J.R. Striker: What I learned in my first 60 days listening to customers

By J.R. Stricker, Chief Customer Officer, Lone Wolf Technologies

When I joined Lone Wolf, I didn’t start by calling customers. I started inside the building.

The first thing I did was ask our HR team for the most recent employee survey. I wasn’t looking at the scores. I wanted the comments. What do the people who serve our customers every day say about working here, what’s working, and where do they keep hitting walls? Then I went and sat with them. About 60 percent of my team works out of a single facility, so I flew there and conducted in-person focus groups and one-on-ones. Everyone else I met over Teams. I talked to my peers, key stakeholders, and anyone who interacts with the customer. Then, and only then, I started calling customers.

I did that on purpose. The experience you create for your employees is the experience they hand to your customers. If I wanted to understand why customers felt what they felt, I had to understand what it’s like to do the work.

The same story, told in every room

Here’s what struck me. The internal feedback and the customer feedback rhymed. I’d go from a focus group to a one-on-one to a customer call, and the same themes kept surfacing. For someone in my seat, that’s a gift, because it means you don’t have to guess. By the third or fourth focus group, it was already clear.

One of the first customers I spoke with has been with us for years and sits on our customer advisory board. She values us as a partner and wants us to win, and she was honest with me about where we come up short. She turned out to be representative of a lot of what I heard. Two patterns came through, loud and clear.

We were getting customers live, not getting them successful

Our onboarding was built around the wrong finish line. The goal had quietly become: get the customer in, get them live, on time and on budget, move on. That sounds efficient. It isn’t, not if the customer isn’t actually doing the thing they bought the software to do.

And this isn’t a people problem. I have genuinely good people on that team. They were pointed at the wrong target. The question we should be asking at the start is simple: what is this customer trying to achieve? In software, we talk about the “aha moment,” the one or two things that, once a customer can do them, mean the product is working for them. That has to become our true north. Get them successful, then go live. Not the other way around.

The burnt popcorn and the house on fire

The second pattern was support, and it’s the one I keep thinking about. Today, if you email us, that becomes a case. We send a note confirming we got it. Then it can sit in a backlog for two days.

Here’s the bad analogy I keep using, because it fits. Right now, we show up the same way whether you burned your popcorn in the microwave or your house is burning down around you. Those are wildly different situations, and we’ve been treating them identically. That’s the part that has to change. When a customer’s house is figuratively on fire, we should be sprinting toward it.

Same as onboarding, this isn’t because the support team doesn’t care or lacks the skill. It’s the structure they work inside, the tooling we’ve handed them, and the way cases route. Good people, set up to lose.

Why 80 percent of the questions start with “how do I”

One number reframed the whole thing for me. About 80 percent of the questions coming into support are how-to questions. Not “something is broken.” Just “how do I do this?”

Sit with that for a second. The average real estate agent sells two or three homes a year. They are not living inside our software every day. So when they do come in, it has to be intuitive, and help has to be easy to reach. Eighty percent how-to tells me two things at once. There’s real room to make the product more self-explanatory, and there’s a support model spending most of its energy on questions a customer should be able to answer in seconds.

What I’m not going to do

I’m not going to tell you it’s all fixed. This isn’t the part where I unveil the plan. It’s the part where I tell you I heard you.

What I can tell you is that I’ve done this work before, more than once, and I know what right looks like. I also know the worst move would be to roll in with a pre-baked answer and skip the listening. So I ran the whole organization to ground first, because everyone deserves not just a voice but a voice that’s actually heard. The plan comes next, and you’ll hear about it. For now, the honest headline is that Lone Wolf is owning where it has fallen short, and the listening was step one.

Frequently asked questions

• Q. What did Lone Wolf’s new Chief Customer Officer find in his first 60 days?
  A. Two consistent patterns: onboarding built around going live rather than customer success, and a support experience that treated urgent and minor issues the same way.
• Q. Why did he start internally instead of with customers?
  A. Because the employee experience shapes the customer experience. Reading employee comments and sitting with frontline teams surfaced the same issues customers were raising.
• Q. What share of Lone Wolf support questions are how-to questions?
  A. About 80 percent, which points both to product usability opportunities and to a support model carrying avoidable volume.
• Q. Is this a staffing problem?
  A. No. The teams are skilled and motivated. The issues trace to structure, tooling, and process, not to the people doing the work.