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

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 [https://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 [https://ecatholic.com/] | LinkedIn [https://www.linkedin.com/in/jasonjaynes/] Connect with Cameron: Website [https://www.cameronherold.com/?_fs=16369989341-15088831188] | LinkedIn [https://ca.linkedin.com/in/cameronherold] Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO" [https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603/] Get Cameron’s online course – Invest In Your Leaders [https://investinyourleaders.com/] Disclaimer: 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 [https://www.optimaoffice.com/] | LinkedIn [https://www.linkedin.com/in/jennifer-barnes-optima/] Connect with Cameron: Website [https://www.cameronherold.com/?_fs=16369989341-15088831188] | LinkedIn [https://ca.linkedin.com/in/cameronherold] Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO" [https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603/] Get Cameron’s online course – Invest In Your Leaders [https://investinyourleaders.com/] Disclaimer: 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 [https://www.life360.com/en-ca] | LinkedIn [https://www.linkedin.com/in/lauren-antonoff-06b2655/] Connect with Cameron: Website [https://www.cameronherold.com/?_fs=16369989341-15088831188] | LinkedIn [https://ca.linkedin.com/in/cameronherold] Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO" [https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603/] Get Cameron’s online course – Invest In Your Leaders [https://investinyourleaders.com/] Disclaimer: 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 [https://www.cameronherold.com/?_fs=16369989341-15088831188] | LinkedIn [https://ca.linkedin.com/in/cameronherold] Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO" [https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603/] Get Cameron’s online course – Invest In Your Leaders [https://investinyourleaders.com/]

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 [https://my.captivate.fm/dashboard/podcast/eff1720e-81d2-4509-b52f-5cf0f1d84afc/episode/57770fb9-a024-409e-8438-7e4548e5a48b] 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 [https://my.captivate.fm/dashboard/podcast/eff1720e-81d2-4509-b52f-5cf0f1d84afc/episode/57770fb9-a024-409e-8438-7e4548e5a48b] 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 [https://www.ameriprise.com/?ref=team%7Ctng-private-wealth] | LinkedIn [https://www.linkedin.com/in/jrschaper/] Connect with Cameron: Website [https://www.cameronherold.com/?_fs=16369989341-15088831188] | LinkedIn [https://ca.linkedin.com/in/cameronherold] Get Cameron’s latest book – "Second in Command: Unleash the Power of Your COO" [https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603/] Get Cameron’s online course – Invest In Your Leaders [https://investinyourleaders.com/]