In this episode of the CTO Compass podcast, Mark interviews Kelsey Daingerfield, founder of Pocket COO, who specializes in bridging the gap between technical teams and executive leadership. Kelsey shares her journey from higher education to entrepreneurship, discussing the importance of the visionary vs. integrator dynamic, the role of a fractional COO, and how to identify operational red flags. She emphasizes the significance of effective delegation, change management, and communication within teams, as well as the need to change the perception of IT departments. Kelsey also highlights the potential of AI in optimizing operations and shares a success story of transforming a business to achieve greater efficiency and work-life balance.
00:00 Introduction & Background
02:13 Visionary vs. Integrator (Rocket Fuel)
05:00 Transition into Entrepreneurship
08:24 Client Work Examples
11:28 Recognizing Operational Red Flags
18:39 Delegation & Leadership Challenges
25:33 Change Management & Communication
31:15 AI in Operations
37:42 Common Leadership Pitfalls
40:14 Success Story
43:23 Final Advice & Wrap-up
Kelsey Daingerfield is the founder of The Pocket COO, where she partners with growth-stage founders to help them scale without burnout. With a background in operations, marketing, and project management—plus early career experience working alongside engineers—Kelsey is a master of translating vision into execution and bridging the gap between technical teams and executive leadership.
Today, she serves as a strategic COO and advisor for founders who are scaling fast but feel stuck in the weeds. Her specialty is turning chaos into clarity by building the operational infrastructure businesses need to run smoothly and sustainably. Whether it’s team delegation, systems setup, or change management, Kelsey brings both structure and soul to her clients’ companies—so they can grow without grinding themselves into the ground.
