CXO Conversations
What does it mean to lead with authenticity in the C-suite? In this episode of CXO Conversations, Doug Gattuso talks about the importance of leaving ego at the door and focusing on creating value for people and organizations. He shares lessons from building teams, returning to companies multiple times, and leading international initiatives across Europe, Mexico, and India. Doug offers candid advice for those aspiring to executive leadership: don’t chase titles—invest in learning, seize opportunities, and always contribute to the bigger picture. For the full interview:...
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In “C-Suite Perspective in Leading with Authenticity,” shares why true leadership is about focusing on opportunities and outcomes—not titles or ego. A veteran of the Naval Academy and Marine Corps, Doug reflects on a career spanning executive roles including President and Chief Customer Officer. He explains why burning bridges is never wise, the lessons gained from international work experiences in Prague and India, and how patience, teamwork, and humility shape long-term success. Doug’s story is a reminder that authentic leadership and continuous contribution create lasting impact in...
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What does it take to admit a prestigious path isn’t for you—and have the courage to pivot? In this episode of CXO Conversations, Casey Woo, CFO of Landing.com, discusses his journey from West Point to Harvard, from Wall Street hedge funds to executive leadership roles at startups like WeWork and Zozi. Casey shares how he found fulfillment in finance by building teams, driving strategy, and embracing the operational challenges of scaling businesses. Along the way, he offers candid advice on following passion over prestige, understanding the differences between CFO and COO roles, and...
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In “Making the Hardest Call – Admitting it’s Not for You,” , former CFO forLanding.com, shares the pivotal moments that shaped his career journey—from starting at West Point and pivoting to Harvard, to walking away from Wall Street to pursue his passion for building and leading companies. With CFO and COO roles at firms including WeWork and Zozi, Casey reflects on following your own path instead of others’ expectations, the lessons he’s learned on his way to the C-suite, and why choosing finance allowed him to combine strategy with impact. His story is a powerful reminder...
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What does it take to plan a career all the way to the CEO chair? In this episode of CXO Conversations, John Oechsle discusses the strategic decisions that helped him rise from technology leadership at J&J and IHS to CEO of Derive Systems. He reflects on how international assignments shaped his leadership style, why embracing “crackpot projects” at Kellogg’s accelerated his growth, and the importance of taking roles for the right reasons—not just for compensation. For aspiring executives, John’s story is a roadmap on career planning, resilience, and the values that define strong...
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In “Career Planning and Strategic Decisions to Become CEO,” was CEO of Derive Systems and now Bolt On Technology, shares how purposeful choices shaped his path from CIO roles at Johnson & Johnson and IHS to leading multiple organizations, including Swiftpage and now Derive. John explains how he set a goal early to become a CEO, took on challenging assignments others avoided, and leveraged international experiences across Europe, Latin America, and Asia to expand his leadership perspective. He also offers candid insights on why money is the wrong reason to pursue the C-suite and why...
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What does it take to transition from the battlefield to the boardroom? In this episode of CXO Conversations, Craig Cummings—Army veteran, Bronze Star recipient, and co-founder of Moonshots Capital—discusses the lessons he’s carried from 17 years of military service into the world of startups and venture capital. He shares practical advice on creating a career-defining elevator pitch, supporting veteran entrepreneurs, and building strong networks that accelerate growth. From deploying with Special Operations to scaling tech startups and investing in extraordinary leaders, Craig’s...
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In “Building Your Career Transition Elevator Pitch,” shares how his journey from Army Intelligence Officer in Afghanistan to General Partner at Moonshots Capital shaped his approach to leadership, entrepreneurship, and investing. A Bronze Star recipient and West Point graduate with a Ph.D. from Columbia, Craig explains how veterans can craft an elevator pitch that opens doors, the importance of building strong entrepreneurship communities like Austin’s, and why investing in talented veteran founders is a mission for him. His story is a powerful reminder that clarity, curiosity, and...
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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...
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