Yes and no. With a shrinking population, the jobs you end up wanting to automate the most are related to elderly care in a lot of cases (see: Japan), which is

Yes and no. With a shrinking population, the jobs you end up wanting to automate the most are related to elderly care in a lot of cases (see: Japan), which is fairly difficult for robots/computers in comparison to factory line operations, cashiers, etc. The other issue is that the timescales don't necessarily match up. It's a pretty safe bet that improvements in robotics, computer vision, machine learning, etc. will outpace the decline in population in most countries, so the net result still stands.