Scaleup Leaders: Stories from Experience

What do you do when you’re suddenly in charge… and totally unprepared?In this episode, I speak with Gillian Davis, leadership strategist and founder of Overtime Leader, who’s spent the last decade helping scaleups grow their leadership and culture as they move from scrappy startup to mature company.Gillian’s journey started with crisis: she took over her family’s business when her father fell ill. She later left corporate “with a vengeance,” and found herself dropped into a high-growth tech company with zero systems, zero onboarding, and a ton to figure out.Since then, she’s served as VP of People at WeTransfer, co-authored the book First-Time Leader with George Bradt, and worked with leadership teams to help them scale intentionally — before chaos sets in.In this conversation, we talk about:* The intern confrontation that reshaped her leadership style* Why she quit corporate without a plan — and what she found instead* How product thinking changed how she does organisational design* Common mistakes founders make when hiring senior leaders* Why fast growth doesn’t mean rushing leadershipWhether you’re a founder, a first-time VP, or just someone trying to lead through uncertainty — this one’s packed with stories and insights you’ll want to remember.🔗 Guest Links* Gillian’s website: OvertimeLeader.com* Gillian on LinkedIn: linkedin.com/in/davisgillian* Her book: First-Time Leader (with George Bradt)🗂️ Timestamps* 00:00 – Intro & Gillian’s origin story* 05:30 – Leading through crisis with no playbook* 15:00 – The intern confrontation that changed everything* 22:00 – Leaving corporate with no plan* 26:00 – Joining a tech startup with no systems* 32:00 – Product thinking meets leadership* 45:00 – Helping founders build leadership post-Series A* 59:00 – The importance of brave, long-term leadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

In a lively discussion, Lidia Oshlyansky, Chief Product Officer at Gillion and former leader at Google and Spotify, shares her unconventional journey from social work to tech. She dives into the complexities of managing large teams, revealing her struggles with existential doubts and the importance of empowering others. Lidia also discusses the chaos of innovation in startups versus the resistance in corporate settings and reflects on fostering collaboration and confronting toxic workplace dynamics. Her insights on balancing pragmatism with ambition are both candid and inspiring.

We often think great leadership is about having all the answers and staying composed under pressure. But what if the real key to leading a high-performing team is being open about your mistakes?In this episode, Kim Wylie reflects on two decades of leadership experience at Google, Farfetch, and scale-ups—sharing what actually builds trust and performance when you’re stepping into a new team.We talk about:• Why trying to be the perfect manager backfires• How Kim built psychological safety in a team that didn’t trust her at first• How to handle resistance to new ways of working in distributed teams• The team rituals she uses to foster connection, even across regions• What to do when your team gives you negative feedback• The neuroscience of why solving everyone’s problems is not good leadership• And how even senior leaders still struggle with imposter syndromeThis is a masterclass in human-centred leadership—with practical tools, real stories, and the kind of honest reflection most leaders wish they heard more often.🧠 Some Takeaways“If you’re a manager and you’re always solving everyone’s problems, you’re robbing them of that dopamine hit.”“One of the biggest lessons I learned is that being vulnerable builds trust—and trust drives performance.”“People need to see that how you show up on day one is how you’re going to keep showing up.”🔗 Links & ResourcesFollow Kim on LinkedInWatch the full video interview on YouTubeSubscribe to the podcast for more real stories and practical leadership insights.Connect to me and ask me about coaching! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

From Google to high-growth scaleups to the boardroom, Maya Moufarek has spent 20+ years helping founders scale their businesses. As the founding CMO of Pharmacy2U, she helped grow the UK’s largest online pharmacy to a scale equivalent to opening a new pharmacy every 2.5 days. Today, she’s a fractional CMO, board member, and angel investor, helping startups build scalable, profitable growth engines.In this episode, Maya shares: • 🚀 Scaling from startup to industry leader: How Pharmacy2U grew and the challenges they faced • 🤝 Cross-functional leadership: Why aligning senior teams (“first teams”) is critical in scaleups • 🔥 Lessons from Google & AMEX: What big tech taught her about stakeholder management • ⏳ Surviving near-failure: What she did when the company was running out of cash • 🏦 Navigating board & investor relations: How to handle tough conversations at the top • 🌍 Building a portfolio career: How Maya balances operator, investor, and board rolesWhere to Find Maya:🌍 Website: MarketingCube.co🔗 LinkedIn: Maya Moufarek This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

Being a scaleup leader can feel like herding cats.- You’re growing, that’s great.- But your growth brings problems.- You have more people but they get less done.- Autonomy used to work, now there is misalignment.- People get in each other’s way and slow things down.Is the solution less autonomy? Or is that too restrictive?Cliff Hazell has the answer.Cliff worked with Spotify to grow from 700 to 5000 people. So he knows a thing or two about scaleups.✅ Have better meetings✅ Focus on a #1 priority✅ Introduce Flight Levels.Flight Levels operationalise strategy - they get people out of each other’s way to get more done.And if this is a new concept for you, then you’ll want to watch this episode where Cliff and I go deep into this whole topic.👉 How to find the sweet spot between autonomy and alignment.👉 Why an outsider is better at unblocking bottlenecks than you.👉 Why most meetings are unfortunately cr*p.👉 How Flight Levels solve all this?And if you'd like to connect with Cliff, you can find him on LinkedIn or at cliffhazell.com-------If you haven't already joined my weekly newsletter for tips and strategies in your inbox, you can join here.Connect with me in LinkedIn. Check out my YouTube channel. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

Christian Meinerding is the Co-Founder and CEO of HiveMQ, a company he founded 11 years ago. He told me about his experience growing a business from scratch, raising a €40 million series A for a total of €50 million raised and growing the team to almost 200 people.When Christian started out, his process of using OKRs was simple and straightforward. However, as his company grew, they started to notice ever increasing problems, and as a result had to make some pretty critical shifts in their OKR thinking.-------You can find Christian here: https://www.linkedin.com/in/goetzchr/Or on his website: https://www.hivemq.com/Follow me on LinkedIn: Richard Russell | LinkedInWant insider access to expert tips and strategies like this every week right in your inbox? ⁠https://richardrussell.co/#subscribe This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

This week I'm joined by Marc Sniukas. Marc is a strategy advisor and he helps CEOs and leadership teams design and execute better strategy.We discuss why strategy can become a big complex monster and how to prevent that. And Marc reveals the three simple steps of strategy - understanding the context, making decisions, and taking action - and how you can use these to steps to creat your own better strategy today.-------------Are you subscribed to my YouTube channel yet? https://www.youtube.com/@richardarussellWant insider access to expert tips and strategies like this every week right in your inbox? ⁠https://richardrussell.co/#subscribe This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

Team meetings feeling lacklustre and unproductive? Do they often turn into lengthy sessions of updates that leave everyone feeling bored and frustrated?The problem is most likely that you're using a people-driven approach in your meetings. They typically mean: Roundtable updates People bored and not engaged No focus on plans and problem solving.In this episode, I explain how you can use an Agenda-Driven approach to transform your meetings so they're more productive and collaborative.----------------------------------Want insider access to expert tips and strategies like this every week right in your inbox?⁠ ⁠https://richardrussell.co/#subscribe⁠Are we connected on ⁠LinkedIn⁠ yet? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

Zoltan Vardy is a startup mentor who helps B2B tech founders struggling with sales to sell and market to enterprise clients. We had a great discussion about: Not adapting for every client to actually help them make a choice. Choosing your battles Goal setting for sales when you don't have any idea what a realistic number would be Shiny object syndrome...and a few more things besides.If you enjoyed this episode, you can subscribe to my newsletter at ⁠https://richardrussell.co/#subscribe and follow me on LinkedIn.If you'd like to connect with Zoltan, you can find him here on LinkedIn, and at zoltanvardy.com/podcast where you can download his free video guide. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com

Many of my clients have had a bad experience of OKRs before working with me. And I noticed that the reasons they had been failing were the same.So I dug out all my past client notes, went through them meticulously gathering the most common mistakes, and finally complied this hit list of the Top 10 Tips to make sure you implement your OKRs right.Want insider access to expert tips and strategies like this every week right in your inbox? Subscribe to my weekly newsletter: ⁠https://richardrussell.co/#subscribe This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit scaleupleaders.substack.com