After more than 20 years of IT experience across different areas (analysis, development, operations, architecture, management, ...) in various industries (e-government, healthcare, manufacturing, consulting, ...), how would you organize your CV well? Would you list all the companies you worked in since your graduation from college and what you did in each (and therefore make a relatively long CV)? Or would you detail only the most recent 3 or 4 companies/projects where you worked along the last 10 years and add a summary of what you did in the older years without listing company names and what you did in each one by one (and therefore limit the CV to round 3 pages)? Any other approaches?
With 20 years of experience this sounds like a rare exception to the one page rule. That being said Alex’s resume here covers 8 years of meaty experience in just a page, without feeling crowded, by being extremely concise. The full resume master class is here. A key from it is to be concise while showing, not telling.
Since I don’t have near that experience myself I’d love to hear more people’s thoughts! In the meantime this is chatgpts slightly useful but mostly parroted opinion:
It's generally recommended to keep your resume to one or two pages, especially if you have a lot of experience. With more than 20 years of IT experience, you may need to be selective about what information to include in your resume. Here are a few options for organizing your resume:
Detail only the most recent 3 or 4 companies/projects: This approach would allow you to focus on your most relevant experience and keep your resume to a manageable length. You could include a summary of your earlier experience, either in a separate section or as a brief paragraph under each job description.
Use a combination of the two approaches: You could list all the companies you've worked for, but only provide detailed job descriptions for your most recent positions. This would allow you to highlight your most relevant experience while still providing a comprehensive overview of your career.
Use a functional resume format: A functional resume emphasizes your skills and achievements rather than your employment history. You could organize your resume by skill or area of expertise, grouping similar positions together and highlighting your relevant skills and achievements.
I really like the answer from Mistplay.
I'd suggest picking the 3-4 most impressive/high-impact jobs, with a bias toward the later part of your career (so not strictly chronological, and not strictly the most well-known jobs).
20 years is the point at which you may have more than 1 page, especially if the roles you're applying for are expecting specialized knowledge.
I'd also look at this from the perspective of "show, don't tell". If you feel like properly talking about your impact in previous roles takes more than a few sentences, I'd prefer that over trying to cram more jobs in the resume.