In this episode of The AI Grapple, Kate vanderVoort is joined by Dr Kyle Elliott, a career coach to tech executives and founder of CaffeinatedKyle.com. From humble beginnings offering £5 CV reviews on Fiverr to coaching leaders into top roles at Meta, Google and Amazon, Kyle shares what’s really happening in the job market - and how AI is shifting everything from CVs to C-suite expectations.

Whether you’re a job seeker, business leader or simply watching the AI wave roll in, this episode delivers grounded, practical advice to help you stay relevant, empowered and ahead of the curve.

What We Cover:

👉 Why middle management is most at risk - and what to do about it Kyle shares what he's seeing across his client base: mid-level roles are often being consolidated or automated. It’s not about roles disappearing completely, but shifting into jobs that involve managing AI-powered processes instead of performing tasks manually. He explains how professionals can identify emerging opportunities and pivot early.

👉 The AI tools job seekers should be using now (and how to train them) AI isn’t magic - it only knows what you give it. Kyle explains how his clients use tools like ChatGPT to write CVs, simulate interviews and even explore new career paths. But success depends on input: the better the data you provide (like performance reviews or personal profiles), the better the output AI delivers.

👉 How AI is changing executive-level hiring and job strategy Even at the top, AI is having an impact. Kyle explains how senior leaders are being assessed differently, what they’re worried about, and how they're learning to talk about AI in ways that show leadership, not fear. It’s about knowing when to use AI - and when to lean on your human skills.

👉 The emotional side of job searching in the age of automation Being made redundant or feeling threatened by change brings real emotional challenges. Kyle talks about the role of mindset coaching and shares an example of a custom GPT built to motivate and coach a client through job hunting - including cheering them on when things got tough.

👉 Why the best AI results come from knowing yourself better To get personalised, useful help from AI, you have to start with self-awareness. Kyle talks about the importance of building a “professional me” document - a profile of your background, skills, preferences and values - that can train AI to reflect who you really are and what you need next in your career.

🔗 Connect with Dr Kyle Elliott:

Website: CaffeinatedKyle.com

LinkedIn: Dr Kyle Elliott

👍 Like what you heard?

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In this episode of The AI Grapple, Kate vanderVoort is joined by Simon Yencken, Founder and CEO of Fanplayr.

What if you could deliver hyper-personalised experiences that delight customers without creeping them out?

Simon is a true pioneer at the intersection of AI, behavioural data, and e-commerce. His career has taken him from global finance and SaaS to founding Fanplayr, a company that's helping brands deliver smarter, faster, privacy-respecting customer experiences.

We dig into how AI is reshaping e-commerce, why privacy-first strategies are critical for survival, and what the future holds for businesses brave enough to embrace the next wave of AI innovation.

If you’re in marketing, business, or tech — this is an episode you won't want to miss.

🎯 Key Highlights

✔️ Simon's Journey to Fanplayr From legal partner in Australia, to global finance at Reuters, through the dot-com boom, SaaS success stories — and finally founding Fanplayr to bring real-time optimisation to e-commerce.

✔️ What Fanplayr Actually Does

Using patented segmentation technology and AI-driven personalization to enhance customer experiences, increase conversion rates, and boost lifetime value — all built on first-party data.

✔️ The Rise of Privacy-First Personalisation Simon explains how Fanplayr helps businesses move beyond third-party cookies, using tools like Privacy ID to comply with GDPR and still deliver tailored experiences.

✔️ How AI is Revolutionising Online Merchandising Beyond basic recommendations, Fanplayr’s AI matches users with exactly what they want — even before they know they want it — using machine learning and personalisation engines.

✔️ The "Creepiness" Factor We discuss how to personalise without feeling intrusive — and why transparency and trust will define the next decade of online customer relationships.

✔️ Regional Differences: US vs Europe Simon shares why privacy regulations are tougher in Europe, and how businesses are adapting differently in the US and UK markets.

✔️ ChatGPT, Hype vs Reality Simon shares his take on large language models like ChatGPT, and why the future of AI won't be one single exponential curve — but rather a series of powerful "S-curves" as new breakthroughs emerge.

✔️ AI’s Impact on SaaS and Business Models

Why the SaaS pricing and licensing world is ripe for disruption — and how traditional tech giants will have to evolve or risk being left behind.

✔️ Avoiding the AI Bubble Simon warns about the huge number of AI startups building on shaky ground — and shares why sustainable innovation will be what separates winners from losers.

✔️ What Excites Simon About the Future AI is at the start of a genuine tech revolution — and it’s opening opportunities that are bigger and more exciting than anything since the rise of the internet.

📌 Connect with Simon Yencken:

• Visit Fanplayr.com: Learn more about Simon’s company and solutions.
• Connect with Fanplayr on LinkedIn

Know a someone who needs to hear this? Share this episode with a friend, team member, or mentor who’s ready to embrace AI and lead with clarity.

👍 Like what you heard?

Subscribe to The AI Grapple on your favourite platform and leave us a rating or review. It really helps others find the show.

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💬 Join the conversation: AI Success Lab Facebook Group

In this episode of The AI Grapple, Kate vanderVoort is joined by Dr Alessandra Wall - psychologist, leadership strategist, and founder of Noteworthy - to explore how AI can help women reshape their careers instead of fearing job loss. Alessandra works with high-performing women in tech who are often juggling expectations, under-recognised achievements, and the ever-growing mental load.

This conversation digs into what’s holding women back in AI and tech, the biases baked into systems, and how AI - when done right - can unlock time, ease, and leadership opportunities for women at every level.

✨ Key Highlights:

➡️ Alessandra’s career journey - from psychology to empowering women in tech Alessandra shares how growing up with ADHD shaped her drive and work ethic, and how that personal experience guided her into a career in psychology. After hitting burnout, she transitioned into coaching, now using those same therapeutic tools to support women navigating the high-stakes world of tech and leadership.

➡️ Being the only woman in the room - and why it’s still happening We unpack the systemic issues that continue to isolate women in tech and AI - from a lack of early representation to high attrition at senior levels. Alessandra shares why women are still fighting for authority, even at the top, and why the system needs more than a token fix.

➡️ Can AI reduce bias? Yes - if we train it right AI reflects the data it’s fed. Alessandra explains how recruitment tools can either reinforce bias or break it - and why the people building these systems need to prioritise diversity and allyship to get meaningful results. Garbage in, garbage out doesn’t have to be inevitable.

➡️ The invisible workload: How AI can lighten the mental load From scheduling appointments to managing family logistics, women often carry the bulk of home-life organisation. Alessandra shares how AI is already helping her - and her clients - reclaim headspace and time, freeing them up to lead more fully at work and live more fully at home.

➡️ AI isn’t just for engineers - how every woman can use it to stay competitive You don’t need a tech background to benefit from AI. Whether you’re in marketing, coaching, or finance, understanding how to use AI as a productivity and strategy tool is a major edge. Alessandra breaks down how women can upskill and support others through this transition.

➡️ Parkour and AI - yes, really! Alessandra compares learning AI to her journey into parkour at 37 - a male-dominated, intimidating space where women hesitate to jump in. Her advice? We need more women teaching women how to navigate and own these tools. The power is in mastering the basics, together.

📌 Connect with Dr Alessandra Wall:

• Website: https://noteworthyinc.co
• LinkedIn: Dr Alessandra Wall on LinkedIn

Know a woman who needs to hear this? Share this episode with a friend, team member, or mentor who’s ready to embrace AI and lead with clarity.

👍 Like what you heard?

Subscribe to The AI Grapple on your favourite platform and leave us a rating or review. It really helps others find the show.

🎧 Listen now → www.aigrapple.com

💬 Join the conversation: AI Success Lab Facebook Group