CXO Conversation Podcast

CFO Jordan Conley, Transitioning from IT to HR

Jordan 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.



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.





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[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.




Obsidian HR




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



Jalan Crossland for the music

Angela Johnson at OC Executive Search

Joseph Batty at Podfly

Corey Coates at Podfly


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