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 37

On uncertainty, randomness, and how OKRs are networks

Chris Butler is a Chaotic Good Product Manager, the Global Head of Product Operations at Cognizant, a writer, and a speaker. He worked previously as a product leader at Microsoft, Facebook, KAYAK, and Waze. Jenny and Chris discuss a broad range of topics including—the future of AI products, uncertainly, randomness, OKRs as networks and trojan horses, issues with hierarchies, and the adversarial mindset.

Episode Notes

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Episode 36

On defining customer value by working backwards

Richard Russell is an independent OKR and Leadership coach who held leadership positions at Amazon, Google, and Deutsche Bank. While working at Amazon, he learned the “working backwards framework” and uses it now in helping companies achieve results using the OKR methodology. Jenny and Richard discuss the advantages of working within large organizations, measuring value, the importance of listening, and more.

Episode Notes

Episode 35

On aligning networks and strategy to drive change

Maya Townsend is the Founder and Lead Consultant of Partnering Resources, a management consulting agency that tackles big-picture organizational challenges. An expert in organizational networks, Maya breaks down the three types of influencers and which type holds the most influence. She shares her most profound insights from her 25-year career and gives examples of times she successfully aligned companies’ networks and strategies.

Episode Notes

Episode 34

What a Chief of Staff brings to a startup

John Quayle is an Operations Professional for small businesses, startups, and brands that are economies of one. Three months ago, he became the Chief of Staff at Four Growers, a startup that’s revolutionizing farming with robots that can pick ripe fruit in green houses. Jenny and John discuss false limitations, OKRs, what exactly is the role of a Chief of Staff, and explore of the art of planning goals.

Episode Notes

Episode 33

Product Strategy, Consumer Science, and Culture at Netflix

In this episode, Jenny Herald is joined by Gibson Biddle, former VP of Product at Netflix and CPO at Chegg. He’s now a speaker, teacher, and workshop host. They discuss many of his tools, models, and frameworks — like GLEE and SMT, how culture is not a touchy-feely soft thing but rather describes the skills and behaviors expected of everyone in an organization. Gib puts Jenny in the hot seat a few times as they examine some Netflix case studies together.

Episode Notes

Episode 32

The Second Order of OKRs Questions, Part 2

Founder of, Ben Lamorte, has more OKR coaching experience than anyone on the planet. In part two of this interview, Jenny and Ben discuss the things that should happen at the end of an OKR cycle, what it means to be a Key Result champion, what to do if you know you won't make any impact on your OKRs this quarter, how to make a metric that matters, and more.

Episode Notes

Episode 31

The Second Order of OKRs Questions, Part 1

Founder of, Ben Lamorte, has more OKR coaching experience than anyone on the planet. In part one of this interview, Jenny asks Ben about his background, latest book, current trends, OKR deployment parameters, and experience working with huge companies.

Episode Notes

Episode 30

To get OKRs right, forget about features

In this episode, Jenny Herald is joined by Mike Pilawski, the Chief Product Officer at Smallpdf where he leads product, design, and data teams. Prior to joining Smallpdf, Mike has held leadership roles in product, engineering, marketing, and data at Typeform, Leanplum, Vungle, and NativeX. In this episode, we chat about the Dimensions of Organizational Blueprints, how one goes about marrying up agility and OKRs for product and engineering teams, and the two camps concerning OKRs and performance management, and more.

Episode Notes

Episode 29

What are you doing to make an impact?

After working years in corporate America, startups, and scaleups, Caroline Franczia founded Uppercut First, a consultancy for startup founders. She’s a columnist for Maddyness UK, the author of Popcorn for the New CEO, an OKR expert, and an advocate for women. Her recent article—“I’ve never felt this awake”: Caroline Franczia on Thelma, Louise and inclusion—is about her personal experience as a woman in tech. She believes diversity and inclusion needs to be baked into the business strategy. In order for employees to stick around, they need to feel a sense of purpose, ownership, and that they make an impact. In this episode, we chat about the ROI of closing the gender gap, using a Value Pyramid to set the foundation for company-level OKRs, and what makes OKR programs fail or succeed.

Episode Notes

Episode 28

Lessons from implementing OKRs at Free Now

In this episode, Jenny Herald interviews Flavia Neves, Director of Product Management at Spotify and former VP of Product at Free Now. Flavia shares Free Now’s OKR journey. Listening to their experience is like going through the hero’s journey. She's gathered some lessons learned and provides advice to organization's considering adopting OKRs. There is pre-work required to make OKRs work. Tune in to find what you need to make your program successful.

Episode Notes

Episode 27

Vessy Tasheva - Diversity & Inclusion Q&A

In this episode, Jenny Herald and Vessy Tasheva answer questions that came from participants that joined a Diversity & Inclusion (D&I) Roundtable discussion. Unfortunately, we did not have an opportunity to cover all the questions during the event and decided to record this episode to cover them.

Episode Notes

Episode 26

Vessy Tasheva - On embedding D&I in business strategy

On this episode of Dreams with Deadlines, Jenny Herald interviews Vessy Tasheva, the founder of, a Diversity & Inclusion, and Mental Health consultancy. Vessy works with clients across Europe and North America, such as Soundcloud, Reward Gateway, and Typeform, to create a healthier and more inclusive purpose-driven culture. D&I efforts shouldn’t be performative or done out of obligation; the baseline is that employees feel like they belong, are safe, and valued, so they have an equal chance to succeed, and, in turn, the business can thrive. How, then, can we embed D&I in business strategy?

Episode Notes

Episode 25

On shaping the future or waiting to be instructed by it

In this episode, Jenny is joined by Peter Kerr, Managing Director of Auxin OKR. He’s had the opportunity and privilege of working with senior executives from some of the largest, most well-known companies in the world. Peter shares some incredible stories from his experiences with these leaders on maintaining relevance in the market, working through political infighting, the need for human connection in a digital world, and how OKRs can help aid all of the above.

Episode Notes

Episode 24

On fast-tracking an OKR program into existence in 3 weeks

In this episode, Jenny Herald interviews Adam Bonifant, VP of Customer Success at ORock Technologies, and Tim Meinhardt, CEO of Atruity. We'll discuss the ins-and-outs of fast-tracking an OKR program into existence. ORock Technologies was able to get OKRs up-and-running in a span of 3 weeks, with Adam co-championing the program and Tim serving as their guide. Find out what they learned at the onset of their OKR journey.

Episode Notes

Episode 23

On the recipe for unleashing enterprise value

In this episode, Jenny Herald is joined by Dan Weikart, Director and Enterprise Agile Coach at Cprime. We discuss the immutable and foundational ingredients necessary for unlocking enterprise value. We’ll get practical and, at times, prescriptive.

Episode Notes

Episode 22

On living the OKR life

On this episode of Dreams with Deadlines, Jenny Herald interviews David Anderson, an OKR Systems Coach at Auxin OKR. David explains what a Blue Zone is and how it relates to OKRs, what it means to live the OKR life, and how motocross racing relates to business. He's passionate about the environment and plans to grow the world’s largest electric bike company. He says it is impossible to scale a belief without a system.

Episode Notes

Episode 21

On building strategic agility

On this episode of Dreams with Deadlines, Jenny Herald interviews Dan Montgomery, author of Start less, Finish More: Building Strategic Agility with Objectives and Key Results, founder and Managing Director of Agile Strategies, and OKR Thought Leader. He goes through the five steps outlined in his book— Assess, Focus, Commit, Act, and Learn. They also discuss OKRs in relation to a concept pilots use called OODA loop (observe–orient–decide–act).

Episode Notes

Episode 20

On delegating decision making so it's safe to be risky

On this episode of Dreams with Deadlines, Jenny Herald interviews Godehard Gerling, Managing Partner at go3consulting in Germany. Godehard shares how he persuades traditional European companies to build products with intent, adopt OKRs, and release their leadership grip to allow teams on lower levels to make decisions. He says that in these uncertain times, being safe in business is risky.

Episode Notes

Episode 19

On the use of storytelling and OKRs to express the case for change

On this episode of Dreams with Deadlines, Jenny Herald interviews Ash Seddeek, Chief Excitement Officer at the Executive Greatness Institute. Ash coaches senior leaders at large companies on storytelling, executive presence, strategic communication, the importance of reflection and ‘meeting with self,’ leadership transitions, and OKR rollouts. He believes the right story can connect, inspire, and move an entire company in the right direction. He is a best-selling author and co-author of Road To Success with Jack Canfield and MEANING, a bestseller on leadership communications.

Episode Notes

Episode 18

On how to make OKRs work for SMBs

Russell Cummings is an experienced Management Consultant and Business Coach with Shifft Consulting. Russ has spent the last 35 years working with dynamic family businesses that want to grow. He is Australian-based but currently services clients across Australia, New Zealand, Canada, and the United Kingdom. In this episode, we cover a lot of ground like the 2 ways OKRs can help small businesses, a walk-through of how to cascade OKRs, how to approach tracking metrics when you’re first starting out, and the dangers of being efficient in the wrong places at the wrong times.

Episode Notes

Episode 17

On the Agile mindset umbrella protecting us from the Waterfall rain

Kit Friend is an Agile Coach, proud geek, and Atlassian Partnership lead for EMEA at Accenture (despite his enthusiasm, these views are currently officially only his own). In this special episode of the Voices of OKRs series, we discuss where it might make sense to apply the Waterfall model (and yes, in some cases this would be a reasonable approach), the many ways to be agile—from the “Seen more rarely currently approaches” like Lean to those we should “Approach with caution” like the “Spotify model,” and how organizations should be thinking about mapping work to value, data to strategy.

Episode Notes

Episode 16

On what it's really like to drive an OKR deployment at scale

Pedro is the founder of Pragmatic Management Consulting. Previously, he was Head of Management at Nextel Brazil where he implemented OKRs for more than 1700 employees. In this episode, he shares his story and experience with us. We get to hear what Nextel Brazil’s OKR lifecycle looked like. We’ll spend some time talking about how their pilot failed and how they were able to turn things around. Pedro goes over the importance of executive sponsorship, how that sponsorship played out in practice, their OKR calendar and check-in process, and how they had tied compensation to OKRs at that time but why he wouldn’t recommend that in practice today.

Episode Notes

Episode 15

On creating situations where everybody can lead

Tim Whitmire is the founder of CXN Advisory, where he coaches executives on strategy, goal setting, alignment and execution. He is the co-founder of F3 Nation and co-author, with David Redding, of Freed to Lead: F3 and the Unshackling of the Modern-day Warrior. F3 is a network of free, peer-led workouts for men in the United States and has grown to more than 30 states and 2,000+ scheduled workouts a week through volunteer efforts. F3 participants apply a distinctive lexicon of terms during their workouts. How do these F3 concepts relate to OKRs? Find out in today’s episode.

Episode Notes

Episode 14

On OKR+As: Objectives, Key Results and Actions

Carsten Ley is the co-founder of Asia PMO – a leading digital transformation & agile consulting company, specializing in implementing OKRs and other revolutionary project management techniques in Southeast Asia. In this first episode of a 12-part series on “Voices of OKR,” Carsten and I discuss:

  • The difference between customer data and feedback
  • How to begin using OKRs via a task force
  • Command-and-control culture vs. participative culture
  • OKRA - Objectives, Key Results, and Actions
Episode Notes

Episode 13

On debugging an organization

Mathias Meyer is an engineer turned founder, a former CEO at Travis CI and CTO at Reaction Commerce. In this episode, we discuss how a simple process, architectural decision records, created the space for his team to make and document decisions; what it means to debug an organization; how to approach OKRs via an evolutionary approach—from not tracking anything to tracking something; the engineering metrics he ended up tracking and more.

Episode Notes

Episode 12

Aligning vectors, cage fighting and PM benching

Srikant Vemuri has held leadership roles in overseeing the design and launch of breakthrough products in the B2B, Adtech, and Big Data spaces for industry innovators such as Seerene, Womply, Aarki, and Adchemy. Currently, he's managing product and technology at Frontier Car Group as the CEO of Technology. In this episode, Srikant shares what he's learned during his journey—filled with bruises, scars, blood, tears, and his share of successes. He's got this exciting idea of balancing great product concepts and a CEO's strategy—he calls it the "cage fight." We discuss Product Management benching. He's taken the term from sports and applies it in business. Find out what he thinks PMs should be doing when benched. And we spend quite a bit of time talking about OKRs, and a personal KPI he monitors to gauge his teams' health. He believes this KPI is foundational for OKRs to be successful.

Episode Notes

Episode 11

Jobs to be Done with Alan Klement, Part 2

Alan Klement is known for developing the theories of Jobs to be Done and Market Modernization and inventing new methodologies and methods for engineering growth. His latest venture is Revealed — a market research and growth guidance firm that helps organizations grow, align, and reveal market insights. He's the author of When Coffee and Kale Compete and is writing a sequel called Jobs to be Done: Understanding Needs. Predicting Adoption. This is part two of our conversation. In this episode, we discuss OKRs and Jobs to be Done, the two goals that product people should take into consideration, the importance of a feed forward communication culture, and we get a sneak peek into some concepts and models from Alan's new book. Let's jump in.

Episode Notes

Episode 10

Jobs to be Done with Alan Klement, Part 1

Alan Klement is known for developing the theories of Jobs to be Done and Market Modernization and inventing new methodologies and methods for engineering growth. His latest venture is Revealed — a market research and growth guidance firm that helps organizations grow, align, and reveal market insights. He's the author of When Coffee and Kale Compete and is writing a sequel called Jobs to be Done: Understanding Needs. Predicting Adoption. It's due in Summer 2020. My conversation with Alan is broken down into two parts. In this episode, we discuss the Taylorism versus Humanism approach to explaining OKRs and how understanding needs means understanding how they're created, how they grow and shrink, and get eliminated. We cover the "voice of the customer" and its flaws and how Lean startup solves problems that come with the "voice of the customer" approach.

Episode Notes

Episode 9

TACOS and OKRs: Values and Frameworks

In this episode, we hear from Scott Shapiro, Principal Product Marketing Manager for B2B/Account Management Customer Experience at Qualtrics. We get an inside look at how it felt when Qualtrics was pre-IPO and everyone thought it was going to happen—but gotcha—it didn't happen. We hear a lot nowadays that things are slowing down due to this global pandemic. Scott shares his findings from research they’ve been doing. They’re seeing an acceleration of what was already happening. Hear what they’ve learned. Qualtrics has a set of principles called TACOS. Find out what that means and how TACOS shape how they operate. We talk about OKRs and how to go from activity to delivering value.

Episode Notes

Episode 8

Balancing autonomy and alignment

Joining me today is Rohit Gupta. He is the Head of Product at and leads the Product Management, Product Design and large parts of the Engineering teams. In this episode, we discuss ways his team is staying socially connected during the Coronavirus pandemic, Honeypot’s dream and how his organization is pursuing it, the power of the reverse recruitment model in hiring, and the key learnings Honeypot weaved into their OKRs process to make the methodology work for them.

Episode Notes

Episode 7

Sold: the journey from mediocrity to excellence

Dennis Gräf is a Business Strategy Manager at Kolibri Games. Ubisoft acquired his company in January 2020. Kolibri is one of the leaders of the “idle” games genre. One of their most popular games, Idle Miner Tycoon, has been downloaded by more than 104 million players. In this episode, Dennis shares Kolibri’s journey with OKRs. We discuss the transition of everyone working from an office to everyone working from home, how he pulse checked the leadership team and the organization before introducing an OKRs tool, how their OKRs process works and has evolved, and the hard lessons the organization had to learn along the way.

Episode Notes

Episode 6

A culture of ownership

Gene Hammett is a leading expert on high-growth company culture and leadership. He has interviewed more than 530 CEOs of high-growth companies to understand the core principles of fast growth. In this episode, we examine what leaders of fast-growth companies have in common and what leaders should anchor to during these challenging times. We discuss what's more important in business, the employees or the customers. In Gene's worldview, accountability is too low a bar. Listen in to hear what he believes we need to strive for instead.

Episode Notes

Episode 5

Create high five situations

Joining me is Blake Thomas, the Director of Engineering at NoRedInk. He’s learned a lot while working with engineers for over two decades. On this episode, you’ll hear us chat about the 2 modes of failure, why we experience issues with people updating their OKRs (and what we can do about it), how to prevent “OKR Theatre,” the universal reality of today’s workforce and more.

Episode Notes

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.

Episode Notes

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 Notes

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 Notes

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.

Episode Notes


Meet Jenny Herald

Jenny Herald
VP of Product Evangelism

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