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Scaleup Leaders: Stories from Experience

Scaleup Leaders: Stories from Experience

By: Richard Russell
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Interviews with successful leaders of scaleups and big techs about the challenges they faced while scaling themselves and their businesses. The host, Richard Russell, has worked at Google and Amazon in product, technology and business leadership roles. He now works as an executive coach helping functional experts transform into strategic leaders in roles like CEO, CPO and CTO in scaleup environments. Learn more about Richard at www.richardrussell.co

scaleupleaders.substack.comRichard Russell
Career Success Economics Management Management & Leadership
Episodes
  • From Corporate VP to Startup CEO — Egil Østhus on Leadership, Culture, and Letting Go of Ego
    Jul 7 2025

    This week, I’m joined by Egil Østhus — co-founder and CEO of Unleash, an open-source feature management platform used by teams at Wayfair, T-Mobile, Allianz, and more.

    Before launching Unleash, Egil led engineering at Visma, a 6,000+ developer SaaS giant. He’s seen both the slow grind of corporate transformation and the chaos of building from scratch — and in this conversation, we talk about what he’s learned from both.

    We get into:

    * Why leadership isn’t so different between big companies and startups

    * How they built a no-ego, high-trust culture at Unleash

    * Why being too frugal nearly slowed them down

    * Egil’s coaching-style approach to leading teams

    * How he handles remote work, loneliness, and vulnerability as a founder

    There’s a moment in this interview — where Egil shares how he felt completely exposed in front of his team — that really stayed with me. If you’ve ever felt the weight of leadership, you’ll hear yourself in this episode.

    Let me know what resonates with you — or forward it to someone building something brave.

    🎧 Timestamps:

    * 0:00 Intro

    * 2:10 Why feature management matters

    * 7:40 What changes (and what doesn’t) when you go from corporate to startup

    * 12:00 Building culture from day one

    * 16:10 Leading with coaching, not command

    * 23:00 Vulnerability, trust, and showing up

    * 28:00 Remote work, loneliness, and presence

    * 33:00 What Egil’s still figuring out

    📌 Subscribe for more interviews with scaleup leaders.

    🔗 Learn more about Unleash: https://www.getunleash.io/

    📣 Follow Egil: https://www.linkedin.com/in/egilosthus/



    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
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    36 mins
  • The Culture Shift After Series A
    Jun 26 2025

    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 leadership

    Whether 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
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    1 hr and 5 mins
  • S2E03: Lidia Oshlyansky on Managing Without Artifacts, Creative Chaos, and When to Walk Away
    May 28 2025

    What happens when you go from designing or building things yourself… to leading a team of 100+? And what if your career didn’t follow the standard product ladder to get there?

    In this candid and funny conversation, Lidia Oshlyansky shares her journey from social worker to backend engineer to product and UX leader at companies like Google, Spotify, and fast-moving startups.

    We explore the invisible work of leadership, the emotional challenges of management, and what it really takes to drive change in complex organisations—without losing your humanity.

    Whether you’re navigating scale, burnout, tough cross-functional relationships, or wondering if you’re still contributing anything at all… this episode will resonate.

    🧠 In this episode, we cover:

    * Why Lidia left social work to become a backend engineer—and how she discovered product along the way

    * The existential doubt of managing managers (“What am I even doing?”)

    * A mindset shift: empowering others is the work

    * How to build better relationships between product, design, and engineering

    * What to do when collaboration breaks down—and why sometimes, the right move is to stop trying

    * How to approach transformation in legacy organisations without arrogance

    * The difference between startup chaos and corporate resistance—and how to lead through both

    💬 Favourite moment:

    “I like that creative innovation chaos—and I like being able to harness it.”

    👤 About Lidia:

    Lidia Oshlyansky is a veteran product, UX, and design leader with global experience across big tech (Google, Spotify), publishing, and startups. She’s currently Chief Product Officerat Gillion, a Stockholm-based fintech. You can find her on LinkedIn (her only public presence—by design!).

    🎯 For:

    * Product leaders navigating growth or career transitions

    * Managers stepping into more abstract leadership roles

    * Anyone wrestling with cross-functional dynamics, change, or self-doubt



    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
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    56 mins
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