Be Kaler Pilgrim - Where Does Product Go Wrong in PE-Backed Firms?

Be Kaler Pilgrim - Where Does Product Go Wrong in PE-Backed Firms?

On this episode, I speak to Be Kaler Pilgrim, founder of Smithfield Search and original founder of Futureheads Recruitment. Be has spent more than three decades helping organisations build technology and product teams, and recently conducted an in-depth study of senior product leaders operating in investor-backed businesses. We explore what effective product leadership really looks like in high-growth environments, why so many organisations still misunderstand the role of product, and how AI is forcing leaders to rethink organisational design, capability and value creation. Episode highlights * Product is still too often treated as a delivery function - One of the strongest themes from the research is that organisations frequently position product management as an execution capability rather than a strategic commercial function, limiting both its influence and its ability to create value. * Leadership roles fail when organisations cannot define the problem - Businesses often hire senior product leaders without first agreeing on what challenge they actually need solving (or whether there's even a challenge to solve), creating misalignment before the role even begins. * Product leadership should be designed around organisational needs, not trends - Whether hiring a CPO, CPTO or another senior product role, organisations need to understand their specific context rather than simply adopting structures that appear fashionable. * Feature factories remain one of the biggest barriers to growth - Teams can become highly efficient at shipping work without creating measurable business impact, leading to activity without meaningful outcomes and missed opportunities to execute the investors' value creation plan. * The "Land of Lost Toys" affects more organisations than leaders realise - Many companies accumulate partially completed initiatives, abandoned priorities and unfinished experiments that reduce focus and create organisational drag. * Technical debt is ultimately a business problem - Whilst often discussed as an engineering concern, accumulated technical debt reduces confidence, slows execution and directly impacts commercial performance over time. * Commercial fluency is becoming a core product leadership capability - Product leaders increasingly need to understand business economics, value creation and financial performance, rather than focusing exclusively on product process and delivery. This enables them to have conversations that resonate with PE leaders. * AI increases the importance of judgment rather than reducing it - Whilst AI can automate many activities, strategic decision-making, prioritisation and organisational leadership remain fundamentally human responsibilities and, thankfully, humans seem to be coming back into fashion! * Product, sales and customer teams succeed or fail together - Sustainable growth requires strong alignment between teams responsible for building, selling and retaining customers, rather than treating commercial outcomes as somebody else's problem. Everyone should care about NRR. * The biggest organisational problems are often hiding in plain sight - Many of the factors that ultimately constrain growth are visible long before they appear in financial performance. PE firms need to look beyond financial metrics and get product experts in early to catch and mitigate these issues earlier. ... and much more. Check Out the CPO Report You can view the CPO Report and take the Smithfield CPO Readiness Index here: https://cpo.smithfieldsearch.com/ [https://cpo.smithfieldsearch.com/] Contact Be If you want to get in touch with Be, go here: * Smithfield Search: https://www.smithfieldsearch.com [https://www.smithfieldsearch.com/] * LinkedIn: https://www.linkedin.com/in/bekalerpilgrimexecsearch/ [https://www.linkedin.com/in/bekalerpilgrimexecsearch/]

Petra Wille - Strong Product Leadership in the Age of AI

On this episode, I speak to the returning Petra Wille, product leadership coach, author of Strong Product People, and founder of the Product at Heart conference. Petra has spent years helping product leaders and organisations develop stronger product cultures, leadership practices, and team structures across a wide range of industries. We went deep into product leadership, especially in an age of AI where we're all being told to be builders again, and how her Product Leadership Wheel helps product leaders up their game. Episode highlights * Leadership is a distinct discipline - Strong individual contributors do not automatically become strong leaders, and leadership requires deliberate development rather than promotion by default. * Product leaders need directional clarity - One of the core responsibilities of leadership is helping teams understand where the organisation is going, why it matters, and how everyday decisions connect to broader strategy. * Coaching is an underused leadership skill - Petra argues that many leaders underestimate the importance of coaching capabilities and fail to invest enough time in helping teams grow and improve. * Culture is often invisible inside organisations - Teams frequently struggle to articulate their company culture because they are immersed in it every day, making reflection and intentional leadership even more important. * AI is changing the demands placed on leaders - Product leaders are being forced to rethink team structures, workflows, decision-making, and product experiences as AI reshapes how organisations operate. * Efficiency gains can create new problems - Faster delivery is not automatically better. Petra warns that organisations risk creating more technical debt, burnout, and shallow thinking if speed becomes the only goal. * Leadership requires optimistic narratives - In periods of uncertainty, leaders play a critical role in creating credible and motivating visions of the future for their teams and organisations. * Feedback gaps exist between leaders and teams - Many product leaders believe they are performing well, while individual contributors often see significant shortcomings, partly because organisations lack shared frameworks for discussing leadership quality. * Reflection matters more than benchmarking - Petra emphasises that leadership frameworks should help people identify growth areas and learning opportunities rather than turn development into rigid performance comparisons. * Leaders should focus on the "shipyard" - Rather than constantly jumping into delivery work, product leaders should concentrate on improving the systems, structures, and environments that enable teams to succeed. ... and much more. Contact Petra * Website: https://www.petra-wille.com [https://www.petra-wille.com/] * Product at Heart: https://www.productatheart.com [https://www.productatheart.com/] * LinkedIn: https://www.linkedin.com/in/petra-wille-b8b1329/ [https://www.linkedin.com/in/petra-wille-b8b1329/]

April Dunford - Obviously Awesome 2.0 : What's New With Product Positioning? (with April Dunford, Author “Obviously Awesome“ and “Sales Pitch“)

On this episode, I am joined for a third (and probably final!) time by April Dunford, renowned positioning expert and author of Obviously Awesome and Sales Pitch. We explore what's changed in her updated edition of Obviously Awesome, what she's learned through delivering hundreds of positioning workshops and how she's honed her approach to reposition positioning to make it clearer for the next generation of product people. Episode highlights * Positioning is how you win - Positioning is the answer to "why pick us now?", grounding your product in real value for a clearly defined customer segment. * Positioning vs strategy - Strategy defines where you're going, while positioning reflects where you are today and must evolve as your product and market change. * AI isn't a position - Simply adding AI is no longer meaningful; if everyone has it, the focus shifts to what tangible value you deliver right now. * From unique to distinct - Capabilities don't need to be truly unique, just meaningfully different in the context of your real competitors. * Trends matter less than clarity - The industry's baseline understanding of positioning has improved, making abstract ideas like "trends" less useful than clear market definitions. * Readiness before action - Teams need to decide what they're positioning, whether they have real customers, and how product structure (single vs multi-product) affects the work. * Positioning as hypothesis - Without customers, positioning is a best guess that must be tested and refined rather than treated as fact. * Sell to the champion - Positioning should resonate with the internal champion, while objections from other stakeholders are handled separately. * Test through sales, not copy - The real validation of positioning happens in sales conversations, not by endlessly tweaking website copy. * AI is a tool, not a shortcut - AI can support positioning work, but it can't replace the thinking, collaboration and deep company context required to define real differentiation. ... and much more. Buy the new version of Obviously Awesome Look for the yellow "updated" sticker! * Amazon: https://www.amazon.co.uk/Obviously-Awesome-Product-Positioning-Customers-dp-1999023056/dp/1999023056/ [https://www.amazon.co.uk/Obviously-Awesome-Product-Positioning-Customers-dp-1999023056/dp/1999023056/] * April's website: https://www.aprildunford.com/books [https://www.aprildunford.com/books] Contact April * LinkedIn: https://www.linkedin.com/in/aprildunford/ [https://www.linkedin.com/in/aprildunford/] * Website: https://www.aprildunford.com [https://www.aprildunford.com/]

The State of B2B Product Management (with me, Saeed Khan and guest host Janna Bastow)

On this episode, we try something a little different. ProdPad and Mind the Product co-founder Janna Bastow joins as guest host to interview me and Saeed Khan about our recently released research report "The State of B2B Product Management". We go deep on the key findings of the report and what to do about them. Episode highlights * The sales-led roadmap reality - In many B2B organisations, roadmap ownership effectively sits with sales, driven by short-term revenue pressures rather than long-term strategy * Customers vs markets tension - Product teams often fail to shift from building for individual customers to designing for scalable market opportunities * The leadership perception gap - A stark ~50-point disconnect exists between how leaders assess themselves and how their teams experience them, pointing to either deluded leaders, poor communication or unreasonable IC expectations * Lack of strategic foundations - Weak or absent vision and objectives create a vacuum where every deal feels equally valid * Product leaders as system designers - Leaders must take responsibility for shaping environments where good product work is actually possible * Discovery isn't just external - Product teams neglect internal discovery, failing to understand stakeholders, sales processes, and organisational dynamics * The cost of short-term thinking - Chasing large deals often creates hidden long-term costs that outweigh immediate revenue gains * AI as efficiency, not transformation - Current AI usage is reported as largely tactical (summarisation, documentation), not fundamentally changing product outcomes * Optimism despite dysfunction - Even with systemic issues, many product managers remain positive about the future of the discipline ... and much more. Check out "The State of B2B Product Management" report You can check the full report here - no email address required: https://b2bproduct.io/?okip [https://b2bproduct.io/?okip] Check out ProdPad Janna is the co-founder of ProdPad, a roadmap, idea management and feedback platform that brings clarity to your organisation. She was kind enough to step in as a guest host for the episode, so why not check what the platform can do for you? https://www.prodpad.com/ [https://www.prodpad.com/] Find us all on LinkedIn * Janna: https://www.linkedin.com/in/jannabastow/ [https://www.linkedin.com/in/jannabastow/] * Saeed: https://www.linkedin.com/in/saeedwkhan/ [https://www.linkedin.com/in/saeedwkhan/] * Jason: https://www.linkedin.com/in/jason-knight/ [https://www.linkedin.com/in/jason-knight/]

CPO Stories: Nick Kenn - Winmau

On this episode, I speak with Nick Kenn, interim Chief Product Officer at Winmau, the world's leading darts brand. Nick's career spans companies such as Betfair and Redbubble, and he now operates in interim and advisory product leadership roles across private equity and venture-backed businesses. He's now on a mission to hit the bullseye and revolutionise a traditional sport with a new, fully digital experience. We cover a lot, including: * Digitising a traditional sport – Building a connected darts experience requires blending physical play with digital layers like tracking, stats, and online competition without losing the tactile essence of the game * Balancing heritage and innovation – Introducing new product experiences in a 100-year-old brand demands careful alignment between modern features and long-standing identity * AI as a pragmatic tool – Rather than chasing trends, AI is applied where it adds clear value, such as computer vision for scoring and an AI referee for dispute resolution * Focus over experimentation – In a high-pressure delivery environment, prioritisation matters more than exploring every new technology or idea * Building inside a non-digital organisation – Establishing product thinking in a manufacturing business requires translation, education, and patience on both sides * Hardware and software alignment – Unlike pure software, product timelines are constrained by manufacturing cycles, creating hard deadlines and forcing disciplined execution * Hiring for passion and proximity – Teams perform better when they have genuine interest in the product domain, especially in consumer experiences tied to physical interaction * Differentiation through awareness – Deep competitor understanding is essential not for copying, but for identifying where to stand apart and create unique value * Private equity vs venture dynamics – Product strategy shifts significantly depending on ownership model, with PE favouring speed and certainty, and VC allowing more exploration * Book smarts and street smarts – The most effective product leaders combine formal knowledge with real-world experience, adapting frameworks to context rather than following them rigidly ... and much more. Find our more about fractional product leadership Nick mentioned an article I wrote about fractional product leadership - you can check it out here: https://oneknightinproduct.substack.com/p/the-ultimate-guide-to-fractional [https://oneknightinproduct.substack.com/p/the-ultimate-guide-to-fractional] Check out Winmau * Winmau: https://winmau.com [https://winmau.com/] * Winmau careers: https://winmau.com/pages/careers-with-winmau [https://winmau.com/pages/careers-with-winmau] Contact Nick * LinkedIn: https://www.linkedin.com/in/nick-kenn/ [https://www.linkedin.com/in/nick-kenn/]