Is it possible to go from a senior financial analyst role at American Express to an investment banking analyst or associate role at a tier 1 or 2 bank?

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If you go to business school

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Analyst with the right undergrad, networking or lots of applications sure, associate unlikely.

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Yes moving to IB as an analyst with that background is possible but will be difficult

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What specific skills would you recommend to pick up?

Uphill climb but think there will be a lot of IB jobs open in 2021. Tier 1 unlikely, maybe tier 2 (depending on what you consider tier 2) but once you are in IB it is really easy to switch banks

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