Jessie Gill leads enterprise strategy at Wheels as chief of staff

Jessie Gill, senior vice president and chief of staff at Wheels, is using 16 years of executive and chief of staff experience to drive strategy, planning and transformation across the company. She also runs a consulting firm and says the role has become a strong training ground for broader enterprise leadership.

Why it matters: - Jessie Gill’s career shows how chief of staff roles can shape enterprise strategy, operations and executive decision-making. - Her work at Wheels, LLC connects CEO priorities to cross-functional execution, a model many growing organizations need as business complexity rises. - Her consulting practice extends that operating approach to founders, CEOs and high-profile clients navigating change.

What happened: - Jessie Gill serves as senior vice president and chief of staff at Wheels, LLC, a fleet management company. - She partners with the CEO on enterprise strategy, long-range planning and transformation initiatives. - Gill has spent 16 years in chief of staff and executive leadership roles across complex organizations. - She also founded JKG Elite Consulting, where she provides fractional executive advisory services. - Gill’s LinkedIn and Influential Women profiles were included for more information: Influential Women profile and LinkedIn profile.

The details: - Gill leads Wheels’ strategic planning process and works to align business units around shared priorities. - She provides executive oversight tied to enterprise accountability and organizational outcomes. - Her responsibilities include decision support, governance coordination and operational execution. - Gill also prepares CEO briefings that incorporate client, market and geopolitical context. - Her career began in 2010 at an energy efficiency software company, where a mentor introduced her to the chief of staff role. - She later held leadership roles at fleet management, Am Law 100 legal services and consumer brands including Dunkin’ Brands, Inspire Brands and Arby’s Restaurant Group. - Gill says the role has given her a broad view of how organizations allocate resources, manage change and translate strategy into performance. - She believes the chief of staff position can serve as a training ground for broader enterprise leadership when it carries real scope and accountability.

Between the lines: - Gill’s message reflects a broader shift in executive leadership: organizations increasingly value leaders who can operate across functions instead of staying inside one silo. - Her career path also underscores how mentorship can change the trajectory of emerging leaders, especially in traditionally male-dominated environments. - The article positions resilience, confidence and discipline as core traits for women pursuing executive roles. - Gill’s consulting work suggests demand for executives who can advise on growth and transformation without being embedded full time.

What’s next: - Gill says she remains focused on helping organizations connect strategy to execution and expand leadership impact. - She expects cross-functional enterprise leaders to become even more important as organizations grow more interconnected. - Her public profiles provide a channel for readers who want to learn more about her work and background.

The bottom line: - Gill’s career centers on one theme: executive vision only matters when it turns into disciplined enterprise execution.