The Tech Trek

In this episode, Rebecca Price joins Amir to discuss the critical transition founders face when evolving into successful CEOs. Rebecca, leveraging her experience as a Partner at Primary Venture Partners, shares insights into the attributes that contribute to a founder's success, the common pitfalls that lead to failure, and actionable advice for navigating this complex journey. This conversation is a must-listen for leaders in tech and startup ecosystems who are eager to enhance their leadership capabilities and scale effectively.

Key Takeaways

Timestamped Highlights

Quote of the Episode

"Organizations become the embodiment of their leaders. A CEO's job is to create alignment, build trust, and set the vision to drive performance." – Rebecca Price

LinkedIn: https://www.linkedin.com/in/rebecca-levine-price

Call to Action

If you enjoyed this episode, please share it with fellow tech leaders and founders. Don’t forget to subscribe, leave a review, and share your feedback!

In this episode, Chris Fahey, SVP of Talent and HR at Volition Capital, discusses the often-overlooked value of org charts for growing companies. He discusses how they can pinpoint hiring gaps and the importance of focusing on roles, not just people. Chris also highlights the importance of aligning your company's strategy with its structure and regularly revisiting this alignment for smoother scaling. Great tips for founders and businesses aiming for efficient growth!

Highlights:

01:47 The Importance of Org Charts in Business

Guest:

Chris Fahey is the Senior Vice President of Talent and Human Resources at Volition Capital. With extensive experience in talent acquisition and HR leadership, Chris deeply understands organizational strategy and scaling businesses. He focuses on aligning a company's talent needs with its broader strategic goals, helping growing businesses optimize their organizational structure and enhance hiring processes. Chris is passionate about building high-performing teams and fostering company cultures that drive success, especially in high-growth environments.

https://www.linkedin.com/in/fahey02

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Thank you so much for checking out this episode of The Tech Trek. We would appreciate it if you would take a minute to rate and review us on your favorite podcast player.

Want to learn more about us? Head over at https://www.elevano.com

Have questions or want to cover specific topics with our future guests?

Please message me at https://www.linkedin.com/in/amirbormand (Amir Bormand)

In this episode, Amir Bormand chats with Christina Stejskalova, Director of Data at Ontra, about the pivotal role of data professionals in startups and the strategic considerations surrounding their hiring. They explore how early investment in data expertise impacts AI strategies, product development, and long-term company success. Christina shares valuable insights from her time at Facebook and leadership roles in Series B startups, offering a fresh perspective on integrating data into business decision-making.

🗝️ Key Takeaways:

⏱️ Timestamped Highlights:

📢 Quote of the Episode:"The best companies in the world use data to drive their revenue growth. Startups need to stop seeing data teams as cost centers and start leveraging them as a strategic asset." – Christina Stejskalova

🔗 Connect with Christina:Find Christina Stejskalova on LinkedIn: https://www.linkedin.com/in/christinastejskalova/

✅ Call to Action:What are your thoughts on when to hire a data professional? Have you seen early data strategies succeed or fail? Share your experiences! Don’t forget to like, subscribe, and leave a review.

In this episode, we dive into how businesses leverage data platforms and AI to serve the business effectively. Addhyan Pandey shares insights into Zoro’s AI journey, the role of machine learning, data technical debt, and the shift toward self-service analytics.

Key Takeaways

🔹 AI vs. ML in Business: While AI is a hot topic, many companies still rely on traditional machine learning (ML) models like recommendation systems and predictive analytics.

🔹 The Data Technical Debt Challenge: Companies struggle with historical data issues, making AI adoption difficult. Addressing data governance and quality from the source is crucial.

🔹 Self-Service Analytics & AI: The demand for self-service analytics is rising, but human oversight remains necessary to ensure accuracy and meaningful insights.

🔹 AI’s Role in Decision-Making: AI can support but not replace business leaders. Decision-making must balance data-driven insights with strategic judgment.

🔹 Stakeholder Collaboration: Business leaders need to be more forward-thinking in adjusting their data processes to maximize AI benefits.

Timestamped Highlights

⏳ [00:01:00] – Introduction: Addhyan shares Zoro’s approach to AI and M

⏳ [00:03:00] – Data quality & technical debt: How companies still struggle with basic BI

⏳ [00:06:30] – Balancing new AI innovations with messy legacy data

⏳ [00:09:00] – The challenges of making AI useful for stakeholders with poor data

⏳ [00:12:00] – The rise of self-service analytics & human-in-the-loop AI

⏳ [00:15:00] – How AI-powered recommendations still need human judgment

⏳ [00:17:00] – Addhyan’s 60-day assessment at Zoro & future AI priorities

Quote of the Episode

"We do not have—and won’t have anytime soon—perfect AI tools. Human oversight is essential to make AI work for businesses effectively." – Addhyan Pandey

Connect with Addhyan

📍 LinkedIn: Addhyan Pandey

📍 Twitter/X: @AddhyanPandey

LinkedIn: https://www.linkedin.com/in/addhyan-pandey

In this episode, I sit down withMatt Birnbaum, Partner atPear VC, to discuss one of the most critical aspects of early-stage startups:structuring equity for early hires. We dive deep intohow founders should allocate equity, common pitfalls, and how to ensure flexibility for future growth. If you’re an early-stage founder, considering joining a startup, or just want to better understand the mechanics of equity distribution, this episode is packed with valuable insights.

We also discuss Pear VC’sstartup equity calculator, amust-have resource for founders and candidates alike. If you're navigating startup hiring or negotiating an offer, this episode is for you!

Key Takeaways

• Equity Allocation Matters: The way you structure early equity sets the tone for compensation and expectations in your startup.
• Early Hires Take More Risk, So They Get More Equity: The first technical hire should receive significantly more equity than the tenth, but many founders don’t account for this.
• Equity Pools Need Strategic Planning: Many founders either set aside too little or too much, leading to dilution or a lack of hiring flexibility.
• Plan for a Buffer: Keeping a25% buffer in your option pool allows flexibility for future hires, key recruits, and strategic pivots.
• Technical vs. Non-Technical Equity: While technical hires often receive a premium, some non-technical roles can be just as critical—founders should plan accordingly.
• Candidates Should Ask Smart Questions: If you’re negotiating equity, ask about the total equity pool, planned headcount, and how your grant was calculated.

Timestamped Highlights

[00:00:00]Introduction – Welcoming Matt Birnbaum, Partner at Pear VC, and discussing the episode’s focus on startup equity.

[00:01:16]What is Pear VC? – Early-stage investment approach and how Pear supports founders beyond capital.

[00:02:37]Why Startup Equity Structure is Critical – How it impacts long-term hiring and company growth.

[00:05:22]Common Mistakes in Equity Planning – Founders often rely too much on benchmarks without understanding the logic behind them.

[00:07:56]Equity Pool Size & Flexibility – Why 10% is the typical equity pool and the importance of maintaining a buffer.

[00:10:44]Negotiating Early Hires’ Equity – How to balance offering enough equity without overcommitting.

[00:14:19]How Founders Should Talk About Equity – Advice on explaining equity offers in a way candidates understand.

[00:19:35]Technical vs. Non-Technical Hiring – Does a non-technical hire deserve as much equity as an engineer?

[00:23:47]The Risk vs. Reward Equation – Why the first hire gets significantly more equity than the tenth hire.

[00:27:28]Final Thoughts & Resources – How to reach Matt and access the Pear VC equity calculator.

Quote of the Episode

"Instead of closing your eyes and picking numbers from a benchmark, take the extra steps to plan your equity spend. It’s the difference between thriving and struggling down the road." –Matt Birnbaum

Resources & Links

• Pear VC Startup Equity Calculator: https://pear.vc/how-to-structure-startup-equity-for-early-hires/
• Matt Birnbaum on LinkedIn: linkedin.com/in/birnbing

Connect with Us

• Subscribe to The Tech Trek for more episodes
• Share this episode with a founder or candidate who needs to hear it!

In this episode, Amir Bormand speaks withSandeep Bhadra, General Partner at Vertex, about the journey and challenges of early-stage founders. Sandeep dives deep into the psychology of being a founder, the importance of support systems, and how investors can serve as mentors. They also discuss essential skills founders often lack, navigating pivots, and the role of distribution in building a business. If you're a current or aspiring founder—or just curious about the world of startups—this episode is packed with valuable insights!

Key Takeaways:

1. The Lonely Road of Founders: Founders often feel isolated as they navigate personal growth and business challenges. A co-founder or coach can make the highs less high and the lows less low.
2. Skills Gaps in Founders: First-time founders often underestimate the importance of distribution and managing teams with diverse skill sets.
3. Pivoting with Purpose: Instead of building endlessly, test new ideas by pre-selling or validating hypotheses before committing resources.
4. The Role of Coaching: Coaching isn't just for founders—investors need to hone their ability to guide without dictating and foster trust with their portfolio companies.
5. Customer-Centric Thinking: Successful founders prioritize understanding customer pain points over the technical capabilities of their product.

Timestamped Highlights:

• [00:01:00] - Introduction to Vertex and Sandeep's role in backing technical founders.
• [00:02:00] - The psychology of founders: loneliness, personal growth, and the need for mentors.
• [00:05:00] - Building non-consensus ideas: What makes a startup truly innovative.
• [00:08:00] - Gaining trust as an investor to help founders open up about challenges.
• [00:13:00] - Founders’ common blind spots: Distribution and managing cross-functional teams.
• [00:16:00] - The art of pivoting: How to avoid endless building and validate ideas effectively.
• [00:19:00] - Amazon’s strategy: Writing the press release first to refine the product vision.
• [00:21:00] - How to connect with Sandeep: Twitter (X), LinkedIn, and Vertex’s website.

Memorable Quote:

"The best athletes in the world have coaches, the best musicians have coaches, and founders are no different. Having someone in your corner who can provide perspective makes all the difference." – Sandeep Bhadra

Connect with Sandeep:

• Twitter (X):@BhadraSandeep
• LinkedIn:Sandeep Bhadra
• Vertex Ventures Website:vvus.com

Call to Action:

If you enjoyed this episode,share it with a friend who’s a founder or considering starting their journey. Don’t forget tolike, subscribe, and comment with your thoughts on the episode or topics you'd like to hear more about!

In this episode, Amir Bormand sits down with John Cottongim, Co-Founder and CTO of Roots Automation, to explore how automation and generative AI (GenAI) are revolutionizing the insurance industry. John brings deep expertise from his 13-year tenure at AIG, sharing insights on legacy systems, data challenges, and the evolving role of digital co-workers. He discusses the intersection of process automation, data quality, AI adoption, and how companies can strategically implement AI without disrupting their workflows.

Key Takeaways

🔹 Insurance’s Tech Debt is Massive – Large insurance companies operate on hundreds or even thousands of legacy systems, making modernization complex.

🔹 Process Automation is a Game-Changer – Digital co-workers can handle high-volume, structured processes like claims intake and underwriting, improving efficiency without drastic process overhauls.

🔹 The Data Quality Dilemma – Poorly structured, inconsistent data has been a barrier to AI adoption, leading many insurance firms to struggle with leveraging data lakes effectively.

🔹 Choosing What to Automate – The best automation candidates are high-volume, repetitive tasks with clear guidelines. Avoid low-impact projects that don’t drive ROI.

🔹 The Future of AI in Insurance – Instead of a single "super AI," the industry will see a network of narrow AI models trained specifically for underwriting, claims processing, and other specialized tasks.

🔹 Adoption Challenges – Employees are often comfortable with inefficient processes. Successful automation integrates smoothly without demanding drastic workflow changes.

Timestamped Highlights

⏳ [00:01:00] – What is Roots Automation? Introducing InsureGPT, digital co-workers designed for insurance automation.

⏳ [00:03:00] – The massive legacy tech burden in insurance: Why do companies still run on decades-old systems?

⏳ [00:06:30] – The data problem in insurance: Why data lakes failed and how AI can improve data capture and structure.

⏳ [00:10:00] – How to pick the right automation projects: Find high-impact, high-volume tasks rather than niche, low-risk ones.

⏳ [00:15:00] – The tech debt of insurance processes: How decades of quick fixes have created a tangled mess of workflows.

⏳ [00:19:00] – Change management and adoption: How to help teams transition from manual work to digital co-workers.

⏳ [00:24:00] – The rise of narrow AI: Why insurance AI models must be specialized rather than all-purpose.

⏳ [00:26:00] – The future of AI in insurance: How companies will need to orchestrate multiple AI models for efficiency.

Quote of the Episode

"The biggest mistake in automation is choosing a process that’s ‘safe’ but not impactful. If it’s not a high-value problem, no one will care when you solve it." – John Cottongim

Connect with John Cottongim

📩 Email: [email protected]

🌐 Company Website: Roots Automation

Enjoying the Podcast?

💡 Share this episode with a colleague who’s interested in AI and automation in insurance!📩 Subscribe, rate, and leave a review to help us keep delivering great conversations.

In this podcast episode, Amir Bormand interviews Michelle Avery, Group VP of AI at WillowTree, a TELUS International Company. They discuss the process of prototyping Generative AI (Gen AI) solutions and transitioning from prototypes to production-ready applications. Key points include identifying business problems, the importance of intentional prototyping, overcoming data access challenges, and ensuring user acceptance and ROI. Michelle shares insights from her work at WillowTree, emphasizing the role of strategic planning and cross-disciplinary collaboration in successful AI implementation.

Highlights

01:34 Prototyping Gen AI Solutions

03:25 Identifying Business Problems for AI Solutions

06:40 Challenges in Prototyping and Data Access

07:55 From Prototype to Production

09:57 Ensuring User Acceptance and Feedback

16:01 Moving Beyond Chatbots

Guest:

With 17 years of experience across engineering, AI, FinTech, and Robotics, Michelle Avery is a technical leader in the Data and AI space. As the Group Vice President of AI at WillowTree, a Telus International Company, Michelle is passionate about building responsible, production-ready AI applications that address real-world business problems. She leads innovative initiatives in generative AI, oversees impactful research projects, and drives the development of data-intensive applications for Fortune 100 clients.

www.linkedin.com/in/michelle-avery-63729bb7

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Thank you so much for checking out this episode of The Tech Trek. We would appreciate it if you would take a minute to rate and review us on your favorite podcast player.

Want to learn more about us? Head over at https://www.elevano.com

Have questions or want to cover specific topics with our future guests?

Please message me at https://www.linkedin.com/in/amirbormand (Amir Bormand)

What if the best way for your child to learn wasn’t in a traditional classroom?

In this episode, Amir Bormand sits down with Amir Nathoo, Co-Founder and Head of Outschool, a live online learning marketplace that’s rethinking how—and where—kids learn. With over a million learners served, Outschool has quietly become a powerful alternative for families looking to break out of the one-size-fits-all education system.

Amir shares the backstory of Outschool’s creation, how the pandemic accelerated online learning, and why education must be rebuilt around engagement, not just content. From the future of AI in personalized learning to working around rigid school systems, this conversation challenges everything you think you know about education.

Key Takeaways:

Marketplace models can drive systemic change in education—not just convenience.

The best teacher for one child might not be the best for another. Fit matters more than credentials.

Online learning isn’t a fallback—it can be a powerful first-choice when designed for engagement.

AI can support personalization in education, but it can’t replace the human element that sparks true learning.

Standardized testing may be holding back students who simply haven’t found the right learning environment.

Timestamped Highlights:

[01:00] – What Outschool is and why piano lessons over Zoom actually work

[04:00] – The “aha” moment: why Amir believed education needed a new system—not just tweaks

[07:00] – What happened when Outschool grew 20x in one year during the pandemic

[10:00] – Why parents now get online learning—and how that changes everything

[14:00] – The hidden tragedy of students thinking they’re “bad at math” because of the wrong fit

[21:00] – The two biggest problems in education: personalization and engagement—and how AI fits in

[24:00] – Why banning AI is the wrong conversation—and how we should be talking about learning motivation instead

Quote of the Episode:

"We created the game. If kids are using AI to jump through hoops, that’s on us—not them. The real problem is they’re not motivated to learn." – Amir Nathoo

Resources Mentioned:

Outschool – Explore the platform and sign up for free

Khan Academy – Referenced in the discussion of EdTech and learning content

ChatGPT / LLMs – Discussed in the context of student use and AI-assisted education

Call to Action:

If you're a parent, educator, or just someone who cares about the future of learning—this episode is a must-listen.

🎧 Subscribe to the show, share this episode with a friend, and explore the classes at Outschool.com.

Let us know what you think learning should look like in 10 years.

In this engaging episode, Amir Bormand sits down with Brian Moseley, Co-Founder and CTO at Sixfold, to explore the nuances of making critical technical decisions. They dive into the concept of technical debt, balancing short-term wins with long-term scalability, and how context plays a crucial role in decision-making. From real-world examples to thought-provoking discussions on collaboration and the evolution of work, this episode offers valuable insights for anyone navigating the challenges of technology leadership.

Key Takeaways:

1. Technical Debt Defined: Brian explains technical debt as a trade-off—achieving short-term goals by borrowing from future scalability or efficiency.

2. Context is King: Decisions made without documented context often face harsh judgments in hindsight. Capturing reasoning through comments or specs builds future empathy.

3. Collaboration & Whiteboards: The role of real-time collaboration tools, like whiteboards, is vital in identifying and solving architectural challenges early.

4. The Role of Experience: As teams grow, written documentation and shared knowledge become critical to avoiding pitfalls of tribal knowledge.

5. Remote Work Challenges: The shift to remote work has impacted collaborative decision-making, with teams grappling to replicate the fluidity of in-person brainstorming.

6. Future of Collaboration: Emerging tools, including VR and Gen AI, may bridge the gap for remote teams in technical discussions and knowledge sharing.

Timestamped Highlights:

• [00:01:00] - Introducing Sixfold and its mission to empower insurance underwriters using generative AI.

• [00:03:00] - What is technical debt? Brian’s analogy of “charging the card” and trade-offs.

• [00:06:00] - The importance of documenting context to avoid harsh judgment on past decisions.

• [00:10:00] - Video snippets and asynchronous communication for capturing context.

• [00:14:00] - Writing, diagramming, and their role in scaling teams effectively.

• [00:16:00] - The value of whiteboard sessions in identifying potential technical challenges.

• [00:20:00] - Work-from-home limitations and their impact on collaboration.

• [00:23:00] - How incorporating collaborative activities can accelerate team productivity.

• [00:24:00] - Looking ahead: VR and advanced tools as potential game changers for remote collaboration.

Memorable Quote:

"If you write down your reasoning around the choices you're making and record them, it helps future engineers understand the context. It builds empathy and keeps you from being judged harshly." – Brian Moseley

Connect with Brian:

• Email: [email protected]

• LinkedIn: Brian Moseley

Follow the Podcast:

Don’t forget to like, subscribe, and share this episode! Have thoughts on critical technical decisions? Leave us a comment or connect on social media to continue the conversation.