About Us
Our Story
At Windward Mark, we are inspired by the discipline, teamwork, and strategic decision-making of one-design sailboat racing. We believe true competitive advantage lies in charting a course that is aspirational yet implementable—anchored in thoughtful planning, seamless collaboration, and a nimble, coordinated approach to changing conditions.
Like the critical windward leg of a race, where success demands skill, timing, and adaptability, we empower businesses to navigate complex financial landscapes with clarity and precision.
Our Mission
Windward Mark LLC exists to bring senior-level financial leadership to companies navigating growth, transition, and transformation. We deliver the strategic clarity and operational precision that high-growth ventures need — without the overhead of a full-time CFO hire. Every engagement is anchored in honest counsel, measurable outcomes, and a relentless focus on our clients’ success.
20+
Years of Experience
Working with startups & established companies
06
Sectors
Innovative and High-growth sectors
92%
Satisfaction Rate
Trusted by businesses for superior service
01
Priority: Value Creation
Financial guidance for sustainable growth
Leadership
Mark Diffley
Founder & Managing Director
Mark is a seasoned CFO and strategic advisor with over 15 years of experience steering financial operations for high-growth technology companies and multinational organizations.
Throughout his tenure as a Chief Financial Officer, Mark has honed wide-ranging growth expertise, focusing predominantly on technology companies and especially on software.
Through his leadership roles at Parity Technologies, SeatGeek, and KAYAK, Mark has specialized in financial strategy, mergers and acquisitions, systems implementation, and scaling operations globally.