CPO Michelle Anastasi, Pros & Cons of Long Tenure at Same Company
Release Date: 01/28/2020
21 Min CxO- Gen. Kevin "Chili" Chilton
CXO Conversations
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...
info_outline
2 Min CxO Clip- David Cox
CXO Conversations
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...
info_outline
10 Min CxO Clip- David Cox
CXO Conversations
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...
info_outline
2 Min CxO Clip- Jack Blaha
CXO Conversations
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...
info_outline
10 Min CxO Clip- Jack Blaha
CXO Conversations
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...
info_outline
2 Min CxO Clip- Laura Ortman
CXO Conversations
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_outline
10 Min CxO Clip- Laura Ortman
CXO Conversations
In “Leading with Impact: Laura Ortman’s Journey to CEO at COLOGIX,” shares how her career path—spanning Lockheed Martin, Jeppesen, VMware, and Hologic—prepared her to lead North America’s leading network-neutral interconnection and Hyperscale Edge data center company. On this episode of CXO Conversations, she discusses the unique challenges of scaling with private equity partners, her customer experience strategy of listening and rebuilding trust, and how her athletic background shaped her “Together We Win” leadership philosophy. From making cold calls to steering a tech...
info_outline
2 Min CxO Clip- Sean Odendahl
CXO Conversations
From Army paratrooper to Chief Transformation Officer, Sean Odendahl’s career path is a masterclass in adaptability and leadership. In this episode of CXO Conversations, discover his lessons on mergers, building high-performing teams, and creating a culture of trust and feedback. For the full interview: https://ocns.co/sean-odendahl-partner-and-chief-transformation-officer/ #mentorship #executiveleadership #careergrowth #careerdevelopment #CXO
info_outline
10 Min CxO Clip- Sean Odendahl
CXO Conversations
Mentorship and direct feedback can make or break a career. , Chief Transformation Officer, joins CXO Conversations to discuss how candid conversations, military discipline, and legal expertise shaped his leadership style. A must-listen for executives and future leaders. For the full interview: https://ocns.co/sean-odendahl-partner-and-chief-transformation-officer/ #mentorship #executiveleadership #careergrowth #careerdevelopment #CXO
info_outline
2 Min CxO Clip- Rand Lewis
CXO Conversations
What makes a successful executive worth following? In this CXO Conversations episode, Rand Lewis—accomplished investor, co-founder of Delta-v Capital, and former McKinsey consultant—shares lessons from hiring and backing leaders across some of tech’s most recognized companies, including Zayo, Iterable, and Chegg. Drawing on more than two decades of experience, Rand explains the traits he looks for in candidates, why decisiveness and followership matter, and how building authentic relationships is just as important as financial investment. A must-listen for founders, CEOs, and aspiring...
info_outlineToday we’re going to discuss the pros and cons of staying with the same company for an extended period, creating an HR organization from scratch, and the lessons that Michelle Anastasi has learned throughout her career.
ABOUT OUR GUEST
Michelle is an outgoing CPO who has worked at CompSych, GiveForward, Dell and ASAP Software. She earned her Business Administration degree from the Indiana University Kelley School of Business and an MBA from Northwestern University’s Kellogg School of Management.
GET IN TOUCH WITH ON LINKEDIN
THANKS TO OUR SPONSORS
Podfly Productions: Podfly.net
Veterans of Foreign Wars: VFWpost1.org
OC Executive Search: OCExecutiveSearch.com
KEY TAKEAWAYS
[1:52] Michael introduces Michelle Anastasi and asks her to share an interesting tidbit about herself — She has had a bear visit her kitchen while she was home!
[4:00] Michelle touches on the roles she embodied and the mentors that guided her during her 16-year stint at the same software company, from the accounting department to building an HR department from scratch.
BUILDING HR FROM THE GROUND UP [6:18] Michelle breaks down how she went about tackling the HR department build with very little experience from establishing priority lists to finding the right mentors.
REGRETS? [11:50] Michelle admits to having made her share of mistakes, but she wouldn’t trade any of them — she does share the one thing she would have done differently: networks and relationships.
STARTING FROM SCRATCH [12:36] Michelle packs so much advice in a minute, you won’t believe it — we counted 11 really important and insightful tips.
SHAKING ASSUMPTIONS [15:30] Behaviors can help in preventing people from pigeonholing you — think about your executive presence and be strategic.
WHY SO LONG? [18:46] Michelle opens up on the reasons why she stayed so long at ASAP, the first of which is that she kept having opportunities to learn and be challenged. She touches on the increasingly short windows companies get to show how engaging they can be to new hires.
THE DELL MERGER [22:21] She did work through a few mergers, but Dell was at a different scale! She talks us through the ups and downs of the experience.
C-SUITE, CPO VS CHRO [25:38] Though there seems to be a push away from the human resources terminology, Michelle sees very little difference between the roles themselves. She delves into what best prepared her for the C-Suite, including a tough boss that knows how to push you outside your comfort zone.
GETTING TO THE C-SUITE [30:04] Michelle hands out fistfuls of advice for aspiring CPOs.
SURPRISES AND REWARDS [33:22] Michelle shares the aspects of being a CPO that she finds surprising and rewarding — even if a lot of the work is covered by NDA!
OVERSEAS EXPERIENCE [33:50] Michelle’s approach to HR is influenced by having lived overseas and being culturally aware.
A BAD CALL [35:18] Michelle shares the time she joined a company led by a narcissist.
MBA [36:56] Michelle touches on the value her MBA has had in her career.
CANDIDATE ATTRIBUTES [38:15] What are the things Michelle looks for in a successful candidate to hire.
BEST WORST JOB MICHELLE EVER HAD [39:19] Waitressing is such a good background for everything in life!
FINAL THOUGHTS AND GOOD READS [42:02] Michelle shares a very generous amount of titles to read and a recap of her tips for emerging CXOs.
[44:20] Michael thanks Michelle for coming on the podcast to share her 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
Linchpin: Are You Indispensable? by Seth Godin
Tribes: We need you to lead us, by Seth Godin
Turn the Ship Around!: A True Story of Turning Followers into Leaders, by L. David Marquet
Start with Why: How Great Leaders Inspire Everyone to Take Action, by Simon Sinek
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers,
by Ben Horowitz
SPECIAL THANKS TO