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Jim Kaskade

Serial Entrepreneur, Global Enterprise Executive

  • Bio Brief
  • Bio Detail
  • I’m an ENTJ
  • Results
  • We’re Hiring!
  • Outside of Work
  • Leadership

A CEO’s journey through culture, strategy, and execution

  • Jim Kaskade
  • January 28, 2026
  • Leadership

Portfolio Companies On The Naughty and Nice List

  • Jim Kaskade
  • December 23, 2025
  • Artificial Intelligence
  • Leadership

Board of Directors at an AI Company

  • Jim Kaskade
  • July 5, 2025
  • Artificial Intelligence
  • Leadership

Corp Dev at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

R&D at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

International Operations at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

Finance at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

HR/People at an AI Company

  • Jim Kaskade
  • July 1, 2025
  • Artificial Intelligence
  • Leadership

Legal at an AI Company

  • Jim Kaskade
  • July 1, 2025
Next-Gen Security (via Cloud): Part 3 – Application and Process
  • Cloud
  • Security

Next-Gen Security (via Cloud): Part 3 – Application and Process

  • Jim Kaskade
  • April 15, 2011
Next-Gen Security (via Cloud): Part 2 – Data and Information
  • Cloud
  • Security

Next-Gen Security (via Cloud): Part 2 – Data and Information

  • Jim Kaskade
  • April 15, 2011
Next-Gen Security (via Cloud): Part 1 – Identity Management
  • Cloud
  • Security

Next-Gen Security (via Cloud): Part 1 – Identity Management

  • Jim Kaskade
  • April 14, 2011
Future of Security (hint: Cloud)
  • Cloud
  • Security

Future of Security (hint: Cloud)

  • Jim Kaskade
  • April 4, 2011
How About a Gaming PaaS?
  • Cloud

How About a Gaming PaaS?

  • Jim Kaskade
  • March 28, 2011
Cloud Security Services
  • Cloud
  • Security

Cloud Security Services

  • Jim Kaskade
  • March 9, 2011
The battle of the business model – Mobile cloud web apps or native handset apps?
  • Cloud
  • Mobile

The battle of the business model – Mobile cloud web apps or native handset apps?

  • Jim Kaskade
  • February 23, 2011
Who Killed The Change?
  • Leadership

Who Killed The Change?

  • Jim Kaskade
  • January 10, 2011
Open (driving more commodity) will become key
  • Cloud

Open (driving more commodity) will become key

  • Jim Kaskade
  • January 6, 2011
SIs are the gateway into large enterprise for new cloud vendors
  • Cloud

SIs are the gateway into large enterprise for new cloud vendors

  • Jim Kaskade
  • January 5, 2011

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Blog Categories

  • Advertising
  • Artificial Intelligence
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  • Broadcast Video
  • Cloud
  • Data & Analytics
  • Digital Media
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  • Identity
  • IoT
  • Leadership
  • Mobile
  • SaaS
  • Security
  • Semiconductors

Jim Kaskade (he/him) Follow 135,542 2,472

CEO for 25 years. Focused on AI, Security, Identity, IoT, Big Data, Social, Mobile, & Cloud. Decade in data warehousing, business intelligence, data mining.

jimkaskade
jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
2h 2078449768519422391

Strategic planning is not a December event. It is a year-round discipline with a Q4 culmination. (Secret: I like to have Board approval to next years budget before the fat man comes down the chimney).

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Strategic planning is not a Twitter feed video.
Reply on Twitter 2078449768519422391 Retweet on Twitter 2078449768519422391 0 Like on Twitter 2078449768519422391 0 X 2078449768519422391
jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
17 Jul 2078087466121056629

Investors do not fund businesses. They fund stories backed by entrepreneurs. Explain "why your business", but also explain "why you".

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Investors do not fund businesses. Twitter feed video.
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jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
16 Jul 2077725109725409407

Every CEO needs at least one session per year (if not per quarter) where the agenda is not about the roadmap. Have you sponsored company-wide Hackathons that can last up to a week?

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Every CEO needs at least Twitter feed video.
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jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
15 Jul 2077362706567323832

Know your competitive position before you update your strategy. SWOT is not a slide. It is a forcing function.

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Know your competitive position before Twitter feed video.
Reply on Twitter 2077362706567323832 Retweet on Twitter 2077362706567323832 0 Like on Twitter 2077362706567323832 0 X 2077362706567323832
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