Episode Summary: Ep. 446 - Team8 COO & CFO, Roy Heldstein

Podcast: Second in Command: The Chief Behind the Chief
Host: Cameron Herold
Guest: Roy Heldstein, COO & CFO of Team8
Release Date: February 4, 2025

1. Introduction

In this episode of the Second in Command podcast, host Cameron Herold sits down with Roy Heldstein, the Chief Operating Officer and Chief Financial Officer of Team8. Roy brings a wealth of experience from the tech and finance sectors, having previously held significant roles in companies like Checkpoint Software and earned an MBA with high distinction from the University of Michigan's Ross School of Business. Together, they delve into the intricacies of Team8's unique venture creation model, the vibrant Tel Aviv tech scene, and the critical role of a COO in steering organizational success.

2. Guest Background

Roy Heldstein provides an overview of his professional journey, highlighting his transition from finance leadership roles in the tech sector to his current position at Team8. With a foundation in economics and strategy, augmented by an MBA, Roy emphasizes his expertise in data-driven decision-making and financial acumen. This blend has been pivotal in his ascendancy from CFO to a dual role encompassing COO responsibilities at Team8.

3. Tel Aviv as a Tech Hub

Cameron Herold expresses his long-standing fascination with Tel Aviv, both as a city and a burgeoning tech hub.

Roy Heldstein [04:56]: "There is something about the way we're being raised and born that make us more techie and more entrepreneurial in nature."

He attributes Tel Aviv's prominence in the tech industry to the inherent entrepreneurial spirit of Israelis, nurtured from a young age, and further fueled by innovation stemming from the Israeli Defense Forces (IDF). The cultural emphasis on creativity and resilience has cultivated a robust ecosystem conducive to technological advancements.

4. Team8’s Business Model and Operations

Team8 is described as a hybrid venture creation and venture capital firm, managing nearly $2 billion in exits and over a billion dollars in assets under management. Unlike traditional venture capital firms that primarily invest in existing ideas, Team8 actively creates ventures by forecasting future market trends and developing products to meet these anticipated needs.

Roy Heldstein [12:53]: "Once we have a good idea for a product, we move these through a real validation process, both technological and market verifications, and only then do we find the right founders and build a company around this idea."

This proactive approach allows Team8 to incubate and scale companies strategically across sectors such as cybersecurity, AI, fintech, and digital health.

5. The Role of the COO and Roy’s Experience

Roy discusses his dual role as COO and CFO, overseeing finance, HR operations, legal, and marketing. He emphasizes the importance of integrating data and analytics into business operations to provide an objective framework for decision-making.

Roy Heldstein [07:40]: "The advantage of having the data sits under finance and operations is the objectiveness of the data."

This integration ensures that strategic decisions are grounded in accurate, unbiased information, fostering more effective debates and problem-solving within the organization.

6. Company Culture and Leadership

A significant portion of the conversation centers around the importance of people in leadership roles. Roy attributes his effectiveness as a CEO to his ability to connect with and understand his team, customers, and stakeholders.

Roy Heldstein [10:19]: "Once you are able to look at the people in front of you... that's what makes a good CEO more than another CEO."

He also shares insights from his time at the University of Michigan, highlighting how teamwork and collaboration principles learned during his MBA have influenced his approach to building company culture at Team8.

7. Building Companies: Milestones and Processes

Roy outlines Team8's meticulous process for venture creation, which includes:

1. Idea Validation: Assessing market and technological viability.
2. Technological Milestone: Ensuring the product's technical feasibility.
3. Product-Market Fit (PMF) Milestone: Confirming that the product meets market demands.

Each milestone involves rigorous evaluation to identify and address potential obstacles early on, thereby increasing the likelihood of a startup's success.

Roy Heldstein [19:39]: "When you do the fine tuning at the beginning... your chances to have a successful startup are increasingly higher."

This disciplined approach contrasts with traditional venture capital methods, positioning Team8 as a leader in venture creation.

8. Work-Life Balance

Roy candidly discusses the challenges of maintaining work-life balance in high-intensity roles such as CFO and COO. He emphasizes flexibility and prioritizing critical family moments over work obligations.

Roy Heldstein [44:33]: "When there's something that is crucial for my wife or for my kids, no matter what, I'll apologize, but I'll be there."

He advocates for remote work models and structured schedules to optimize productivity while safeguarding personal time.

9. Leadership Meetings and Communication

Roy describes Team8's approach to meetings, focusing on efficiency and effectiveness. They limit the number and size of meetings, prepare agendas in advance, and encourage open dialogue during one-on-ones.

Roy Heldstein [40:26]: "We are trying as the meeting, first of all, we're trying to keep a limited amount of meetings with a limited number of people in each one of the meetings."

By minimizing reliance on communication tools like Slack, Team8 fosters deeper, more meaningful interactions and reduces distractions.

10. Advice for the Younger Self

Reflecting on his journey, Roy offers invaluable advice to his younger self and aspiring leaders:

Roy Heldstein [45:56]: "Run as much as you can. Don't look back... Remember, when it's painful, that's when you are growing up."

He underscores the importance of perseverance, continuous learning, and embracing challenges as opportunities for growth.

11. Conclusion

The episode concludes with Roy Heldstein reiterating the core mission of Team8: "making our companies successful." His strategic vision, combined with a people-centric approach, exemplifies the qualities that make him an effective COO and CFO. Cameron Herold thanks Roy for his insights, wrapping up a conversation rich in practical wisdom for aspiring second-in-command leaders.

Roy Heldstein [47:28]: "It's a great conversation. Thank you for having me."

Notable Quotes

• Roy Heldstein [04:56]: "There is something about the way we're being raised and born that make us more techie and more entrepreneurial in nature."

• Roy Heldstein [07:40]: "The advantage of having the data sits under finance and operations is the objectiveness of the data."

• Roy Heldstein [10:19]: "Once you are able to look at the people in front of you... that's what makes a good CEO more than another CEO."

• Roy Heldstein [19:39]: "When you do the fine tuning at the beginning... your chances to have a successful startup are increasingly higher."

• Roy Heldstein [45:56]: "Run as much as you can. Don't look back... Remember, when it's painful, that's when you are growing up."

Final Thoughts

This episode offers a deep dive into the operational strategies and leadership philosophies that define successful second-in-command roles. Roy Heldstein's experiences and insights provide a blueprint for COOs and aspiring leaders aiming to drive organizational excellence and foster sustainable growth.

For more episodes and insights from top COOs, visit COOAlliance.com.