About Us

DSS Advisory is the boutique coaching and leadership development group founded by Deanna Siegel Senior.

Drawing on more than two decades of coaching, research, and internal leadership experience, we offer coaching and advisory services rooted in the science of self-discovery and proven to drive impact at organizations of all sizes. We’re also pretty fun to work with.

 
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Deanna Siegel Senior, Ph.D.

Founder and Executive Coach

Deanna Siegel Senior, PhD, is a certified executive coach and accomplished Head of Talent with more than two decades of experience coaching high-performing leaders and teams. In her coaching practice, she specializes in executive transitions and focuses on how the most effective executives inspire their teams through authentic leadership and radical candor. Her guiding approach is to help leaders identify their motivations and values in order to effectively tailor their leadership style and discover greater levels of success and ease in all areas of life.

Deanna received her PhD in Organizational Psychology from Columbia University, and has coached C-suite executives, start-up founders, mid-career managers and emerging leaders as well as led large teams in People and Talent at brands including Tiffany & Co., WW (reimagined from Weight Watchers), Deloitte and Pfizer.

Throughout her career, Deanna has built a solid reputation as a pragmatist who builds strong relationships, and acts boldly to identify and address challenges.

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Rachel Bridgeman

Director of Operations

Rachel Bridgeman is a strategic and resourceful project management, operations and human resources professional. She began her career in financial services as a recruiter before moving to a Human Resources Business Partner role. Always being asked to join special projects teams, she found her calling in operations and project management.

Rachel had the pleasure of creating career growth & development initiatives, designing custom leadership and team building sessions, and building mentor programs (though some colleagues may say her favorite assignment was managing the budget!).

As an Operations Professional, Rachel derives joy from filling in the white space and anticipating business and client needs at every turn. She had a professional reputation for removing barriers to create cross-functional partnerships and this became her legacy both at Tiffany & Co. where she worked for ten years before relocating from New York City to Raleigh, NC and at Epic Games, where she was the Human Resources Operations Manager. There she managed the executive coaching program, tripled the HR Operations team and implemented an employee engagement survey.

Rachel now enjoys her life on a suburban cul de sac. When she’s not working to support DSS Advisory clients, she is building LEGO with her son, playing Barbies with her daughter, baking for friends and neighbors, and avoiding necessary yard work.

 

STRATEGIC PARTNERS

Our global network of coaches and leadership development consultants helps us design the perfect approach for you and your organization.

I have benefited tremendously from Deanna’s radical candor both professionally and personally, and I can’t say enough about Deanna’s strengths as a coach and mentor.
— Lisa Itzkowitz — Director, Change Management and Organizational Effectiveness at Tiffany & Co.