Amelia Rossi-Doyle

Have you heard of a “Specialised Generalist”? It’s a term I’ve been thinking about a lot as I reflect on the future of work. We’re at an inflection point - not just because of AI, but because of how work itself is evolving. Teams are leaner. Expectations are more complex. And linear careers are quickly giving way to hybrid, fluid ones. Someone who combines: • Depth in 1–2 key disciplines • Breadth across functions, sectors, or mindsets • And the ability to connect dots and adapt fast In this new landscape, the people who’ll thrive are those who can go deep and wide. If you’ve worked across industries, led cross-functional teams, or picked up “adjacent” skills outside your job description - you’re already training your Specialised Generalist muscle. If you’ve ever felt like your skills don’t fit in just one box, that might be your superpower, not your liability. Do you agree?

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Yesterday, I had the privilege of participating in an international customer panel on mental well-being, with teams from across Europe. One story stayed with me. A person spent nearly a year in isolation after their divorce, without telling a single person. Not privately. Not at work. The impact on their well-being and performance was clear. Another panelist offered a quiet but powerful invitation: "If you're struggling, reach out. I'm here." They shared how they personally manage difficult moments. That simple act created space for others to speak up. It was a clear reminder that challenges are universal. But stigma often begins with how we're raised, and it still shows up in the workplace. This is where leadership matters. If you hold influence, you shape culture. People notice what you say, and what you choose not to. When leaders go first, it shows that vulnerability is not a liability. It is a sign of strength and trust. I’m proud to be part of an industry that is prioritising these conversations. Not as a side topic, but as a core part of how we build healthy, high-performing teams.

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Self-promotion gives me the ick 🤢... and I know I'm not alone! 2 tips have helped me 'conquer' this task, which IS important, especially if you work at a big company. 1. 🖼️ Re-frame: Promote the work for the sake of all the people you worked *with* to make sure *they* get recognition... Not just you. 2. 🔄 Switch the task: Work with someone awesome? Send a note of kudos to their manager. This isn't promoting yourself necessarily, but the good karma will come back to you. Trust me. And don't forget... Nobody else is gonna do it for you! Other tips for promoting your work, in a less-icky way? And who do you think saved me from being trapped in the stairwell?

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What if your seemingly unrelated career experiences were the exact springboard you needed to thrive in AI? In a recent Business Insider article (𝘀𝗲𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗰𝗼𝗺𝗺𝗲𝗻𝘁𝘀), Jon Flynn shares his unconventional journey from filmmaking to leading AI sales at Google. 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 𝗼𝗳 𝗙𝗮𝗰𝘁𝘀: Jon Flynn began his career producing music videos and commercials in southern Africa. Despite his creative background, he maintained a strong interest in technology, earning a Microsoft engineering certification. This technical foundation facilitated his transition into roles within financial services, product management, and business leadership. Flynn emphasizes that curiosity, effective communication, and understanding customer needs are more critical than advanced technical degrees in AI sales. 𝗧𝗵𝗿𝗲𝗲 𝗞𝗲𝘆 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: 1️⃣ 𝗘𝗺𝗯𝗿𝗮𝗰𝗲 𝗗𝗶𝘃𝗲𝗿𝘀𝗲 𝗕𝗮𝗰𝗸𝗴𝗿𝗼𝘂𝗻𝗱𝘀: Non-traditional career paths can provide unique perspectives and skills valuable in AI roles. 2️⃣ 𝗖𝘂𝗹𝘁𝗶𝘃𝗮𝘁𝗲 𝗖𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝗮𝗻𝗱 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻: A genuine interest in technology and the ability to convey complex concepts are essential for success in AI-related positions. 3️⃣ 𝗣𝗿𝗶𝗼𝗿𝗶𝘁𝗶𝘇𝗲 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗨𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱𝗶𝗻𝗴: Aligning technological solutions with customer needs fosters stronger relationships and drives innovation. 𝗠𝘆 𝗣𝗼𝗶𝗻𝘁 𝗼𝗳 𝗩𝗶𝗲𝘄: Flynn's career trajectory underscores the value of diverse experiences in the AI industry. His story illustrates that a non-linear path, driven by passion and adaptability, can lead to leadership roles in cutting-edge fields. This perspective is particularly encouraging for professionals considering a shift into AI from unrelated sectors. I have a very diverse background myself. From Culinary Arts, to gaining my Hospitality Management Degree, which I obtained with the intent of leaving the industry, to successfully managing a $14M business with 45 employees before transferring to the US, where my trajectory brought me to Customer Success and Support. My biggest mistake? Undervaluing my Culinary Arts and Hospitality background and particularly how it shaped me in the early stages of my career. 𝗖𝗮𝗹𝗹 𝘁𝗼 𝗔𝗰𝘁𝗶𝗼𝗻: Reflect on your career journey and consider how your unique experiences can contribute to the evolving AI landscape. Share your thoughts and stories in the comments below. 𝗗𝗶𝘀𝗰𝗹𝗮𝗶𝗺𝗲𝗿: 𝘛𝘩𝘪𝘴 𝘱𝘰𝘴𝘵 𝘸𝘢𝘴 𝘢𝘶𝘵𝘰𝘮𝘢𝘵𝘪𝘤𝘢𝘭𝘭𝘺 𝘥𝘳𝘢𝘧𝘵𝘦𝘥 𝘣𝘺 𝘊𝘩𝘢𝘵𝘎𝘗𝘛 𝘢𝘴 𝘱𝘢𝘳𝘵 𝘰𝘧 𝘮𝘺 𝘰𝘯𝘨𝘰𝘪𝘯𝘨 𝘦𝘹𝘱𝘭𝘰𝘳𝘢𝘵𝘪𝘰𝘯 𝘰𝘧 𝘈𝘐 𝘢𝘯𝘥 𝘤𝘰𝘮𝘱𝘭𝘦𝘮𝘦𝘯𝘵𝘦𝘥 𝘣𝘺 𝘮𝘦 𝘸𝘪𝘵𝘩 "𝘔𝘺 𝘝𝘪𝘦𝘸". 𝘈𝘭𝘭 𝘳𝘦𝘧𝘦𝘳𝘦𝘯𝘤𝘦𝘥 𝘢𝘳𝘵𝘪𝘤𝘭𝘦𝘴 𝘸𝘦𝘳𝘦 𝘳𝘦𝘢𝘥 𝘣𝘺 𝘮𝘦, 𝘢𝘯𝘥 𝘵𝘩𝘦 𝘰𝘱𝘪𝘯𝘪𝘰𝘯𝘴 𝘦𝘹𝘱𝘳𝘦𝘴𝘴𝘦𝘥 𝘪𝘯 𝘵𝘩𝘦 "𝘔𝘺 𝘝𝘪𝘦𝘸" 𝘴𝘦𝘤𝘵𝘪𝘰𝘯 𝘢𝘳𝘦 𝘴𝘰𝘭𝘦𝘭𝘺 𝘮𝘺 𝘰𝘸𝘯.

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She scaled Booking.com across 225+ countries over 20 years. Here's what she'd do differently if she started today. Gillian Tans didn't just grow Booking.com, she lived through every stage of its evolution from Dutch startup to global giant, serving as COO, CEO, and Chairwoman. In a session moderated expertly by Ingrid Tappin 🏳️‍🌈 CEO, at the Valencia Digital Summit , Gillian revealed the leadership lessons that only come from watching what breaks at scale: What she wished she'd known about middle management: ↳When you're high growth and moving fast, middle managers are where things start breaking at scale. ↳Embrace the chaos and seize the opportunity in it. On the founder's obsession with perfection: ↳Don't worry if it's ugly. Worry if there's real product-market fit. ↳ In the early days people complained that Booking's UI was ugly ..but they booked! On how competitive advantage has shifted: ↳More people have access to tech today, so think about what makes you stand out. ↳Having the best product is not enough. There's new complexity in marketing, sustainability, remote work. Her take on AI: ↳ AI is probably your best co-founder. What leaders must unlearn: ↳Growth at all costs ↳ Control-based leadership (yaaasss!) What to embrace instead: ↳ Decentralize decisions as low as possible ↳ Accountability and ownership ↳ Spend 25% of your time on talent (yaaasss!) Her three pillars for sustainable scale: ↳ Focus (simplicity scales) ↳ Transparency (essential) ↳ Don't assume (validate everything) When hiring, she asks: ↳ Can this person last 3 years from now? ↳ And tie performance to behaviours, not just outcomes. The final piece of wisdom that stayed ↳ Don't let failure get into your heart and success into your head. Gillian emphasized that building a people-first organization means partnering with experts who understand talent and culture deeply. Organizations like Diverse Leaders in Tech are critical to making this shift real, not performative. Gillian Tans built one of the world's most successful travel platforms. Now she's teaching founders to build smarter, not just bigger. What would you unlearn from your scaling journey? #VDS2025 #leadership #leadershiplessons

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