We’re proud to share that Denise Pickering, Obie’s Lead Program Manager, has been named a 2025 HousingWire Insider. This national award honors the behind-the-scenes leaders driving innovation and progress across the real estate and insurance industries.
At Obie, we know that great technology means nothing without great execution. Denise is the force behind some of our most complex and critical initiatives, from leading the successful rollout of Obie’s company-wide rebrand to building systems that improve efficiency across our service, data, and finance teams.
In 2024 alone, her leadership helped reduce manual processing time by 50%, contributed to a significant decrease in employee burnout, and ensured that product improvements were delivered on time and with precision. She also oversees Obie’s Business Quality Assurance function, ensuring that every platform enhancement meets the highest standards before it goes live.
With nearly two decades of insurance experience and a rare ability to bring clarity to complexity, Denise has become a cornerstone of operational success at Obie. Her work helps ensure we consistently deliver the seamless experience our clients, partners, and internal teams count on.
“Denise brings a rare combination of deep expertise, precision, and a people-first mindset to everything she touches,” said Laura Olson, Chief Insurance Officer at Obie. “She has a gift for turning complexity into clarity and vision into results, making her an invaluable leader and partner. Her positivity, empathy, and relentless drive for excellence make her not only effective but a true pleasure to work with. This recognition is incredibly well-deserved.”
Behind every efficient process and scalable partnership is someone like Denise. She drives impact, solves problems, and keeps teams aligned. We’re honored to have her at Obie and proud to see her leadership recognized by the HousingWire Insiders program.
Congratulations, Denise, and thank you for everything you do!
Learn more about how Obie supports smarter, more scalable insurance solutions at obieinsurance.com.
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