The Ops Drop Podcast
Welcome to The Ops Drop, a podcast designed for business operators who want actionable insights to build solid foundations for scalable growth. Created by Darren Fay and Mackenzie Hughes—industry veterans with deep expertise in Revenue Operations and Product Operations—this show brings quick, focused content perfect for professionals with busy schedules and short attention spans.
At The Ops Drop, we explore every facet of operations—vision, culture, processes, tools, and strategies—because operations is at the heart of everything a business does. Whether you’re in a startup or a public tech company, operations evolve, and so do we. Tune in for expert-led discussions packed with real-world experience to help you stay ahead in a fast-changing world.
S2.E5 Why You’re Really Losing Deals - And What to Do About It
Why You’re Really Losing Deals - And What to Do About It
Most companies think they know why they’re losing deals. In reality, they’re relying on generic Salesforce picklists and half-hearted notes that offer zero insight.
The truth is, win-loss data isn’t just for Sales or GTM. It’s strategic intel that fuels smarter product decisions, sharper messaging, and more accurate forecasts. If you’re ignoring it, your product roadmap, marketing spend, and revenue targets are probably off-track.
Brady Jensen, Founder of Clear Go-To-Market, joins us on The Ops Drop to talk about why most closed-lost analysis falls short - and what high-performing teams are doing instead. With a background spanning sales and product marketing, Brady now helps businesses uncover the real reasons behind lost deals and use that data to drive measurable growth.
If you’re serious about product-market fit, cross-functional alignment, and building a business that actually wins - this episode is for you.
S2.E4 Leading Design Teams in the Age of Commercialization
Hiring & Growing Your Startup Team
In this episode of The Ops Drop, we chat with Natalie Ledbetter. Natalie cut her teeth in the startup world as a Chief People Officer - she has also worked in VC, and has now brought her show on the road as a Fractional/Advisory CPO with Ledbetter Advisory. When you're building a company - your first few hires matter the most - and figuring out the right fit can be daunting. Natalie has worked with many startups on hiring and retaining their greatest resource: their people.
S2.E3 Hiring & Growing Your StartUp's Team
Hiring & Growing Your Startup Team
In this episode of The Ops Drop, we chat with Natalie Ledbetter. Natalie cut her teeth in the startup world as a Chief People Officer - she has also worked in VC, and has now brought her show on the road as a Fractional/Advisory CPO with Ledbetter Advisory. When you're building a company - your first few hires matter the most - and figuring out the right fit can be daunting. Natalie has worked with many startups on hiring and retaining their greatest resource: their people.
S2.E2 Get Your Engineers Out of the Basement!
Get Your Engineers Out Of The Basement!
In this episode of The Ops Drop, we talk with Ed Morgan — a 20+ year software engineer and founder - about what it takes to build an effective, business-savvy engineering team in 2025.
We dive into engineering team structure, hiring the right engineers, working with outsourced vs in-house teams, and how to align engineering metrics with business outcomes. Whether you're a CTO, VP of Engineering, or product leader, this conversation will help you rethink how engineering teams should operate in today’s tech landscape.
S2.E1 Navigating The Beautiful Mess of Product Leadership
Navigating The Beautiful Mess of Product Leadership
In this episode of The Ops Drop, we sit down with John Cutler, CPO at DotWork, to explore the complexities of product leadership, from navigating The Beautiful Mess to bridging the gap between GTM and product teams. John shares his unique journey into product, how to adapt leadership styles based on company maturity, and the right ways to approach product metrics and team models. We also dive into how product operators can gain executive support, where leaders should invest their time for the biggest impact, and the unspoken challenges companies face today. Whether you're a product leader or operator, this conversation is packed with insights to help you build better teams and drive meaningful outcomes.