Podcast Summary
Podcast: Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: Ep. 502 – Anthony Petitte – Thriving in the Digital Age: How to Empower Remote Teams with Heart
Guest: Anthony Petitte, COO of Finpark (division of Finlock 2000)
Host: Savannah Brewer
Date: August 19, 2025
Episode Overview
This episode dives into the unique, often underappreciated world of the Chief Operating Officer. Guest Anthony Petitte, COO of Finpark, explores the realities of “being the chief behind the chief,” tackling everything from building connected remote teams and combating burnout to innovating with AI, all while supporting company vision from the operational back seat. The honest and heart-forward discussion emphasizes the real impact of COOs, the nuances of executive dynamics, and practical strategies for flourishing as a leader in today’s rapidly evolving business landscape.
Key Discussion Points & Insights
1. Anthony’s Role, Company Structure & Operational Complexity
- Finlock 2000: Long-established ($400M) player in transportation finance with three divisions:
- Finpark (Anthony’s focus): Pay-to-park marketplace for commercial drivers/fleets (~$1–2M, fast growth startup within the group)
- VHub: Asset repositioning tool for trailers (historical $5–7M)
- Parent Company: A Canadian manufacturing & distribution multinational facing headwinds from recent tariffs.
- Anthony leads operations, marketing, partnerships, and strategy for Finpark and supports VHub.
- Daily Focus: Process-building, strategy development, benchmarking against competitors, and preparing CEOs for execution.
- Quote:
“All grit and no glory...I put together the strategy on a day to day and then it gets executed by the CEO. So CEO goes out and executes it, gets all the glory, where it was really much my work at the end of the day.”
(07:13, Anthony)
2. The Reality of Being COO vs. CEO
- Having sat in both seats, Anthony provides a realistic look:
- COO Pros: No direct board or investor pressure, focus on efficiency/strategy, chance to empower the CEO.
- COO Cons: Less public recognition and affirmation.
- Highs: Seeing strategies lead to successful investment or growth outcomes—even if others get the public credit.
- Advice: Despite lack of recognition, it’s a prime role for impactful company-building.
- Quote:
“You're just basically prepping them up, right? So they go…and investors love what they see. And they love what they saw because it was the time and effort that myself, as well as CFO…have put in.”
(10:43, Anthony)
3. CEO-COO Relationship
- Essentials: Deep trust, friendship, personal connection outside office walls.
- Quote:
“You’re basically like best friends…If you’re not best friends, it’s probably not a right environment...”
(12:17, Anthony) - Tension & Clashing Styles:
- Anthony values creativity, CEO is more rigid—requiring negotiation and factual persuasion.
- Quote:
“We have a different lens on building company…That colorful, that creativity, that, that thinking outside the box, he doesn’t like. So...it creates some tension. But we figure out…how we want to approach certain things.”
(13:36, Anthony)
4. Leading Up: Making a Case for Change
- Principle: Always bring data and evidence when proposing creative/new approaches.
- Preparation builds credibility and helps manage resistance to new ideas.
- Quote:
“If I’m trying to create something that’s different…It has to be fully documented…and it allows that person to go, ‘Well, I can’t deny facts.’”
(16:46, Anthony)
5. Remote Culture: Creating Cohesion without Walls
- Team Structure: 100% remote in the US (~20), major teams in Montreal & St. Georges, QC (50–150+).
- Culture-building Tactics:
- In-person meetups (e.g. Nashville, trips to Canada for exposure to HQ), pairing teammates regionally for face-to-face connection.
- Emphasis on open communication, diverse and creative environments.
- Stat: Engaged employees are up to 23–46% more productive.
- Quote:
“Culture is everything. If you don’t have a good culture, you’re not going to be successful in your company…”
(21:40, Anthony)
6. Remote Burnout: Recognizing and Addressing It
- Proactive Approach: Regular personal check-ins, honest conversations, direct support—even helping team members find better-fit opportunities if needed.
- “If it’s not the right environment here for you, then please let me know…I am very connected to other individuals…that could be a better environment for you.”
(28:31, Anthony)
- “If it’s not the right environment here for you, then please let me know…I am very connected to other individuals…that could be a better environment for you.”
- Retention: Being seen, heard, and supported—at all levels.
- “It doesn’t matter if they’re an intern or…another…C level position. I’m just built like that…I want to make sure they’re okay…”
(33:26, Anthony)
- “It doesn’t matter if they’re an intern or…another…C level position. I’m just built like that…I want to make sure they’re okay…”
7. AI – The Real Impact vs. the Buzz
- Reframing AI:
- AI is not new (spellcheck, Siri, Alexa are all AI): hype is recent, but the substance is long-standing.
- Balance: AI can streamline or automate work, but shouldn’t be seen solely as a threat—rather, a way to elevate people into more meaningful or strategic roles.
- “What if you allow those executive assistants to take a larger role in the company?”
(36:48, Anthony)
- “What if you allow those executive assistants to take a larger role in the company?”
- Leadership Mindset: Encourage becoming indispensable by mastering and integrating AI, not replacing human contribution.
- “It’s just how you understand it and how you can utilize it to be the best in your industry, your company, and also use it as the best practice.”
(37:48, Anthony)
- “It’s just how you understand it and how you can utilize it to be the best in your industry, your company, and also use it as the best practice.”
8. AI as a Tool—Not a Crutch:
- AI is everywhere but should be used responsibly—avoid “false productivity.”
- Leaders must check for overuse (e.g., formulaic reports) and encourage true, authentic work.
- Quote:
“I want to make sure when you’re generally writing up a report, it’s coming from here and it’s coming from knowledge—not just AI that can write it in 30 seconds…”
(40:12, Anthony)- Fiduciary duty: Use AI to support, not replace, responsible leadership and company interests.
Notable Quotes & Memorable Moments
-
On COO Recognition:
“I’m the behind the scenes guy. It’s a great position, a great role…I just don’t get the glory I want.” (07:13, Anthony) -
On Relationships:
“Relationships run the world. And it’s true.” (12:13, Anthony) -
On Creativity vs. Tradition:
“We should do something completely different that no one else is doing…How are we going to stand out against competition?” (13:54, Anthony) -
On Burnout:
“I want you to be seen, I want you to be heard. I want to make sure that whatever you’re going through…I can help out with.” (28:00, Anthony) -
On AI’s True Nature:
“AI has only been a buzzword for two years, but really, AI has always been there… when you’re running a text message, for example, and it fixes the word…that’s AI.” (35:35, Anthony) -
On Responsibility Amidst Tech:
“I have a financial, fiduciary, operational responsibility to my company to make sure that you do everything the right way…” (41:38, Anthony)
Timestamps for Important Segments
- 00:40–04:50: Anthony’s background, company structure, and responsibilities
- 05:19–09:16: Day-to-day COO operations, “all grit, no glory,” role execution
- 09:16–11:49: Highs & lows of COO vs. CEO, lessons from both seats
- 12:10–13:25: Building the CEO-COO relationship, trust, and personal connection
- 13:36–16:19: Working through tense or divergent views; creativity vs. tradition
- 16:19–18:02: Persuading with data, leading up, making cases for innovation
- 19:48–24:46: Remote team culture—building cohesion, meetups, engagement stats
- 26:52–33:26: Spotting and addressing remote burnout, retention, and genuine support
- 35:35–38:00: AI’s real role, reframing fear, and upskilling for the future
- 39:43–42:09: Using AI responsibly—balancing efficiency with authenticity
- 44:41–46:34: Productivity tools, the value of handwriting, and cognitive strategies
- 47:40–49:30: Personal and professional outlooks for the next six months
Practical Takeaways & Tools
- Culture & Connection: Make time for team building—offsites, pairing up, and informal interaction matter in remote settings.
- Burnout: Regular, empathetic check-ins; prioritize individual well-being over immediate productivity.
- AI: Embrace AI as an enhancer, not a replacement. Use data, but maintain authentic, original work. Encourage upskilling.
- Data-Driven Leadership: Always back strategic pitches with data to gain consensus across leadership divides.
- Personal Productivity: Keep a handwritten journal or notebook to stay organized and reduce mental stress from “open loops.”
Final Reflections
Anthony’s appearance on the Second in Command podcast offers a rich, honest look at what it takes to thrive in operations leadership today—balancing creativity and rigor, tech innovation and human connection, and supporting the company (and its people) through both uncertainty and opportunity. His people-first approach and authentic leadership style set a high bar for COOs, especially in remote, rapidly evolving industries.
Listen to the full episode for more actionable wisdom and real-world insights from top operational leaders.