Advice on (drastically) switching markets?

I made a similar move you are describing and am based in Southern California. I also have been selectively looking at moving to other cities for the past year or so at the EVP/Managing Director level. Feel free to DM me for more details but I wanted to reply for the forum’s benefit.

The biggest factor I would consider is your level of seniority. Generally the younger, the easier it is to make this type of market switch. Once you hit the Director/VP level is when it gets significantly more difficult because at that point you likely have some level of sourcing responsibilities and/or are running projects so local knowledge becomes more valuable. Once you have reached SVP/Managing Director level I would plan for at least 6+ months of looking/recruiting time in a normal job market and up to 1+ year or more in bad times. Even that can be extremely variable as there are a very limited number of seats and if one opens up, you’re still likely going against other professionals with similar years of experience but all in that local market so you better have a compelling story or better yet, deal experience in the market you are looking to move to.

Another consideration is what slice of industry are the positions you’d like and/or how selective you are being. Generally, jobs within asset management will be easier to recruit for in a different market while development and construction roles likely will require more localized knowledge.

Based on the above and your years of experience, the move you are proposing should be doable in a normal job market. Times are tough out there right now with ample candidates so that will certainly be more difficult in the intermediate term.

Some tips I would offer for someone looking or determined to make a market switch would be:

1. Have a great story or better yet, experience in that market - ideally this is a bunch of deals you’ve done in the new market but even if you have a couple projects and a really great story as to why you want to work there (and how it fits into your long term plan) then that can get it done as long as they really like you. I would make sure your significant other/family are on board before you begin the recruiting process because being able to answer with confidence you’ll move is vital during interviews/conversations.
2. Utilize your alumni and personal network as much as possible - reach out to every connection you have to the area, no matter how vague. Whoever hires you moving markets is betting on you the person so the more people who can advocate for you on a personal level, the better.
3. Consider an MBA or MRED - this will be dependent on your experience and financial status but this is one of instances where a graduate degree or certificate makes sense. It lets you meet talent your age and build your local network, employers often recruit at certain schools and it helps you get acclimated to the area. 
4. Risky but save the initial funds and make the move - keep in mind this is very situational so this will only apply to a very small slice of job seekers in the right situation but if you’ve saved a significant amount of funds and have great experience or brand name as well as a fall back plan then it can be a big help to either make longer trips out to the new market you want to move to so you can meet face to face or actually move ahead of the job so you focus full time on recruiting and networking. In Southern California in particular, employers are very sensitive to talent that lives elsewhere and will actively screen out those who are not local (unless you’re a rockstar) because too many have wasted a ton of resources pursuing talent that falls in love with the idea of living out here but when rubber hits the road, they won’t move or expect a bunch of additional costs to move them out here. 

This is Southern California specific advice but if you’re willing to be flexible, you’ll have much more luck finding a position in LA or OC. SD has a significant lack of major employers and most real estate firms choose those two markets for their west cost HQ. Keep in mind culturally these are very to pretty different than SD (LA being very different, OC being pretty different depending on what city you live in).

Those are just some thoughts that come to mind but feel free to send anymore my way.