The Coaching Clinic: Tax Season Strategies

Busy season is where tax strategy, risk management, and execution converge. Watch The Coaching Clinic: Tax Season Strategies, led by Megan Leesley, CPA, Director of Tax at Dark Horse CPAs, as she breaks down real-world tax scenarios, high-stakes decision points, and practical techniques firms can apply immediately as deadlines approach. Ramp will close with a brief overview of its 1099 capabilities as one operational lever to support busy-season execution.


You’ll learn:

  • How mid-market and enterprise firms prioritize tax strategy versus compliance under tight timelines
  • Key judgment calls that impact client risk, advisory value, and downstream outcomes
  • Approaches to managing complex tax scenarios without overextending teams
  • Ways to create capacity while maintaining consistency and quality at scale

About the speakers

Megan Leesley's profile picture
Megan Leesley
Director of Tax, Dark Horse CPAs
Megan Leesley is a seasoned CPA with a robust background in public accounting, currently serving as the Director of Tax at Dark Horse CPAs. With over a decade of experience in management and product management prior to beginning her career as a CPA over 11 years ago, Megan brings a unique blend of strategic insight and practical expertise to her role, offering a fresh perspective in the industry. Megan is also an active member of various focus groups and councils, where she collaborates with other tax professionals and firm owners to shape the future of public accounting. She is a sought-after speaker at industry conferences, having presented on planning strategies for tax law changes, making the transition from compliance to advisory services, and various other topics designed to help practitioners see their value, embrace learning and growth, reduce burnout, and elevate their relationships with both clients and peers.  She is committed to helping other professionals navigate the complexities of the industry and achieve their career goals. 
Nigel Reiff's profile picture
Nigel Reiff
Sr. Solutions Consultant, Ramp
Nigel is a Sr. Solutions Consultant at Ramp, dedicated to serving our partners with the upmost experience and knowledge. With years of experience delivering ERP and FP&A solutions from mid-market to enterprise businesses, Nigel brings valuable accounting and technical solutioning expertise to the team. Originally from Boston and a Bentley University graduate, Nigel has called Denver home for the past three years, where he can be found exploring the mountains—especially on his skis!