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

In today's episode of the Second in Command podcast, Cameron explores a common business gripe that everyone knows all too well: why meetings (or rather, the way they're run) are so unproductive. Cameron offers a fresh perspective by focusing on *why* this problem persists and how to fix it with simple, practical skills. You'll hear how he challenges the widespread belief that meetings are inherently awful, arguing instead that most people have never been taught how to run or participate in them effectively. Without that foundational training, leaders and employees alike contribute to the frustration, making meetings drag on or feel pointless.The discussion then uncovers some easy-to-implement habits that can transform meetings into productive, respectful experiences. From ensuring meetings end early to setting clear agendas with defined purposes and time allocations, Cameron shares real-world examples and personal coaching insights. These small adjustments not only help curb the common problem of lateness but also create a culture where time is valued and meetings are more efficient.This episode shows you how, by tailoring meetings to your true goals and attendees, your business can streamline communication and get better results—without sacrificing the human connection and spontaneous collaboration that meetings can foster.Know someone who runs meetings like a hostage situation? Share this episode with them—it might just save their team. 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:Why most people lack proper training in running meetings, leading to inefficiency and lack of productivity.The problem with complaining about business issues without proper training in essential skills, such as interviewing, coaching, and conflict resolution.The importance of reviewing the purpose, outcome, and agenda of each and every meeting to ensure clarity and efficiency.How to handle informal meetings by setting clear purposes and outcomes, even in casual settings.The challenge of managing large meetings with multiple topics and the importance of inviting only necessary participants.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 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.

What does it really take to steer a fintech through a growth reset—and come out stronger? In today's episode of the Second in Command podcast, Cameron is joined by COO Rina Jariwala, who takes us inside the transformation of Fundbox, where operational precision meets people-first leadership.In this insightful conversation, Rina shares a compelling journey through rapid growth, transformation, and the challenges of steering a company toward profitability. You'll get an inside look at the strategic pivots and cultural shifts necessary when a high-growth organization recalibrates its priorities to build a sustainable and thriving future. The discussion reveals how transparency, clear goals, and leadership resilience play pivotal roles in navigating tough transitions.Beyond the company’s financial and operational evolution, you'll hear about the nuances of leadership itself. Rina reflects on the importance of execution over theory, the emotional intelligence required to manage diverse demands, and the continuous learning mindset that fuels personal and professional growth. The exploration of coaching as a vital leadership skill—contrasting it with mentoring—highlights how fostering curiosity and empowerment can transform teams and organizations alike.This episode offers inspiring insights into how leaders can cultivate trust, build culture, and approach challenges with grace and determination.Want more conversations like this—where coaching meets execution? Follow the show and get inside the minds of next-gen operators. 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 importance of empathy and understanding Rina's team's motivations, which she believes are crucial for effective leadership.The underwriting process, which involves analyzing data from small businesses to provide quick funding decisions.Fundbox's growth strategy, focusing on platform and distribution partners that serve a multitude of small businesses. The cultural shift required to achieve profitability and the importance of maintaining a strong team.Rina's journey of pursuing a master's degree in leadership and organizational development with an emphasis on executive coaching.And much more...Guest Bio:Rina Jariwala is the Chief Operating Officer of Fundbox, known for her authentic, high-energy leadership and a passion for driving operational excellence. With extensive experience across technology, data, and service delivery, Rina specializes in turning around organizations and helping them reach peak performance. She excels at elevating service delivery, improving efficiency, and driving profitability through strategic planning and seamless execution. A dynamic communicator and influential leader, she motivates high-performing teams, spearheads complex process improvements, and fosters cross-functional collaboration. Her key strengths include business process re-engineering, change management, coaching, and organizational development. With a strong focus on customer impact and innovation, Rina brings a bold, people-centered approach to operational leadership that consistently delivers lasting results.Resources:Connect with Rina: 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 breaks down the misunderstood and often misused role of the Chief Operating Officer. Drawing from both personal experience and established research, he uncovers how the COO is not a one-size-fits-all title—it’s a role that shifts depending on the needs of the CEO and the stage of the business. With anecdotes from his own time at 1-800-GOT-JUNK and references to thought leaders in the field, Cameron explores how many leadership titles are incorrectly handed out, and why defining the true second in command begins with understanding the personality and skill gaps of the CEO.The conversation dives into seven key archetypes of COOs, from executors and change agents to mentors and MVPs—each fulfilling a unique function within a company. Whether serving as a stabilizing force in turbulent times, guiding a young founder through explosive growth, or acting as a public-facing counterpart to an introverted CEO, the COO’s impact is always rooted in complementing leadership. Cameron also explores the often unseen dynamic of the CEO-COO relationship, likening it to a marriage where balance, trust, and mutual respect drive real progress.This episode shows that the role of the COO is anything but static; it’s a powerful, adaptive force that, when aligned correctly, becomes the backbone of growth, execution, and sustained 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:The common misconceptions about COOs and how they are often confused with other leadership roles, like directors or VPs.The seven main categories of COOs identified by Nate Bennett and Stephen A. Miles in their book "Riding Shotgun." The importance of finding a COO who complements the CEO's strengths and weaknesses.How the role of the COO has evolved over time, with more CEOs investing in their own leadership growth and involving their senior leadership in coaching and mentorship.Why the role of the COO is seen as a source of culture through their vision, core values, and motivation towards goals.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 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.

What does it really take to lead a mission-driven company from the inside out? In today's episode of the Second in Command podcast, Cameron is joined by Jason Jaynes, former CO and now CEO of eCatholic, creator of digital tools and services tailored to Catholic parishes, schools, and dioceses.In this insightful conversation, you'll be taken behind the curtain of a rapidly evolving organization as its leadership navigates succession, growth, and transformation. Jason reflects on the decision-making process involved in identifying and promoting the right internal talent, exploring how mentorship, trust, and long-term planning played key roles in building a strong leadership team. Get a glimpse into how one leader balanced humility with decisiveness in preparing both himself and his team for the future.The discussion also explores the personal growth journey of the guest as he transitions from a behind-the-scenes operator to the public face of the company. He opens up about the challenges of stepping into the spotlight, embracing new responsibilities, and learning the nuances of strategic sales and marketing leadership in a niche space. The discussion explores the courage to seek help, partner with outside experts, and shift perspectives in order to lead effectively.This episode offers a candid, inspiring look at how thoughtful leadership can shape not only a company’s trajectory but also its culture and impact. Curious about how eCatholic helps faith-based organizations thrive online? Visit eCatholic.com to explore their suite of digital tools.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:An overview of eCatholic, a company founded to provide digital tools for the Catholic Church, as well as their focus on helping churches reach their communities online.Jason's previous role as COO, focusing on systems, processes, and scaling the company in the first two years.The transition from COO to CEO, focusing on becoming, in his words, "three miles wide and one inch deep." The process of identifying and grooming Karen (Lackey) for the COO / VP of operations role, including her previous roles and responsibilities.The importance of hiring experts in areas where one lacks expertise, such as sales and marketing.And much more...Guest Bio:Jason Jaynes is the CEO of eCatholic, a company that provides a suite of digital tools and services tailored specifically for Catholic parishes, schools, and dioceses. With over 27 years of experience in the software and technology industry, Jason has held a wide range of leadership roles, including Co-founder, COO, CTO, VP of Product, VP of Business Marketing, and Senior Systems Engineer. His diverse background reflects a deep expertise in both technical innovation and strategic business development. Jason holds a Bachelor of Science in Computer Science from Texas A&M University and earned his MBA from the University of Texas, equipping him with the skills to lead mission-driven digital transformation within faith-based organizations.Resources:Connect with Jason: 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 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