Second in Command with Cameron Herold

Episode 518: “How to Lead Through Feedback, Focus, and Follow-Through” with Brent Hagen
Guest: Brent Hagen, Chief Supply Chain Officer at Lob
Date: October 14, 2025

Episode Overview

In this episode, Cameron Herold speaks with Brent Hagen, Chief Supply Chain Officer at Lob, about the art and science of effective leadership as a COO. They cover leading through feedback, focus, and follow-through, and dive into how Brent manages logistics for billions of mail pieces, drives operational excellence, and helps his team grow into future leaders. The discussion is pragmatic, candid, and filled with actionable insights for second-in-command executives and aspiring leaders.

Key Discussion Points and Insights

What Is Lob? (02:23–03:52)

• Lob Overview: A direct mail automation platform, orchestrating personalized mail via a network of third-party print houses and logistics partners. The company operates as an orchestration engine, streamlining mail campaigns for customers.
• Market Context: Brent notes the stark difference between U.S. and Canadian direct mail markets, attributing it mostly to postal cost barriers.
  • Quote: “This year the USPS will probably send 90 billion pieces of mail. If you were to look at Royal Mail in the UK or Canada Post, you might do 9 billion pieces...” (03:52, Brent Hagen)

The “Second Act” at Lob (06:23–08:16)

• Launching a New Business Line: Brent describes Lob’s fresh focus on integrating distribution between clients, print manufacturers, and the USPS, using technology to solve for market fragmentation and barriers to entry.
• The initiative both expands Lob’s customer base and improves economics and reliability for existing customers.
• Quote: “We’re excited about [our new initiative] not just because of the new customers and incremental revenue, but also what it presents to our existing customers.” (08:16, Brent Hagen)

Balancing Vision and Execution / Operating at Multiple Altitudes (08:32–10:56)

• Navigating Daily Priorities: Brent explains the importance of working at different “altitudes”—high-altitude strategic thinking and low-altitude operational detail—and the discipline required to know when to zoom in or out.
• Emphasizes establishing clear “cadences” for surfacing issues and knowing when to intervene vs. when to let teams find their own solutions.
• Quote: “A part of them having autonomy is also taking ownership... I take pride in helping my team get there, but not crossing the finish line for them.” (09:49, Brent Hagen)

Growing Future Leaders (12:19–14:40)

• Tailored Development: Brent likens talent development to parenting: recognize employees have different levels of readiness and provide support accordingly.
• Focus on growing people’s business acumen—especially financial literacy (e.g., understanding FP&A, ROI, P&L)—alongside their instinctive or technical skills.
• Quote: “If they want my job... the next thing they’re going to do is go explain it to the board. And the board’s going to ask, ‘How is it tied back to the P&L?’” (12:19, Brent Hagen)

Feedback As a Leadership Superpower (14:40–18:25)

• Learning to Accept Feedback: Brent shares candidly that embracing feedback did not come naturally, and he had to learn it through structured development programs and mentorship.
• He credits early-career exercises—like building a “career flight plan” and receiving honest input from mentors—for helping him see feedback as essential for growth.
• Quote: “It’s not just about this project... It’s about continuing those relationships over time and watching them build on each other.” (16:24, Brent Hagen)

Authenticity in Leadership (18:30–20:37)

• Professional vs. Personal Alignment: Brent recounts a turning point during an “Insights color” exercise at Amazon, where a consultant confronted him about acting differently at home and work. Realizing the exhaustion that comes from “faking it,” he began leading with greater authenticity.
• Quote: “I’m faking it... I think my team wants me to interact with them one way... but that’s not who I am. She’s like, ‘You must be exhausted.’ I was like, ‘I am exhausted.’” (19:09, Brent Hagen)
• Authenticity led to stronger team alignment and ongoing relationships with talent across roles and companies.

Identifying and Growing Emerging Leaders (20:37–22:36)

• What to Look For: Brent seeks subject-matter expertise, a willingness to become well-rounded, and at least one strong skill in managing up, down, or laterally.
• Cross-Functional Growth: Those who manage laterally well—without direct control or authority—stand out and can be coached to broaden their impact across the organization.

Aligning Teams to Vision (22:50–24:19)

• KPI Cascading: Brent advocates a “top-down vision, bottoms-up planning” approach: set North Star metrics at the top, then have teams build plans and metrics that roll up into the vision, driving ownership and accountability.

Channeling Team Creativity & Saying No (25:32–28:09)

• Objectives Drive Priorities: Brent discusses using prioritization (e.g., C&E matrices) to objectively tie ideas and projects back to business goals and financials.
• Quote: “When you can move that into objective [criteria], it’s going to be a benefit.” (26:42, Brent Hagen)
• Avoids “because I said so” leadership, instead explaining the rationale behind prioritization/exclusion of ideas.

Intelligent Headcount Decisions (29:47–32:45)

• Avoiding Reflexive Hiring: Both Cameron and Brent note a common manager mistake: believing every problem can be solved by hiring more people.
• Brent shares a story of challenging even experienced execs on this assumption, advocating for better problem-/skills-gap definition and tying hiring decisions directly to measurable outcomes and ROI.
• Quote: “...what problem are you trying to solve?... has that problem changed over time? And how did we establish these skill set gaps?” (29:47, Brent Hagen)

Mastering Context Switching (32:45–35:31)

• Coping with Executive Whiplash: Brent shares that as a COO, he must regularly set aside the emotional residue of previous meetings—good or bad—to show up effectively for each new audience.
• He describes himself as a “shock absorber,” filtering both pressure and information downward and upward, and deliberately reflecting after meetings about what’s noise versus what matters.
• Quote: “Don’t let that pressure influence your next conversation, your next call, your next day, your next week. I also call it being the shock absorber.” (33:31, Brent Hagen)

Filtering Communication Up and Down (35:31–37:21)

• Information Triage: Brent emphasizes sparing both the board and his teams from unnecessary detail (“noise”), ensuring each group gets relevant, actionable information.
• Practices active reflection on what teams and boards really need, not just what’s been discussed.

Consistent Team Debriefs & Gemba (“Go Look”) Mindset (37:44–39:37)

• Regular Reviews: Brent instills daily, weekly, monthly, and quarterly cadences for “what went right, what went wrong, what did we learn, what’s next, and how do we know it’ll work?”
• Adapts the depth of review to the timeframe, focusing on reliability and continuous improvement over blame.
• Quote: “If you had a really bad Monday, don’t let that influence necessarily the entire month review... unless you believe what went wrong on Monday can happen on any given day ever again.” (39:05, Brent Hagen)

Critical Feedback Without Fear (39:57–41:08)

• Failure is Learning: Brent reframes operations “misses” as learning opportunities and urges his team not to fear constructive criticism.
• Quote: “We shouldn’t look at this as a failure... we shouldn’t be scared of that sort of thing... we’re going to get better as a result of it. That’s absolutely winning.” (40:04, Brent Hagen)

Advice to the Younger Self (41:33–43:21)

• Say Yes, Build Relationships: Brent urges young professionals to accept new challenges, but not at the expense of forging human connections. He admits he focused too much on task completion early in his career and not enough on the relationships that could have made it easier—and more collaborative.
• Quote: “I was so focused on task management versus building the relational rents... that led to me having to do more work than I needed to do because I was doing it by force, and not by leveraging the people around me.” (41:33, Brent Hagen)

Memorable Quotes

• On Letting Teams Own Outcomes
  “I take pride in helping my team get there, but not crossing the finish line for them.”
  — Brent Hagen (09:49)

• On Authentic Leadership
  “You must be exhausted.” // “I am exhausted.”
  — Consultant and Brent Hagen on professional authenticity (19:09)

• On Systematic Feedback
  “Every day, every week, every month, every quarter—what went right, what went wrong, what did we learn, what are we doing next, and how do we know if that’s going to work?”
  — Brent Hagen (37:44)

• On Filtering Information
  “I try to eliminate unnecessary noise on either side.”
  — Brent Hagen (35:31)

• On Embracing Mistakes
  “We shouldn’t look at this as a failure... every time that something goes wrong, we learn something as a result of it.”
  — Brent Hagen (40:04)

Episode Takeaways

• Top COOs work at “multiple altitudes,” shifting seamlessly between strategy and execution.
• A commitment to authentic leadership liberates energy and builds trust.
• Honest, constructive feedback is essential—both given and received—to grow as a leader.
• Building durable internal relationships is as critical as hitting milestones.
• Align all projects to vision and KPIs, and regularly solicit team input on what’s working or not.
• Objectivity and transparency in saying “no” fosters trust and helps teams focus on what matters most.
• Filter and contextualize information for each audience—don’t broadcast all details up or down the org.
• Consistent reflection and learning cycles drive continuous improvement and resilience.