From earliest stage start-up to coveted unicorns status, few people have had more of a front-row seat on helping grow businesses than Jenny Herald’s guest on this episode of Dreams With Deadlines. Luca Cipriani, who is Head of Architecture and OKR Coach at Jimdo, knows intimately the strategic elements that make scaling ventures fly or fail – and he’s sharing his rules of the road. It all starts, he says, with building nimbleness and psychological safety into the blueprint from your...

In this episode of Dreams with Deadlines, Rianne Roggema, CEO of Practic, shares her journey as a successful business leader and entrepreneur. She started her career at 25 as a managing director for Rocket Internet in Myanmar and later started her own digital marketing agency, Irie Digital. After struggling with managing her growing team, she got introduced to OKRs (Objectives and Key Results) and found them to be an effective tool for setting clear goals and direction for her team. She...

In this episode of Dreams with Deadlines, Jenny Herald and Jonathan Alloy take a deep dive into the strategy execution challenges that organizations face when implementing a customer-centric approach. Jonathan Alloy, a seasoned leader in banking and financial services, takes us through the journey of creating a microsite that puts the needs of customers first and the obstacles he faced along the way. Join us as we discuss these challenges and more as Jonathan shares his experience, insights...

In this episode of Dreams With Deadlines, Jenny Herald talks with agile expert Yuval Yeret about the connection between business agility and OKRs, specifically in the context of private equity. They discuss the role of OKRs in aligning the goals of a portfolio company and how they can be used to facilitate cross-functional collaboration and focus on outcomes. They also discuss the importance of going beyond the surface level of frameworks like OKRs and Scrum to truly understand and utilize...

When we leverage the right recruitment and hiring tools, talent and retention follow! It’s just a question of taking a strategic approach, explains Jem Pauley, who is featured on this episode of Dreams with Deadlines. In her role as Senior Operations Partner at the global embedded recruitment services firm Talentful, she has developed OKRs and systems that are clear, replicable and hold space for both innovation and ongoing process improvement.

This episode of Dreams With Deadlines is laser-focused on all things ESG. Host Jenny Herald starts by inviting her guest, Guenter Rottenfusser, to brief us on the basics – defining the “E,” “S” and “G” of it all. As a social impact entrepreneur and Environmental, Social and Governance expert, Guenter is here to provide an inside look at the global business landscape and help answer the question: How do we design a more sustainable future?

The featured guest on this episode of Dreams with Deadlines has done it all: Global consulting on major corporate transformation initiatives, overseeing M&A integrations and holding influential positions on multiple boards. Karen Thomas-Bland, whose highly successful career with KPMG and IBM hopscotched across the UK, the US, the Middle East and Latin America, joins Host Jenny Herald to share insights gleaned during complex corporate integrations. As Founder & Director of Seven...

If taking any legacy organization into a new era of enterprise agility poses challenges, then doing so for a 200-year-old bank is a special mountain to climb. Host Jenny Herald’s guest on this episode of On Dreams With Deadlines is Michael Goitein, an agility expert who has been coaching KeyBank – the 20th largest in the U.S. – through an exciting digital transformation and using an OKR-based methodology to help get the job done.

On this episode of Dreams With Deadlines, Host Jenny Herald sets the stage for OKR adoption success with Antonio Civita, an innovative “design thinker” who has written a book on the topic. With his unique blend of experience leading high-level workshops for large companies looking to become more agile and outcome-driven, Antonio shares the toolkit that he and his team have developed – and are continuing constantly to evolve to support optimal OKR outcomes.

This episode of Dreams With Deadlines features a seasoned marketing pro who heart-centered approach has special resonance as employees adapt to evolving hybrid conditions. Host Jenny Herald talks with Gideon Pridor, CMO and Chief Storyteller at the internal enterprise communications platform Workvivo, who explains why emotional connection and community are more important than ever in a post-pandemic world. Leadership teams that embrace storytelling and value personal engagement do better...

Consumers and regulatory bodies are continually turning up the pressure, demanding that industry offenders reduce their ongoing environmental harms in meaningful ways. Host Jenny Herald’s guest on this episode of The Dreams with Deadlines podcast spotlights the new data-driven platform his team at Pledge have created using fintech tools to track carbon footprints and remediate emissions. CEO and Co-Founder David DePicciotto explains why their new methodology is a gamechanger when it comes...

The special challenges confronted by a legacy media giant are the focus of this episode of Dreams With Deadlines, featuring Chief Marketing Officer Mayur Gupta. Host Jenny Herald elicits nuts-and-bolts details about how the Gannett – USA Today Network has moved to broaden its platform and shift to a subscriber-based model. Mayur offers insights into designing a dynamic team structure, embracing a customer-obsessed focus and implementing synergistic, methodical OKRs across departments.

When Jenny Herald’s guest on this episode of Dreams With Deadlines went to work for the startup kick scooter company Circ in 2018, he was handed a beautiful blank canvas onto which he was quickly able to project a highly effective culture built on thoughtfully designed teams, dynamic communication and the robust use of data. Markus Müller, who also guided product management teams at N26, is giving us a detailed look at the nimble management structures he favors, procedures that foster team...

The Objectives and Key Results (or OKR) approach is a great way to reorient organizations to challenging, ambitious goals with measurable results. But the collaborative, goal-setting methodology so popular in Silicon Valley is anything but one-size-fits-all. Host Jenny Herald’s guest on this episode of Dreams With Deadlines is Felipe Castro, an OKR evangelist who walks us through the many variables that enable the mindset shift and preparation that ultimately ensure successful adoption...

On this episode of Dreams With Deadlines, we learn why today’s Environmental, Social and Governance standards – or ESG – are about a lot more than aspirational, check-the-box marketing. Not in the face of accelerating climate change impacts and social inequity! Guest Catherine Duggan, Head of Sustainability for Financial Services Advisory at the consulting firm Grant Thornton Ireland, briefs Host Jenny Herald on why robust ESG standards are critical to corporate resiliency and risk...

On this episode of Dreams With Deadlines we meet a dynamo who has converted lessons learned over many years of serving as chief of staff to various C-suite executives at AT&T into a professional development program with bespoke coaching and tools you won’t find anywhere else. Laurie Arron breaks down exactly what it means to be a chief of staff and how the role shapes, protects and advances leadership agendas.

Human relations leaders are uniquely positioned to leverage OKRs cross-functionally – an impact-driven approach that yields transformational benefits across the enterprise. This episode of Dreams With Deadlines features Bradford Wilkins, a visionary Chief People Officer who has successfully rolled out data-driven programs that have measured and optimized OKR initiatives executed by C-level leaders through teams from sales, marketing, logistics, product development, and beyond.

In 2019, Lavanya was seeing a need to align priorities between teams and make them more visible and transparent. This led her down the journey of making the decision to implement a company-wide OKR system. On this Journey, she learned many lessons along the way and shared the most important ones with me today.

How can we make hybrid work really work? How can we facilitate better OKR setting sessions? Do individual incentives get in the way of driving collaborative behaviour? In this episode of Dreams with Deadlines, Jenny talks with Alexis Monville. Alexis is Chief of Staff to the CTO at Red Hat, a long-time hybrid open-source software company with more than 100 office locations in 40 countries, where half of the 20,000 people work remotely.

Christine Stone joins me in this episode of Dreams with Deadlines. She's the global head of technical program management at Groupon. We discuss her personal OKR—to help women in tech gain influence, Groupon's unique experience of starting OKRs during the COVID crisis, and the three measurements that matter—business growth, business strength, and personal development.

How do you move from a strategy that feels like a list of projects to focusing on the outcomes? Strategic agility is all about being flexible in how you get there, beginning with the end in mind rather than focusing on a to-do list. In this episode of Dreams with Deadlines, Jenny speaks with 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 explains...

So, your organization has passed down a mandate that you’re going to do OKRs. Now what? In this episode, I’m joined by Allan Kelly. Allan is an agile coach, author of 7 books, and keynote speaker. His introduction to OKRs was exactly this—it came down as a mandate and he had to figure things out. He’s got some controversial ideas around maintaining a backlog (spoiler: he thinks it’s okay to nuke your backlog and start anew every quarter). He believes it’s okay to not achieve your Key Results....

What is a planning season? Why is idea agility so important, and how can we achieve it? And what does this have to do with OKRs? In today’s episode of Dreams with Deadlines, Jenny talks to Jeff Gothelf. Jeff is a coach, speaker, author, and consultant who helps organizations build better products, and executives build the culture that builds better products. Listen to the episode to hear Jeff explain what a planning season is and why it’s important to be able to adjust the borders of a...

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.

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.