A Digital Strategy Podcast

What We Cover Why delivery on time and on budget is not the same as project success The 'meeting of the minds' problem: how misaligned expectations sink projects before kickoff Free text fields vs. structured data — and why that distinction matters for every dashboard you want to build Why AI makes strategy more important, not less: if you don't know where you're going, it'll get you there fast The warehouse problem: why the people closest to the work always know something leadership doesn't Technology adoption as the real success metric — and what training actually needs to look like How to run discovery when clients say it isn't necessary (and why that response is a red flag) Past state / future state: mapping where you are vs. where you want to be before touching a platform Key Takeaways Technical decisions are business decisions. If they're being made without input from operations, finance, or end users, the scope is already wrong. Shadow IT is a symptom. When people build workarounds, it's because the official system didn't solve their actual problem — and your data is now fractured across both. Discovery is not optional. If a client won't let you talk to stakeholders before scoping, they are setting you up to build the wrong thing with confidence. The goal is adoption, not deployment. A project isn't done when it's launched. It's done when people are using it and it's doing what it was supposed to do. Slow down to go fast. The foundational work — workflow mapping, stakeholder interviews, requirements definition — is the work that prevents the $80K change order. About the Guest Deborah Kaminetzky is the founder of Defacto Project Management. She brings a background in law, mediation, and corporate operations to high-complexity technical implementations — specializing in ERP, CRM, and platform projects where business requirements and technical execution need to stay tightly aligned. She works across industries and is known for being the person in the room willing to ask the questions nobody else will. Website: https://defactoprojectmanagement.com/ LinkedIn: https://www.linkedin.com/in/deborah-kaminetzky-pmp-fractional-project-manager/ About the Hosts Symon Oliver, RGD is Design Director and Marcello Gortana is Executive Director at Tennis — a B2B web design and product development agency. The Weekly Set covers the decisions, patterns, and hard truths behind technical projects, vendor relationships, and agency operations. Chapter List 00:00 — Navigating Complex Technical Projects 02:16 — Common Failure Patterns in Project Management 05:52 — The Role of AI in Project Efficiency 10:20 — Understanding Client Needs and Workflows 14:45 — The Importance of Business Outcomes in Tech Decisions 18:21 — Breaking Down Communication Barriers 21:58 — Defining Project Success and Adoption 25:48 — The Foundation of Successful Projects LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

Product teams don't miss deadlines because they're slow. They miss them because no one ever defined what "done" actually means. In this episode, Symon and Marcello dig into the structural and cultural gaps that quietly blow up product timelines — and what you can borrow from the services world to fix it. What we cover: No governance = no finish line. Without a roadmap and defined milestones, scope is infinite. Teams can take as many liberties as they want with what counts as complete — because nothing ever officially is. You can't think and make at the same time. Conceiving a feature and building it simultaneously is one of the most common (and costly) product anti-patterns. Strategic thinking has to happen before the work starts, not during. Agile isn't a cure-all. Every Agile project Symon and Marcello have joined without managing themselves has introduced friction. Scrum roles, dashboards, ceremony overhead — it's not wrong, but it's also not free. Feature creep needs a scorecard. We reference the RICE framework (Reach, Impact, Confidence, Effort) as a baseline for evaluating whether any feature is actually worth building — before anyone opens Figma. The HiPPO effect is real. When the highest-paid person's opinion drives the roadmap, you get flavor-of-the-week features and no strategic coherence. Investor-clients can quietly hijack your roadmap. When early clients are also investors, their feature requests carry disproportionate weight — often at the cost of actual product direction. Stakeholder alignment is your first deliverable. Before scope, before design, before a single line of code — get everyone at the table and make the plan the first collaborative output. Resources mentioned: RICE Scoring Framework (Reach, Impact, Confidence, Effort) r/buildinpublic on Reddit Chapters 00:00 Intro — Why speed is the promise, delay is the reality 00:43 Who we are and what we're covering today 01:21 Deliverables world vs. product world — a culture clash 02:10 Root cause #1: No roadmap, no governance 03:15 Root cause #2: Thinking and making at the same time 04:00 Root cause #3: Agile's hidden baggage 04:30 Root cause #4: Feature creep and RICE scoring 05:16 The HiPPO effect — when the highest-paid opinion runs the roadmap 06:20 What mature product orgs do differently 07:14 The investor-client trap — when funding steers features 08:00 Why teams struggle with "done" — too many stakeholders 09:30 What happens after launch (the part nobody plans for) 10:40 Sequencing as a discipline — installing a mini operating system 11:36 Practical advice: where to start depending on your lifecycle stage 13:29 Stakeholder alignment IS a deliverable 14:22 Hard truths and closing takeaways LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

Key topics: The concept of the SaaS apocalypse and its driving factors How AI tools like Claude Code, Claude, ClawdBot and others are enabling bespoke app development The declining economics of SaaS subscription models The impact of AI on employment, stock markets, and investor behavior The importance of UX and integration in product development Strategic shifts for SaaS companies: focusing on core features and tight integrations The probable future: distributed, fragmented software ecosystems with interoperable components Timestamps: 00:00 - Introduction to the SaaS apocalypse and its relevance 02:17 - How ChatGPT and AI tools are simplifying development workflows 05:04 - The disruption of traditional SaaS pricing and value propositions 07:55 - What is the SaaS apocalypse? Overview and core fears 09:20 - Impact on stock markets and investor sentiment 11:27 - AI's rapid evolution and implications for white-collar jobs 12:23 - Key technical drivers: Claude code, agent reasoning, and automation 14:49 - Lowering costs and decentralizing software creation 16:05 - Consumer versus enterprise AI adoption challenges 18:14 - Adoption rates in AI: lessons from color TV history 19:03 - User behavior trends and incremental AI adoption 21:04 - Market shifts: smaller, focused tools vs. bloated platforms 22:36 - Importance of UX and strategic integrations in product success 24:06 - Building with network effects: integrations over feature bloat 25:37 - The future landscape: distributed, interoperable, fragmentated SaaS ecosystem LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysTotal cost of ownership includes hidden costs like hosting and labor.Organizations often underestimate the costs associated with website redesigns.Hosting costs can vary significantly and are often overlooked.Labor costs related to managing technology can add up quickly.RFPs rarely include detailed descriptions of hosting and management costs.Cultural attitudes towards websites affect how costs are perceived.Incremental delivery can help manage costs more effectively.Clients often lack awareness of their total spending on technology.Effective communication is key to understanding project costs.Managed hosting can provide peace of mind despite higher costs. Chapters00:00 Introduction to Total Cost of Ownership04:28 Understanding Hidden Costs in Website Redesigns10:16 The Role of Hosting and Labor Costs16:14 Challenges in RFPs and Cost Management22:08 Cultural Perspectives on Website Value25:55 Hard Truths About Total Cost of Ownership LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysOrganizations often lack a structured way to evaluate vendors.A scorecard can help monitor vendor performance over time.Identifying triggers for audits can prevent larger issues.Communication is a critical factor in vendor relationships.Documentation is essential for transparency and accountability.Systemic issues can often be masked by one-off problems.Regular evaluations can help maintain healthy vendor relationships.Quality drift should be monitored to ensure standards are upheld.Establishing clear criteria for success is vital.Future planning can alleviate pressure during vendor evaluations. Chapters00:00 Evaluating Vendor Relationships01:56 Understanding Audits and Scorecards03:04 Ongoing Evaluation of Vendor Success05:51 Identifying Triggers for Vendor Audits09:03 Distinguishing Between One-off Issues and Systemic Problems10:41 Establishing Evaluation Criteria13:40 The Importance of Communication and Reporting14:57 Key Categories for Vendor Evaluation LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysThe importance of a flexible process in project management.Documentation is critical for continuity and clarity.Scope should be viewed as a hypothesis, not a contract.Effective communication is key to navigating project risks.Governance helps promote decision clarity and accountability.Understanding client expectations is crucial for project success.Regularly reviewing and updating processes is essential for improvement. Chapters00:00 Introduction and Weekly Recap11:14 The Importance of Documentation in Processes13:33 Process Philosophy and Governance16:27 Navigating Project Risks and Flexibility19:25 The Role of Communication in Project Management22:14 Understanding Scope and Change Management25:14 Final Thoughts on Process and Client Relationships LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysMVPs aren't about shipping fast, they're about learning fast.The term MVP has been misunderstood and often co-opted.Validation should come from real user engagement, not speculation.A good MVP strategy involves identifying risky assumptions and defining success metrics.An MVP can be a scrappy version of a product, but it must still show commitment to the idea. Chapters00:00 Introduction to MVPs01:28 Understanding the Misconceptions of MVPs06:37 Real-World Examples of MVPs09:38 MVPs in Product Thinking11:11 When to Use an MVP14:19 The Importance of Speed in MVP Development15:30 Crafting an Effective MVP Strategy24:01 Hard Truths About MVPs29:36 Conclusion and Key Takeaways LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysThe trend of single user apps will continue to grow.Compliance will increasingly involve product and design teams.Dynamic web pages may become a reality this year.Websites should be treated as living systems, not static products.Customer journeys are becoming more complex and non-linear.Sales tech stack integration with websites is essential for success.AI will play a significant role in web design and functionality.Accessibility compliance will become a standard expectation.The importance of design systems will increase as technology evolves.Understanding customer data and behavior is crucial for effective marketing. Chapters00:00 Welcome Back and Personal Updates01:53 Predictions for 2026: Trends in Web and Product Design05:38 The Rise of Compliance in Design09:38 Dynamic Web Pages and AI Integration13:18 Websites as Living Systems19:13 Customer Journeys: A Non-Linear Approach24:59 Sales Tech Stack Integration with Websites LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysDesign is interpretive and has a rich history.Aesthetics is often mistaken for the entirety of design.Design involves planning and execution, not just visuals.The complexity of a project influences the design approach.Research and problem identification are crucial in design.De-risking the design process helps in decision-making.Accuracy in design outcomes is essential for success.Agility allows for effective pivots in design projects.Documentation aids in maintaining clarity during pivots.Design should be evaluated beyond just aesthetics.Chapters00:00 Introduction to Design Perspectives02:49 Defining Design: A Multifaceted Approach06:12 The Four Pillars of Design08:59 Aesthetics vs. Functionality in Design11:48 De-risking the Design Process14:41 The Importance of Accuracy in Design18:00 Agility and Flexibility in Design20:56 Conclusion: The Depth of Design Beyond Aesthetics LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysWebsites can now serve as growth engines.Defining clear goals is crucial for website success.Sales and marketing teams must collaborate effectively.Data analytics is essential for informed decision-making.A strong content strategy is foundational for growth.Eliminating unnecessary tools can streamline processes.Long-term planning is vital for website design.Understanding lead movement through the organization is key.Integrating technology into marketing strategies enhances effectiveness.The website should be part of a larger growth ecosystem. Chapters00:00 Website as a Growth Engine07:32 Defining Website Goals and Success Metrics08:00 Understanding SaaS and B2B Marketing Dynamics10:18 The Importance of Metrics in Marketing12:38 Integrating Website with Growth Ecosystem16:12 Sales and Marketing Collaboration18:21 Essential Technologies for Growth27:50 Redesigning Websites for Sales and Marketing34:16 The Hard Truths of Website Strategy LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

AEC is facing a perfect storm + digital disruption. Johanna Hoffman (Oomph Group) explains what’s happening, why it won’t revert, and how firms can reposition, align BD/marketing, and turn their website into a growth engine.Find Johanna Hoffman: https://www.linkedin.com/in/johanna-hoffmann-b35b251/ Find Oomph Group: www.oomphgroup.com Find Marcello Gortana: https://www.linkedin.com/in/marcellogortana/ Find Symon Oliver: https://www.linkedin.com/in/symonoliver/ Find Tennis: www.designtennis.com   LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysAssociations have unique digital needs due to their member-driven nature.Building in public can lead to valuable feedback.Monolithic systems are tightly coupled and may limit flexibility.Modular systems allow for more customization and scalability.Portals are essential for member engagement and retention.Requirements gathering is crucial for effective technology solutions.Mapping out existing systems can reveal inefficiencies.Testing software before commitment is vital for long-term success.Associations often struggle with outdated technology solutions.The right tech stack depends on the specific needs of the organization.Chapters00:00 Introduction to Building in Public05:23 Understanding Associations and Their Digital Needs07:10 Exploring the Tech Landscape for Associations11:20 Monolithic vs. Modular Systems17:50 The Importance of Portals in Member Engagement20:01 Requirements Gathering and Future Planning LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysBuyers often mistrust vendors due to past negative experiences.A comprehensive brief is essential for effective agency selection.Understanding your needs is crucial before searching for an agency.Evaluating an agency's process can de-risk your investment.Outdated portfolios can indicate a lack of current expertise.Cultural fit is important for a successful partnership.Asking for recent references can provide insight into agency performance.Support philosophy should be clear and value-driven.Measuring success should be a collaborative effort with clear metrics.Agencies that own the CMS they sell may not have your best interests in mind. Chapters00:00 Introduction and Personal Updates02:37 Understanding Buyer Mistrust in the Industry05:30 Selecting the Right Design and Development Agency08:38 The Importance of a Good Brief11:32 Evaluating Agency Processes and Expertise14:33 Analyzing Portfolios and Case Studies17:23 The Balance of Specialization and Generalization21:51 The Importance of Transparency in Development24:13 Cultural Fit: Aligning Values with Vendors25:18 Support Philosophy: Planning for Post-Launch27:04 Key Questions to Ask Before Hiring34:47 Evaluating Technology and Vendor Intent37:25 Recap: Navigating the Vendor Selection Process LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysThe more plugins you use, the higher the cybersecurity risk.WordPress remains a dominant CMS but has its challenges.Webflow is emerging as a leading web experience platform.Open source CMS can lead to maintenance overhead.Site builders are suitable for small businesses but may not scale well.Headless CMS is ideal for complex, multi-platform content delivery.Enterprise CMS offers governance and workflow benefits but at a high cost.The editor experience is critical for content management success.Chapters01:51 Understanding CMS Platforms and Categories05:57 What to Look for in a CMS11:42 Evaluating Traditional CMS Options16:26 The Rise of Webflow and Migration from Drupal20:01 Debating the Pros and Cons of Drupal21:32 Visual Development Platforms: Framer and Webflow26:58 Headless CMS: The Future of Content Management28:27 Enterprise CMS and Digital Experience Platforms (DXP) LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysExplore different types of CMS: traditional, headless, and enterprise.Understand the pros and cons of each CMS type.Learn what to look for and avoid in a CMS.Discover the scalability of different CMS platforms.Gain insights into CMS suitability for various business needs.Symon Oliver shares his expertise on CMS.Marcello Gortana discusses CMS categories.The importance of choosing the right CMS for your business.Common misunderstandings about CMSs.Why open source CMS might not always be the best choice.Title OptionsNavigating the CMS LandscapeUnderstanding CMS TypesChoosing the Right CMS for Your BusinessThe Pros and Cons of CMS PlatformsScalability in CMS: What You Need to KnowInsights from Symon Oliver and Marcello GortanaAvoiding Common CMS PitfallsThe Future of Content Management SystemsWhy Your CMS Choice MattersExploring Headless and Enterprise CMSChapters00:01:05 Introduction to CMS Types00:01:17 What to Look for in a CMS00:01:29 Categories of CMSs00:02:18 Headless and Enterprise CMSs00:03:00 Scalability and Suitability00:04:11 Specialty CMS Platforms00:05:27 Risks and Considerations00:08:46 Fun with Headless CMSs LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysClients often feel restricted by rigid website layouts.Content management can become a frustrating experience.A lack of flexibility in design can lead to client disengagement.Mental barriers can prevent clients from updating their sites.User experience is heavily influenced by website design.Clients may lock themselves into systems that don't meet their needs.The process of uploading content can be time-consuming and discouraging.Effective website design should prioritize user flexibility.Understanding client frustrations is key to improving design.Open communication can help alleviate client concerns. LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysComplexity arises from various factors including technology, people, and governance.The more people involved in a project, the more complex it can become due to internal politics.Discovery is crucial for understanding project scope and requirements.Budget and time constraints are key considerations in project feasibility.Clarity in project goals and deliverables is essential for success.Engaging stakeholders early can mitigate complexity and decision fatigue.A structured approach is necessary for managing complex projects effectively.Discovery should be treated as a standalone phase to ensure thorough planning.Understanding the audience and their needs is vital for project success.Communication is key to aligning expectations and understanding project complexity. Chapters00:00 Understanding Project Complexity06:56 The Impact of Complexity on Projects11:08 Navigating Complex Projects: Discovery and Strategy16:54 The Importance of Structure in Complex Projects LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysBad support is a primary reason for vendor switching.Good support should be proactive and value-driven.Traditional support models often prioritize agency profit over client needs.A shift in mindset is needed from support to partnership.Value-driven retainers focus on measurable improvements, not just maintenance.Knowledge transfer is essential for client self-sufficiency.Red flags include lack of documentation and predatory retainer models.Clients should conduct a cost-benefit analysis for support needs.Finding a good vendor is challenging and requires due diligence.Partnerships should align with client goals for success. Chapters00:00 The Importance of Vendor Support03:02 Defining Good vs. Bad Support05:52 The Pitfalls of Traditional Support Models08:46 Shifting Mindsets: From Support to Partnership11:45 Value-Driven Retainers and Their Benefits14:43 Red Flags in Vendor Relationships17:43 Navigating the Support Landscape20:38 Finding the Right Vendor Partner LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysUser experience (UX) design is often misunderstood and conflated with web design.Web design focuses on aesthetics and marketing, while UX design emphasizes functionality and user engagement.The evolution of design roles has led to a complex landscape where UX, UI, and web design intersect.Websites should be treated as products to ensure long-term engagement and optimization.Continuous improvement is essential for maintaining effective websites.Aesthetic design alone does not solve business problems; UX-driven design is necessary.The ideal designer possesses skills in UX, UI, and web aesthetics, often referred to as a 'unicorn.'Organizations need to understand the value of UX to avoid poor design decisions.The conversation highlights the importance of bridging marketing, business, and technology in design.Defining clear roles and expectations in design teams can lead to better outcomes. Chapters00:00 Understanding UX and Web Design12:47 Defining User Experience and Web Design23:52 The Role of UX Designers in Web Development29:34 Wrapping Up: UX vs Web Design LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter

TakeawaysStart with problems, not solutions.Define the objectives and outcomes clearly.Setting a realistic budget early is crucial.Involve decision makers early in the process.A strong brief is the cheapest way to de-risk a project.Vague features can lead to project failure.Understand your commitment during project phases.Budget transparency helps everyone self-qualify.Frame the problems, not the solutions.Manage decision makers and involve them early.Chapters00:00 Introduction and Lunch Conversations02:18 Project Management and Vendor Sourcing05:27 Scoping and Briefing for Digital Projects08:12 The Importance of Clear Objectives11:11 Understanding Audience Priorities14:07 Budgeting for Digital Projects17:03 Defining Features and Requirements20:08 Stakeholder Involvement in Projects22:54 Recap and Key Takeaways LinksYou can learn more about Tennis at our website. Be sure to follow us at LinkedIn, YouTube, Instagram, or Twitter