The Ops Drop

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.

Remember in the ZIRP days when design was all about "the art of the craft"? These days, the best design leaders are thinking differently about design. We met with Juli Duffer, who has been leading design and research teams for 20 years, and is currently the SVP of Design at FactSet. As an established design leader, her emphasis has been in defining and driving UX strategy, establishing UX as a key business function, and building and scaling design organizations. She spent seven years teaching and loves mentoring and coaching the wonderful humans on her team. This episode explores how design teams are adapting to a more commercial, resource-constrained tech environment - highlighting how to assess org maturity, tie design to business outcomes, operate in different team models, and stay relevant amid AI, CMS tools, and rising complexity.

Time Stamps:

00:30 Major tech trends impacting how we approach design 

03:00 Designing for business impact 

05:10 Design and the customer journey

07:15 Business metrics for designers 

10:10 Finding design-friendly environments

14:35 How to measure research and design impact 

16:15 Finding design leaders in the age of commercialization 

17:55 How designers can work better within their teams, post ZIRP 

26:05 Setting up the best organization structure for design 

27:45 Best design resources

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.

Timestamps:

01:00: Natalie's journey into HR (from London to Indonesia to Texas) 

04:20 When do Founders need HR support? 

06:25 Hiring and your balance sheet 

10:00 Managing across generations 

13:35 Everyone is really unhappy in tech right now - what do we do about it? 

19:40 Hiring as a grow - what NOT to do 

28:45 Best practices for people operations

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.

Timestamps:

00:40- Ed Morgan: journalist turned engineer

03:30- STEM vs Non-STEM educated engineers

05:50- What to look for in your engineering candidates

08:20- Outsourcing vs hiring in-house engineers

10:35- How hiring trends have changed over time in engineering

14:15- Working with outsourced vs in-house teams

16:00- The ROI of your engineering team

18:00 What does a healthy engineering org look like?!

22:00- Aligning engineering metrics with business outcomes, and where to get started

23:45- Optimal engineering team structures

26:00- How to get your engineers "out of the basement" and closer to the business

29:45- Top 3 things engineering leaders need to be thinking about in 2025

Connect with Ed Morgan 🔗 LinkedIn:   / edwardpmorgan   🌐 Gordian Knot: https://www.gordianknot.company/our-team

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.

00:40 Who is John Cutler...beyond The Beautiful Mess

4:20 Getting into Product from a non-traditional background

7:35 How John Cutler came up with The Beautiful Mess

10:15 How to approach being a product leader in different environments

14:15 Understanding your company/product on the maturity curve

16:00 How to bridge the gap between GTM and product teams with metrics

18:00 How to get started with product metrics with the right team models

22:00 Getting support from Execs as a product operator

23:45 How product leaders should invest their time and their teams' time

26:00 What's going unsaid right now at companies

29:45 Advice for product operators from John Cutler