
Absolutely. Appreciate it.
25:03.90
Niraj Ranjan Rout
Thank you.
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