CXO Conversation Podcast

CSO David McDougall, The Management Skills for Success

David 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.



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.





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[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.



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


Sales Hacker podcast



Jalan Crossland for the music

Angela Johnson at OC Executive Search

Joseph Batty at Podfly

Corey Coates at Podfly



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.




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