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_outlineDavid McDougall joins the show to share his 20- year-plus expertise on what it takes to make a good Chief Sales Officer (CSO) and what sales management professionals need to foster in themselves in order to run better teams.
Ever wonder how big game deals pursuit prepare a future CSO? Tune in to hear some seriously insightful advice on what it takes to take on the C-Suite.
ABOUT OUR GUEST
David McDougall is Vice President, Cloud and Managed Services at ConvergeOne. His career spans over two decades and he has held the position of Executive Vice President and Chief Sales Officer at CSS Corporation, as well as senior positions at firms including Capgemini, T-Systems, Siemens, and Inacom Corporation.
GET IN TOUCH WITH DAVID ON LINKEDIN
THANKS TO OUR SPONSORS
OC Executive Search: OCExecutivesearch.com
Podfly Productions: Podfly.net
Veterans of Foreign Wars: VFWpost1.org
KEY TAKEAWAYS
[1:51] Michael introduces David McDougall and asks him to share an interesting tidbit about himself.
[3:03] David touches on the multiple ways in which sales skills translate to different roles and even transcend the professional sphere.
ON MENTORING [5:25] There are people who play a seminal role in shaping our professional futures; David shares the impact one of his superiors had on him as well as the organic nature of this mentoring relationship, as opposed to formal. He also shares what being a mentor himself has taught him.
[9:11] David and Michael discuss the importance of mentoring at the C-Level in terms of promoting company culture.
ADVICE FOR CSOs [10:11] Listening may be the one most important sales skill according to David; he breaks down the ways its consultative aspects can impact your interactions. David shares what it takes to become a Chief Sales Officer, from getting the numbers to being perceptive with your human resources — as well as some important KPIs to track performance. He opens up about the things he’s learned in his two sojourns as CSO:
- People are everything so build a great team
- Take the time to understand your organization
- Set very clear timelines and makes sure everyone is on the same page
- Don’t move away from what you know works
[21:17] David explains how the CSO leads the charge to get deals done and touches on all of the working parts that need to work together for it to happen. This means that your team has to trust you and you have to be the head cheerleader for the overall organization!
RAPID FIRE CSO QUESTIONS [23:24] The surprising, the rewarding, and the overlooked.
SALES MANAGERS [26:18] David dives deep into what teams working well together look like and the opposite while weaving in necessary attributes of a good sales manager and how they affect a team’s performance:
- Be in the trenches — don’t micromanage
- Get to know your people and keep up to date with them
- Find, palliate, and improve on your team’s weaknesses
- Showcase your team’s strengths
- Be ready and willing to make difficult decisions
- When the vibe is off, start probing your team!
- Build trust
- Ask for and be open to feedback; you can always get better
[35:51] If you’ve exhausted every possible option — repurposing, new talent, multiples — to resolve performance issues, it may be time to rebuild your team from scratch. If you’re there, you’ll want to over-communicate why you need to do this; what’s working, what’s not working, what you tried, so as to not negatively impact your recruiting process.
[38:12] How do you manage your top prima donna?! David shares his advice on this prickly beast.
CSO AND C-SUITE [41:14] The relationship you build with the CEO and the CFO is critical and it starts at the interview process. Everyone needs to be on the same page, understand the go-to-market strategy and the strategic plan to get there. David touches on the slight differences between being a newly hired CSO and a long time CSO in the company.
[45:13] David talks about what you should be doing and the skills you should be building if you aim to become a VP or a CSO. Go read! Learn!
BIG DEALS [46:34] David and Michael discuss how big game deals are unique and different from normal-sized deals and how they contribute to the ability to run a sales organization.
DAVID’S ADVICE FOR HIS YOUNGER SELF [51:34] Continue being positive, stay on your vision, work hard, be grateful and there will be setbacks.
BEST WORST JOB DAVID’S EVER HAD [52:13] David goes back to his help desk days, getting unhappy customers with problems... It taught him a few lessons!
[55:09] Michael thanks David 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.
MENTIONED IN THIS EPISODE
Leaders Eat Last, by Simon Sinek
Execution: The Discipline of Getting Things Done, by Larry Bossidy, Ram Charan,
and Charles Burck
Grit: The Power of Passion and Perseverance, by Angela Duckworth
SPECIAL THANKS TO
Angela Johnson at OC Executive Search
ABOUT YOUR HOST
For the past 20 years, Michael Mitchel, B.A., has been interviewing leaders in their fields. He started his career recruiting for United Parcel Service in Seattle, where he implemented the company's Welfare to Work program for the Washington State District. He has recruited for Federal agencies and U.S. Department of Defense contractors for classified programs internationally. He Founded OC Executive Search in 2001 to serve companies ranging from startups to Global F10.
Michael is an honorably discharged veteran of the U.S. Navy and enjoys skiing, cycling, traveling, photography as well as hiking in the Colorado Rockies with his cattle dog, Kala the Wunderdawg.