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.
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.
Rachel Bridgeman
Director of Operations
Rachel Bridgeman brings over 20 years of experience in operations, HR, and leadership development to her role as Director of Operations at DSS Advisory. She partners with HR leaders and executive sponsors to design custom coaching engagements and leadership programs, tailoring each one to the needs and culture of the organization. Behind the scenes, she keeps operations running seamlessly—managing business processes and anticipating client needs. Her thoughtful, people-first approach is a key part of what makes DSS Advisory a trusted partner to clients.
Rachel began her career in financial services as a recruiter before moving into an HR Business Partner role at Tiffany & Co. There she spent five years supporting business leaders before her her work transitioned into project, program, and HR operational management. At Tiffany & Co., Rachel helped to build leadership and development initiatives, established a mentorship program, and improved processes that supported cross-functional collaboration. After relocating from New York City to Raleigh, NC, she joined Epic Games as HR Operations Manager, where she tripled the HR operations team, implemented an employee engagement survey, and managed the executive coaching program. She now brings that same sense of structure, clarity, and follow-through to her work at DSS Advisory—always focused on streamlining operations and supporting clients with consistency, care, and connection.
STRATEGIC PARTNERS
Our global network of coaches and leadership development consultants helps us design the perfect approach for you and your organization.
