The Tech Trek

What happens when UX design collides with generative AI? In this episode of The Tech Trek, Amir sits down with Mickey Alon, CEO and co-founder of Eucera, to explore how AI-first design is redefining SaaS product experiences. Mickey shares his vision for conversational UX, why menus are becoming obsolete, and how intelligent agents will soon become the most valuable “team member” in your product. If you build, lead, or design in tech—this one will get you thinking differently.

Key Takeaways

• Traditional UI can't keep up with modern feature sets—AI-first UX unlocks faster access to value

• Conversational interfaces offer personalization and productivity that static workflows can't match

• User expectations are evolving rapidly thanks to tools like ChatGPT—SaaS must catch up

• AI-first design challenges product teams to rethink roadmaps, roles, and even user trust

• Future UX will be hybrid: visual, prompt-driven, and increasingly agentic

Timestamped Highlights

03:12 — Why traditional menus break as SaaS features grow

04:45 — The gap between AI-powered hype and true AI-first product experiences

08:25 — How AI can personalize UX based on user skill level and intent

17:50 — The need for audit trails and observability in AI-driven workflows

21:30 — Will UX roles shrink or expand in the age of AI-first design?

25:20 — What happens when every product is just an agent? Where do you differentiate?

Quote of the Episode

“The companies that will deliver AI-first experiences will outperform—because you're deploying the best person in the company, which is the agent, to assist any number of users in real time.”

Call to Action

If this episode made you rethink the future of product design, share it with a teammate or PM who needs to hear it. Subscribe to The Tech Trek for more smart conversations at the edge of tech, product, and leadership. And connect with Mickey Alon on LinkedIn if you want to dive deeper into AI-first UX.

How do we ship code faster without sacrificing quality or accountability? Greg Foster, co-founder and CTO at Graphite, joins the show to unpack how AI is reshaping code reviews, developer workflows, and the very definition of software engineering. From AI-assisted reviews to the challenge of maintaining context in a world of auto-generated code, Greg shares hard-won insights from the front lines of dev tools innovation. If you care about shipping fast, staying secure, and evolving your engineering org for what’s next — this one’s for you.

Key Takeaways

• Code review is becoming more about collaboration and less about bug catching

• AI-generated code introduces a new challenge: how engineers maintain context without writing the code themselves

• Developer experience is shifting toward orchestration, not just authorship — prompting, reviewing, shipping, and owning

• Stack-based workflows are essential for speed, safety, and parallel progress in an AI-assisted world

• Even with AI in the loop, human accountability — especially for security and architecture — remains critical

Timestamped Highlights

2:10 – Why Graphite calls itself “code review for the age of AI”

4:50 – What code review really means today (hint: it's not just about bugs)

8:40 – The hidden cost of losing context when you’re not writing the code

12:05 – How the developer experience is evolving with AI-generated code

16:10 – Is tech debt still a problem if code becomes disposable?

21:00 – Inner vs. outer loops of development — and why the bottleneck is shifting

26:10 – Why we hold AI to a higher standard than human engineers

Quote of the Episode

“We used to get context for free — just by writing the code. But in a world of AI code gen, we’re going to need new ways to absorb and maintain that context.” – Greg Foster

Resources Mentioned

Graphite: https://graphite.dev

Greg on LinkedIn: https://www.linkedin.com/in/gregmfoster

Email Greg: [email protected]

Pro Tips

Stack your PRs to keep shipping fast and safely. Whether it’s AI or human writing the code, small, parallelized changes are easier to review, test, and deploy — especially when you're operating at high velocity.

Call to Action

Enjoyed this episode? Share it with a fellow engineer, follow the show, and leave a review on Apple Podcasts or Spotify. For more insights like this, connect with us on LinkedIn or subscribe to our newsletter.

What does it take to build startups that last and come back for more? In this episode, Amir sits down with Russ Fradin, serial founder, longtime investor, and now CEO of Larridn. With nearly 30 years of experience and billions raised across multiple ventures, Russ shares what he’s learned about founding companies, hiring the right people, navigating pivots, and representing other people’s money with integrity. This isn’t a highlight reel. It’s a grounded, real-world look at what actually makes a great founder.

Key Takeaways

• Great founders haven’t changed. The barriers to entry have

• The best ideas evolve constantly. Early-stage success is about the team

• Founding with the right people creates longevity and joy in the journey

• Angel investors are betting on judgment, not just ideas

• Fulfillment comes from building with people you respect and admire

Timestamped Highlights

00:53 Why Russ and his co-founder launched Larridn to reimagine productivity in the age of AI

03:48 Lessons from 29 years of company building, from pre-Netscape to today

05:36 How the startup world has changed and what hasn’t since the 90s

12:06 What makes the journey worthwhile even when startups fail

14:56 How Russ chose the right co-founders and why it still matters most

17:52 Knowing which idea to chase and when to pivot with purpose

21:24 What representing other people’s money really means to him as a founder and angel investor

Quote of the Episode

“There’s just nothing better you can do with your time than go to work every day trying to build something amazing with amazing people.”

Pro Tips

When choosing your next venture, ask: where do I have unfair advantage? It’s not just about solving a big problem. It’s about solving the one you’re uniquely qualified to tackle.

Call to Action

Enjoyed this episode? Share it with a founder or investor in your circle. Subscribe to The Tech Trek for more conversations with leaders who’ve done the work and are still doing it. Follow Amir on LinkedIn for more insights and episode drops.

What do founders get wrong when trying to build a startup? Jeff Gibson, CTO and co-founder at Kintsugi, joins the show to break down how he approaches building around real business problems—not flashy features. Drawing from pre-IPO roles at Atlassian and his journey scaling Kintsugi, Jeff shares why understanding cash flow, revenue mechanics, and operational bottlenecks is critical for building something that lasts. Whether you're a startup founder or tech leader, this one’s full of sharp insights on building with purpose.

Key Takeaways

• Solving “boring” problems can be wildly valuable—if you understand where the money flows

• Great businesses start with a clear grasp of what companies actually value, not just what users say they want

• Pre-IPO cleanup reveals hidden complexity in compliance, revenue recognition, and internal tooling

• Pivoting without a strong North Star leads to wasted cycles; solve for the cause, not just symptoms

• Not every successful business needs to be venture scale—but it does need to be viable and focused

Timestamped Highlights

01:17 — What Kintsugi actually does, and why indirect tax is a massive hidden challenge

03:49 — The “pre-IPO cleanup” playbook and how it shaped Jeff’s understanding of business systems

06:52 — Why chasing product-market fit is risky if you don’t deeply understand the business problem

09:44 — Talking to 100 customers before writing a single line of code

12:57 — The opportunity in low-innovation, high-value spaces (think CRMs, billing, compliance)

16:44 — Niche wins: why a $10M business in a focused segment can be more valuable than chasing unicorn status

Quote of the Episode

“You don’t want to find a boring problem that’s commoditized. You want a boring problem that’s valuable.”

Resources Mentioned

• Kintsugi: https://www.kintsugi.com

Call to Action

If you found Jeff’s insights helpful, follow The Tech Trek for more conversations with builders and leaders shaping the future of tech. Share this episode with a founder friend, and don’t forget to subscribe wherever you listen. Want to keep the conversation going? Connect with Jeff on LinkedIn.

Ashok Srinivasan, SVP of Engineering at Aledade, joins The Tech Trek to break down what it really means to have impact as an engineering leader. With experience at Microsoft, Snapchat, Indeed, Dropbox, and now Aledade, Ashok brings clarity on how to assess your value, earn trust, and align technical strategy to business outcomes. Whether you're leading at a scrappy startup or an enterprise giant, this conversation offers a grounded and practical lens on leading with purpose, adjusting your playbook, and knowing when to pivot.

Key Takeaways

• Your first 90 days as a leader should be about listening, learning the culture, and earning trust

• Technical strategy only matters if it maps to business value—long-term bets need short-term execution

• Engineering leadership changes based on company stage: wartime vs peacetime, scale vs speed

• Culture and resilience matter more than expertise—especially in remote, high-change environments

• Great leaders don't just bring the right tools—they know when to use them, and when to stay curious

Timestamped Highlights

00:36 — What Aledade does and why healthcare impact is personal

02:14 — From chip design to engineering leadership: Ashok’s career journey

04:09 — Matching your leadership style to company stage and market dynamics

06:39 — Why trust-building matters more than early change-making

10:24 — How Ashok evaluates engineering impact across people, product, and execution

13:13 — The thrill of learning new business models—and why he keeps switching industries

16:41 — Aligning OKRs with team performance while still shipping hands-on

21:51 — The most underrated skill in engineering orgs: resilience in the face of ambiguity

Quote of the Episode

“Strategies change all the time. If your team isn’t aligned through culture, they won’t be ready to pivot—and that’s what really holds you back.” — Ashok Srinivas

Resources Mentioned

• Radical Candor by Kim Scott

Call to Action

Enjoyed the episode? Share it with an engineering leader you respect. Then subscribe to The Tech Trek so you never miss conversations like this—real insights from people building the future.

Vijaye Raji, CEO and founder of Statsig, left two decades of success at Microsoft and Facebook to start from scratch—at age 41. In this episode of The Tech Trek, we unpack the mindset, planning, and trade-offs that come with becoming a first-time founder later in life. If you've ever wondered what it really takes to leave the safety of big tech to chase a startup dream, this one’s for you.

What You’ll Learn

• Why Vijaye treated the decision to become a founder separately from the idea for Statsig

• How he de-risked the leap by financially preparing his family for the journey

• The emotional rollercoaster of being a solo founder—and how he stays grounded

• The biggest blind spots coming from big tech to startup life (hello, sales and SOX compliance)

• How he thinks about pivoting, product strategy, and avoiding the “limping-along” trap

Timestamps to Catch

02:03 – Why he walked away from Meta and Microsoft

04:32 – The real difference between “wanting to start a company” and knowing what to build

06:17 – How he set a 10-year plan—and avoided the dangerous middle zone

11:54 – What he didn’t know until he had to do it himself: sales, marketing, compliance

15:28 – How he structured support at home to take the leap without a co-founder

21:40 – Tactical advice for future founders to build toward entrepreneurship intentionally

Quote of the Episode

“Startup is not an individual affair—it’s a family affair. It affects people around you in subtle ways, and some not so subtle.”

Resources Mentioned

• Statsig: https://www.statsig.com

• Connect with Vijaye on LinkedIn: https://www.linkedin.com/in/vijaye

Pro Tip from Vijaye

If you’re planning to start a company in the next five years, structure your career today to pick up the missing skills: sales, marketing, financials, hiring, and firing. Be intentional about it.

Enjoyed the episode?

Follow The Tech Trek for more real conversations with startup builders, tech leaders, and product thinkers. Like, subscribe, and share this episode with someone who’s thinking about taking the leap. And if you’ve got thoughts or feedback—drop a comment or connect on LinkedIn.

What if your data science team could drive business outcomes across products, not just models? In this episode, Hicham El-Hassani shares a tested blueprint for building data teams that are adaptable, retention-proof, and ready to ship.

With 18 years of experience, Hicham has led high-impact data science orgs across insurance and software—and he’s not afraid to challenge the standard playbook. He explains why most teams fail to scale, how generalist data scientists can outperform specialists, and what actually matters in model success (hint: it’s not just the algorithm).

Whether you’re a technical leader, hiring manager, or data practitioner, this conversation is packed with insights on how to design for execution, avoid attrition, and get your models into production—fast.

Key Takeaways

Data science orgs need flexible, crew-style structures—not rigid vertical silos

Generalists thrive when given exposure, ownership, and tailored training

Feature engineering and domain context often beat algorithm tuning

Execution and documentation matter more than flashy tools

GenAI will boost productivity—but won’t replace real data science judgment

Timestamped Highlights

02:00 — Why rigid, specialized teams backfire in data orgs

06:45 — The real value of domain knowledge and how to build it quickly

11:50 — How data scientists can shape sales, pricing, and go-to-market strategy

17:30 — A four-phase matrix to structure projects and reduce context switching

23:00 — How AI tools are already speeding up DS workflows (and what’s next)

26:00 — One habit that separates scalable teams from forgettable ones

Quote of the Episode

"Cross-pollination is the best thing—when data scientists are exposed to different business problems, they evolve faster and stay longer."

Call to Action

Enjoyed the conversation? Share this episode with someone building or managing a data team. And if you haven’t yet, subscribe to The Tech Trek for more no-fluff insights from leaders building the future of tech.

What does the “long tail” of AI really look like in a highly regulated industry? In this episode, Dave Wollenberg, VP of Enterprise Data & Analytics at Scan, breaks it down. From cautious experimentation to enabling non-technical users to build AI-driven POCs, Dave shares a grounded, practical perspective on AI adoption inside a Medicare Advantage organization.

You’ll hear why the real transformation isn’t just technical—it’s cultural. We talk about how to shift employee mindsets, educate business teams, and unlock self-service analytics while staying compliant. If you’re a tech or data leader trying to separate hype from real value, this one’s for you.

Key Takeaways:

The long tail of AI means rethinking roles—not just automating tasks

Real AI enablement starts with data quality, governance, and semantic clarity

Non-technical employees can (and should) build AI proof-of-concepts

Change management will make or break your AI strategy

In regulated industries, open source and secure deployment models matter

Timestamped Highlights:

00:55 – What Scan Health Plan does and why AI matters in healthcare

03:10 – From machine learning to generative AI: how use cases have evolved

08:15 – Three types of business users and how to upskill them for AI

12:40 – Shifting expectations: stakeholders want AI-powered insights, now

15:20 – Why self-service BI still falls short without a solid data foundation

18:35 – AI adoption isn’t just IT’s job—business users need to lead too

22:15 – Navigating AI in regulated industries: risks, rules, and realities

Quote of the Episode:

“It's not as if there's a certain amount of work in the world, and if AI takes some, there's nothing left to do. When you make people more powerful, they add more value—and you want more of them, not fewer.”

Pro Tips:

Host internal hackathons to build excitement and break down resistance

Use sandbox environments to safely encourage experimentation

Don't wait for technical users—give your business teams the tools to try

Call to Action:

Like what you heard? Share this episode with someone exploring AI adoption in their org. Subscribe to The Tech Trek for more candid conversations with tech leaders on building, scaling, and leading through change.

What happens when you bring Silicon Valley tech thinking into an “unsexy” industry? Alex Jekowsky, Co-founder and CEO of Cents, shares how his vertically integrated platform is quietly transforming garment care—starting with laundromats. In this conversation, Alex breaks down what it takes to digitize an analog industry, earn operator trust, and build deep value with a lean team. If you’ve ever wondered what it really means to build vertical SaaS for SMBs, this is a masterclass.

Key Takeaways

Start with digitization, not disruption—operators don’t need revolution, they need visibility and options.

Building for SMBs means listening first, innovating later. Reliability beats cleverness early on.

A lean team can deliver better quality by being more deliberate, but it comes with execution risk.

Cents’ growth isn’t about horizontal expansion—it’s about going deeper with each customer.

Clear alignment on mission—“garment care”—enables scale without complexity.

Timestamped Highlights

[01:50] – Why laundromats? The overlooked opportunity in an “unsexy” industry

[06:30] – Digitize first, then provide optionality: Cents' real value proposition

[09:40] – Why innovation is an earned right in SMB SaaS

[12:50] – The tradeoffs and benefits of building vertically with a small team

[16:40] – How Cents plans to grow deeper in garment care without chasing new verticals

[21:50] – Culture, clarity, and staying anchored to the mission—how Cents keeps its edge

Quote of the Episode

"Nobody works with you because you're innovative—they work with you because you work."

Resources Mentioned

Cents: https://www.trycents.com

Call to Action

If this episode changed how you think about vertical SaaS or SMB tech, share it with a founder or product leader who needs to hear it. And don’t forget to follow The Tech Trek for more behind-the-scenes stories on building products that actually move industries forward.

How do you turn GenAI excitement into real enterprise value—without leaving people behind?

In this episode, Amir talks with Mike Urban, Chief Technology Operations Officer at Best Egg, about the overlooked muscle every company needs to build: change management. Mike shares how his team is navigating the real-world complexity of bringing GenAI into production across a highly regulated fintech org—while aligning control and risk teams as unexpected champions of innovation.

If you’re trying to move fast without breaking trust, this conversation is packed with lessons.

Key Takeaways:

Change management isn’t a framework—it’s a living process, just like the changes you’re navigating.

GenAI adoption starts with personalized enablement, not just tooling. Everyone has a different “light switch.”

Risk and control functions can be powerful allies in innovation, not blockers—if brought in early.

Gamified onboarding and grassroots advocacy can shift perception and accelerate adoption.

The real value of GenAI isn’t replacement—it’s amplification. Think "thought partner," not "automation engine."

Timestamped Highlights:

00:47 – What Best Egg does and who they serve in the fintech landscape

01:46 – Why traditional change management often fails in tech orgs

07:42 – The GenAI learning curve: why every employee needs their own light switch moment

10:18 – Risk and control teams as enablers of innovation (not roadblocks)

12:39 – A clever GenAI onboarding experiment with Best Egg’s control team

17:01 – Framing GenAI as a productivity co-pilot, not a job replacer

22:33 – Why GenAI's constant evolution might actually make it easier to adopt

Quote of the Episode:

“Every person has their own GenAI light switch—and once it’s on, it doesn’t turn off.”

Call to Action:

If this episode sparked new ideas for how your team can embrace GenAI more effectively, share it with a colleague or drop us a review. And don’t forget to subscribe so you never miss an episode of The Tech Trek. You can also connect with Mike Urban on LinkedIn to continue the conversation.