Dreams with Deadlines

Join our discussions with thought leaders and learn how to shrink the gap between strategy and its day-to-day implementation. Let us guide you through the intricacies of holistic Objectives & Key Results at scale.

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The Latest Episode

Episode 4

The continuous improvement mindset

Joining me today is Rob Bayley. Rob is currently a Senior Product Manager at Auvik Networks Inc. Previously, he was a Director of Product at Roadmunk and a Senior Product Manager at NetSuite. He's got a decade of Product Management experience under his belt. On this episode, Rob shares his thoughts on Product Management from the lens of an individual contributor, manager and leader, the dangers of cascading goals, the key to making OKR work, and how to utilize evidence based decision making when you're at a pre-product stage.

All Episodes

Episode 3

Build teams of changemakers

Prar Johnson’s a changemaker who has over 19 years of experience—spent some time shaping products at Nokia, T-Mobile, Skype Microsoft, Soundcloud, Shopify, and now Atlassian. On this episode, you’ll hear her explanation for why product strategy is hard, the time she made a tough call using a consensus-driven approach, what data the Atlassian design team uses to shape their OKRs, how she got involved with the birth of what is now known as Microsoft Teams and more.

Episode 2

Process can drive outcomes

Our guest for Episode 2 is Andrew Wallace. He’s the Managing Director and CPO of SmileBack. Previously, he was the Director of Product Management at Chefs Plate. Chefs Plate was acquired by the German meal kit company, HelloFresh, in 2018. In this episode, you’ll hear Andrew’s thoughts on the importance of knowing and having a shared vision, how Chef’s Plate planned to exit with a certain buyer in mind who ended up not being the buyer in the end, how sometimes a business needs to build unique technology in-house, why simple dreams are good, what Andrew’s learned from his experience at Chefs Plate and transferred to SmileBack and more.

Episode 1

Always take accountability

There are no shortcuts to learning. We learn by doing and failing. We can learn from what others do but, sometimes we need to experience things on our own. In this episode, you’ll hear from Ryan McMinn, Head of Product and current steward of Microsoft OneNote & Sticky Notes. Ryan joined Microsoft in the doldrums between the Department of Justice antitrust days and Satya’s revival. Ryan shares how the company and the way teams approach building product has changed since then.

The host

Meet Jenny Herald

Jenny Herald
CPO, Gtmhub

Jenny Herald is currently the Chief Product Officer of Gtmhub, where she champions the company’s efforts to help customers bridge the gap between strategy and execution via the world’s most powerful OKRs platform. Jenny has spent more than 8 years accelerating growth for enterprises such as Microsoft and Wunderlist.

The Company


Founded in 2015, Gtmhub is the world’s most powerful Objectives and Key Results (OKRs) platform, enabling companies to connect Strategic Priorities and daily Execution in order to accelerate growth. The Gtmhub platform helps businesses improve internal alignment, clarify focus and amplify goal achievement. For more information, please visit