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Jim Kaskade

Serial Entrepreneur, Global Enterprise Executive

  • Bio Brief
  • Bio Detail
  • I’m an ENTJ
  • Results
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  • 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
Look out – Here comes Microsoft Azure
  • Cloud

Look out – Here comes Microsoft Azure

  • Jim Kaskade
  • March 11, 2010
Virtualization Management Gap
  • Cloud

Virtualization Management Gap

  • Jim Kaskade
  • March 10, 2010
More than HA/DR, More than VM Management
  • Cloud

More than HA/DR, More than VM Management

  • Jim Kaskade
  • March 6, 2010
SIOS to Showcase Comprehensive Cloud Management Solution for Hybrid and Federated Clouds at CeBIT 2010
  • Cloud

SIOS to Showcase Comprehensive Cloud Management Solution for Hybrid and Federated Clouds at CeBIT 2010

  • Jim Kaskade
  • March 2, 2010
SIOS Unveils Strategy to Lead Enterprises Safely into the Cloud
  • Cloud

SIOS Unveils Strategy to Lead Enterprises Safely into the Cloud

  • Jim Kaskade
  • February 22, 2010
Infrastructure is out, Applications are in
  • Cloud

Infrastructure is out, Applications are in

  • Jim Kaskade
  • February 6, 2010
Migration to Private or Public Clouds Difficult
  • Cloud

Migration to Private or Public Clouds Difficult

  • Jim Kaskade
  • January 25, 2010
Capacity Management Challenging
  • Cloud

Capacity Management Challenging

  • Jim Kaskade
  • January 18, 2010
Economy hits the data center
  • Cloud

Economy hits the data center

  • Jim Kaskade
  • January 13, 2010
Economy hits the data center
  • Cloud

Economy hits the data center

  • Jim Kaskade
  • January 13, 2010

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Blog Categories

  • Advertising
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  • SaaS
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  • 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.
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