CXO Conversation Podcast

COO/CFO Todd Siegler, Focus on Impact, Not Money

Todd Siegler joins the show today to shed some light on the differences in C-suite roles depending on the organization, C-suite interactions, management of direct reports and aiming at having an impact, above all else.


Join us today for an in-depth discussion about the inner-workings of the C-suite.



Todd Siegler graduated from Princeton University and Tulane Law School — talk about a well rounded CXO! He has been a CFO, a COO, Chief Administrative Officer, Chief Development Officer, General Counsel and saved the CEO title for his own company.





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[1:52] Michael introduces Todd Siegler and asks him to share an interesting tidbit about himself.


[3:05] Todd talks about the two things his firm currently does and the one product he is poised to launch in the next quarter.


ACCIDENTALLY INTENTIONAL CAREER PATHS [3:54] Todd and Michael discuss the often convoluted paths that take you on your professional journey.


SO, WHAT’S A CAO? [6:28] Todd touches on the nature of the CAO role, from human resources to legal counsel, with a stopover on infrastructures, as well as the differences in how companies tackle this role with regards to the importance they place on HR.


Todd also shares his takeaways from nine years of experience wearing and stacking different hats from Corporate Development, General Counsel, to finance and even technology.


MULTI-BILLION TRANSACTIONS [10:25] Having been privy to 100+ mergers and acquisition deals, Todd speaks of his involvement in two major transactions and shares a war story!


PREPPING FOR CEO/COO [13:50] Todd highlights the two principal ways being a CAO prepared him for higher positions:

  1. Hiring —  it offers you an opportunity to get a first-hand understanding of what it takes to build a successful team.
  2. Multiple facets of business — being a CAO lets you stick your fingers in many aspects of the business; you can learn a lot.


Todd shares tips and best practices for building great teams as well as the importance of clear expectations and building good structures.


FOR INFLUENCE: CFO OR COO? [17:32] Todd speaks to the wide span of company structures, and how a variety of C-suite structures can fit into each according to their primary needs and goals. This makes it harder to determine which has the most strategic influence and overall impact since from one company to the next, their effective reach may differ.


Todd’s advice? When looking for new opportunities, you should really focus on people as opposed to title.


[21:45] Why aim for a COO position? It’s a question of impact in mentoring and growing people, as well as on the business and the strategy. Todd shares a story from his time at Marketforce that emphasizes the importance of building people — and companies — up to the point where they don’t need you.


[24:30] What’s your legacy? Is a question I like to ask prospective candidates. Todd shares his view on the importance of the impact you have


ADVICE FOR A VP [25:39] You’re aiming for C-suite? Stretch yourself. Feel uncomfortable.


C-LEVEL SURPRISES [26:41] Todd opens up about what surprised him when he made the C-suite. Impact first, but also the titles may be the same but the job is different according to the company.


This last one leads him to underscore the important questions to ask when moving into a role:

  • What does it mean to be Cxx here?
  • What decisions can you make?
  • What role can you have?


THE REWARDS [28:01] The rewards are all about people for Todd: mentoring, seeing people grow, seeing your teams do well and having an overall positive impact on the company.


MANAGING DIRECT REPORTS [28:53] Todd discusses best practices when it comes to managing your direct reports. It’s about them.


But really, hire great people and let them do their job, and lead by example.


BOARD EXPERIENCE (IS IT A BLESSING OR A CURSE?) [31:02] Todd breaks down the steps to getting a good balance on your board — it’s really about relationships — as well as how to properly prepare for meetings.


MAKING BAD DECISIONS [34:51] You will never have perfect information; don’t be afraid to make a mistake: it’s a chance to learn. Todd can tell you every detail of the three to four bad mergers and acquisitions he was a part of, he learned.


Making mistakes is par for the course to becoming CXO.


TODD’S ADVICE FOR HIS YOUNGER SELF [37:40] Continue to push on the opportunities that deliver experience, not money. Stay you, and if it doesn’t fit with you, you can say no. Finally, live below your means.


BEST WORST JOB TODD’S EVER HAD [39:55] Todd shares his worst job but really, all his jobs have had some bad.


[42:23] Michael thanks Todd 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 gives us five stars on iTunes and share your comments so we can improve and ask the questions you want to hear.



Malcolm Gladwell


Lean startup



Jalan Crossland for the music

Angela Johnson at OC Executive Search

Joseph Batty at Podfly

Corey Coates at Podfly


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