Improving Your World?


We help mission-driven organizations execute

Deep Why picks up where strategy leaves off. If you’ve got a bold new strategic plan, a great idea for a new service, or any other big change you need to make, we guide your team through the operational changes that will make it real.

humanized systems

Deep Why exists to help organizations transform and humanize their operational systems. Humanized systems are transparent, equitable, and effective. They allow you to pursue operational excellence without burning out your team.

What’s In a Name

Our name is a nod to the 5 Whys practice of continuous improvement. This approach to problem solving and design allows us to ultimately get down to the root cause of many inter-related problems or pain points, which we call the Deep Why. This Deep Why provides simplicity and clarity and allows us to design and implement enduring, resilient operations.


Experienced Guides


Human-Centered Doers Who Know the Territory

We’re human-centered doers: combining all of the stakeholder engagement, iteration activities, and design thinking that make human-centered design so powerful with a practical, implementation-focused approach shaped by years of experience getting things done.

Jenn Bender, Partner

People, Process, and Strategy Alignment

Jenn has spent her career helping mission-driven organizations align their operations with their strategies so they can more effectively achieve their intended impact, pursue their growth goals, and improve the experiences of their stakeholders. Read more…

Jenn Taylor, Partner

Information, Process & Technology Systems

Jenn has worked directly with more than 100 nonprofits and educational organizations of all types and sizes to help them implement new (or transform existing) digital systems, adjust processes accordingly, and problem-solve throughout implementation to ensure successful adoption. Her current focus is humanizing digital systems in the social sector. Read more…

Dave Borgal, Consultant

Process Design and Management

Dave is the founder of Bottom Line, a nationally-recognized non-profit with a mission to help first-generation students from low-income backgrounds get in to college, graduate from college and go far in life.  Under his guidance, Bottom Line grew from its start with 25 students in 1997 to serving nearly 8,000 students per year in Boston, New York, and Chicago in 2018. Read more…


Patricia Holliman, Consultant

Technology Innovation

Trish has worked with dozens of nonprofits to help them envision, architect, design, and implement better ways to capture program data and support program staff with technology. As an architect and engineer, Trish brings more than 30 years of full lifecycle technology experience to bear on her solutions design. Her career in local government and higher education technology lends a public sector expertise to her work at Deep Why. Read More…