Scaling Tech - The Blueprint for Successful Tech Teams

Hosted by Debbie Madden

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Jan 2025

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Are you a CTO, Chief Product Officer or Tech leader? Then this one's for you: If there was one tool that would help you learn best practices and avoid top mistakes so that you can achieve your goals, would you consider that tool? If you answered "yes," this is the tool you've been looking for. Debbie Madden is a serial tech entrepreneur. She is well known for helping teams scale in ways that result in measurable outcomes paired with a strong culture. She is the founder & chair of Stride, a national agile software development consultancy. Stride helps the world's top brands like SeatGeek, Spotify, Codecademy, and Casper get high-quality products to market while modeling the way for tech and product best practices that upskill and enable tech teams. Episode after episode, you'll hear top tech leaders and experts in their fields sharing first-hand successes, failures, and lessons learned about the topics that are a high priority for today’s tech teams. Let the technology leaders of our time share first-hand stories of successes, failures, and lessons learned as they lead and grow their teams amid an ever-changing landscape. For more information on Debbie Madden and Stride visit https://www.stride.build/

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45 recent

January 30, 202529 min

How GenAI + Automation Are Going to Revolutionize Legacy Code Migration

Stride’s Michael Carlson and Michael Wytock join this week’s episode to share how Stride’s groundbreaking 100x service is transforming legacy code modernization. They explore how Generative AI and automation are breaking down the barriers that have long made updating outdated systems slow, risky, and politically challenging.The duo shares how Stride 100x streamlines the modernization process by automatically tracing and understanding even the most complex legacy systems. The approach reduces what used to take weeks—or even months—to mere hours, enabling companies to modernize without disrupting their day-to-day operations. Plus, the two explore real-world legacy software challenges, from unknown system dependencies to hidden code risks, and explain how 100x eliminates these pain points through cutting-edge technology. They also explore how Stride 100x differs from popular tools like GitHub Copilot. If your organization is stuck in the old legacy systems, tune in now and discover how Stride 100x can help you modernize your systems. You can learn more about the service at https://www.stride.build/100x or chat with the team for a personalized demo. “Re-architecting and modernizing your applications as the business needs arise is not something that's going counter to what the business is trying to do. Actually, it will help the business move forward.” ~  Michael CarlsonIn This Episode:- Introducing Stride 100x: modernizing legacy applications- The birth of 100x from understanding client pain points- Identifying common legacy software struggles- Step 1 of 100x: code tracing in legacy systems- Speeding up the modernization process: real-world examples - Continuous monitoring and iteration with 100x- Stride 100x vs. popular AI coding tools- The future of legacy code modernization with Stride 100xAnd much more!Learn More About Stride 100x:https://www.stride.build/100xConnect with Debbie Madden:Website - https://www.stride.build/LinkedIn - https://www.linkedin.com/in/debbiemadden1/LinkedIn - https://www.linkedin.com/company/stride-consulting/

December 3, 202427 min

The Intersection of GenAI and Real Business Value with Mark Kasdorf

Mark Kasdorf, a serial entrepreneur and founder of Forge, joins today’s conversation on the transformative power of generative AI in traditional industries. Mark previously founded Intrepid, a pioneering mobile agency that he successfully scaled to a $25 million exit with Accenture. Mark explains Forge’s approach to addressing real-world challenges in the trades, from recruiting and training Gen Z workers to equipping them with AI-enabled tools to replace fossil fuel-dependent systems. He shares how Forge integrates generative AI into its processes, such as using GPT-4-powered systems to gather job-site feedback and improve efficiency. Mark also highlights how AI and extended reality (XR) will transform trades by combining human expertise with AI-guided solutions. From AI-powered glasses to systems capable of managing complex tasks, he predicts a future where technology amplifies human capabilities rather than replacing them. The insightful conversation also addresses concerns about workforce skepticism of AI and emphasizes the importance of integrating AI into existing processes to drive efficiency and business growth.Tune in to discover genAI’s potential to not only transform individual industries but also redefine the way businesses operate in an increasingly tech-driven world. “I think in the next three years, we will see AI capable of guiding you to do anything that's within your hard skills and take off 100% of the problem-solving load.” ~  Mark Kasdorf In This Episode:- Applying Generative AI in business- The Bluon tool for HVAC contractors- Build vs. buy: the AI dilemma- How GenAI is transforming the trades- Human judgment in AI-driven trades- AI for skilled labor transformation- Addressing workforce skepticism of AI’s role- Harnessing AI for business growth or development Connect with Mark Kasdorf:- LinkedIn - https://www.linkedin.com/in/markkasdorf Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn - https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

November 19, 202420 min

Stride Conductor vs Copilot

Stride’s Rob O’Brien and Stephen Meriwether join this week’s conversation highlighting the impact of AI on software development. The duo demonstrates how Stride Conductor, a multi-agent GenAI tool, differs from single-user CodeGen tools like GitHub Copilot by offering tailored solutions for team-based workflows.Unlike cloud-based tools, Stride Conductor operates within a secure company environment, offering complete control over AI model usage. It also supports team-specific customization, ensuring code aligns with established standards, reducing mental overhead, and improving code consistency across large organizations.In a live demo, Stephen contrasts Copilot's single-user model with Stride Conductor’s automated testing capabilities. While Copilot requires frequent manual interventions, Stride Conductor completes tests with a single command, which is efficient in collaborative environments. Stride Conductor is currently supporting Java, JavaScript, TypeScript, and Python.Visit https://www.strideconductor.com/ to sign up for a live demo.“When we talk about Stride Conductor, we think of three key differentiators: secure, tailored, and automated. This is not a cloud-based SaaS product; it’s running in your environment.” ~ Rob O’BrienIn This Episode:- Introduction to Stride Conductor - What makes Stride Conductor different?- Demo preview: using Copilot vs. Stride Conductor for testing- Using Stride Conductor for testing- Addressing unique use cases with Stride Conductor - How to book a Stride Conductor live demo  And much more!Learn More About Stride Conductor: - https://www.strideconductor.com/ Connect with Rob O’Brien:- LinkedIn - https://www.linkedin.com/in/rob-o-brien-82865b25Connect with Stephen Meriwether:- LinkedIn - https://www.linkedin.com/in/stephenmeriwether Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn - https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

October 8, 202428 min

Product Management Across 4 Startups: Lessons Learned with David Hersh

Building and scaling startups involves numerous uncertainties and complexities, from ideation to exit. Many entrepreneurs and tech leaders struggle with innovation risks, team cohesion, and the fear of failure. Today, serial entrepreneur David Hersh shares his lessons from founding and exiting four large companies.David discusses key tech startup challenges, such as product ideation, early monetization, and building strong teams. He offers tech leaders and aspiring founders valuable lessons on adapting to market needs, making strategic pivots, and navigating the journey from startup to acquisition.David highlights the critical role of teamwork in navigating the ups and downs of startup life, noting that building a trusted, cohesive team can be more important than the idea itself. He also shares the importance of building the products that customers want and the value of embracing external ideas.Tune in to hear David’s candid reflections on the highs and lows of entrepreneurship, his best and worst decisions, and his advice on managing post-acquisition transitions in large companies.“Scratching your own itch is effective because if you’re solving a problem for yourself, you’re likely solving it for others.” ~ David HershIn This Episode:- Lessons from product ideation to execution- Monetization strategies and business viability analysis- David’s best and worst decisions: the role of teamwork- Reflecting on mistakes and pivots- How to choose an exit strategy as an entrepreneur- How to navigate post-acquisition challengesAnd much more!Connect with David Hersh: - LinkedIn:https://www.linkedin.com/in/dhersh/ Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

September 24, 202421 min

How Business Leaders Should Think About Labor Mix Today with Hugo Malan

Over the past 18 to 24 months, temporary labor usage in the U.S. has dropped by 15%, despite the strong economic performance. This surprising decline in temp labor penetration highlights a critical shift in workforce strategies and the need for companies to evaluate their labor mix. Hugo Malan, President of Kelly Science, Engineering, Technology, and Telecom, is here to discuss one of the most pressing issues for business leaders today: finding the right labor mix. As a seasoned leader in workforce solutions, Hugo shares valuable insights on how companies can achieve the right balance between permanent, temporary, and consulting labor to drive flexibility, continuity, and innovation.Hugo explains how short-term economic fears, such as concerns about a recession, have led companies to reduce their use of temporary staff and maintain permanent staff. He anticipates a normalization in the demand for temporary staffing by 2025 as economic anxiety decreases and companies look for more flexible labor options.Tune in to learn how to prepare your company for future demand fluctuations and maintain a flexible, high-performing workforce.“If you don’t have a flexible component in your labor force, it becomes more difficult to respond fast enough to an upturn or downturn in demand, and that can have significant negative impacts on your bottom line.” ~ Hugo MalanIn This Episode:- Defining labor mix: permanent, temporary, and consulting- The importance of finding the right labor mix- Surprising shifts in the U.S. labor market- The root causes of labor market changes- The impact of economic anxiety on temporary labor- Future trends and predictions for the staffing industry- Advice for business leaders on finding the right labor mixAnd much more!Connect with Hugo Malan: - LinkedIn: https://www.linkedin.com/in/hugo-malan-0994191/Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

September 10, 202424 min

Ethical AI: How Tech Leaders Can Balance Innovation with Transparency, Ethics, and Human Value with Ken Judy

As AI continues to shape the future of tech, leaders must ensure they're using it responsibly while maintaining human-centric values. Navigating the ethical complexities of AI is crucial to avoid costly mistakes that could compromise both teams and technology.Today’s episode features Ken Judy, a partner at Stride. Ken has over 30 years of experience in the tech industry, with 15 years spent in executive leadership roles. He highlights the need for accountability and professional ethics in AI development, emphasizing that adopting AI should enhance human roles, not replace them. Ken highlights potential risks, such as intellectual property violations and misuse of AI outputs. He advocates for proactive efforts to avoid these issues, including new governance roles to oversee AI ethics within organizations, much like Agile's Scrum masters ensure accountability.Are you ready to lead your team into the future of AI responsibly? Tune in to this insightful episode and learn how to align tech practices to long-term values so that AI supports human potential and organizational goals.“If you care about people, your first instinct will not be how many of these people I can replace. It'll be, "How can I help these people get their jobs done better?” ~ Ken JudyIn This Episode:- Ethical principles in AI development- Transparency and best practices in AI- Governance and accountability in AI- Agile principles and AI integration- Final thoughts on ethics in AIAnd much more!Connect with Ken Judy: - LinkedIn - https://www.linkedin.com/in/kenjudy Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

August 27, 202420 min

The Impact and Potential of AI on Project and Program Management with Adam Roberts

AI's rapid evolution is impacting the project management profession. It’s shifting the focus from manual crisis management to strategic oversight, enabling tech leaders to deliver higher-quality outcomes faster and more efficiently.Today’s guest, Adam Roberts, is a seasoned project management expert with over 20 years of experience at major companies such as Disney, Viacom, and NBCUniversal. We are talking about the role of AI in project and program management, exploring its potential, and the challenges it presents.Adam shares how AI is already reshaping routine tasks, such as note-taking and scheduling, allowing project managers to focus on more strategic responsibilities. He also addresses AI's inherent risks and limitations, emphasizing the need for vigilance and human oversight in leveraging these technologies.If you’re a tech leader aiming to stay ahead of the curve and effectively lead your teams in an AI-driven world, this episode is a must-listen. You will learn how AI can drive efficiency, reduce project risks, and potentially redefine the future of project management roles.“The notion of 80 percent of project management work being handled by AI can be a very frightening statistic, but it might mean there is capacity to take on more and deliver more.” ~ Adam RobertsIn This Episode:- AI's impact on project and program management- Challenges and limitations of AI in project management- The impact of AI on the project and program managers’ profession- The future of AI in project management- Myths and misconceptions about AI- Organizational responsibilities and AI policiesAnd much more!Connect with Adam Roberts:- LinkedIn - https://www.linkedin.com/in/scrumexpert/ Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

August 13, 202430 min

Data Science Decoded: The Academia vs Industry Showdown with Marco Morales

The Harvard Business Review once called data science the “sexiest job in the 21st century.” A decade later, a significant gap exists between academic training and the practical demands of data science in business. Educational programs focus heavily on technical skills without preparing students for real-world challenges.Marco Morales, a seasoned professional, has spent the last decade at the intersection of business and technology, leading data science initiatives in media and entertainment. Marco explains why tech leaders should care about this gap and offers actionable steps, such as dedicated data science internships, to help new graduates transition smoothly into the industry.Marco emphasizes the importance of upskilling data scientists to collaborate effectively with non-technical stakeholders in a typical business setting.Tune in to learn key methodologies and best practices for building impactful data products and mitigating the experience gap for new data scientists entering the workforce.“As a tech leader, you’ll find that people don't usually hit the ground running. There's a learning curve, and it's a cost that any company ends up incurring for getting people ready to be contributing as data scientists.” ~ Marco MoralesIn This Episode:- Marco Morales’ background and experience in data science - The gap between academic and business data science- The challenges in applying academic data science- Problem-solving in a controlled academic setting vs in the real world- Teaching data scientists to collaborate with other specialized professionals - Best practices for data science in business- How tech leaders can mitigate the gapAnd much more!Connect with Marco Morales: - LinkedIn - https://www.linkedin.com/in/marcomoralesbarba Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

July 30, 202420 min

Deciding When to Ditch Versus Reuse Software with Nolan Frausto

How do you decide between ditching and reusing software? Nolan Frausto, the CTO of AdaptedMind, discusses his experience leading a complete software rewrite at the education technology startup. AdaptedMind experienced rapid growth during the COVID-19 pandemic, exposing significant issues with its outdated codebase, which had been developed over ten years by a very small team. Nolan explains his process of assessing the current code, identifying fundamental issues, and deciding to rebuild from the ground up.He emphasizes the importance of hiring the right people and gaining trust from the founders and team members for a successful migration.If you are a tech leader tasked with deciding whether to reuse or rewrite software, Nolan’s experience and lessons will help you make the right choice for your organization. Tune in for this and more!“Spending an extra month or extra time with your hiring will pay dividends across the board down the line. It's a cliche; hire good people, hire the best, but it's a cliche for a reason.” ~ Nolan FraustoIn This Episode:- Assessing the code quality before the decision to rewrite- AdaptedMind’s software rewrite journey: Steps and challenges- Executing the switchover seamlessly - Migration strategy, timelines, A/B testing, and team growth - The importance of gaining trust from the founders - Reflections and lessons learned in the migrationAnd much more!Connect with Nolan Frausto:- LinkedIn -  https://www.linkedin.com/in/nolanfrausto Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/

July 9, 202427 min

Exploring GenAI’s Impact on Tech Debt with Dan Mason

Are you a tech leader struggling to control tech debt while navigating the rapid advancements in AI? Stride’s Head of AI, Dan Mason, is here to help us unravel the complexities of using generative AI to manage and prevent the tech debt spiral.Dan explains that GenAI's effect on tech debt largely depends on how organizations use it. With proper guidance and context, GenAI can improve code quality, but without oversight, it can lead to bad code and increased tech debt.Dan highlights the necessity of providing GenAI with detailed human-level documentation and instructions for teams to achieve better code quality. Also, the benefits of AI tools differ across industries. Cautious industries like banking may see a reduction in tech debt, while fast-moving startups might incur more debt.Consequently, Dan emphasizes the need for tech leaders to have a strategic plan and ensure AI-generated code is thoroughly reviewed to prevent tech debt accumulation and maintain code integrity. He also warns about the potential pitfalls of ignoring GenAI’s impact on tech debt.Listen to the full episode to understand how thoughtful integration of AI tools can enhance team capacity and lead to more intelligent decision-making in your organization."The best way to avoid incurring new debt is to be honest about what GenAI can do. You can't plan your workflows around 'GenAI will just do everything.' Find the things that it's good at and figure out which constraints GenAI can loosen for you. " ~  Dan MasonIn This Episode:- The impact of AI on code quality- The role of human language instructions and human oversight- How to determine the right AI strategy and tools- Strategic application of AI in various industries- How to use Stride Conductor to remediate tech debt- The evolution of the relationship between GenAI and tech debt- Best development practices to prevent the tech debt spiral- Consequences of ignoring GenAI's impact on tech debtAnd much more!Connect with Dan Mason : - LinkedIn -  https://www.linkedin.com/in/dnmason Connect with Debbie Madden:- Website - https://www.stride.build/- LinkedIn – https://www.linkedin.com/in/debbiemadden1/- LinkedIn - https://www.linkedin.com/company/stride-consulting/