CXO Conversations
What can hundreds of transactions and decades of leadership teach us about CEOs? In this episode of CXO Conversations, Chris Younger, CEO of Class VI Partners, reflects on buying, selling, and leading companies across industries. He shares candid insights on managing the stress of leadership, why presence and transparency matter, and how servant leadership builds lasting teams. From his experience acquiring 27 companies to guiding CEOs through exits and growth strategies, Chris highlights both the rewards and the realities of C-suite life—and why prioritizing self-care is as important as...
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In “CEO Insights & Self Care with Chris Younger,” shares lessons from a career spanning telecom, private equity, and advisory leadership. As President of Expanets, he acquired 27 companies in just 3 years before selling to Avaya, and today, as CEO of Class VI Partners, he advises middle-market businesses and family offices on transactions and growth. Chris opens up about the physical toll of overwork, the importance of managing stress, and why diet, sleep, and exercise are critical for executives. He also explains his “Dinner Test” for CEOs and why executive presence sets the tone...
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What does it mean to be truly intellectually curious as a leader? In this episode of CXO Conversations, Christine Gagnon, CFO of African Asset Finance Company at time of interview, discusses the value of continuous learning and the global perspective she’s gained from international assignments and advanced education at top institutions. From her early career at PwC and EY to her current role financing critical sectors across Africa, Christine shares how ongoing education enriches her work, enhances strategic planning, and opens new angles of business she would have never seen otherwise. Her...
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In “Christine Gagnon CFO, the Importance of Being Intellectually Curious,” shares how a lifelong passion for learning has shaped her global career. During recording, she was the CFO of African Asset Finance Company, she reflects on her journey through leadership roles at EY, PwC, and OneWest Bank, as well as earning multiple advanced degrees and executive certifications from Harvard, Stanford, and Washington University. Christine explains how international experiences, from Johannesburg to London, shaped her global market perspective, and why intellectual curiosity allows her to better...
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In “General Kevin ‘Chili’ Chilton, Board Member, Astronaut and Flying the Space Shuttle,” shares lessons from his extraordinary 34½ years in the U.S. Air Force and his successful transition into corporate leadership. On this episode of CXO Conversations, Chili reflects on problem-solving and leadership training, the astronaut band Max Q, and the experience of flying three space shuttle missions. From serving as Deputy Program Manager of Operations for the International Space Station to becoming the only astronaut to achieve the rank of 4-star General, Chili’s story is a powerful...
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What does it take to transform one of the world’s most respected publications without losing its identity? In this episode of CXO Conversations, David Cox discusses his 14 years at The Economist, including his role as CFO and COO, where he spearheaded the company’s global shift from print to digital and live events. He explains how he balanced editorial independence with client demands, why pricing digital at the same level as print was a pivotal decision, and what he learned about storytelling, teamwork, and leading large-scale transformation. David’s lessons remain invaluable for...
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In “Leading an Iconic Brand Through a Global Transformation,” former CFO of The Economist, shares how he helped guide the publication through its bold shift from weekly print to a digital-first and live events model. On this episode of CXO Conversations, David reflects on early digital adoption, the value of listening to clients, and how consultative selling reshaped the way advertisers and subscribers engaged with the brand. From launching Economist Espresso to hosting government roundtables across the globe, David’s story is a playbook for executives leading organizations through...
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What does it take to go from West Point to the corner office? In this episode of CXO Conversations, Jack Blaha, CEO of Cendyn, opens up about his path from Army officer to five-time SaaS CEO and the lessons he’s learned along the way. He emphasizes the importance of adaptability, continuous leadership development, and building a strong professional network, while sharing strategies for excelling in current roles and preparing for future opportunities. For aspiring and current leaders alike, Jack offers practical insights on team building, mentorship, and how presence and emotional...
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In “West Point to CEO,” , CEO of Cendyn, shares his remarkable journey from Army veteran to seasoned executive leading multiple SaaS companies. On this episode of CXO Conversations, Jack reflects on how military-honed adaptability and leadership shaped his transition into the corporate world, from hospitality to social media marketing software. He discusses the impact of emotional intelligence on company culture, the value of mentorship, and the importance of building strong teams—including bringing trusted colleagues to ensure operational success. Jack’s story is a masterclass in...
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What does it take to go from making cold calls to leading a hyperscale data center company powering the cloud? In this episode of CXO Conversations, Laura Ortman, CEO of COLOGIX, shares her journey through pivotal roles across tech, the lessons she carried into the C-suite, and why broad business experience is critical for informed leadership. She reflects on perseverance, mentorship, and transforming challenges into opportunities for growth, while emphasizing the importance of corporate culture, strong networks, and risk-taking. Laura’s story is a masterclass in resilience, relationship...
info_outlineJordan Connely joins the show today as the President of Obsidian HR and CFO of ProService Hawaii (Obsidian's parent company). He and Michael share some interesting practices when it comes to HR as well as Jordans’ thoughts on how to improve your career, how to transition from consulting to the C-suite, and the many roles he’s held throughout the years.
ABOUT OUR GUEST
Jordan Conley is President of Obsidian HR, as well as the current CFO of ProService Hawaii (Obsidian’s parent company). He is responsible for the strategy, customer experience, culture, and profitability of the business.
Leveraging over 20 years of experience in the HR outsourcing industry, he brings a unique perspective to the evolving needs and definition of “HR” in the modern workplace.
Prior to being appointed President of Obsidian HR, he was a founding member of ZeroChaos (now Workforce Logiq) and has held senior leadership roles at CoAdvantage (a large national HR outsourcing firm).
As a natural entrepreneur, Jordan is passionate about seeing opportunities where businesses need help and partnering with leaders to protect their operations and make growth a reality. Jordan attended the University of Central Florida and Crummer School of Business at Rollins.
He is married with three sons and currently resides in Denver, CO where he is an active car aficionado, an avid reader, and a connoisseur of Colorado beer.
GET IN TOUCH WITH JORDAN CONLEY ON LINKEDIN
THANKS TO OUR SPONSORS
Podfly Productions: Podfly.net
Veterans of Foreign Wars: VFWpost1.org
OC Executive Search: OCExecutiveSearch.com
KEY TAKEAWAYS
[2:49] Michael introduces Jordan and asks him to share a little bit about what ProService Hawaii and Obsidian HR do as well as the differences between working in Hawaii and on the mainland.
A LITTLE BIT OUT OF THE BLUE [8:44] What Jordan didn’t realize at the time was that in consulting he had been doing a year-long interview for the CTO position!
CXO PATH [10:30] Having dropped out of undergraduate school to launch a startup, Jordan speaks to his non-linear path to the C-suite by way of an MBA. He shares an anecdote about staying in touch with some of his classmates and even having some of them now working out of Hawaii.
SLOW BUT STEADY [15:19] From CTO to COO Jordan talks about the slow transition he made from IT to HR as well as playing both roles for a period of time. Jordan also shares his most rewarding and challenging moments as a COO.
KEEPING TRAINS ON TIME [19:10] Jordan shares his take on the COO role as well as the period of time when the COO was living out of Sweden and traveling to Honolulu regularly, requiring Jordan to fill a lot of roles.
LEGACY AND ADVICE [20:51] Jordan touches on what he hopes are the traits people will remember him by at ProService. He shares one of his proudest moments at ProService, as well as some critical advice for aspiring c-suite.
[24:00] Jordan explains why you need to make sure you’re never a bottleneck as well as relentless prioritization.
MANAGEMENT STYLE [26:49] Jordan walks us through the leader-leader style of management and talks about the great advantages and difficulties of Topgrading.
RECRUITING [32:10] Recruiting and hiring is one of the most important aspects of Jordan’s job, and he will spend around 40% of his time on it.
DECISIONS [33:22] Jordan shares a decision he made that didn’t go as planned.
BEST WORST JOB JORDAN EVER HAD [35:30] Bussing tables at a restaurant!
[39:26] Michael thanks Jordan for coming on the podcast to share his insight and closes out the podcast with his favorite takeaways.
We hope you learned something today and enjoyed the conversation. Please give us 5 stars on iTunes and share your comments so we can improve and ask the questions you want to hear.
MENTIONED IN THIS EPISODE
Books:
Turn the Ship Around!: A True Story of Turning Followers into Leaders, by L. David Marquet
The Oz Principle: Getting Results Through Individual and Organizational Accountability,
by Craig Hickman, Tom Smith, and Roger Connors
Scaling Up: How a Few Companies Make It…and Why the Rest Don’t, by Verne Harnish
Riding Shotgun: The Role of the COO, by Nathan Bennett
SPECIAL THANKS TO