A quick glimpse into what happened in the world of AI in April 2025!

THE SHOW

AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools!

THE LINKS

Recommendations

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

Polly Allen

LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠

AI Career Boost: ⁠https://www.aicareerboost.com/⁠

Yuying Chen-Wynn

LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠

Blog: https://yuying.substack.com/

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

THE GUEST
Dr. Yisha Stiskala-Yu is a clinical psychologist, scientist, and AI product leader transforming the digital health and medtech innovation landscape. With over a decade of experience at the intersection of psychology and technology, she advises VCs, startups, and investment firms on AI-driven healthcare solutions, clinical governance, and go-to-market strategy. A former clinical lead for elite athletes at the Australian Institute of Sport and a hospital-based psychologist, Yisha is now focused on advancing digital therapeutics, healthcare AI, and precision medicine. Through her work with What If Ventures, VentureBlick, and global innovation initiatives, she is helping shape the future of emotionally intelligent, evidence-based care.

THE SUMMARY
Shallow Mental Health Apps Don’t Cut It: Calm and Headspace are great for general wellness, but Yisha argues they fail people facing real trauma and emotional pain. We need tech that actually heals, not just soothes.

Software as Care, Not a Connector to Care: Yisha’s startup treats software itself as the intervention—delivering personalised, evidence-based learning journeys that reduce symptoms and empower users.

AI That Responds in the Moment: Instead of AI chatbots or “companions,” MyndStrong Health uses AI to intelligently surface the right tool at the right time—especially in moments of distress.

No AI Hype, Just Clinical Rigor: Forget flashy features. Yisha’s focus is safety, empathy, and real clinical outcomes. Healthcare tech should be built with integrity, not buzzwords.

Want to Pivot to AI? Study First: Yisha didn’t guess her way into AI—she took a full MITxPro course. Her advice: be humble, stay curious, and actually learn the tech before you build with it.


THE SHOW
Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

THE LINKS
Have a question you want us to answer? Send it through to support@aicareerboost.com

Yisha Stiskala-Yu
LinkedIn: https://www.linkedin.com/in/yishastiskalayu/

My links
LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠
AI Career Boost: ⁠https://www.aicareerboost.com/⁠

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

THE GUEST

Kelli "Rua" Klein is a seasoned Product Manager and board member at Firebrand Resiliency Collective, where she leads innovative, AI-powered tools and helps streamline operations to support wildfire resilience. With over 14 years at Nike, Kelli honed her expertise in digital product management, cross-functional collaboration, and user-centered design. She has successfully led high-impact projects, leveraging AI-driven technologies for global customers, and has a track record of driving financial success and improving customer experiences. Kelli’s work with Firebrand focuses on empowering communities to prepare for and recover from natural disasters by leveraging community-driven processes and technology for long-term resilience. Her diverse career reflects a passion for strategic problem-solving and creating meaningful, user-driven products.

THE SUMMARY

From Curiosity to Capability: Kelly Klein’s journey into AI wasn’t sparked by a technical background—it was fuelled by curiosity and a passion for problem-solving. Hands-on experimentation with tools like ChatGPT, Midjourney, and Voiceflow helped her rapidly upskill and start building real-world solutions.

AI for Real Problems, Not Just Big Tech: Kelly used AI to tackle wildfire preparedness in rural Oregon—creating an advisor tool that helps residents assess home risks and access grants. Her work proves AI can thrive outside Silicon Valley, especially when it's built for communities often left out of tech innovation.

Start With the Problem, Not the Tool: Kelly stresses that effective AI products start with deep user understanding. Jumping into solution mode without discovery is a recipe for wasted effort. Instead, focus on the pain points—tech should come after the insights.

Advice for New AI Builders: Don’t wait for permission—just dive in. Start with something you care about, play with no-code tools, and use AI to solve a real problem in your life or community. It’s not about having the right degree—it’s about asking the right questions.

THE SHOW

Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

THE LINKS

Have a question you want us to answer? Send it through to support@aicareerboost.com

How to contact Kelli:

LinkedIn: https://www.linkedin.com/in/kelliruaklein/

Website: https://kelliruaklein.com/

Email: kelliruaklein@gmail.com

Firebrand Resiliency Collective: https://firebrandcollective.org/wildfire-home-risk-assessment-program/

Link to FRC Donation Post in LinkedIn: https://www.linkedin.com/posts/kelliruaklein_donate-to-firebrand-resiliency-collective-activity-7300576574280474624--Vpj?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAAkm8sBh0j0hoJyBtRoEbjK_zKYHLb33ig

FRC HomeSafe Fire Resiliency Advisor - Beta: https://chatgpt.com/g/g-74t55OjF7-homesafe-fire-resiliency-advisor-beta

My links

LinkedIn: ⁠

A quick glimpse into what happened in the world of AI in March 2025!

THE SHOW

AI After Hours with Polly Allen and Yuying Chen-Wynn is an irreverent attempt to 'edutain' about the latest AI headlines & tools!

THE LINKS

Recommendations

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

Polly Allen

LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠

AI Career Boost: ⁠https://www.aicareerboost.com/⁠

Yuying Chen-Wynn

LinkedIn: ⁠https://www.linkedin.com/in/yuyingchenwynn/⁠

Blog: https://yuying.substack.com/

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

THE GUEST

Vasuki Chilukuri is a dynamic product leader known for driving impact at scale. At Intel, she pioneered the company’s first 'as-a-Service' model for data center products, generating billions in revenue, and launched AI-driven manageability strategies for 200M+ devices annually. Previously at Model N, Vasuki was instrumental in enabling its successful IPO by transforming products into scalable SaaS platforms, achieving 25% YoY growth. Her expertise in product strategy, SaaS, and AI fuels her ability to deliver innovation and measurable results. She’s currently serving as Fractional VP of Product at Ambient Enterprises.

THE SUMMARY

From Technical Expertise to Product Leadership: Moving from software engineering to product management requires significant mindset shifts, including a focus on empathy, people-oriented problem-solving, and strategic vision.

The Data Layer in AI Innovation: The data layer forms the foundation of AI solutions, influencing how data is sourced, stored, and utilised to enable actionable insights and efficient systems.

Securing Data Ownership: Innovative solutions are emerging to help users take control of their data, ensuring security, sovereignty, and the ability to monetise digital assets responsibly.

Navigating AI Product Development: AI-driven product strategies often require long-term planning, adapting to rapidly changing market trends and technological advancements.

THE SHOW

Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

THE LINKS

Have a question you want us to answer? Send it through to support@aicareerboost.com

Vasuki Chilukuri

LinkedIn: https://www.linkedin.com/in/vasukic/

My links

LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠

AI Career Boost: ⁠https://www.aicareerboost.com/⁠

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

THE GUEST

Matt Wei has built a remarkable career in product management and agile transformation, driving impactful innovation at VMware Tanzu Labs. With experience delivering over 10 software products across six industries, Matt has transformed teams and modernized critical applications, boosting efficiency, user satisfaction, and organizational agility. Recently, he’s been expanding his expertise into AI, so he can further help organizations harness cutting-edge technology for real-world solutions. From improving government systems to accelerating Fortune 500 initiatives, Matt combines strategic vision with a hands-on approach to shape the future of digital transformation.

THE SUMMARY

Breaking Into AI 🚀: Hands-on learning is the best way to transition into AI. Dive into tools like ChatGPT, experiment with workflows, and troubleshoot to understand how AI can solve real-world problems.

Transforming Prototyping With AI 💡: AI accelerates prototyping, turning static designs into interactive, functional models. This enables faster iteration, real-world testing, and a more collaborative process with design and engineering teams.

AI in Enterprise Modernization 🤖: AI tools can slash software development timelines, automate compliance and security processes, and even perform user validation. Enterprises can achieve in days what once took months or years.

Collaboration in the AI Era 🌟: AI is blurring the lines between traditional roles like product management, design, and engineering. Building shared mental models and maintaining clear responsibilities are crucial for effective teamwork.

Lessons for Aspiring AI Product Leaders ✨: To succeed in AI product management, focus on experimentation, practical experience, and learning from failure. Transitioning to AI is about building confidence through action, not just theory.

THE SHOW

Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

THE LINKS

Have a question you want us to answer? Send it through to support@aicareerboost.com

Matthew Wei

LinkedIn: https://www.linkedin.com/in/matthewhdwei/

Spring Labs: https://springlabs.io/

My links

LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠

AI Career Boost: ⁠https://www.aicareerboost.com/⁠

For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested

THE GUEST

Flora Wu is a trailblazing program management leader redefining what’s possible at the intersection of technology and AI. With over a decade of experience leading cross-functional teams at Microsoft and Seagull Scientific, she has delivered groundbreaking results—migrating enterprises to cloud solutions, driving 80% efficiency gains, and slashing crash rates by 12% in flagship software releases. With a Bachelor’s in Electrical Engineering and an MBA in Technology Management from the University of Washington, Flora has been learning the best ways to leverage AI-driven strategies to tackle complex challenges. An innovator, builder and collaborator, she’s shaping the future of program and product management through cutting-edge technology.

THE SUMMARY

The Power of Hands-On Learning 🚀: Flora’s transition into AI started with practical projects that tackled real problems. Tools like ChatGPT were instrumental in accelerating learning and getting her started on building impactful solutions.

Problem-Solving With AI 💡: Flora created a swimming coach bot to simplify complex logistics for parents in competitive swimming. By using custom GPT models, she streamlined schedules, rules, and updates—saving time and reducing confusion for parents and coaches alike.

Turning Frustration Into Innovation ✨: Personal pain points, like managing swim meet logistics for her children, sparked Flora’s motivation to explore AI. Her work highlights how lived experiences can inspire tech solutions that benefit entire communities.

Learning AI From Scratch 🌟: Flora emphasizes the importance of guided learning combined with hands-on experimentation. Online resources, structured courses, and capstone projects provided the accountability and depth she needed to succeed.

Advice for Aspiring AI Enthusiasts 🔑: Start with tools like ChatGPT to build familiarity with AI, then take it further with structured programs that offer project-based learning and mentorship. Deadlines and real-world applications are game-changers.

THE SHOW

Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.

THE LINKS

Have a question you want us to answer? Send it through to support@aicareerboost.com

Flora Wu

LinkedIn: https://www.linkedin.com/in/floraflorawu/

My links

LinkedIn: ⁠https://www.linkedin.com/in/pollymallen/⁠

AI Career Boost: ⁠https://www.aicareerboost.com/⁠