[nathanwallace]

Career change is often best one variable at a time. For example, change company size but stay in the same industry. Double jumps are generally harder.

Perhaps, focus on startups that reduce the number of change variables. For example, startups focused on satisfying the needs of enterprise IT customers should value your inside knowledge of the pain points.

Keep looking - the right thing will be out there. (For example, my company, Turbot, is actively seeking remote employees with enterprise experience and a pent up hunger to get stuff done.)