Stephen Shivers, Director of Product Management at Lone Wolf, has been named to HousingWire's 2026 Insiders list. The award recognizes the people HousingWire calls operational all-stars, the ones who work mostly out of view and are still the reason a company holds together. He earned the recognition for the way he builds products and for paying attention to the people who use them.
Who is Stephen Shivers?
Before Stephen ever shipped a product for real estate agents, he spent more than a decade at RE/MAX, a lot of it working shoulder to shoulder with agents and brokers. He learned how they actually work, where they get stuck, which shortcuts they trust, and what tech they abandon after a week.
That field experience became a standard he holds his teams to now. Build for how agents really work, even when the version that looks impressive in a demo would be easier to ship. It is a harder way to run a product team. It is also why the things his team builds tend to stick.
What did Stephen build this year?
Over the past year, Stephen led the work to give brokers direct control over their Cloud CMA listing presentations. In the past, a broker who wanted to rebrand a report, adjust colors, or add their own content had to file a request and wait on Lone Wolf's onboarding team. Even a small change could create a real delay. Stephen's team built an admin area that hands that control back. Brokers update their own branding, change colors, and add or edit pages themselves. For larger companies, the controls expands to the office and team level. The idea came straight out of conversations with brokers about a specific frustration, and the result gave them back two things at once: their time, and ownership over how they show up to clients.
That instinct connects across his work. On Boost, Lone Wolf's advertising product, his team kept hearing the same wish from agents. They wanted to be the local market expert their clients remember, and they wanted it to take almost no effort. So the team built a market-stats ad that an agent can launch in a single click, branded to them, with the technology doing the heavy lifting quietly in the background. The agent gets to be the expert. The software stays out of the way.
He recently took on the Transact product line after years leading Lone Wolf's agent-facing products, including Boost and Cloud CMA.
What makes his approach different?
Plenty of product leaders say they listen to customers. Stephen's version has teeth. His team gathers feedback on the products and then follows up on it, including with the customers who are unhappy.
He is candid about where Lone Wolf has been and how the company is working to change how customers experience it. He handles that history openly rather than defensively, which is its own kind of leadership.
"The person who emails me to say 'I hate this' is exactly who I want to talk to. That is where a one-star experience turns into a five-star one. You just have to be willing to hear it."
"Stephen builds the way we want the whole company to build. He starts every decision with a real conversation with the people who use our products. This recognition from HousingWire is well earned."
Where does this fit for Lone Wolf
Lone Wolf has been shifting toward more listening, faster iteration, and real care for the people its software serves. Stephen has been working this way for years, so the direction is not new to him. It is a habit he already had.
Congratulations, Stephen — from all of us at Lone Wolf.
Frequently asked questions
- What is the HousingWire Insiders award?
The HousingWire Insiders award recognizes operational all-stars in housing and real estate, the professionals who often work behind the scenes and are vital to their company's success. HousingWire selects the list annually. - Who won the 2026 HousingWire Insiders award at Lone Wolf?
Stephen Shivers, Director of Product Management at Lone Wolf, was named to HousingWire's 2026 Insiders list. - What does Stephen Shivers do at Lone Wolf?
Stephen Shivers is Director of Product Management at Lone Wolf. He has led the company's agent-facing products, including Boost and Cloud CMA, and recently took on the Transact product line. - What did Stephen Shivers build for Cloud CMA?
His team built an admin area that lets brokers control their own Cloud CMA listing presentations. Brokers can update branding, change colors, and add or edit pages themselves, with controls that reach down to the office and team level for larger companies, without waiting for a manual onboarding request. - When was the award announced?
Lone Wolf announced Stephen Shivers' recognition on August 3, 2026.
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