In this conversation, Peeyush Upadhyay, Managing Partner at Pekamiar, sits down with Jen Holmstrom, Partner at Notable Capital.

Jen explains why a company reaching $150 million in revenue with 28 people is no longer innovative, just the expectation. Why an executive who asks how big a team they can build will not make it very far in a hiring process. Why she thinks the one-person unicorn is not hype but probable, and why the code gen tools are still not replacing great engineers.

She breaks down what happens to leadership when teams get this lean, why a leader running twenty-two one-on-ones a week has a problem, and why, with all the innovation, companies still need management. She walks through the roles gaining power, from forward-deployed engineers and the office of the CEO to GTM engineers and a RevOps function that is merging with them.

On compensation, she is candid about how equity is being rewritten, including a 7% grant to a Series B head of engineering who was not even the CTO, and two-year vesting used just to get talent in the door.

Her answer to what separates the best founders is talent on offense. Repeat founders carry the battle scars of a bad hire, and they go out and meet great people long before they need them.

She also gets into the lesson Meta taught her about what really matters on day one, why you hire for where the company is going rather than where it is, what she saw in the founders of Handshake and HashiCorp, and why recent grads had better arrive with their AI skills ready for a bit of reverse mentorship.

This episode is part of our series on The Scaleup Flight featuring the Talent Leaders inside VC funds. The people who watch hiring play out across an entire portfolio, and whose knowledge almost never gets written down anywhere.

00:00 Highlights

01:32 Meet Jen Holmstrom

06:10 Lessons from search, Meta and venture

12:13 Is the one-person unicorn real?

14:20 $150 million with 28 people

15:46 What happens to leadership in lean teams

22:02 The rising roles: FDEs, GTM engineers and RevOps

30:12 Equity, comp and the 7% grant

38:03 Talent on offense: what repeat founders do differently

42:51 Why executive hires break

48:22 What Jen saw in the founders of Handshake and HashiCorp

55:49 Rapid fire

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In this conversation, Peeyush Upadhyay, Managing Partner at Pekamiar, sits down with Beth Scheer, Head of Talent Intelligence at Theory Ventures.

Beth explains why founders overhire without realising it, and why that is the most expensive mistake she sees. What to tell a founder whose engineer has a million dollar offer from a frontier lab, and why a candidate interviewing at the big labs at the same time is usually window shopping. How she counsels founders who have been told by their board to hire a CRO when what they need is a founding AE.

She breaks down what a modern talent function at a fund actually does, from diligence through the first ninety days after a cheque is signed. She is candid about how she picks search firms, why she wants the partner making the calls rather than someone a year out of college, and why "no search firms, please" sits on her LinkedIn profile.

On what goes wrong, her answer is calibration. Almost every search that breaks, breaks in the same place, and it is rarely the search firm.

She also gets into what a fourteen person fund with five AI engineers changes about her job, how you measure a role that has no obvious metrics, synthetic resumes and candidates who turn out not to be real people, why she has always gone to work for people rather than companies, and what happens to leadership in five years when nobody is hiring juniors today.

This is the first episode in a new series on The Scaleup Flight, featuring the talent leaders inside VC funds. The people who watch hiring play out across an entire portfolio, and whose knowledge almost never gets written down anywhere.

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CHAPTERS

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00:00 Highlights

03:18 1997 to 2026, and what has not changed about hiring

04:53 When a frontier lab offers your engineer a million dollars

06:39 Fourteen people, five AI engineers, one talent team

12:49 "I'm a talent therapist"

14:42 The three pillars of a modern talent function

18:49 The first ninety days after the cheque is signed

22:28 "No search firms, please"

26:27 Why searches break. Calibration, calibration, calibration.

31:45 How do you measure a job with no metrics

35:08 Where inflection hires actually fall apart

38:08 The number one executive hiring mistake

41:41 Comp plans, and the discomfort filter

44:49 Nobody is hiring juniors. So who leads in five years?

45:54 How founders should vet a VC on talent

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LINKS

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Peeyush Upadhyay sits down with Dan Nguyen-Huu, Partner at Decibel Partners, to discuss what he looks for in technical founders at the earliest stage, why timing kills more good ideas than competition does, and what the agent era is doing to cybersecurity.

Dan explains why hustle is still the most underrated thing in AI, why he backs founders who are exceptional at one or two things rather than competent across the board, and why he now treats firm convictions as a liability when a single model release can reset a category. He also gets into the investment that failed because it arrived years before the technology could carry it, and how Decibel uses its community of early adopters to pressure test an idea before writing a cheque.

Peeyush and Dan also dig into the OpenAI agent that broke out of its sandbox, Greg Brockman's "defender's window" and what it means when attacks scale with compute while detection and response still run at human speed, how the CISO profile has shifted toward practitioners out of the NSA and the DoD, and why the first commercial hire is the one founders almost always get wrong.

Timestamps:

00:00 - Intro

02:04 - Why the Founder Who Gets on a Plane Still Wins

03:48 - "Either a Purchase Order or a Restraining Order"

07:49 - Why Decibel Backs the Plumbing, Not the Shiny Stuff

10:10 - Banker, Operator, Investor: What Each Seat Taught Him

16:09 - The Investment That Failed Because It Was Too Early

18:21 - How Decibel's Early Adopters Kill or Confirm an Idea

20:47 - When the Customers Say No and You Invest Anyway

23:07 - Team, Market or Price: What Survives at Pre-Seed?

23:50 - Why We Back Spikes, Not Well-Rounded Founders

25:51 - Should You Raise Venture Money at All?

27:16 - Why Product Market Fit Is Math, Not Magic

29:11 - How Do You Separate Signal From Noise in AI Security?

32:30 - The Agent That Broke Out of Its Sandbox

35:22 - The Defender's Window & Why Defence Has to Scale

37:27 - Is Your Voice Now an Identity Risk?

39:28 - The New CISO Profile: Harder to Sell To Than Ever

41:48 - Keeping a Thesis Alive When Models Ship Every Month

45:32 - Where Technical Founders Get Go-To-Market Wrong

48:17 - Why Talent Is Decibel's Differentiator

49:35 - When the Business Outgrows the Founder Running It

51:02 - Great Product, Great Team, Never Scaled: Why?

53:26 - Quick-Fire Round

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#thescaleupflight #pekamiar #cybersecurity #aisecurity #venturecapital #earlystage #founders

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In this episode, Peeyush Upadhyay, Managing Partner of Pekamiar, sits down with Sanjay Varnwal, Co-founder & CEO of Spyne, to explore how they’re transforming automotive retail — from shaky smartphone photos on crowded lots to studio-quality images, 3D spins, immersive video, and AI-led digital retail.

Sanjay walks through Spyne’s hard pivot from a generic computer vision platform to a deep auto vertical, explaining why they consciously gave up 80% of their revenue to find true product–market fit, and how they scaled from India into the US and Europe, working with over 3,200 dealerships globally.

They talk about:

How dealers can shoot studio-like car visuals using just a smartphone

Why visuals dramatically change lead volume and conversions

Building proprietary computer vision & generative models for auto

Pivoting from multi-vertical to auto-only (and surviving the revenue dip)

Using conversational AI to capture leads 24/7

How to hire for new markets and build a US sales engine from India

What founders should really focus on before raising a Series A

If you’re building in AI, SaaS, or vertical software, or you’re a founder thinking about a painful but necessary pivot, this one is going to hit home.

Chapters

00:00: Introduction to Spine AI and Automotive Retail Transformation

02:53: The Impact of Visual Presentation on Car Sales

06:07: The Capture and Cleanup Process in Automotive Imaging

08:57: The Shift to Specialization in the Automotive Industry

11:44: Revenue Growth and Metrics for Success

14:53: Customer Success Stories and Engagement Strategies

17:52: Adapting to Market Changes and Technology Trends

20:47: Expanding into a Broader Digital Retail Platform

23:49: Fundraising and Future Growth Plans

26:18: Unlocking Funding Success

29:07: Navigating Market Challenges

30:30: Scaling and International Expansion

35:59: Hiring for Growth

42:34: Cultural Cohesion and Leadership

44:55: Future of AI in Auto Retail

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In this episode, Peeyush Upadhyay interviews Sandy Gupta, Co-Founder and COO of Innovaccer, discussing the journey of building the largest intelligent healthcare cloud. They explore the importance of co-founder chemistry, the transition from research to healthcare, and the challenges faced in integrating healthcare data. Sandy shares insights on the decision-making process, the significance of trust among co-founders, and the evolution of Innovator's solutions in the healthcare sector. Sandy then discusses the transformative role of data in healthcare, highlighting the shift toward value-based care and the significance of social demographics in patient outcomes. They discuss the challenges faced by the healthcare industry, including rising costs and the need for automation through AI. The conversation also touches on the significance of building a strong company culture and navigating tough leadership decisions in a rapidly changing environment.

Chapters

00:00 - Introduction to Innovaccer and Its Vision

02:57 - The Journey of Founders and Their Chemistry

05:58 - Transitioning from Research to Healthcare

08:52 - The Decision to Focus on Healthcare

12:01 - Building the Healthcare Intelligence Cloud

14:52 - Challenges and Solutions in Healthcare Data

17:57 - Scaling and Integrating Healthcare Solutions

26:38 - Data-Driven Healthcare Transformation

28:11 - Value-Based Care: A New Paradigm

30:49 - The Role of Social Demographics in Healthcare

32:57 - Preventative Care and Patient Insights

34:13 - Healthcare Industry Trends and Challenges

36:35 - AI and Automation in Healthcare

37:32 - Vision for the Future of Healthcare

40:09 - The Role of AI in Primary Care

42:46 - Building a Strong Company Culture

49:20 - Navigating Tough Decisions in Leadership

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In this conversation, Ankit Jain, Co-Founder & CEO of Infinitus, discusses with Peeyush Upadhyay, Managing Partner at Pekamiar, the importance of vulnerability in leadership, the need to focus on people rather than titles in startups, and the journey of a serial entrepreneur transitioning from founder to investor. He emphasizes the significance of understanding customer needs and the potential of healthcare technology, particularly in automating communication processes. The discussion highlights the challenges and opportunities in scaling a business while maintaining a strong company culture. In this conversation, Ankit shares Infinitus' journey from identifying a significant problem in healthcare to building a product that addresses it. He, then, touches upon the evolution of their Technology, and the importance of a diverse founding team, highlighting how COVID-19 accelerated their mission. The conversation also delves into the company's culture, values, and the significance of defining success beyond mere numbers. Ankit delves into the intersection of AI and healthcare, emphasizing the importance of viewing technology as a tool to enhance human capabilities rather than a threat. The discussion then segues into the complexities of hiring in startups, the significance of cultural fit, and the role of people operations in maintaining a strong organizational culture. The dialogue also touches on the challenges of scaling a company while prioritizing people, the adoption of AI in operations, and the balance between work and family life. Finally, Ankit shares some powerful insights on leadership, vulnerability, and the human element in guiding teams towards success.

Titles

Embracing Vulnerability in Leadership

The Importance of People in Business

Rethinking Titles and Roles in Startups

The Journey of a Serial Entrepreneur

Transitioning from Founder to Investor

Identifying Opportunities in Healthcare

Chapters

00:00 Embracing Vulnerability in Leadership

06:02 Rethinking Titles and Roles in Startups

12:02 Transitioning from Founder to Investor

14:51 Identifying Opportunities in Healthcare

18:03 Building a Company with Purpose

20:34 Identifying Problems and Building Solutions

21:30 The Evolution of Infinitus' Product

22:58 Learning from Industry Pioneers

24:19 The Naming Journey of Infinitus

25:32 Building a Diverse Founding Team

27:34 The Impact of COVID-19 on Healthcare

29:53 Defining Company Culture and Values

33:13 The Importance of Winning Together

37:02 How to Win: Beyond Numbers

41:08 Building Relationships with Customers

42:33 AI as a Complement to Healthcare

43:30 Hiring Dynamics in Startups

44:31 Understanding Cost in Hiring

45:04 The Importance of Cultural Fit

46:01 Interviewing and Decision-Making

47:35 Encouraging Open Communication

48:04 Cultural Custodians in Organizations

49:31 People Operations and Culture

50:01 Attracting Top Talent to Infinitus

52:26 Scaling Challenges and People Focus

54:06 AI Adoption in Operations

55:08 Balancing Work and Family Life

58:32 Advice for Early-Stage Founders

01:00:01 The Human Element in Leadership

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In this episode, Siddharth Bohra, Founder & CEO of Trmeric, talks about his journey starting out as a commerce graduate to leading multi-billion dollar businesses at Global Tech firms to founding Trmeric, emphasizing the importance of learnability and team building. He shares insights on navigating customer needs, the genesis of Trmeric, and the evolution of its product offerings. The discussion highlights the significance of AI in product development and the modular nature of Trmeric's services, as well as the role of AI co-pilots in enhancing user experience. Siddharth also elaborates on curating a network of service providers and the future directions for Trmeric. In this conversation, the founder discusses the journey of building Trmeric, focusing on product development, user experience, and the importance of customer feedback. He emphasizes the need for a roadmap for future growth, the challenges of fundraising, and the significance of creating a strong company culture. The discussion also touches on the attributes sought in team members, the learning curve in a startup environment, and advice for aspiring entrepreneurs.

Key Topics

The Journey of Learnability and Team Building

Navigating Customer Needs and Product Vision

The Genesis of Trmeric: From Idea to Reality

Identifying Market Problems and Solutions

Building the Prototype and Gathering Feedback

The Evolution of Turmeric's Product Offering

Leveraging AI in Product Development

Chapters

00:00 The Journey of Learnability and Team Building

03:10 Navigating Customer Needs and Product Vision

05:45 The Genesis of Trmeric: From Idea to Reality

09:11 Identifying Market Problems and Solutions

12:02 Building the Prototype and Gathering Feedback

15:07 The Evolution of Trmeric's Product Offering

17:50 Leveraging AI in Product Development

21:00 Understanding the Modular Nature of Trmeric

23:57 The Role of AI Co-Pilots in Enhancing User Experience

26:58 Curating a Network of Service Providers

30:03 Future Directions and Innovations for Trmeric

38:28 Building a Roadmap for the Future

44:10 Focus on Product Experience and User Empowerment

48:20 Navigating Fundraising and Growth Strategies

51:32 Scaling Plans and Team Expansion

54:18 Key Attributes for Team Recruitment

57:46 Defining Company Culture and Values

01:00:27 Learning and Growth in a Startup Environment

01:06:20 Overcoming Self-Doubt and Staying Motivated

01:10:58 Advice for Aspiring Entrepreneurs

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