10 Min CxO Clip- Todd Siegler
CXO Conversations
In “Focus on Impact, Not Money,” shares candid lessons from a career spanning nearly every C-suite role—CFO, COO, CAO, CDO, General Counsel, and eventually CEO of his own company. A Princeton and Tulane Law graduate, Todd reflects on the differences in executive roles across organizations, the dynamics of C-suite interactions, and how managing direct reports effectively builds trust and results. His message is clear: the best leaders aim to create impact, not just chase titles or compensation. For aspiring executives, his story is both an insider’s view of the C-suite and a roadmap...
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10 Min CxO Clip- Jamey Seely
CXO Conversations
In “Being a Blue Collar LGBTQ Executive,” Chief Legal Officer at Gates at time of recording and now General Counsel for Crusoe, shares her journey to the C-suite and what it means to lead authentically in traditionally blue-collar industries like energy, manufacturing, and nuclear. Named one of Denver Business Journal’s Top 25 Most Powerful Women in Business, Jamey reflects on her career path, the two common legal career tracks, and why inclusivity, resilience, and curiosity have shaped her leadership. She also discusses the importance of mentorship, board interactions, and building...
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10 Min CxO Clip- Michelle Anastasi
CXO Conversations
In “Pros & Cons of Long Tenure at Same Company,” shares how she built an HR organization from scratch and the lessons she learned across leadership roles at ASAP Software, Dell, GiveForward, and CompPsych. A graduate of Indiana University and Northwestern’s Kellogg School of Management, Michelle reflects on the advantages and challenges of staying with one company for 16 years, the importance of aligning HR with business needs, and why self-advocacy, curiosity, and developing others are essential for long-term success. Her perspective offers valuable guidance for HR leaders and...
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10 Min CxO Clip- Bill Wosilius
CXO Conversations
In “CEO Bill Wosilius, Why and How to Prepare for CEO Chair,” , who was CEO of NexusTek at the time of recording, shares candid insights on declaring your career goals, assessing situations with clarity, and making the tough executive calls that define leadership. A graduate of the U.S. Air Force Academy, Bill served eight years before moving into executive roles at InFlow, Sungard, Healthgrades, CoreSite, and Optiv, ultimately preparing him for the CEO role. He emphasizes why the best job is the one you have right now, how every experience builds toward the moment of leadership, and...
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2 Min CxO Clip- Steve Joanis
CXO Conversations
What does it take to get noticed by both venture capitalists and C-suite recruiters? In this episode of CXO Conversations, Steve Joanis—CEO of PlanetIQ and veteran of more than $200M in venture fundraising—shares how his career path from Army combat aviator to consultant, investor, and CEO shaped his leadership style. Drawing on decades of experience scaling startups and serving on 20+ boards, Steve highlights why relationships matter more than résumés, how to present yourself authentically to investors, and the strategic decisions that define a CEO’s success. His advice is invaluable...
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10 Min CxO Clip- Steve Joanis
CXO Conversations
In “CEO Steve Joanis, Getting Noticed for C-Level & by VCs,” , the CEO of PlanetIQ (at time of recording, now a PE Managing Director), shares lessons from 25+ years in management consulting, venture capital, and executive leadership. A West Point graduate, decorated Army aviator, and Wharton MBA, Steve has served as CFO, President, board member, and investor across more than 20 companies with multiple successful exits. In this episode of CXO Conversations, he explains how to stand out to venture capitalists, what personality traits the most successful C-suite candidates share, and how...
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2 Min CxO Clip- Carlos Perez
CXO Conversations
What does it take to build a high-performing sales organization from scratch? In this episode of CXO Conversations, Carlos Perez, CRO of Simuwatt, shares lessons from leading revenue teams at startups, global enterprises, and everything in between. He talks about the changing nature of sales leadership, the importance of aligning marketing and sales under a unified revenue vision, and why adaptability is critical in a post-COVID world. From closing his first $25M outsourcing deal to scaling SaaS organizations, Carlos offers actionable advice for leaders building sales orgs designed to last....
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10 Min CxO Clip- Carlos Perez
CXO Conversations
In “CRO Carlos Perez, Building a Sales Org from Scratch,” shares how he’s grown revenue organizations across startups and billion-dollar companies alike. From his early consulting days to CRO roles at Wowza and now Concept3D, Carlos reflects on the evolving role of the Chief Revenue Officer, aligning sales, marketing, and customer success to accelerate growth. He also discusses how sales has changed post-COVID, why trust and creativity matter more than ever, and how to build scalable sales teams from the ground up. For executives and entrepreneurs, this episode is packed with insights...
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2 Min CxO Clip- Heather Callender-Potters
CXO Conversations
What does it take to know when to step aside and hire the right CEO? In this episode of CXO Conversations, Heather Callender-Potters—global investor, co-founder of PharmaJet, and experienced board member—discusses the lessons she’s learned from founding companies, navigating leadership transitions, and serving on boards. From her international upbringing to launching one of the first private equity funds in Eastern Europe, Heather’s journey offers a unique perspective on resilience, cultural awareness, and executive selection. Her advice for aspiring leaders and board members...
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10 Min CxO Clip- Heather Callender-Potters
CXO Conversations
In “Heather Callender-Potters, Founder and Board Member. Hiring a CEO and Board Member Perspectives,” shares lessons from a remarkable career that began in Poland just after the fall of the Berlin Wall, bringing access to capital during a time of historic transformation. Now co-founder of PharmaJet and a seasoned board member, Heather reflects on the challenges of handing over leadership to a CEO, the importance of cultural fit versus just résumé credentials, and why resilience and trust are critical in executive roles. She also offers candid advice for first-time board members on...
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