As lead program manager at Obie, Denise Pickering is the driving force behind the company’s most complex, cross-functional initiatives. In the past year, she led the successful execution of Obie’s full rebrand — an eight-month effort spanning engineering, product, design, marketing and executive teams. The launch went live on schedule and without incident, a direct result of Pickering’s disciplined project management, clear communication and unwavering attention to detail.
Beyond the rebrand, Pickering has overseen automation and infrastructure improvements that cut manual processing time in half across key departments, contributing to increased efficiency and a measurable improvement in employee well-being. She also manages Obie’s Business quality assurance function and plays a central role in the company’s strategic planning and objectives and key results (OKR) process — bringing structure and consistency to areas that impact every team.
With nearly two decades of insurance experience and eight years in program management, Pickering is known across Obie for her operational fluency and calm, pragmatic leadership. She leads through clarity, not command — guiding teams through complex challenges with empathy and precision. Her ability to synthesize moving parts and keep cross-functional projects aligned has made her a trusted partner across departments.
Pickering has been promoted twice since joining Obie and was recently recognized as the company’s 2024 “Top Dog of the Year,” a reflection of her influence and steady contributions behind the scenes. Whether mentoring colleagues or leading mission-critical initiatives, she brings consistency, care and a deep commitment to progress.
Name:
Denise Pickering
Title:
Lead Program Manager
Company Name:
Obie
