Boutique RE & VC fund (2yrs analyst + 1yr associate) to IB: how realistic?

Background: I spent two years as an analyst and just finished a year as an associate at a boutique real estate fund. My work covered deal underwriting, fund administration, seed stage investing/valuations, LP reporting, and compliance. I went to a non-target school.

I want to move into investment banking. The fund has given me solid underwriting and financial analysis experience, but the team is small and the pace isn’t what I’m looking for. I want a bigger grind, a more competitive environment, and the training that comes with a proper bank.

Questions for people who’ve seen this from either side:

  1. How realistic is a lateral into IB at the associate level from a boutique RE/VC fund, versus resetting to analyst or taking a lower title?
  2. Does RE underwriting experience translate, or do banks see it as too narrow? Would RE or REIG be the natural landing spot?
  3. How much does the non-target background hurt at this stage, and can experience offset it?
  4. What’s the best route in: direct applications, recruiters, networking into middle-market banks, or something else?
  5. Is a boutique or middle-market bank a smarter first step than going straight for a bulge bracket?

I’m willing to take a step back in title if that’s what it takes. Appreciate any honest takes, including “it’s a long shot.”

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