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

Maggie May is a sharp, high-velocity product and tech executive who has built and scaled lovable products across real estate, accessibility, and fintech. From the startup trenches to CPO seats, she’s known for pairing speed with substance—shipping fast while never losing sight of user trust and delight. At Tomo and AudioEye, Maggie led teams with a relentless focus on impact, inclusive design, and staying one step ahead of what customers and markets actually need. Now, through AskAndBeFound.com, she’s focused on helping service-based businesses get discovered on ChatGPT, bridging the gap between AI-era search and the real humans ready to serve.

THE SUMMARY

AEO/GEO is the new SEO power play: The episode dives deep into why AI-engine optimisation matters more than people realise. Traditional SEO alone won’t get you discovered in LLM search — and many businesses are flying blind thinking Reddit comments or keyword-stuffing will save them. The real levers are directories, reviews, and structured data that AI can actually understand.

The 3-part framework every business should use: Maggie breaks it down to Off-Page (directories + reviews), On-Page (classic SEO), and Technical SEO (schema files + inline markup). If any of these pieces are missing, AI simply won’t trust your content or know who you are. She makes it clear: this isn’t optional anymore — it’s the minimum viable digital presence.

Myth-busting what doesn’t work in AI search: There’s a widespread belief that you need to grind on Reddit or that AI suppresses AI-generated content. Both are wrong. The episode makes the argument that AI rewards clarity and structure, not internet folklore. If reviews and directories aren’t part of your strategy, you’re wasting your time.

Schema is the unsung hero of AI discovery: The conversation highlights how installing the right schema can transform visibility — sometimes in under an hour. Not because it's a “hack,” but because it gives AI exactly what it wants: clean, structured context. Most businesses don’t even know this step exists.

If AI doesn’t understand who you are, you don’t exist: One of the strongest opinions throughout the episode: ambiguity kills discoverability. If your business name, phone, and address aren’t consistent across platforms, AI drops you instantly. The margin for error is zero — AI doesn’t “kind of guess.”

Entrepreneurship + multi-passionate careers are a feature, not a bug: Maggie’s career arc reinforces that being multi-passionate is now an advantage — not something to hide. Each curiosity thread strengthens the others. The episode makes a strong case that exploring multiple domains is the modern form of career compounding.

Start building with AI, even if you’re intimidated: The final takeaway: the only way to learn AI is hands-on. Break things. Save versions. Ask the model questions. Whether you’re using LLMs to build products or grow your service business, the barrier to entry is the lowest it’s ever been — and the upside has never been higher.

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

Maggie Mae

LinkedIn: https://www.linkedin.com/in/maggie-mae-seattle

My links

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

AI Ca

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

Sudha Kumar is a powerhouse product leader who thrives at the intersection of data, compliance, and user impact. With more than a decade of experience scaling B2B SaaS platforms and modernizing federal IT systems, she has delivered measurable outcomes across sectors, from accelerating healthcare audits by 30% to driving product revenue across more than 50 companies. Known for her ability to simplify complex workflows without sacrificing rigor, Sudha brings deep technical fluency and a sharp sense of user empathy to every challenge. Now focused on shaping the next generation of AI-powered enterprise tools, she is dedicated to advancing system compliance, reliability, and trust in the AI age.

THE SUMMARY

Data is the real truth-teller in product work — The conversation emphasises that users rarely behave the way product teams expect. Data becomes the only reliable signal to understand real usage patterns and close the gap between intention and reality.

Technical fluency massively elevates a PM’s impact: Being able to query raw logs, validate theories, and guide engineering with precision turns a PM into a high-leverage operator—especially in platform roles, where hidden complexity and technical debt drive long-term success or failure.

Compliance is an AI goldmine: Compliance work is repetitive, high-stakes, and deeply dependent on human interpretation. Automating the mapping of findings to regulatory standards shows immediate value, especially when errors can trigger hospital shutdown risks.

AI performance reflects the clarity of the human behind it: Iterating on prompts, supplying examples, and defining rules tightly is what improves accuracy. AI only becomes “smart” when the PM is intentional, structured and thorough with the inputs.

Data harmonisation is the hidden prerequisite for real AI adoption: At Renovo, six companies with six definitions for basic concepts made clear that most AI problems are data problems. Without consistent definitions and clean context, AI becomes a guessing machine—not a reliable system.

Mindset is the real barrier to entering AI, not skill: Sudha describes the early fear of being “left behind” and how the shift happened when she realised AI is a partner that frees PMs from tactical noise so they can do the strategic work they’re actually paid for.

Feeling behind means you’re already ahead: The episode closes on a strong, counterintuitive insight: the moment you worry you’re behind is the moment you’ve already started moving. Diving in early, experimenting, and iterating is the real differentiator.

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

Sudha Kumar

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

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

Taylor Algren is a product leader, founder, and strategist with over a decade of experience tackling real-world challenges at the intersection of tech, health, and global operations. He’s launched scalable platforms, advised early-stage startups, and brings a unique mix of systems thinking and human-centered design to every project. Now building a stealth-mode AI health-tech startup focused on chronic disease care, Taylor is known for his execution, mentorship, and commitment to meaningful, equitable innovation.

THE SUMMARY

Impact starts with lived experience — and this founder proves it. The episode dives into how years navigating the healthcare system as a cardiomyopathy patient revealed just how broken, bureaucratic, and non-human-centric chronic disease care really is. The constant cycle of refills, prior authorisations, pharmacy stock outages, and insurer rules creates a system that pushes patients to give up — at the cost of their long-term health.

AI isn’t a buzzword here — it’s a survival tool: The conversation highlights how agentic AI can step into the administrative chaos patients face: tracking expiring prescriptions, pre-auth deadlines, pharmacy stock issues, and even escalating tasks clinicians don’t have time for. The strong opinion: AI isn’t replacing clinicians — it’s replacing the waste that’s burning them out and harming patients.

Easy Medicine" tackles the most painful, immediate problem: cost: Instead of starting with the flashy stuff, the MVP focuses on something every chronic patient feels — medication prices. By pulling manufacturer coupons, GoodRx prices, and Cost Plus Drugs data, the tool delivers real savings instantly. It’s practical, high-impact, and built entirely using modern AI coding tools, no traditional coding required.

Rapid AI-powered building is the new superpower: The episode pushes a strong stance: don’t start with a course — start by building. A one-hour prototype is now more valuable than weeks of prep. The biggest skill in AI product building isn’t knowing how to code; it’s knowing what’s worth building, validating fast, and iterating with real users. Tools like Lovable, Bubble, Replit, and Figma have lowered the barrier to near-zero.

Purpose drives better products: Taylor’s journey from Botswana to Google to chronic illness to founder underscores a theme: when you’ve lived the problem, you build differently. His story is a reminder that the most meaningful AI solutions don’t start with technology — they start with empathy and frustration with the status quo.

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

Taylor Ahlgren

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

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

Daryl Teo is a technology strategist and seasoned CTO known for turning bold business vision into practical, scalable technical execution. Over the years, he has led engineering organizations of up to 150 developers, guided product and platform strategy across multiple industries, and built high-performance teams grounded in clarity, culture, and strong delivery. Today, Daryl advises companies as a fractional CTO—doubling down on AI-driven automation and transformation. With a rare blend of deep technical expertise and sharp business intuition, he brings the kind of leadership that helps startups, scale-ups, and SMBs move from idea to impact with confidence.

THE SUMMARY

Small, agile teams outperform large ones: when rapid change is required. Working with compact, high-calibre teams lets leaders drive meaningful shifts in weeks instead of months — a pace larger organisations struggle to match thanks to bureaucracy and slow decision-making.

Remote teams make junior hiring far harder: Without shoulder-to-shoulder mentoring, junior developers often become a net cost. In services-based environments, the margin pressure makes it almost impossible to justify the overhead of training juniors without a dedicated program.

AI adoption starts with a mindset shift, not a technical one: The moment you stop treating AI as a novelty and start treating it like a collaborator — one whose output you audit with healthy skepticism — everything changes. This “AI-first” approach is now non-negotiable.

The fastest wins come from augmenting existing capabilities: Some of the easiest, highest-ROI applications of AI aren’t glamorous. A 24/7 voice agent for a laundromat chain is a perfect example: humans sleep, machines don’t. Businesses gain capability they simply couldn’t afford before.

AI is a weapon for speed in operational bottlenecks: Even shaving a few minutes off time-sensitive workflows — like sourcing inventory prices from multiple vendors — can materially shift conversion rates. AI becomes a force multiplier in places humans didn’t even realise they were inefficient.

There’s no single “best” coding agent — the value is in speed, not purity: For rapid prototypes and short-lived projects, the differences between tools like Cursor, Claude Code, and Codex barely matter. What matters is delivering value, not endlessly comparing models.

The most important advice for anyone entering AI? “Lean in and commit: Half-adopting AI is as useless as not adopting it at all. Treating models as capable collaborators — while still verifying their output — is the mindset that unlocks real leverage.

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

Daryl Teo

LinkedIn: https://sg.linkedin.com/in/thedarylteo

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

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 support@aicareerboost.com

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 support@aicareerboost.com

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 support@aicareerboost.com

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 support@aicareerboost.com

Rachel Beck

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

Email: rach.beck@gmail.com

My links

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

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