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

Sanjay Robson is a seasoned product leader with over 15 years of experience building digital experiences that make life simpler for customers and drive growth for businesses. His career spans industries like energy, insurance, and telecommunications—where he’s led strategy, innovation, and delivery with a reputation for turning complexity into clarity and results. A lifelong technology enthusiast, Sanjay is now channeling his product expertise into the world of AI. He’s the creator behind several innovative tools, including Moontail’s AI and Planly, and currently leads Product and AI Transformation at Compare Broadband.

THE SUMMARY

From Call Centre to Head of Product: Sanjay’s career began in a contact centre — but curiosity, not credentials, drove his growth. He proved that execution beats theory, moving from junior support roles to Head of Product without completing a degree. His story is a masterclass in learning by doing.

The MVP Mindset That Actually Works: Instead of over-engineering AI solutions, Sanjay’s philosophy is to “build first, plan later.” His spreadsheet-powered chatbot for Compare Broadband became a working MVP before full integration — showing that proving value early is the fastest path to real innovation.

AI Meets Compliance and Scale: He’s turning compliance monitoring — once a painfully manual process — into a scalable AI-driven system. By flagging “ambiguous” calls for human review rather than aiming for perfection, he’s saving massive amounts of time while meeting strict regulatory standards.

Building Planly: Lesson Plans in Minutes: Frustrated watching his wife spend hours planning lessons, Sanjay built Planly.com.au — an AI tool that creates lesson plans, worksheets, and slides aligned with the Australian curriculum. It’s proof that personal pain points can become products with real-world value.

The Real AI Lesson: Sanjay had zero AI development experience before joining Polly’s course — now he’s launched multiple projects. His advice? “Don’t overthink it — just start.” The tech will frustrate you, but you’ll be amazed at how fast you can go from idea to 80% done.

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 [email protected]

Sanjay Robson

LinkedIn: https://au.linkedin.com/in/sanjay-robson

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

Joe Sessions is the COO and co-founder of Optimize, where he helps companies automate routine tasks and build the foundation for scalable AI adoption. With a career spanning hands-on software development, product leadership, and operational strategy, Joe brings a rare blend of technical depth and big-picture vision. He’s known for his ability to dive into the details when needed, while also guiding teams to step back and think strategically about long-term impact. A lifelong innovator and educator, Joe is passionate about empowering people and leveraging cutting-edge tools to drive meaningful growth—for businesses and individuals alike. Today, he joins us to share his insights on how thoughtful automation and AI can transform the way organizations work, scale, and lead in the digital age.

THE SUMMARY

RPA Before AI: Joe Sessions, COO and co-founder of Optimize, argues that most mid-sized companies shouldn’t start with AI at all — they should start with automation. Robotic Process Automation (RPA), he says, is the real foundation that enables scalable AI adoption later on.

Simple Beats Flashy: Joe believes too many businesses jump straight into AI experiments without solid systems in place. His advice: simplify your workflows first. No databases, no endless code updates — just connect the dots between tools and eliminate repetitive tasks.

Real-World AI Use Case: Joe shares his capstone project — an AI-powered document extraction system that detects features like fences in construction PDFs. He breaks down how he used workflows and Gemini to handle complex image data, showing how AI can add value only after automation does the heavy lifting.

AI with Ethics and Practicality: A former Microsoft Responsible AI developer, Joe brings a measured view to the hype. He’s writing a book on ethical AI, aiming to ground the conversation in realism and responsibility — not fear or hype.

Advice for Newcomers: Start small. Joe recommends OpenAI’s $20 plan and experimenting with custom GPTs for repetitive tasks. The ROI? He cut a five-week project down to three days using smart automation.

Takeaway: Stop “AI-washing” your business. Nail your processes, automate smartly, and let AI follow naturally.

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 [email protected]

Joe Sessions

LinkedIn: https://www.linkedin.com/in/joe-sessions

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

Zak Wiatr is a product leader at the intersection of fintech, higher education, and emerging technology, with a career spanning Air Force intelligence operations to scaling payments infrastructure for a $50 billion-plus education ecosystem. Currently leading product at Transact Campus, Zak helps universities modernize and simplify the student payment experience, while also driving digital solutions for government clients and delivering millions in cost savings through strategic data and client experience initiatives. A former Air Force officer and architecture graduate turned product strategist, he brings a unique blend of systems thinking, precision execution, and human-centered innovation to every challenge. Passionate about shaping technology that serves real people, Zak joins us today to share his journey from military intelligence to AI-driven product leadership.

THE SUMMARY

From Air Force Intel to Product Leadership — Zak’s journey from military intelligence to product management shows how skills in risk analysis, systems thinking, and competitive intelligence translate directly into building and scaling software products.

AI in Higher Education — At Transact Campus, Zak is driving AI adoption in student payments and university operations. His team’s approach: start with the question “what work do you not want to do?”—focusing on removing friction rather than chasing hype.

Building Without a Coding Background — Despite not being an engineer, Zak built working AI apps with tools like Replit, Magic Patterns, and Claude. His bold take: real estate agents may not exist in 15 years because AI can automate core steps in home buying and selling.

AI-First Household — As a father, Zak applies AI not just at work but in parenting—using tools like NotebookLM for research hacks and AI-powered storybooks for kids. His stance: parents must teach AI safety alongside internet and social safety.

Empowering Others with AI — Zak even coached an Uber driver who wanted to launch a farm-to-table delivery startup, showing them how to use ChatGPT and Replit to spin up a business plan and prototype without coding skills.

Advice to Beginners — Fear and FOMO pushed Zak into AI, but his message is clear: it’s easier than most people think, and anyone—even a 93-year-old—can build apps with today’s tools.

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 [email protected]

Zak Wiatr

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

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

Rachel Beck is a global leader in business intelligence and analytics with 15 years of experience transforming complex data into actionable insights that drive program impact and investment. She has led business intelligence strategies for portfolios exceeding $70 million, launched global management systems used in over 50 countries, and unified KPIs that unlocked tens of millions in additional funding. With dual master’s degrees in data science and public administration, Rachel is now focused on integrating AI into inclusive, user-centered systems that scale social impact, while also mentoring the next generation of analytics and product leaders

THE SUMMARY

From Conflict Zones to AI Leadership — Rachel draws parallels between navigating civil war in South Sudan and today’s AI landscape. Both require rapid pivots, scenario planning, and risk management under uncertainty.

Risk Isn’t Optional — In both war zones and AI adoption, “doing nothing” is itself a risk. Organisations must decide whether to stand still, retreat, or transform—and the biggest gains come when they embrace intentional change.

The Human Side of Data — Rachel stresses that the real value in analytics lies in messy, qualitative insights—the “why” and “how” behind the numbers. In AI, the challenge is turning subjective evaluations (like “is this summary better?”) into meaningful, measurable metrics.

Trust Over Technology — Partnerships built on trust (like with community leaders in crisis zones) translate to AI too. A prototype can’t replace alignment, risk management, and stakeholder trust. Those who ignore this lose credibility fast.

AI for Social Impact — Rachel’s new AI tool helps product managers and researchers perform deep competitive analysis with human-in-the-loop oversight. It blends automation with expert steering, ensuring outputs are meaningful, not shallow.

Advice for Newcomers to AI — Start small. Use AI tools to solve real pain points in your daily life (even as simple as dinner recipes). Curiosity and iteration matter more than expertise when getting started.

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 [email protected]

Rachel Beck

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

Email: [email protected]

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

Grace Wu is a visionary fintech product leader with over two decades of experience transforming the global payments and risk ecosystem. She has shaped platform strategies at Apple, Uber, and Alipay, and launched revenue-generating products across Asia, Latin America, and the U.S., bringing deep expertise in card issuing, acquiring, alternative payments, and identity. Holding a patent in alternative payments, Grace has led teams responsible for more than $500 million in revenue and transaction volume while significantly reducing fraud and loss. Now a trusted advisor to early-stage startups, she is focused on AI and next-generation risk intelligence, leveraging her real-world experience with cutting-edge technology to shape the future of global commerce.

THE SUMMARY

AI in Payments Is About Trust, Not Just Tech — Grace Wu argues that without consumer trust, even the most advanced AI-driven payment systems will fail. Platforms must offer protection — like credit card chargebacks — to drive adoption.

Agentic AI: Still More Rules Than Autonomy — Despite the hype, most “AI agents” in commerce are still rule-based, not fully autonomous. True agentic AI will require mastery of both knowing and doing, plus robust human validation.

Security Risks Multiply with AI Agents — Giving AI spending power creates new vulnerabilities — think of it as an eager intern who can be misled. Guardrails, spending limits, and behaviour-based trust are essential before handing over more control.

Data Quality Is the Real AI Power Source — The future of AI is a trifecta: data, model, and context. Without high-quality, relevant data, even the best models fail — making data readiness a critical first step in AI adoption.

Career Tip: Build Before You Talk — Grace’s advice for AI newcomers: ground yourself with fundamentals, find trusted sources, and build something hands-on to truly understand the possibilities and limits of AI.

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 [email protected]

Grace Wu

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

Website: https://paymentsoperator.substack.com/

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

Don Stoddard is a powerhouse product leader with over two decades of experience driving SaaS innovation across B2B and B2C markets. From scaling global platforms at Monster and SumTotal to launching AI-powered strategies through his consultancy, Blueprint Product, he is known for leading high-impact teams and unlocking product–market fit at scale. With a foundation in computer science and a career spanning enterprise tech, HR platforms, and martech, Don brings deep operational expertise and a passion for emerging technology. Now at the forefront of AI enablement, he helps companies modernize product strategy, execute with speed, and mentors the next generation of product leaders along the way.

THE SUMMARY

AI as a Force Multiplier for Product Leaders — Don shares how tools like Replit can deliver up to a 90% boost in efficiency for building and integrating AI features, from CRM hookups to mobile optimization, in minutes.

Avoiding “Vibe Coding” Pitfalls — While AI can rapidly generate code, Don stresses the importance of guiding it with prompts that explore multiple options first, preventing costly missteps like accidental site-wide navigation changes.

Turning AI into Actionable Insights — His site, BlueprintProduct.com, not only assesses product leadership skills but also uses AI to analyse industry newsletters, validate insights with a second model, and distil them into actionable trends.

Practical On-Ramps to AI — For senior product leaders new to AI, Don recommends building a custom GPT—whether to recommend conference sessions or decode the Marvel Universe—as a quick, hands-on way to learn.

AI Enablement Consulting — Don helps companies integrate AI into products so it’s relatable, user-aligned, and value-adding—bridging the gap between cutting-edge tech and real business goals.

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 [email protected]

Don Stoddard

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

Website: https://www.blueprintproduct.com/

Blueprint Product Capability Assessment: https://www.blueprintproduct.com/assessment

Blueprint Product Trends: https://www.blueprintproduct.com/insights

ProductCamp Conference GPT: https://chatgpt.com/g/g-681cc789dc9c8191a62e8602060be080-productcamp-conference

Marvel Cinematic Universe GPT: https://chatgpt.com/g/g-6817ad8808a88191a2769110bc6995f1-marvel-cinematic-universe?model=gpt-4o

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

Kelly-Ann Bakhos is a dynamic product leader with a diverse career spanning healthcare, retail, gaming, data analytics, and election systems. She has led high-performing teams, driving innovation in data governance, AI-driven analytics, and user experience. With leadership roles at renowned companies such as EBSCO Information Services and Riot Games, she excels at integrating AI to enhance decision-making and automate workflows. Continuously pushing the boundaries of product development and leadership, Kelly-Ann is also a passionate advocate for the positive impact of responsible AI.

THE SUMMARY

Data Governance as a Revenue Driver: Kelly argues that data governance isn't just about compliance—it's a critical enabler of speed, trust, and revenue. Without clarity on metrics or confidence in definitions, decisions slow down or misfire. True governance allows teams to move fast because the foundations are solid.

From Games to Government: Kelly's career spans gaming and now election systems. At Riot Games, she saw the power of AI in action. Now, she's applying that mindset to design a transparent, AI-enhanced election system for Los Angeles County—where governance and public trust are everything.

AI in Elections—With Guardrails: AI can support secure elections without compromising integrity. Kelly explores use cases like signature verification and summarising voter guides—but always ensures human oversight, audit trails, and full transparency to build public trust.

Getting Into AI: Play, Don’t Just Study: Her advice to AI newcomers? Treat AI tools like video games—play with them daily, explore workflows, and learn through doing. The #1 skill? Fearless tool adoption. It's not about being perfect—it's about being willing to dive in and figure things out.

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 [email protected]

Kelly-Ann Bakhos

LinkedIn: https://www.linkedin.com/in/kelly-bakhos-205690a/

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

Dave Stys is a product leader with one of the most fascinating paths into tech—starting his career calibrating instruments on the Hubble Space Telescope before moving into reimagining the future of email at AWeber. Blending scientific precision with sharp marketing instincts, Dave has led initiatives in dynamic content, AMP for email, and deliverability. Now, he's stepping into a bold new chapter, exploring how AI can enhance content creation and streamline product workflows across the email ecosystem. Whether he’s mentoring teams or decoding spam signals, Dave is shaping the future of communication one message at a time.

THE SUMMARY

Prototype First, Permission Later: Dave didn’t wait for roadmap approval—he just built it. His AI newsletter builder solved a real problem, got internal traction, and shipped. Action beats alignment.

Blank Pages Kill Momentum: Email editors shouldn’t feel like Photoshop. Dave’s AI-generated “block layouts” let users skip the design paralysis and drop in beautiful, functional content instantly.

Cursor Over No-Code: No-code tools felt like config hell. Cursor gave Dave just enough coding power to move fast without being an engineer. The takeaway: pick tools that suit how you think.

Real Adoption = No Edits: Users hit “send” on AI-generated emails without changing a word. That’s the bar for useful AI—not engagement, not hype—trust.

Don’t Chase the Shiny Stuff: AI image generation wasn’t ready—yet. Dave’s experiments bombed early on. Know where AI adds value now, and where it still lags.

Invest, Then Build: Whether it’s buying a tool, joining a course, or staying up late, Dave’s message is simple: no one’s coming to upgrade you. Do it yourself.

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 [email protected]

Dave Stys

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

Website: https://www.aweber.com/

My links

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

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

AI After Hours – Summer Edition: Copyright showdowns, reasoning meltdowns, and HR mayhem!

Anthropic scores a legal win that could reshape LLM training. Apple releases a reasoning paper that stirs up more drama than insight. And HR? They're drowning in AI-generated résumés while legally barred from using AI themselves. Oh, and did we mention robots folding laundry offline?

Join Polly Allen (AI Career Boost) and Yuying Chen-Wynn (Wily Ventures) as they serve up their no-BS takes on the month’s juiciest AI headlines. From wild research reactions to workplace adoption struggles, we call out what’s real, what’s hype, and what’s just plain ridiculous in AI.

Irreverent. Insightful. Slightly buzzed. It’s AI After Hours.

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

Rebeca Assunção is a senior product leader driving innovation at the intersection of AI, mobility, and no-code tools. With over a decade of experience across e-commerce, transit tech, and smart cities, she currently leads the digital product team at NEOM, shaping a seamless AI-powered system for one of the world’s most ambitious urban development projects—an entirely new, future-forward e-city in Saudi Arabia. Known for her hands-on leadership style, Rebeca builds rapid local prototypes to accelerate validation and guides teams through complex, enterprise-scale launches. Outside of her professional work, she is an active investor championing tech-for-good ventures in fintech, sustainability, and health.

THE SUMMARY

AI is a multiplier, not a magic wand: Rebeca uses AI to extend her tiny team’s reach—writing specs, validating vendors, and building working prototypes solo. It’s not just about innovation; it’s survival when you’re understaffed and under pressure to deliver fast.

The “average” product manager is done: AI will automate the middle. Rebeca argues PMs need to pick a lane: either go deep into growth or become technically fluent. The days of generalists writing Jira tickets are over.

Don’t build unless you must: Her rule is simple—only build in-house if the product is unique, high-impact, and the team has the skills. Otherwise, buy or license. Time, expertise, and complexity should dictate, not ego.

NEOM’s ambition? Kill the UX entirely: The vision is frictionless transport. If a bus is cancelled, the system quietly rebooks you. No alerts, no stress. But this requires deep hardware integration, not just clever software.

Internal tools matter too: She built a roadmap assistant that lets teams chat with strategy docs and get feature suggestions. Not just a cool demo—it’s a real step toward aligning product culture in a non-product-native org.

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 [email protected]

Rebeca Assunção

LinkedIn: https://ae.linkedin.com/in/rebecaoramassuncao

My links

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

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