Hi, I’m Dillon Ferdinandi

I’m a performance coach and the founder of Grandview. I help startup founders, CEOs, and executives navigate the emotional and tactical challenges of building both a successful company and a fulfilling life. Here you’ll learn more about me and hopefully get a good sense of our potential working relationship. 

Operator > Investor 

My professional journey began at venture-backed start-ups (Typekit & Zemanta). As an early-employee I learned firsthand how products, teams and companies are built – including how to navigate product outages, launch deadlines, fundraises, and quarter closes. I had the opportunity to wear many hats – from partnerships and sales to operations and even the occasional dishwashing. 

These early-stage experiences led me to Slack’s platform team in 2016. There I helped shape the company’s platform and developer ecosystem and expand its presence across EMEA and APAC. After 3 years I took the opportunity to launch and run Slack Fund, where I invested in and partnered with over 100 companies, including 1Password, Oyster, Glean, Hightouch, and Loom.

Investor > Coach

My coaching journey started during a particularly challenging time at Slack. Slack’s rapid pace and complexity initially overwhelmed me and constantly highlighted areas where I needed to improve to keep up. At the same time, my wife and I discovered we were expecting twins, further intensifying my personal and professional pressure.

Coaching was transformative. I started out looking for quick solutions and practical tools, but instead my coach challenged me with deeper, more introspective questions like, “Why do you work?” Over the next year and a half, this inner exploration reshaped my perspective and helped me build clarity and resilience.

After experiencing my own transformation through coaching I knew that the founders and leaders I worked with at Slack Fund could also benefit. But to build genuine trust, I also knew I needed to step away from the investor-founder power dynamic – so I decided to create Grandview to exclusively focus on supporting founders and leaders on their journeys. 

Why Performance Coaching?

Performance coaching is traditionally associated with athletic training, but I believe that founders, builders, and executives share striking similarities with elite athletes—they’re fully committed and give everything in their pursuit of excellence. Athletes have structured off-seasons and dedicated coaching teams; similarly, founders and builders deserve the same comprehensive support to consistently achieve and sustain peak performance.

Aligning Grandview’s vision closer to athletic coaching than traditional management or life coaching models is intentional. While I draw from diverse coaching disciplines to create highly personalized programs, performance coaching remains my north star—sharpening all my efforts toward helping clients excel holistically throughout their lives. (Note: you don’t have to be an actual athlete for us to work together :))

What I Bring to Our Work

• Professional Training: I’m an ICF-certified coach, trained in both Co-Active Coaching and Conscious Leadership, with extensive hours in coaching education, group facilitation, and supervisory practice.
• Whole-Person Approach: I integrate health and wellness strategies into coaching, recognizing true performance requires attention across all life domains.
• Real-Life Experience: Beyond my professional credentials, I’m a husband and father to three daughters, a brown belt in Brazilian Jiu-Jitsu, and a cancer survivor. These experiences have deeply informed my understanding of resilience, authenticity, and the ability to challenge personal limits.

Who I Work With

My clients often share similar traits—they push themselves relentlessly, sometimes to the point of burnout or significant deficits in other life areas, and often find that the results they once achieved are no longer sustainable. Together, we address these challenges directly, recalibrating to achieve consistent, balanced peak performance.

Like in my initial coaching experience, clients often initially seek tactical guidance, but our true work delves deeper, addressing underlying fears, overwhelm, and self-doubt. Together, we set ambitious goals and actionable plans before moving to tactical execution:

Clients frequently collaborate with me to:

• Resolve conflicts or better communicate with co-founders or key stakeholders.
• Build, scale, and nurture high-performing teams and cultures within the fast paced, high stress start up environment. 
• Navigate critical strategic decisions, from product roadmaps and fundraising to mergers and acquisitions.
• Develop essential leadership skills for transitioning from builder to effective manager and inspiring leader.
• Strategically plan career transitions following significant leadership tenures.

Let’s chat

Each founder and startup journey is different. If this resonates with you, let’s have a conversation about your unique business, goals and challenges.