Second in Command: The Chief Behind the Chief with Cameron Herold

In today's episode of the Second in Command podcast, Cameron is joined by Jennifer Barnes, CEO and Founder of Optima Office, a fractional CFO service provider.During the conversation, you'll get a glimpse behind the curtain of business leadership to explore one of the most misunderstood yet essential disciplines for sustainable growth. Cameron and Jennifer discuss how executives can move from instinct-driven decisions to data-informed strategies, and why the ability to forecast with precision might be the difference between thriving and simply surviving. With real-life examples and personal anecdotes, Jennifer highlights how even successful leaders can miss critical signs when they aren’t looking in the right places.You'll hear cautionary tales from companies that looked strong on the surface but were blindsided by deeper operational missteps. These stories serve as powerful reminders that misjudging certain internal dynamics can have cascading effects—especially when scaling, managing rapid change, or weathering financial uncertainty. Yet, within each challenge lies a roadmap toward clarity, if you're willing to look under the hood.Whether you're an entrepreneur wearing too many hats or part of a leadership team seeking sharper insights, this episode sheds light on how the right support structure can bring discipline, flexibility, and strategic alignment to your organization.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The differences between the roles of a CFO and a controller, including why a CFO looks forward to strategy and forecasting, while a controller focuses on historical accuracy and processes. (0:14)Common pain points such as not knowing gross margins by customer or product, and the importance of understanding these metrics. (8:35)The process of balance sheet cleanup and the importance of having accurate balance sheet accounts to ensure the P&L is correct. (14:11)Creating a P&L budget, balance sheet forecast, and cash flow forecast to predict future financial performance. (16:20)The potential for fractional CFOs to help companies build out their finance teams and eventually replace themselves as the company grows. (22:24)And much more...Guest Bio:Jennifer Barnes is the CEO and Founder of Optima Office, a firm that provides outsourced accounting, fractional CFO, and human resources support to nearly 300 companies nationwide, with a strong focus on the West Coast. With a commitment to flexibility and employee satisfaction, Optima operates on an hourly billing model and embraces a hybrid work environment, guided by the motto “Happy Staff = Happy Clients.” Jennifer earned her Finance and Marketing degree from the University of Arizona, completed her MBA at San Diego State University, and brings over 15 years of experience as a Controller. She has received numerous accolades, including SDBJ’s Woman of the Year and the Top 50 Women of Influence in Accounting and Finance. Jennifer currently serves on several boards and is active in multiple leadership and mentorship organizations.Resources:Connect with Jennifer: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your LeadersDisclaimer:The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Second in Command podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Lauren Antonoff, COO of Life360, a leading family safety and social networking business.In this insightful conversation, Sivana and Lauren discuss the art of effective team management, focusing less on rigid reporting and more on meaningful outcomes. They explore how focusing on key results rather than micromanaging daily activities can drive better performance and foster a culture of trust. The discussion touches on how teams can prioritize what truly matters, making sure efforts align with the overall progress of the business.You'll hear about the evolving role of technology in the workplace, particularly how new tools can empower rather than replace team members. There’s an emphasis on navigating change with openness and creativity, encouraging teams to see innovation as a way to amplify their strengths and take ownership of their work. Cultural values play a crucial role here, shaping how teams adapt to new challenges while staying true to their core mission.This episode invites you to rethink leadership dynamics and encourages a mindset that combines strategic focus, technological adaptability, and authentic human connection.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Lauren's career journey, starting at Microsoft through an acquisition, where she was 'diagnosed' as a product manager. (2:30)The challenges of integrating the Tile app into Life360 and the decision to pull resources from a standalone product launch. (6:27)Lauren's experience of hiring a CMO and CTO to help manage the marketing functions and ensure accountability. (18:37)Why focusing on a few key areas and making disciplined choices to drive success is key to Life360's future growth. (25:38)Her approach to supporting leadership, including regular meetings and in-person gatherings to develop shared views and tackle problems together. (35:22)And much more...Guest Bio:Lauren Antonoff is the Chief Operating Officer of Life360, a leading family safety and social networking app. She brings decades of experience as a product and technology leader, known for driving growth through a focus on customer value, organizational alignment, and execution. Prior to joining Life360 in 2023, Lauren held senior executive roles at GoDaddy, where she led product and services development to empower small businesses. She also spent over 18 years at Microsoft, overseeing major initiatives such as SharePoint and Office 2007, and founded the Step Up Program to advance women in leadership. A former board member of Momentive, Lauren holds a BA in Rhetoric and Political Science from UC Berkeley and began her tech career through the acquisition of ResNova Software.Resources:Connect with Lauren: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your LeadersDisclaimer:The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Second in Command podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

In today's episode of the Second in Command podcast, Cameron reveals a transformative approach to measuring and improving workplace culture—one that many businesses overlook despite its powerful potential: The employee Net Promoter Score. (NPS)You’ll hear about a deceptively simple metric that goes beyond typical satisfaction scores, revealing the true pulse of a company’s internal health. The conversation digs into why traditional methods often miss the mark and how a single question can unlock deep insights about employee sentiment, driving meaningful change without breaking the bank.Get a look behind the scenes of real companies that leveraged this tool to climb the ranks of the best workplaces nationwide, illustrating how culture can become a strategic advantage. From thoughtful ways to gather actionable feedback to surprising tactics that boost morale and loyalty, the discussion explores how cultivating happiness at work directly fuels productivity and profitability. Along the way, you’ll discover how leaders can shift mindsets, set ambitious goals, and create a workplace where people genuinely want to stay—and thrive.Whether you’re aiming to retain top talent, enhance teamwork, or simply understand what truly matters to your people, this conversation offers a roadmap to reimagine what a workplace can be.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:How a simple one-question survey, the Net Promoter Score (NPS) can gather important feedback and improve company culture. (3:27)Why the process of gathering employee feedback is similar to writing a letter to Santa, as well as the importance of acting on that feedback. (4:33)Strategies for improving NPS, including setting ambitious goals and celebrating achievements. (10:59)The need to balance employee happiness with profitability, and why a high NPS can lead to increased revenue and profitability. (11:46)The impact of external competition and the importance of a strong company culture to retain employees. (12:27)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron is joined by Jeana-Rae Kendall, COO of TNG Private Wealth, a private wealth advisory practice of Ameriprise Financial Services, LLC.In this engaging conversation, Jeana-Rae shares her journey from corporate America to the entrepreneurial world, offering a candid look at the evolution of her leadership style and the strategies that helped shape a thriving business. She discusses the unique mindset shift that occurs when transitioning between sectors, emphasizing the surprising realizations and lessons that come with stepping behind the curtain of business operations.You'll hear how her team has built a cohesive and agile remote workplace, where onboarding, accountability, and communication are thoughtfully structured for both efficiency and adaptability. Discover how personal assessments and intentional hiring play a role in aligning company culture, supporting autonomy, and creating a highly collaborative environment.This episode also highlights how growth challenges leaders to develop new skills, particularly in the areas of sales and marketing, and what it means to guide rather than micromanage.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The unique structure of the women-led team and TNG Private Wealth, as well as the benefits of having a diverse leadership perspective.Jeana-Rae's background, including her previous experience at a different brokerage firm and her decision to take a career break during COVID.TNG's onboarding process for new employees, which includes a structured first week to provide a comprehensive overview of the company. The restrictions on marketing and sales communications in the financial services industry and how the team manages within these constraints.The importance of accountability and the role of the COO in fostering a culture of responsibility and performance.And much more...Resources:Connect with Jeana-Rae: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron explores the rapid evolution of cutting-edge tools that are reshaping the way businesses operate. The discussion highlights real-world examples of how quick thinking and innovative approaches can transform seemingly complex tasks into simple, streamlined processes. With insights from industry leaders, You'll hear about the power of leveraging new technology to create impactful solutions on the fly—often with surprising results.  The conversation also explores strategies for driving team adoption of emerging tools, emphasizing the importance of experimentation, collaboration, and internal engagement. Creative approaches, such as friendly competitions and structured learning initiatives, demonstrate how organizations can build a culture of curiosity and efficiency.With practical takeaways and compelling anecdotes, this episode serves as both a wake-up call and a roadmap for those looking to stay ahead in an ever-changing landscape.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:The importance of finding experts who can help automate processes and save time.Why training employees on AI tools and encouraging them to share their learnings with colleagues is vital.The importance of hiring sales and marketing people first to grow revenue before developing leadership skills.Cameron's approach to hiring offshore talent to save costs and increase efficiency.And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron is joined by Brennan Pothetes, current CEO and former COO of Infinity Constellation, a holding company with eight AI-focused companies.In this fascinating conversation, Cameron and Brennan take you behind the scenes of a fast-growing and highly innovative company that’s reshaping an entire service industry. Brennan shares his perspective on what it takes to build multiple successful ventures simultaneously, while maintaining a high bar for leadership, execution, and strategic vision. Through the lens of real-world experience, he offers insight into the principles that drive long-term growth, the importance of founder mindset, and the structures that support sustainable scale.You'll hear about the complexities of aligning people, purpose, and performance in a high-stakes environment. From early-stage incubation to strategic talent selection, the guest explores the nuances of equity, compensation, and cultural alignment—laying out a model that favors ownership and trust over traditional hierarchies. There's also an honest look at how economic conditions and past market cycles influence today’s decisions around valuation, fundraising, and team incentives.This conversation is both a roadmap and a rallying cry for anyone serious about building transformational ventures in today’s evolving business landscape.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Brennan's career path, starting in risk and compliance in banking, moving to Neo banks, and eventually becoming a Chief Operating Officer.The importance of mental health, fitness, and personal well-being for high performance. Infinity Constellation's model of building and scaling AI-driven businesses, including design as a service and executive assistance.The challenges of transitioning from COO to CEO, and the differences in focus between the two roles.Why aligning with like-minded investors who understand the company's vision and strategy is vital to success.And much more...Resources:Connect with Brennan: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron shares unconventional strategies for leadership, team building, and decision-making. Throughout the conversation, he challenges traditional hiring methods, advocating for a deeper, more intuitive approach to evaluating potential team members. The discussion touches on the importance of behavioral assessments over standardized profiling tools, emphasizing the need for leaders to sharpen their ability to assess talent beyond surface-level metrics.  You'll learn about the complexities of organizational transitions, offering practical advice on maintaining stability and focus during times of uncertainty. Cameron highlights the necessity of clear communication, structured short-term planning, and fostering a culture of transparency to ensure alignment within a team. With an emphasis on collaboration, adaptability, and intentional leadership, this episode will provide you with actionable insights you can apply immediately to strengthen your teams and organizations.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:The motivation behind the COO Alliance: the need for a community specifically for COOs and second-in-command roles.The benefits of attending in-person events, participating in monthly calls, and utilizing the member portal for resources.The value of the Colby profile for understanding and working with CEOs and other team members. Cameron's approach to interviewing and hiring, focusing on behavioral profiling and past performance.And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Ted Collins, Chief Operating Officer of Forensic Psychiatric Associates (FPA Med).During this fascinating conversation, you'll hear how Ted's career has taken him through high-pressure corporate environments and into a leadership role that demands both empathy and operational clarity. Discover a world where precision, timing, and emotional intelligence intersect to build strong client relationships and cohesive internal teams. The discussion touches on the subtle art of exceeding expectations while remaining grounded in clearly defined boundaries and agreements.Ted shares thoughtful strategies for protecting visionary leaders from unnecessary decision fatigue while still ensuring they’re looped in when their insight is most valuable. You'll learn practical tools and routines that help manage both external client expectations and internal workflow tensions—especially in high-stakes, detail-sensitive industries.This episode is a must-listen for anyone interested in sustainable leadership, operational finesse, and thoughtful growth.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:FPA Med's evidence-based process, involving psychological testing, record review, and psychiatric evaluation, followed by reports and testimony.How Ted improved the intake process, reducing administrative hassle for Dr. Levy and the experts, and creating a more efficient team. The importance of collaboration among experts, including consultations and pairing psychiatrists and psychologists.The challenges and rewards of handling multi-plaintiff or mass tort cases, such as the assessment of 46 Navy sailors claiming PTSD. Ted's process of negotiating with clients to maintain positive retainer balances and avoid administrative delays.And much more...Resources:Connect with Ted: Website | LinkedIn | EmailConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron discusses the process of identifying and attracting the right leadership talent who not only possess the necessary skills but also align deeply with your company’s vision and core values.You’ll discover the importance of building a “virtual bench” of potential candidates and why proactive recruiting beats passive job postings when searching for a high-impact executive. Discover a structured interviewing process that evaluates both cultural fit and technical expertise, ensuring your new leader complements the CEO and drives the company forward. You’ll also understand how rigorous reference checks provide critical insights into a candidate’s true character and capabilities before making a hiring decision.Cameron uncovers best practices for defining compensation, clarifying roles, and setting organizational expectations that attract and retain top executives. You’ll learn how to balance respect for existing leaders while empowering your new hire to remove obstacles and foster alignment across the company, creating a strong foundation for long-term success.The podcast explores how careful alignment of expectations and responsibilities can help create a harmonious, effective leadership structure that drives a company forward without unnecessary friction.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The difficulty of finding COOs as they are rarely unemployed and often need to be poached. (1:05)Why the old adage of 'hire for attitude, train for skill' no longer applies, and why you must hire for both cultural fit and skill set. (4:15)The importance of choosing the right job title to match the responsibilities and compensation. (7:11)The concept of maintaining a "virtual bench" of potential candidates for future roles. (23:04)The role of HR in supporting the search 9not recruiting) and the importance of rigorous interviews. (24:32)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, co-host Sivana Brewer is joined by Polina Mireau, co-founder of Scale It Simply.In this fascinating conversation, Sivana and Polina discuss the often unseen emotional layers that come with leadership, especially from the perspective of younger professionals navigating roles traditionally dominated by older, more experienced individuals. They explore how genuine connection and authentic care within an organization can transform workplace culture and foster a sense of belonging that goes beyond titles and tenure.They touch on the subtle challenges faced by women stepping into leadership roles, highlighting the unique pressures to prove themselves repeatedly despite their qualifications. The discussion reveals how shifting focus from self-doubt to relationship-building can empower leaders to break through preconceived notions and create meaningful impact—not just through their work, but through the human connections they nurture.This episode is an insightful exploration of leadership that encourages embracing imperfection, leaning into growth, and fostering trust as the true foundation for success.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Polina's upbringing in Canada, where she learned the importance of hard work, organization, and independenceHer formal transition to the COO role, and her experience in fractional and full-time capacities.The negative impact of siloed communication on team efficiency and customer experience.The differences between fractional and full-time COO roles, and the need for clear expectations and boundaries in fractional roles.The challenges of being a young female leader, and the need to focus on relationships and genuine care for the team.And much more...Resources:Connect with Polina: LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders