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How to Get Hired by a CIO: Resume Tips and $200K+ Retail IT Paths
What do CIOs really look for when they’re hiring — and which tech roles in enterprise retail are secretly paying the most? 💰
In this Tech Jobber Podcast episode, Ken Widener (CIO at Do it Best) pulls back the curtain on CIO hiring decisions, high‑paying enterprise IT roles, and the hidden‑gem jobs in retail tech that can quietly pay FAANG‑level compensation over time.
If you’re a Software Engineer, Architect, Data/Analytics pro, or IT Leader who wants to move into higher‑pay, higher‑impact roles (and eventually CIO/CTO track), this episode is your playbook.
What you’ll learn in this episode:
• How CIOs actually review resumes (and the #1 mistake that gets candidates skipped)
• The highest‑paying roles in enterprise retail IT — and why some beat FAANG on stability & upside
• Hidden‑gem retail IT jobs (integration, mainframe modernization, ERP, supply chain) most engineers ignore
• How to position your experience for Director, VP, and CIO‑track roles
• Skills and project types that justify $200K+ total comp in enterprise tech
• How Ken led IT through a massive retail acquisition without breaking the business
• Why mainframe–to–Oracle Fusion ERP and AI/data work are career goldmines right now
• How CIOs think about AI, automation, and the future of software engineering jobs
⏱️ CHAPTERS:
00:00 – Introduction to Ken Widener and Do it Best Group
08:34 – Tech challenges in the retail space and the role of IT
15:34 – High‑paying and in‑demand tech roles in retail IT
23:08 – Implementing AI and working with data engineers
36:09 – Challenges and opportunities in the tech industry
🎯 WHO THIS EPISODE IS FOR
• Mid–Senior Software Engineers & Architects
• Data Engineers, Analytics & BI professionals
• IT Managers, Directors, and aspiring CIOs/CTOs
• Anyone targeting high‑impact, high‑pay roles in enterprise tech & retail IT
📌 To Access All My Resume/Linkedin/Interview Prep Templates: https://techchris6.gumroad.com/l/xjxkbs
📱 CONNECT WITH CHRIS (HOST)
LinkedIn: / christopherschwenk
Twitter/X:
/ techjobberpod
🤝 WORK WITH ME For all of your hiring needs, go to https://www.delostaffing.com
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
View all episodes
By Chris SchwenkWhat do CIOs really look for when they’re hiring — and which tech roles in enterprise retail are secretly paying the most? 💰
In this Tech Jobber Podcast episode, Ken Widener (CIO at Do it Best) pulls back the curtain on CIO hiring decisions, high‑paying enterprise IT roles, and the hidden‑gem jobs in retail tech that can quietly pay FAANG‑level compensation over time.
If you’re a Software Engineer, Architect, Data/Analytics pro, or IT Leader who wants to move into higher‑pay, higher‑impact roles (and eventually CIO/CTO track), this episode is your playbook.
What you’ll learn in this episode:
• How CIOs actually review resumes (and the #1 mistake that gets candidates skipped)
• The highest‑paying roles in enterprise retail IT — and why some beat FAANG on stability & upside
• Hidden‑gem retail IT jobs (integration, mainframe modernization, ERP, supply chain) most engineers ignore
• How to position your experience for Director, VP, and CIO‑track roles
• Skills and project types that justify $200K+ total comp in enterprise tech
• How Ken led IT through a massive retail acquisition without breaking the business
• Why mainframe–to–Oracle Fusion ERP and AI/data work are career goldmines right now
• How CIOs think about AI, automation, and the future of software engineering jobs
⏱️ CHAPTERS:
00:00 – Introduction to Ken Widener and Do it Best Group
08:34 – Tech challenges in the retail space and the role of IT
15:34 – High‑paying and in‑demand tech roles in retail IT
23:08 – Implementing AI and working with data engineers
36:09 – Challenges and opportunities in the tech industry
🎯 WHO THIS EPISODE IS FOR
• Mid–Senior Software Engineers & Architects
• Data Engineers, Analytics & BI professionals
• IT Managers, Directors, and aspiring CIOs/CTOs
• Anyone targeting high‑impact, high‑pay roles in enterprise tech & retail IT
📌 To Access All My Resume/Linkedin/Interview Prep Templates: https://techchris6.gumroad.com/l/xjxkbs
📱 CONNECT WITH CHRIS (HOST)
LinkedIn: / christopherschwenk
Twitter/X:
/ techjobberpod
🤝 WORK WITH ME For all of your hiring needs, go to https://www.delostaffing.com
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.