The Digital Diaries Hosted by Peter Woods

#62 | The Future of TV Advertising, Category Creation & AI with Amit Sharan

Overvoew What does it take to build a category when customers do not yet know they need what you are selling? In this episode of The Digital Diaries, Peter Woods speaks with Amit Sharan, SVP of Marketing at Tatari, about building brands, marketing teams and entirely new markets. Amit shares lessons from helping build LiveRail into a leading video advertising platform before its acquisition by Facebook. He also reflects on his time at Meta, where he worked across advertising and products including Facebook Watch, Facebook Live and video monetisation. The conversation explores why Amit prefers building over maintaining. He explains why clarity of positioning was so important at LiveRail and why marketing needs to do more than generate demand. It also needs to build the value and reputation of the company. Amit explains what category creation really means. Sometimes customers are not actively searching for your solution. You first need to show them why the category matters before explaining why your company does it better. Peter and Amit also explore the evolution of TV advertising. TV is becoming more measurable, targeted and accessible. Connected TV, retargeting and new advertising formats are bringing it closer to the performance marketing world. They also discuss the growing role of AI in marketing. This includes how brands appear in LLMs, AI-powered media planning and AI-generated advertising. Amit shares why AI can reduce production costs, but also raises questions around consumer trust, synthetic talent and regulation. Finally, Amit explains why he believes TV remains one of the most powerful brand-building channels available. Social media might amplify cultural moments, but many of those moments still begin on television. Why Amit prefers building businesses from zero to one Lessons from scaling LiveRail and working at Meta Why clear positioning can create a competitive advantage The difference between demand generation and category creation Why digital-first brands eventually need new channels to grow How connected TV is changing television advertising The opportunity for TV retargeting in B2B marketing How AI is changing search, media planning and advertising creative Consumer trust and regulation around AI-generated talent Why TV and social media can be stronger together Why leaders should give people problems to solve, not just tasks to complete Great marketing is not only about capturing existing demand. Sometimes you need to create the market first. That means educating customers, establishing the category and building trust before someone is ready to buy. For Amit, the same thinking applies to leadership. Give talented people a meaningful problem to solve and the space to work out how to solve it.

#61 | Fixing Broken Meetings with Dr Rebecca Hinds

In this episode of The Digital Diaries, host Peter Woods speaks with Dr Rebecca Hinds, author of Your Best Meeting Ever, founder of the Work AI Institute at Glean, and former head of the Work Innovation Lab at Asana. They discuss why workplace meetings have become so dysfunctional and how applying product design principles can transform collaboration. Dr Hinds reveals actionable frameworks like the 4D CEO test, methods for managing calendar overload, and how artificial intelligence is reshaping modern work practices. Treat Meetings like Products: Organisations should view meetings as critical internal products, using intentional design principles to optimise alignment and decision-making. Meeting Doomsday: Conducting a calendar cleanse at the team level can reclaim substantial time, including up to 11 hours per person each month. Combating Parkinson's Law: Work expands to fill allotted time; setting shorter meeting durations (such as 50 minutes) or wrapping up once goals are achieved prevents wasted effort. Verb-Driven Agendas: Structuring agendas around actionable verbs ensures attendees understand the exact objective of each item. Measuring True Costs: Beyond direct salary calculations, unoptimised schedules inflict heavy cognitive costs and fatigue across organisations Navigating AI and "Bot Sitting": AI can streamline operations, but poor setup forces workers to spend up to 6.5 hours weekly supervising automated too Key Takeaways Treat Meetings like Products: Organisations should view meetings as critical internal products, using intentional design principles to optimise alignment and decision-making. Meeting Doomsday: Conducting a calendar cleanse at the team level can reclaim substantial time, including up to 11 hours per person each month. Combating Parkinson's Law: Work expands to fill allotted time; setting shorter meeting durations (such as 50 minutes) or wrapping up once goals are achieved prevents wasted effort. Verb-Driven Agendas: Structuring agendas around actionable verbs ensures attendees understand the exact objective of each item. Measuring True Costs: Beyond direct salary calculations, unoptimised schedules inflict heavy cognitive costs and fatigue across organisations. Navigating AI and "Bot Sitting": AI can streamline operations, but poor setup forces workers to spend up to 6.5 hours weekly supervising automated tools.

#60 | Why Authenticity Is the Future of Employer Branding, with Bryan Adams

This week Peter is joined by Bryan Adams — CEO and founder of Happy Dance, best-selling author, TEDx speaker (1.4M+ views), and one of the leading voices in employer branding and candidate experience. Over two decades, Bryan has helped nearly 200 global organisations — including Apple, Canva, Salesforce and Johnson & Johnson — rethink how they attract talent. In this conversation, Bryan and Peter dig into why the best employer brands are built on honesty, not hype — and why "selling the truth" beats selling the perfect story every time. The origin story — how a workshop moment that "gave Bryan goosebumps" set him on the path from marketing to employer branding, before the term even existed Sell the truth, not the perfect story — why leading with the real challenges of a role (not just the perks) attracts the right candidates and repels the wrong ones The imposter syndrome fix — how radical clarity about what a job actually demands removes the guesswork for new hires Why career sites still fall short — page speed, legacy tech, and the risk-aversion of large organisations AI and conversational candidate experience — how career sites are moving from static job boards to systems that "listen before they speak," cutting a 1,200-job firehose down to the 3 roles that actually fit Good friction vs. bad friction — why re-typing your CV into an ATS is needless friction, and what good candidate experience removes The three layers of story every organisation needs — reputation (what you're known for), expectation (the deal you're offering), and experience (the stories only your employees can tell) Leadership advocacy — why employer brand only works when it's championed from the C-suite down, not run as an HR side project Bryan's own story — nearly going out of business from a fear of public speaking, and the standup comedy course that changed everything Five years out — Bryan's prediction that transparency, not perfection, will become the ultimate measure of emplyer brand About Bryan Adams Bryan is CEO and founder of Happy Dance, and author of Give and Get Employer Branding. His new book, Sell the Truth — a storytelling playbook for leaders who want to build cultures that win — is out 17 September in all good bookstores and on Amazon. Learn more about Bryan's work at Happy Dance Pre-order Sell the Truth, out 17 September

#59 | einventing the Everyday: Building Smarter Products with Oscar Hedaya

Overivew What does it take to reinvent a product that hasn't meaningfully changed in decades? In this episode of The Digital Diaries, Peter Woods is joined by entrepreneur and product innovator Oscar Hedaya, founder of Space and creator of the Space Safe, a connected smart safe that combines modern technology with traditional physical security. Oscar shares his journey from growing up with limited means to building multiple consumer product businesses, revealing how necessity sparked an entrepreneurial mindset that continues to shape his approach to innovation. Together, they explore what it really takes to bring hardware products to market, why customer feedback is the foundation of great product development, and how solving genuine problems is far more important than chasing the next big idea. The conversation also dives into the unique challenges of hardware versus software, the future of connected security, and the realities of entrepreneurship that rarely make it into the headlines. How adversity can become an entrepreneurial advantage Why successful founders solve real problems—not imagined ones The hidden complexity of building hardware products What differentiates physical product innovation from software development Why customer feedback should shape your roadmap How connected technology is changing the future of home and hotel security The financial realities every founder should understand before launching a business Why AI is becoming an invaluable tool for aspiring entrepreneurs Oscar's entrepreneurial journey and early businesses Building companies with limited resources Spotting opportunities through everyday frustrations Designing and launching the Space Safe Hardware development challenges and manufacturing lessons Cybersecurity versus physical security Smart home technology and connected devices Customer-led product innovation Startup funding, runway and financial planning Using AI to validate business ideas What success looks like after building multiple companies Innovation starts with observation. Many of the best products don't invent something entirely new—they improve products people already use every day. Hardware is unforgiving. Unlike software, physical products can't simply be patched after launch. Small design decisions can have expensive long-term consequences. Build for genuine customer pain points. The strongest businesses solve problems customers are already experiencing and are willing to pay to eliminate. Think lean from day one. Managing cash flow, understanding runway and validating demand are often more important than perfecting the product. Listen to your customers. Some of Space's most valuable product features, including its innovative Panic PIN functionality, came directly from customer suggestions. "The entrepreneur isn't the person who spots the problem, it's the person who builds the solution." "Hardware is a nightmare. Software can be updated. Hardware has to be built right." "Never ask your family and friends if your idea is good, they'll tell you what you want to hear." "The day you open your business is the day you're open to selling your business." "Innovation doesn't have to be complicated. Sometimes it's simply upgrading something people already use." Oscar Hedaya is a serial entrepreneur and product developer with more than 15 years of experience bringing innovative consumer products to market. Having worked across manufacturing, retail and global distribution, he has launched products into major retailers including Walmart, Target, Costco and Best Buy. Today, he's the founder of Space, creator of the Space Safe—a next-generation smart safe featuring touchscreen controls, built-in cameras, mobile notifications and advanced security features designed for both homes and hospitality environments. Space Smart Safe Amazon Web Services (AWS) Tesla's touchscreen-first design philosophy AI tools for market research and business planning 🌐 Space: https://thespacesafe.com

#58 | Data Inspired: Why Better Decisions Start With Better Questions with Sebastian Wernicke

Overview In this episode of The Digital Diaries, Peter Woods sits down with data scientist, consultant and author Sebastian Wernicke to explore why the biggest obstacle to digital transformation isn't technology—it's organisational courage. Drawing on two decades of experience leading data science teams, advising Fortune 500 companies and working on national-scale innovation projects, Sebastian challenges the idea that becoming "data-driven" is enough. Instead, he argues that organisations should aspire to become data inspired—using data not just to optimise existing processes, but to unlock entirely new ways of thinking. From luxury car manufacturers predicting bespoke customer demand before an order is placed, to the hidden politics behind boardroom decisions, this conversation dives into why successful transformation is fundamentally about people, trust and decision-making—not algorithms. If you're leading digital transformation, building AI capabilities, or trying to create a culture where better decisions happen, this episode offers practical insights that go far beyond dashboards and analytics. Why being data-driven isn't the same as being data inspired The surprising luxury car case study that generated millions through predictive manufacturing Why stakeholder alignment matters more than building the perfect algorithm The biggest mistake data professionals make when presenting to executives Why decisions are rarely made in the boardroom How organisational politics shape successful transformation Why culture cannot be "fixed" in a 12-week engagement The hidden role of psychological safety in better decision-making How companies like Amazon and Netflix intentionally design decision-making processes Why many failed technology projects are actually failures of culture The inspiration behind Sebastian's new book, Data Inspired Technology is rarely the hardest part. The real challenge is aligning people across functions and building trust before implementation begins. The best data projects create new possibilities. Rather than simply optimising existing processes, truly data-inspired organisations use data to rethink how business is done. Boardroom meetings don't change minds. Successful decisions are usually made through conversations and stakeholder alignment long before executives gather around the table. Culture cannot be mandated. Sustainable transformation requires leadership commitment, psychological safety and deliberate behavioural change over time. Decision-making deserves intentional design. High-performing organisations don't leave important decisions to chance—they build repeatable processes that encourage challenge, curiosity and evidence-based thinking. "The thing holding organisations back isn't their tooling—it's their nerve." "The hard part wasn't building the algorithm. It was getting everybody into the same boat." "The decision is never made in the decision meeting." "Culture is not a project." "Technology often becomes the lightning rod for cultural problems." This episode is for: Business and technology leaders Data and AI professionals Digital transformation teams Strategy and innovation leaders Consultants and change managers Anyone interested in how organisations make better decisions Sebastian Wernicke is a data scientist, consultant and author of Data Inspired. With over twenty years of experience helping organisations use data more effectively, he has worked across Fortune 500 companies, public sector initiatives and large-scale transformation programmes. His work focuses on helping organisations move beyond optimisation to create genuinely data-inspired cultures and decision-making. Data Inspired by Sebastian Wernicke Amy Edmondson's work on Psychological Safety Amazon's six-page memo decision-making process Netflix's approach to empowered decision-making Adam Grant's endorsement of Data Inspired Don't forget to subscribe, leave a review and share it with someone.

#57 | From Army Commander to AI Entrepreneur: Leadership, Execution & Building Businesses with Rob Wright

What does it take to transition from commanding 350 people in military aviation to flying commercial aircraft while simultaneously building technology companies? In this episode of The Digital Diaries, Peter Woods sits down with Rob Wright, a former U.S. Army Special Operations Aviation commander, commercial airline pilot, and entrepreneur. Together they explore leadership under pressure, making difficult decisions, the realities of entrepreneurship, and how AI is changing the way businesses operate. Rob shares lessons from military leadership, explains why execution beats ideas every time, and discusses how his company, Waffl, helps organisations build AI-powered software that solves real business problems—not just shiny technology. Whether you're leading teams, building a startup, or trying to understand where AI creates genuine business value, this conversation is packed with practical insights. Why military leadership is built on trusting the people around you The biggest adjustment from Army command to commercial aviation Why time—not money—is your most valuable resource How Rob balances multiple businesses alongside a flying career The story behind Waffl and building custom AI solutions for businesses Why AI alone isn't a competitive advantage The difference between automation and creating real business value How businesses can identify hidden inefficiencies in their operations Why execution consistently beats great ideas The importance of validating customer demand before building a product Great leaders don't make decisions in isolation—they rely on experienced teams and proven processes. AI should create new value or remove unnecessary costs, not simply make existing tasks slightly faster. Every business has operational bottlenecks that become opportunities when they're properly measured. Owning your own software and intellectual property can become a long-term competitive advantage. Entrepreneurs often overestimate ideas and underestimate execution. Positive feedback doesn't equal paying customers—market validation is everything. "The best ideas don't win. The best execution does." "Time is the most valuable resource." "You're not really using the power of AI unless you're creating new value for your company or eliminating unnecessary spend." "There's a big difference between someone saying your idea sounds great and someone writing you a cheque." Military leadership Decision making under pressure Commercial aviation Entrepreneurship Startup growth AI implementation Digital transformation Business automation SaaS development Product-market fit Operational efficiency Leadership lessons Rob Wright is a former U.S. Army aviation commander, commercial airline pilot, and entrepreneur. Alongside his aviation career, he helps organisations build custom software and AI solutions through Waffl, focusing on practical technology that delivers measurable business outcomes. LinkedIn: Robert Wright Website: GoWaffl.com If you enjoyed this episode, subscribe to The Digital Diaries, leave a review, and share the episode with someone interested in leadership, entrepreneurship, or the future of AI in business. New episodes released every week. Episode SummaryWhat You'll LearnKey TakeawaysMemorable QuotesTopics CoveredAbout the GuestConnect with Rob WrightConnect with The Digital Diaries

#56 | From IT Leader to Commercial Strategy: Building Trust, Data, and AI That Actually Works with Sean Collins

🧭 Episode Overview In this episode of The Digital Diaries, Peter Woods sits down with Sean Collins. A rare operator who has lived on both sides of the technology buying journey. From 20+ years in IT leadership to commercial director and UK General Manager at Tech Enable, Sean brings a grounded, real-world perspective on how enterprise decisions actually get made. Together, they unpack the evolution from technical delivery to commercial strategy, the psychology of trust in B2B sales, and why most AI initiatives fail long before the technology becomes the problem. 💡 Key Themes 1. The power of “both sides of the table” experience Sean shares how moving from IT leadership into consultancy and commercial leadership gave him a rare ability to understand both operational pain and commercial pressure — especially when signing off major systems. 2. Trust is the real currency in enterprise salesTechnology matters, but decisions are ultimately made on trust. Sean explains why credibility, honesty, and sometimes even walking away from deals is what builds long-term relationships. 3. Why most AI projects fail (it’s not AI)A recurring theme: AI doesn’t fail — data does. Sean breaks down why poor CRM hygiene, broken processes, and inconsistent adoption undermine even the most advanced AI tools. 4. CRM, ERP, and the myth of “one system to rule them all” From Salesforce to ERP systems like Microsoft Business Central, Sean explains why successful transformation depends on integration, not replacement. 5. The real starting point for AI adoptionInstead of chasing AI use cases, organisations should start by identifying operational friction: Where are teams overloaded? Where are processes breaking? What would genuinely save time?

#55 | Don't Believe the Hype: Why AI Has Already Taken Your Brand Narrative Away (with Gal Borenstein)

Episode Overview What happens to your brand's reputation when AI agents, not your marketing team, are the ones answering questions about your company? This week Peter is joined by Gal Borenstein, founder and CEO of The Borenstein Group and author of Don't Believe the Hype: When Trust Is on the Line. Gal has spent close to 30 years building and protecting brands for clients including Airbus North America and Forrester Research, and his book argues that generative AI has fundamentally broken the old model of brand control. Gal explains why narrative ownership has shifted away from companies and towards AI search engines and anonymous online voices, why deploying AI agents without institutional knowledge is like handing your brand to a junior employee with no real-world experience, and why the businesses most at risk are the ones rushing to "keep up" without first getting their internal house in order. The conversation covers his GUARDIAN Digital Trust Framework, the Boeing case study on what happens when problems don't travel up the chain of command, why "vanity metrics" won't save a damaged reputation, and a candid challenge to Gal himself: is there a conflict of interest in a branding agency owner writing a book that says companies need outside help? What you'll learn: Why AI search engines and generative answers have removed companies' control over their own brand narrative The "junior employee" problem: why agentic AI without institutional knowledge creates real reputational risk The three ways companies typically respond to AI disruption, and why the seemingly safest option is often the most dangerous How the GUARDIAN Digital Trust Framework helps leaders build resilience before a crisis hits What the Boeing case reveals about reporting culture and reputational collapse Why "private company" is no longer a real strategy, and what a proper digital footprint actually involves How to tell genuine trust signals apart from vanity metrics like follower counts Gal's own answer to the "Start With Why" challenge, and what he changed his mind about in the last 12 months About the guest: Gal Borenstein is the founder and CEO of The Borenstein Group, a branding and PR agency, and the author of Don't Believe the Hype: When Trust Is on the Line, Activate!, and What Really Counts for CEOs. He has spent close to three decades advising C-suite executives on brand resilience. Connect with Gal on LinkedIn or find his books on Amazon. Mention this episode when you message him for a complimentary copy of his latest ebook, Beating Goliath with AI. The Digital Diaries is where we explore what it actually takes to lead, build, and transform in a world that won't slow down. Follow Peter Woods and The Digital Diaries for new episodes every week.

#54 | Human Infrastructure: Why People Are the Real AI Advantage | Barbara Wittmann

Episode OverviewAfter 25 years inside enterprise transformation projects, Barbara Wittmann, Founder of the Digital Wisdom Collective, reached an uncomfortable conclusion: most technology projects don't fail because of the technology. They fail because organisations never built the human infrastructure to support it. In this episode, Barbara and Pete unpack why she treats people as infrastructure in exactly the same way IT treats servers, including test environments, upgrade cycles and ongoingmaintenance. They get into alignment debt, the hidden cost that builds up when leadership assumes consensus that was never actually verified, and why 70 per cent of project time is spent solving the wrong problem entirely. Barbara also shares her four-pillar framework for collective problem-solving,why she believes organisations need “chiefs” rather than managers, and why AI's biggest gift might be forcing us to finally get honest about our own hallucinations. This conversation is forleaders under pressure to show AI results fast, anyone running (or living through) a transformation project, and anyone curious about what “wisdom” actually means in a digital-first world.

#53 | The Most Distinctive Claim from My Conversation with Dr Victoria Mensch

Almost every executive will tell you they are committed to AI. Very few organisations are actually being transformed by it. So what is really happening in the gap between what leaders say about AI and what they do? This week, Pete sits down with Dr Victoria Mensch, Founder and CEO of the Silicon Valley Executive Academy. With a PhD in Psychology, an MBA from UC Berkeley and over 25 years in Silicon Valley technology including 14 years at SAP, Victoria spends her working life helping senior leaders lead AI transformation. As a psychologist, she has a sharp diagnosis of what is actually holding them back, and it is not strategy. It is identity. This is a conversation about the human side of AI adoption: the identity crisis it triggers in senior leaders, the quiet sabotage that follows, and what genuine transformation looks like once you stop treating AI as just another efficiency play. In this episode: - Why AI adoption stalls long after the strategy is signed off - The difference between using AI to do existing work faster and using it to transform the work itself - The identity crisis hitting senior leaders: if AI can do intellectual work better, what is left for me? - Why fear of replacement quietly shows up as sabotage at every level of an organisation - The unbundling of job roles, and how to take ownership of your career inside it - What the Silicon Valley Innovation Playbook offers leaders in more traditional industries - Why genuine transformation requires the courage to push back on pure efficiency pressure - How AI amplifies burnout by setting false expectations of human output volume - A practical, science-backed approach to replenishing energy in a high-pressure environment - Why we overestimate AI's short-term impact and underestimate how it reshapes work over time - The mindset that will separate leaders who genuinely transform from those who only perform it Standout moment: Victoria reframes AI resistance as an identity crisis rather than a strategy debate. The private question every executive is asking, she argues, is "if AI can do it better, what am I?", and it often shows up as sabotage rather than honest pushback. About Victoria: Dr Victoria Mensch is Founder and CEO of the Silicon Valley Executive Academy (SVEA), a boutique executive education and innovation consulting firm. She designs immersion programmes that equip global leadership teams to lead AI transformation, drawing on her V.I.T.A.L. method and the Silicon Valley Innovation Playbook. Her work sits at the intersection of psychology, executive performance and technological change. Connect with Victoria: - Sign up for SVEA's weekly newsletter at svexecutive.academy - LinkedIn: linkedin.com/in/victoriamensch If this conversation resonated, please follow, rate and share The Digital Diaries. It is the single most useful thing you can do to help the show reach the leaders who need it.

#52 | AI Doesn't Rank You, It Chooses You | Jimi Gibson on AI Visibility

Episode OverviewJimi Gibson spent 25 years as a professional magician before becoming VP of Brand Communication at Thrive Internet Marketing Agency. In this episode he explains why that pivot makes more sense than it sounds: the structure of a magic trick and the structure of a marketing message activate the same psychology, built on curiosity, anticipation and a satisfying close. The conversation moves into the heart of Jimi's current work: a study of 400 businesses across five industries and roughly 2,400 prompts put to AI tools, which found that 46% of businessowners were invisible when AI was asked about them. He unpacks why AI favours people over logos, how large language models build their picture of a business (his "pizza dough and toppings" analogy), and the principles behind what he calls Answer Engine Optimisation. Jimi closes with a practical framework for leaders and business owners who want to start showing up: from cleaning up LinkedIn profiles and Google Business listings, to a five-pointcontent framework built around promise, relationship, passion, defiance and identity, that AI cannot replicate.

#51 | The Human Side of AI: Why Better Tools Don’t Fix Broken Collaboration with Rujuta Singh

Episode Summary What happens when the smartest people in the room still can’t make a decision? In this episode of The Digital Diaries, Peter Woods speaks with Rujuta Singh, founder of Solve Together, about the hidden human challenges behind business transformation, AI adoption, and organisational change. Rujuta shares how her experience leading complex transformations across global organisations led her to question why teams could spend months discussing the same problems without moving forward. The answer wasn’t better technology. It was better collaboration. Together, they explore why clarity and alignment are the foundations of successful transformation, why most AI strategies fail because organisations start with tools instead of problems, and how companies can use structured experimentation to move from ideas to working prototypes in weeks rather than months. From leadership meetings and AI implementation to recruitment technology and the future of work, this conversation examines the gap between what organisations say they want from technology and what they actually need from people. Key Topics Discussed Why smart teams still get stuck The hidden cost of unclear goals and misalignment Why meetings often create the illusion of progress without decisions The difference between having expertise in the room and actually using it Why transformation failures are often collaboration failures Why diverse perspectives create better solutions — but require structure How facilitation helps teams separate ideas from egos Moving from discussion-heavy meetings to outcome-driven collaboration The “together alone” approach: giving people space to think independently before group discussion Why quieter voices often hold the insights organisations need Why buying ChatGPT, Copilot, or other AI tools does not equal an AI strategy The importance of understanding business problems before selecting technology How structured experimentation can help companies test AI solutions safely The risks of AI-driven recruitment systems Why organisations need AI confidence at leadership level How executives can better understand AI capabilities before making investment decisions The missing ingredient in transformation: humansDesigning better meetingsAI adoption: start with the problem, not the toolThe future of work and AI Key Takeaways ✅ Transformation succeeds when people have clarity on what they are solving and alignment on why it matters. ✅ The best technology strategy starts with a business problem, not a software purchase. ✅ Meetings should be designed around outcomes, not conversations. ✅ AI adoption requires experimentation, learning, and human validation. ✅ Leaders don’t need to become AI engineers — but they do need enough understanding to make better decisions.

#50 - Partner Success in AI with Joanne John

Episode Overview Partner programmes are the invisible infrastructure behind most enterprise software revenue, yet they rarely get airtime. In this episode, Pete talks to Joanne John, who spent over nine years at Salesforce moving from incident management through partner operations into transformational change leadership, about what partner success actually means, how AI is reshaping partner programmes without replacing the trust at theircore, and the real mechanics behind a major attrition-risk reduction programme she led.Key Takeaways • Partner success is ultimately measured by customeroutcomes, not just deal size; a poorly fitted solution damages trust even whenthe deal closes. • According to Joanne, roughly 70 to 80% ofpartner-related escalations at Salesforce traced back to communicationbreakdown rather than product or delivery failure. • AI's role in partner programmes is in surfacing betterdata for decisions (referral fee structures, certification value, partner motivations), not in replacing the relationship-building that still drives trust. • Leading cross-functionally without direct authority depends on transparency and finding a genuine win-win, not positional power. • One simple structural fix, mandating partner involvement within 24 hours of an escalation, was, according to Joanne, the central driver behind a measured year-over-year improvement in partner-related account risk. 🌐 Connect with Joanne John on LinkedIn

#49 | David Homan: Building Trust at Scale in the Age of AI

Episode overviewDavid Homan has spent more than a decade building a private community of over two thousand connectors, founders, family offices and impact investors. In this conversation with PeteWoods, he explains why he eventually decided the analogue version of his work needed an AI engine behind it — and how that became SOAR Connect, his relationship intelligence platform currently in beta. It is a wide-ranging conversation about the things technology has quietly broken about human connection: the way contact data evaporates after every conference, why most introductions are wasted, and why the people who built the social platforms we use every day are themselves the loudest critics of how cold those platforms have become. David also tells the story of taking the phone call, at 28, that wiped out the fourteen-million-dollar endowment of the foundation he ran at the time — a call from a fund managernamed Bernie Madoff. The fallout from that single moment, and the way most of his network walked away rather than helped, became the real beginning of everything he has built since. There is also a vacuum cleaner, a ballet at the Joffrey, an encounter with Steven Spielberg, and a genuinely useful reframe of the well-worn phrase “give without expectation of return.” For anyone trying to figure out how to use AI thoughtfully in the parts of work that are most human relationships, trust, asks, follow-up, this episode is worth your time.

#48 | Joshua Gould on Running thebigword, AI as Speed Not Strategy, and the Discipline of Managed Risk

Episode OverviewJoshua Gould is Group CEO of thebigword, one of the world's largest language service providers, handling around 50,000 assignments a day across translation, interpreting and localisation. He took the company through a majority private equity sale, stayed on to run it, and has spent the last few years rebuilding the business around AI orchestration, automated workflows and the WordSynk platform. In this conversation, Josh walks through the journey from a £44-a-week room and a sales job at Coors Brewers to running a tech-enabled language group across more than 80 countries. He's refreshingly blunt on what AI actually does inside a real operation, why "AI strategy" is the wrong starting question, and how the unsexy work of fixing broken processes is what compounds. If you're a leader being told to "have an AI strategy in 90 days", this one is for you. Key Learnings Why AI is "like taking speed" and what that means for broken processes How thebigword drove operations from 20% of revenue down to 9% (and why that doubles profit) The questionnaire Josh would send to every department head on day one of an AI mandate Why companies that called themselves "internet businesses" all failed, and what that tells us about today's "AI businesses" The difference between data-informed and data-driven decisions Managed risk over blind gambling: how to size AI bets when token costs are unpredictable Why a zip manufacturer is suddenly more attractive to buyers than a flashy tech business Resources mentioned: thebigword: https://www.thebigword.com WordSynk platform Joshua Gould on LinkedIn

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47 | The Hidden Risks in Every Ad You Run with Pamela Slea, CEO Boltive

Episode OverviewOne in eight ads running across the internet today containsmalware. Most marketing teams have no idea. In this episode, Pete talks to Pamela Slea, CEO of Boltive and a two-decade veteran of ad tech, about the invisible security and privacy risks baked into modern digital advertising and why AI is making the problem dramatically worse. Pamela has led at Google, YouTube, AppNexus, Index Exchange,and InMobi. Her contrarian view: compliance is no longer a quarterly checkbox. It needs to be always-on, agentic, and built into production not just policy. What We Cover • WhyAI is a double-edged sword in ad tech -- accelerating both innovation and th capabilities of bad actors • The 1 in 8 ads contain malware' statistic and why CMOs are not reacting with theurgency it demands • The shift from periodic compliance audits to continuous, agentic monitoring • Why the regulatory spotlight is moving from web cookies to in-app and connected TV environments • What streaming companies are being forced to confront about cross-device data and consent flows • Who actually owns responsibility for ad security today -- and why the answer has changed • How AI-generated sales outreach is forcing a return to relationship-led selling • The biggest mistake advertisers will regret not having fixed in the next 12 months The same AI tools accelerating legitimate softwaredevelopment are being used by the people building malware. Security solutions from two years ago may already be obsolete. The threat landscape is not static it is moving at the same pace as the technology. Brands can have a perfectly designed consent managementplatform that completely breaks in production -- because a new partner was added to the page, the CMP loads too slowly, or a third-party script fires before consent is collected. Regulators do not care about intent. They care about what the consumer actually experienced. Historically, ad security and privacy compliance weretreated as periodic audits. The expectation from regulators -- and from the market is now continuous monitoring. This is not just best practice; in many jurisdictions, it is becoming a legal requirement. As advertising budgets move heavily into streaming,regulators are following the money. The CTV ecosystem involves multiple data handoffs -- OEMs, content partners, ad servers -- and consent signals can break at any one of those touch points. Streaming companies are now actively seekingexternal validation that their privacy posture matches what is actually happening in their systems. The traditional view was that the publisher owns thewebsite, so the publisher owns the liability. Litigation in both the US and Europe is shifting that. If your ad tech pixels or tags are on someone else's page and they behave improperly, the brand may now find itself on the hook. Pamela notes that the volume of AI-generated cold outreachhas become so overwhelming that senior buyers are increasingly only engaging with people they already know. Some CEOs are now explicitly hiring salespeople based on their existing relationships rather than their process skills. Key Insights From This EpisodeBad actors are keeping pace with the best AI toolsPrivacy intent and production reality are two different thingsThe compliance model is shifting from quarterly to always-onConnected TV is the new frontier for privacy riskResponsibility for ad security is no longer the publisher's problem aloneAI-saturated outreach is driving a return to relationship-led sales

#46 | Why Your Marketing Strategy Isn't Working — and What Behavioural Science Says to Do Instead

Rich Smith has spent 30 years as a CMO inside financial services, healthcare, and mortgage — managing $100M+ budgets and leading companies through crisis, hyper-growth, and turnaround. He is the founder of Rich M. Smith Growth Studio and host of The Revenue Science Podcast. In this episode, Rich and Pete pull apart why most companies jump straight to tactics without a strategy behind them, what behavioural science actually means in practice, and how marketing leaders consistently lose the boardroom by speaking the wrong language. They also cover the AIG Bank crisis playbook, the future of AI search, and why distribution is the most underrated factor in sustainable growth. Key Learnings Tactics without strategy is just noise. Most CEOs are asking "should we do more on social media?" before they have a repeatable strategy. Without intentional architecture, even a win can't be scaled — because you don't know why it worked. If you can't use a superlative, go back to the drawing board. First, fastest, only, cheapest, proprietary — if you can't describe what you do with a word like that, you are part of the sea of sameness. Customers cannot tell who is telling the truth until they buy. Capture the heart before the mind. People make decisions emotionally and rationalise them later. Leading with ROI charts and features at the top of the funnel is a guaranteed way to lose attention before you've earned it. The boardroom disconnect is a marketing leadership failure. Talking about MQLs and engagement metrics in front of a CEO is speaking the wrong language. Reframe website traffic as "demand capture potential" and watch the conversation change. You never fail your way out of a crisis — you succeed your way through it. During the 2008 AIG crisis, Rich proposed launching a direct-to-consumer online bank and kept the AIG brand. The logic: a sophisticated depositor understands FDIC insurance. An unknown brand would have taken years to build trust they simply didn't have. Intent data has a longer lead time than most marketers expect. At Jornaya, Rich found that consumers begin active shopping behaviour far earlier than credit triggers or late-stage signals suggest. Most businesses are reacting far too late. Alignment decays — you have to apply energy to maintain it. Ask a CEO what the company's top priorities are, then ask a leadership team member the same question. The answers will not match. The further from the original plan, the worse the matching gets. Connect with Rich on LinkedIn 🌐 http://www.richmsmith.com

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#45 | From Luxury Watches to Agentic AI: The Future of Sales

Episode Overview Michael Kalinichenko has earned six promotions across a decade in SaaS, leading high-performing sales teams atIntercom, Zendesk, and Rieke — all while maintaining under 10% voluntary attrition across seven years of management. Before tech, he was selling Swiss-made luxury watches in one of the most relationship-driven, paper-based industries imaginable. In this conversation, Michael and Pete trace the arc from manual relationship selling to the age of agentic AI — and find that the most durable competitive edge in sales has nothing to do withsoftware. They cover the hidden spectrum of AI adoption across European markets, why the world's most advanced LLMs carry a Western cultural bias that EMEA sellers must account for, and how to lead a team through constant disruption without letting uncertainty become anxiety. Connect with Michael on LinkedInBook mentioned — The Choice: by Dr Edith Eger

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#44 | Why ERP Implementations Fail (And It's Not the Software) | Kevin Patrick

EPISODE OVERVIEW Kevin Patrick has spent over 30 years in operations, manufacturing and enterprise technology. He has led more than 120 SAP Business One deployments, launched a brand new Acumatica practice that generated $2 million in revenue within 17 months, and earned Softengine the Acumatica Rookie of the Year award at the 2025 Summit. Today, through his company Trinity One Consulting, he works as a fractional CEO, EOS integrator and certified Dream Manager, blending operational rigour with a deeply human approach to workplace performance. This conversation explores the pattern Kevin noticed across hundreds of ERP projects: the system is almost never what breaks. It is the people asked to use it who were never consulted, never brought in and never cared for. From that insight, Kevin found the Dream Manager methodology, developed by Matthew Kelly and delivered through Floyd Consulting, a programme that helps employees define and pursue personal goals across 12 life categories, with the aim of reigniting engagement, reducing turnover and driving business results from the inside out. Pete and Kevin also go deep on AI adoption, the EOS framework, the cost of employee disengagement and what it really takes to build a podcast audience worth having. KEY LEARNINGS 1. The four red flags that signal an ERP implementation is heading sideways Kevin identifies the warning signs he looks for from day one: only managers in the room with no frontline workers, bad or incomplete data, no testing plan and no genuine employee buy-in. Any one of these is a problem. More than one and the project is in trouble before it starts. 2. Frontline workers are stakeholders, not afterthoughts When management runs an implementation and then arrives on the floor six months later to say "here's your new system," they communicate something powerful without saying a word: your opinion does not matter. Kevin builds subject matter experts from the floor into every project from the outset. 3. Employee disengagement is measurable and expensive The cost of replacing a consultant or manager typically runs to 20,000 to 30,000 euros in recruitment fees alone, before you factor in ramp-up time, lost tribal knowledge and the customers who follow the departing consultant to their next employer. The Dream Manager programme addresses the root cause, not the symptom. 4. The Dream Manager works across 12 life categories Developed by Matthew Kelly, the programme structures monthly one-to-one meetings across areas including physical wellbeing, financial health, legacy and relationships. Participants often report coming to work in noticeably better spirits within three to six months, with downstream improvements in customer satisfaction, output and retention. 5. AI is a force multiplier for the operational consultant Kevin was sceptical of AI until about 18 months ago. Now his entire practice runs on it. He has built a custom Dream Manager tracking application, an EOS management tool and automated his outbound sales pipeline, all without being a technical developer. His view: the fear of AI taking jobs is holding back the people it could help most. 6. Authenticity wins audiences faster than polish Kevin's two biggest podcast episodes by a wide margin are his addiction recovery story and a raw episode he calls The Reckoning, in which he admitted to his audience that he was still in the middle of the journey, not beyond it. Audiences can hear when someone is performing. They stay when someone is telling the truth.

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#43 | Why Frontline Leadership Fails — and the System Built to Fix It

EPISODE OVERVIEW Most leadership frameworks were built for a world that no longer exists. Jon Dario has spent over three decades operating at the sharpest end of retail — from managing the flagship Gap store on 34th Street in Manhattan to overseeing $1.7 billion in operations across North America for Travelex, to sitting in the CEO chair of a 60-property real estate portfolio. Along the way, he kept running into the same problem: good managers with good intentions who still couldn't execute consistently. His answer was AIM — Action Item Management — a practical framework built not for the theory of leadership, but for the reality of the frontline. In this episode, Jon breaks down exactly how AIM works, why most digital transformation efforts fail at the human layer, and where AI genuinely enhances structured leadership systems rather than replacing them. This is a conversation for anyone who has ever been frustrated by the gap between what a team should deliver and what it actually does. What you'l get in this episode 1. Structure isn't a crutch — it's the foundation for good judgment. The AIM framework doesn't remove decision-making from managers; it gives them guardrails within which to exercise it. Jon's GPS metaphor is worth holding on to: a GPS defines the destination and recalibrates when roads are closed. The manager's job is the same. 2. The equation that explains every result. Jon teaches: actions + external influences = results. Managers who ignore external influences and follow the system blindly will always underperform. Monitoring what's happening around the plan and adjusting accordingly is the actual job. 3. Accountability flows upward before it flows downward. When someone is underperforming, Jon's default assumption is that the leader failed to explain, train, or remove obstacles effectively. That reframe changes how every difficult conversation goes — and dramatically reduces the frequency with which those conversations are needed at all. 4. AI's best role in leadership is buying back human time. Jon is direct: AI should not replace face-to-face management. But it can handle the administrative load that prevents managers from doing it. Tools like Microsoft Copilot extracting action items from a Teams call is a concrete, practical example of AI serving a structured system rather than substituting for it. 5. The management pyramid solves the multi-location consistency problem. Across 240+ Travelex locations, the challenge wasn't what the standards were — it was what happened when standards came into conflict. The pyramid of priorities gives every manager a shared hierarchy so decisions made independently still land in the same direction. 6. The hiring process is quietly breaking down. Since ChatGPT, Jon has seen assignment results at Seton Hall flip: 90% of students now get the hardest questions right, but through AI rather than understanding. His point — that people can feign knowledge in interviews without a real human conversation exposing it — is one every hiring manager should hear. 7. Leadership is ultimately about character, not competence. Jon's closing answer is the one to remember: influence comes from character, and character is how you treat people. You can be a tremendous leader without superior knowledge or technological fluency. You cannot be one without genuine human connection.

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