I have enough experience under my belt to feel comfortable approaching fuzzy engineering problems that span relatively unfamiliar domains but I feel it's quite difficult to convey this when applying for positions.
I'm also sure to fail googlable technical questions so I was wondering how others might approach this.
Don’t try to join startups or cool SV companies unless you have an inside track. Their recruiting and hiring practices are mostly geared to ensure “culture fit.” That’s code for young single male who will work 12 hrs/day and think free beer and pizza makes it cool.
Focus on measurable accomplishments rather than languages, frameworks, tech buzzwords.
Learn to solve business problems rather than “engineering problems.” No one needs 2,000 more lines of Javascript. Lots of companies need business problems addressed.
If you’re applying for jobs you’re hobbling yourself. If you have years or decades of experience you should have a large network of colleagues to get leads and jobs from.