In this episode of Software Without Borders, hosts Thomas Hilliard and Olivier Pollard sit down with Ben Coffman, SVP of Engineering and Product, to break down how AI is being implemented inside modern software organizations. From computer vision and 3D modeling workflows to large-scale data infrastructure, Ben shares real-world insights on scaling engineering teams, improving system performance, and building AI-driven platforms. This conversation dives into software development, engineering leadership, artificial intelligence, and the strategies teams are using to turn emerging technology into real business results.

Guest Introduction:

Ben Coffman is the SVP of Engineering and Product at STACK Construction Technologies, where he leads high-performing teams at the intersection of software development, product strategy, and business execution. With a background spanning engineering leadership, AI-driven platforms, and large-scale data systems, Ben brings a practical, real-world perspective on how modern software organizations are built and scaled. Known for combining technical depth with strategic thinking, he focuses on improving workflows, accelerating performance, and helping teams turn complex systems into measurable business outcomes.

Key Takeaways:

• How AI is actually being deployed inside real software systems, not just discussed in theory
• What it takes to scale engineering teams from early-stage builds to complex, high-performance platforms
• How computer vision, 3D modeling, and data infrastructure are shaping the future of software development
• The mindset leaders need to successfully implement AI and adapt to constant technological change
• Why improving system speed and performance is critical when building AI-driven platforms
• How modern engineering teams are turning emerging technology into measurable business results
• What separates teams that successfully build AI systems from those that get stuck in experimentation
• How early curiosity in technology can shape a career in engineering leadership and innovation

Chapter Markers:

00:00 – Introduction to the Show

00:45 – Ben’s Background and Leadership Experience

01:10 – How Did Your Career in Technology Begin?

03:00 – What Shaped Your Professional Journey?

05:00 – What Drew You to Software and Engineering?

07:00 – Early Inspiration: Thinking About the Future of Technology

09:00 – Transitioning from Interest to Real-World Systems

11:30 – What Does It Take to Build Real Software Systems?

14:00 – How Is AI Actually Implemented in Production?

17:00 – Where AI Fits in Modern Software Architecture

20:00 – Challenges of Integrating AI into Existing Systems

23:00 – How Do You Scale Engineering Teams Effectively?

26:00 – Improving Speed, Performance, and Output

29:00 – Leadership Lessons from Scaling Complex Systems

32:00 – How Do You Drive Real Business Results with Technology?

35:00 – The Mindset Required to Lead Through Change

38:00 – What Teams Get Wrong About AI and Innovation

41:00 – Looking Ahead: The Future of AI and Software

43:30 – Final Thoughts and Takeaways

Keywords:

AI, artificial intelligence, software development, software engineering, engineering leadership, AI in production, machine learning, data infrastructure, scalable systems, system architecture, computer vision, 3D modeling, tech leadership, engineering teams, building AI systems

AI is accelerating software development at a pace most organizations aren’t ready for. In this episode of Software Without Borders, Duncan Grazier, Chief AI Officer at Build, breaks down what happens when code creation becomes nearly free—and why that doesn’t translate to better outcomes. From broken pipelines to misaligned metrics, this conversation explores how AI is forcing leaders to rethink how teams operate, how performance is measured, and what actually drives value.

Duncan shares why judgment and “taste” are becoming the most important skills in engineering, where AI is delivering real impact today, and how companies can avoid the trap of moving faster without moving smarter.

Guest Introduction:

Today’s guest is Duncan Grazier, Chief AI Officer at BuildOps, where he’s helping lead the shift from traditional software companies to AI-native organizations. Duncan has spent his career scaling engineering teams and building high-performance systems, including taking an organization from roughly 30 engineers to over 300 through hypergrowth and IPO.

Beyond his leadership roles, Duncan is known for his deep thinking around engineering, AI, and how companies actually operate under rapid change. He’s focused on how AI is reshaping not just how software gets built, but how teams are structured, how performance is measured, and how businesses create real leverage in this next era of technology.

Key Takeaways:

• AI has made code creation fast and cheap, but it has exposed bottlenecks in validation, alignment, and decision-making across teams.
• More output does not guarantee better outcomes; organizations must shift from measuring activity to measuring real business impact.
• The gap between junior and senior engineers is shrinking, which puts greater emphasis on judgment, context, and decision quality.
• The biggest breakdowns are not technical—they come from misaligned metrics and lack of coordination between leadership, product, and engineering.
• Companies that win with AI will focus on integrating it into systems that drive core business results, not just using it to increase speed or volume.

Chapter Markers:

00:00 – Intro & Guest Introduction

02:30 – Why AI Is Breaking Traditional Software Models

05:00 – The First Bottleneck: From Code to Production

08:30 – Why More Output Doesn’t Mean Better Results

10:00 – Rethinking Teams, Roles, and Headcount

11:30 – Where AI Is Actually Delivering Value

13:30 – The Gap Between Prototype and Production

15:00 – Where Companies Are Getting AI Wrong

18:30 – The Real Challenge: Organizational Alignment

21:30 – Final Thoughts & Key Takeaways

Keywords:

AI, artificial intelligence, software development, engineering leadership, AI tools, machine learning, software engineering, product development, tech leadership, startups, scaling teams, automation, developer productivity, SaaS, digital transformation

In this episode of Software Without Borders, Andy and Tomás sit down with Justin Bankston, CTO of South by Southwest (SXSW), to explore the remarkable evolution of one of the world’s most influential cultural and technology events. Justin shares his journey from playing in rock bands and reviewing demo CDs to leading the software, IT, and innovation groups that power SXSW’s massive annual footprint. We dig into the behind-the-scenes engineering challenges, the explosive impact of Twitter’s 2007 debut at SXSW, and the technical coordination required to support tens of thousands of attendees across multiple venues. Justin reflects on leadership, scaling teams, and what it takes to deliver a flawless experience when failure becomes instantly public. If you’ve ever wondered how innovation, culture, and infrastructure collide at global scale, this episode pulls the curtain back.

Guest Introduction:

Justin Bankston is the Chief Technology Officer at South by Southwest, where he has spent nearly 20 years shaping the technical backbone of one of the world’s premier events in music, film, and technology. From his early days as a full-stack developer to leading SXSW’s software, IT, and innovation teams, Justin has guided the organization through explosive growth, digital transformation, and cultural shifts — all while ensuring the attendee experience remains seamless and world-class.

Key Takeaways:

• SXSW’s uniqueness creates massive technical complexity. Three industries, three conferences, one seamless attendee experience.
• Justin’s journey was entirely organic. From musician → volunteer reviewer → contractor → leader → CTO.
• Twitter’s 2007 debut changed SXSW forever. Attendance spiked, expectations shifted, and technical resilience became paramount.
• Custom software was born from necessity. When SXSW started, no event platform could handle its hybrid creative/tech experience.
• Invisible infrastructure is intentional. If the Wi-Fi isn’t perfect, attendees notice — and complain loudly.
• Remote and global teams helped SXSW scale sustainably. Nearshore partners expanded engineering capacity without sacrificing collaboration.

Chapter Markers:

00:00 — Andy welcomes listeners to Software Without Borders

01:12 — Guest introduction: Justin Bankston, CTO of SXSW

03:18 — Justin’s backstory: bands, demo CDs, and first touchpoints with SXSW

04:16 — Contracting beginnings and early software challenges

07:58 — The unique blend of artist, audience, corporate, and technical needs

08:35 — How SXSW grew organically — and fast

10:32 — Leadership lessons from early career mentors

11:32 — The uniqueness of SXSW vs. other global festivals

13:13 — Stakeholder alignment and balancing competing priorities

14:57 — Inside SXSW’s custom software ecosystem

15:49 — The complexity of event IT & multi-venue Wi-Fi at scale

17:57 — The stakes of real-time attendee experience

18:58 — PanelPicker: the origin story

22:16 — Twitter’s SXSW launch and the ripple effects

24:14 — Strengthening infrastructure amid explosive growth

26:34 — Beginning remote/global engineering partnerships

29:26 — Process, communication, and the reality of global development

31:00 — How remote teams support SXSW’s “lights-on” needs

Keywords:

Software Without Borders, SXSW, Justin Bankston, Andy Hilliard, Tomás Hilliard, Accelerance, event technology, global engineering teams, festival tech infrastructure, Twitter SXSW launch, custom software development, nearshore engineering, CTO insights, large-scale event operations.

In this episode of Software Without Borders, Andy and Scott sit down with Steve Petersen, a veteran software architect and engineering leader known for building collaborative, high-trust technical teams across global environments. Steve shares the lessons he’s learned from decades of experience—coding, mentoring, scaling engineering orgs, and navigating the cultural and communication challenges that come with distributed teams.

Guest Introduction:

Steve Petersen is a seasoned software architect, engineering leader, and mentor with deep experience designing scalable systems and guiding teams through growth and transformation. Known for his calm leadership style, technical clarity, and focus on people-first engineering cultures, Steve has spent his career helping developers elevate their craft while strengthening communication and trust across globally distributed organizations.

Key Takeaways:

Communication is the real bottleneck, not code. Highly distributed teams succeed when they over-communicate clearly and consistently.

Pairing senior and junior engineers is a force multiplier, accelerating learning for both sides and strengthening team cohesion.

Humility makes great engineers—those willing to ask questions, seek clarity, and challenge assumptions collaboratively.

Technical leadership is not about having all the answers, but about creating a space where the best ideas surface.

Avoiding unnecessary complexity leads to higher velocity and more maintainable systems.

Global engineering teams thrive on structure, predictable rhythms, and clear expectations that support asynchronous work.

Chapter Markers:

0:00 Welcome to Software Without Borders

0:21 Introducing Steve Petersen

1:13 Steve’s Background & Early Career Path

2:46 Technical Leadership vs. Individual Contribution

4:05 How Engineering Teams Break Down Communication

5:32 The Power of Pairing Senior & Junior Engineers

7:01 What Makes an Engineer Truly Great

8:44 Curiosity, Humility & Asking the Right Questions

10:12 Reducing Complexity for Better Outcomes

12:09 Leading Distributed Engineering Teams

14:03 Building Predictable Rhythms & Expectations

15:58 Technical Debt vs. Necessary Complexity

17:30 Creating a Culture Where Engineers Feel Safe Speaking Up

19:03 What Steve Looks for When Hiring Developers

21:18 Why Mentorship Accelerates Team Growth

22:40 When to Step Back as a Technical Leader

24:11 Coaching Engineers Through Hard Problems

26:05 Final Thoughts & What Steve Wishes He Knew Earlier

End: Closing Remarks

Keywords:

Software Without Borders, Andy Hilliard, Scott Pollov, Steve Petersen, engineering leadership, software architecture, distributed engineering teams, global teams, technical mentorship, engineering culture, communication in engineering, technical debt, software development leadership, scaling teams

In this episode of Software Without Borders, we sit down with Joe Forgét—founder of Igniting Momentum and a leader who has lived through mergers, global team integrations, and the uncomfortable-but-necessary transitions that define high-growth companies. Joe breaks down what really happens when organizations hit those inflection points: culture drift, misalignment, operational chaos, and the quiet pressure founders and leaders carry while trying to scale.

Guest Introduction:

Joe Forgét is the founder of Igniting Momentum, a leadership and operations coach who helps growing companies rebuild clarity, alignment, and execution discipline. With deep experience leading global teams through mergers, restructures, and rapid scale, Joe blends operating system rigor with human-centered leadership. His work centers on creating momentum through intentional rhythms, strategic alignment, and practical accountability structures.

Key Takeaways:

Companies often realize they need help when they hit the moment Joe calls: “The business owns me now.”

Momentum comes from structured operating rhythms — not heroic effort.

Frameworks like EOS, Pinnacle, and System & Soul provide scaffolding, but must be tailored to each organization.

Early-stage founders may not need full frameworks yet, but scale-ups absolutely do.

Mergers & acquisitions create cultural collisions; alignment must come before acceleration.

Empowerment only works when role clarity and accountability structures are in place.

Progress must be viewed through “the gap and the gain,” recognizing wins instead of only missing pieces.

Chapter Markers:

0:00 Welcome back to Software Without Borders

0:23 Introducing guest Joe Forgét

2:17 Joe’s discovery of coaching

4:11 The Ignition Framework (Align → Activate → Accelerate)

6:22 EOS, Pinnacle, System & Soul explained

8:04 Coaching in fast-growth organizations

9:47 The moment leaders realize the business owns them

11:35 Measuring early momentum

15:51 The Gap and the Gain mindset

17:02 People-first additions in newer operating frameworks

20:03 Why implementation must be customized

23:35 Cultural blending in mergers

26:58 Choosing between scale, exit, or reinvention

30:25 Post-inflection indicators that help is needed

33:12 Role clarity as empowerment

35:05 Why coaches need their own coaches

End: Closing insights and wrap-up

Keywords:

Software Without Borders, Andy Hilliard, Scott Pollov, Joe Forget, Igniting Momentum, leadership coaching, operating rhythms, EOS, System and Soul, business scaling, mergers and acquisitions, organizational alignment, executive coaching, leadership frameworks, global team leadership

In this episode of Software Without Borders, Andy and Scott sit down with Kristina Crane, transformational executive, fractional COO/CSO, and CEO of The Canyons Group, to unpack what it really takes to lead organizations through AI-driven change. Kristina draws on 25+ years across SaaS, government tech, and operational transformation to explain how companies can embrace AI without losing their people, culture, or strategic focus. From building a “culture of curiosity” to using proven software-industry frameworks for prioritization, Kristina brings a grounded, practical perspective on how leaders can move fast and smart.

Guest Introduction:

Kristina Crane is a transformational executive and fractional COO/CSO with deep expertise in AI adoption, organizational change, and strategic operations. As CEO of The Canyons Group, she helps government agencies, enterprises, and growth-stage companies navigate complex transitions with a framework centered on “Navigate to Elevate.” Kristina spent 12+ years at STC Health leading a major shift from a dev-shop model to a scaled SaaS organization, driving 10x revenue and 60% efficiency gains through AI.

Key Takeaways:

• AI transformation is a people problem first—tech only works when teams understand the “why” and feel empowered. episode-37

• Companies must balance curiosity with prioritization to avoid shiny-object chaos.

• The software industry provides proven frameworks (like RICE) that non-tech organizations can use to evaluate AI opportunities.

• Old-school executive teams need a business-first, tech-translated approach to adopt AI successfully.

• Strategic planning cycles must speed up—leaders should revisit their business model, ICP, and value proposition every 12–36 months.

• Consultants accelerate outcomes not because of frameworks, but because of pattern recognition and objective accountability.

Chapter Markers:

0:00 Intro

1:07 Welcome to Software Without Borders

1:12 Introducing Guest — Kristina Crane

1:56 Kristina’s Background in Strategy, SaaS & GovTech

3:41 Teaching Roots → Consulting → SaaS Incubation

5:58 Transition to STC Health & Leading SaaS Transformation

6:34 Difference Between Kale Crane & The Canyons Group

8:08 AI FOMO, Human Intelligence & Organizational Change

9:03 Navigating Noise & Extremes Around AI

10:26 What AI Forces Every Organization to Learn

12:30 How Old-School Exec Teams Can Embrace AI

14:14 Culture of Curiosity & Empowering Teams

15:34 Guardrails, Governance & Safe Experimentation

16:57 When to Bring in Technologists

17:12 Prioritization Frameworks (RICE & ICE)

18:54 Governance Policies & Early-Stage Experimentation

19:29 Curiosity Champion Groups & Brown-Bag Cycles

22:22 Training Teams to Think Like Product Organizations

23:19 Overcoming Fear & Starting Small

23:46 Strategy vs. Operations — Big Picture Impacts

24:58 Business Model Iteration in the AI Era

26:51 The SaaS Business Model Shift as an Analogy

28:12 Professional Services & White-Collar AI Disruption

29:37 Innovating Without Breaking the Core Business

30:01 Leading Large-Scale Change Inside Mature Organizations

32:21 Why Consultants Matter in AI Transformation

33:15 Seeing Blind Spots & Reading Culture

34:10 Accountability, Execution & “Skinned Knees”

35:13 The Hardest Transformation Leaders Will Face

End Closing Thoughts

Keywords:

Software Without Borders, Andy Hilliard, Scott Pollov, Kristina Crane, The Canyons Group, AI transformation, organizational change, SaaS transformation, leadership, culture of curiosity, AI adoption, operational strategy, RICE prioritization, business model evolution, enterprise AI, government tech

In this episode of Software Without Borders Podcast, Andy Hilliard sits down with Olivier Poulard, Accelerance’s Head of Global Software Engineering Strategies, to unpack one of the biggest myths in global software delivery: that adding more people solves delivery problems. Olivier shares what really drives predictability—clear alignment across people, process, technology, and data—and why so many organizations unknowingly “scale chaos.” Together, they dive into recurring SDLC pitfalls, hidden costs, and proven frameworks to turn fragmented delivery into a cohesive, measurable system. If you lead distributed teams or manage offshore partners, this conversation delivers a playbook for building sustainable, high-quality software outcomes.

Guest Introduction:

Olivier Poulard leads Global Software Engineering Strategies at Accelerance, bringing decades of experience on both sides of the delivery equation—as a global client managing teams of over 1,000 engineers and as a strategic partner architecting offshore and nearshore delivery systems. His practical, systems-level insights help clients design efficient, scalable, and high-performing software operations built on clarity and alignment rather than chaos.

Key Takeaways:

You can’t scale chaos—adding people only multiplies inefficiency without fixing underlying issues.

True delivery success requires alignment across people, process, technology, and data.

Clear, complete requirements (including transition and information requirements) prevent rework and estimation failures.

“Definition of Done” is critical for predictability—teams need shared clarity on what completion means.

Leaders must control scope and observe team dynamics to restore stability before scaling again.

Context switching, unclear requirements, and unmanaged change requests are among the costliest hidden inefficiencies.

Chapter Markers:

0:00 Intro

0:09 Guest Introduction: Olivier Poulard

1:16 Evolution of Accelerance’s Consulting Arm

3:03 The Myth of “Adding More People”

5:09 Aligning Clients and Partners for Real Outcomes

8:18 Why You Can’t Scale Chaos

10:46 The Two-to-Tango Rule in Global Delivery

12:28 Top SDLC Bottlenecks: Ambiguous Requirements & Bad Estimation

18:42 Building Predictable Estimation Models

21:19 The Power of a Strong Definition of Done

22:24 Using Checklists to Stabilize Teams

24:00 The Hidden Costs of Context Switching

27:13 Controlling Change Before It Controls You

29:11 Restoring Predictability Without Stalling Delivery

32:37 Measuring Team Health and Stress Indicators

34:03 Final Thoughts on Effective Partner Collaboration

Keywords:

Software Without Borders, Andy Hilliard, Olivier Poulard, Accelerance, software delivery, global engineering, software development lifecycle, SDLC bottlenecks, outsourcing strategy, agile transformation, software estimation, offshore teams, nearshore delivery, global software operations, leadership in tech

On today's episode, we sit down with Raja Musunuru, CPO at Tiffin and a seasoned leader with over 25 years across Fortune 500 companies and innovative startups. Raja shares how AI is transforming the way products are built—shortening cycles from months to days, empowering small but mighty teams, and reshaping the global talent model. From crisis leadership lessons at Gaylord Hotels to redefining donor-advised funds with AI-driven innovation, Raja brings a wealth of insight into what it means to lead in today’s era of rapid disruption.

If you’re a leader looking to understand how AI impacts product development, talent strategies, and business growth, this conversation is one you won’t want to miss.

Guest Introduction:

Raja Musunuru is the Chief Product Officer at Tiffin, with an impressive background spanning 25 years at organizations like Sony, AAA, Amicus, and Gaylord Entertainment. Today, Raja is at the forefront of AI-powered product innovation, blending technical depth with visionary leadership. He’s passionate about building lean teams that deliver with speed, excellence, and purpose—shaping the future of wealth management, investment intelligence, and beyond.

Key Takeaways:

• True leadership shines in crisis: Raja’s experience during the 2010 Nashville flood taught him radical prioritization that still guides his approach.

• AI isn’t just hype—it’s slashing product development cycles from months to days, enabling faster feedback and clarity between product and engineering teams.

• Small, focused teams deliver better results than bloated headcount—especially when empowered by modern AI tools.

• Senior engineers who adapt thrive with AI, while new grads must become “AI natives” to succeed in today’s market.

• Success doesn’t come from selling AI—it comes from solving real problems better than anyone else.

• The global outsourcing model is shifting from “more people” to “more excellence.”

Chapter Markers:

0:00 Intro

0:15 Guest Introduction – Raja Musunuru’s career highlights

3:00 Defining moments in leadership: lessons from the Nashville flood

7:00 Radical prioritization and the “tour of duty” mindset at Tiffin

10:00 Building lean product teams and rapid MVP cycles

12:00 Where AI creates true disruption in product development

17:30 Aligning stakeholders in a fast-moving AI environment

19:00 How AI is reshaping engineering talent and global delivery models

23:00 Senior vs. junior engineers in the age of AI

26:00 Lowering barriers: from AWS to AI-powered MVPs

29:00 Redefining donor-advised funds with AI and automation

31:00 Global teams: from volume outsourcing to excellence-driven delivery

35:00 What AI means for hiring and talent pipelines

40:00 Closing thoughts and key advice for leaders

Keywords:

Raja Musunuru, Rich Wanden, Tomas Hilliard, It Comes Down To This podcast, AI disruption, product development, lean teams, MVP cycles, global talent model, outsourcing, engineering productivity, donor-advised funds, wealth management innovation, Tiffin, product leadership