Our startup is looking for second-act career seekers to be our local representatives. As it is commission-based, we are looking for people able to invest a little bit of time.
Paid advertising on social media, particularly Twitter, Facebook and LinkedIn can be highly targeted and so I am sure you could find relevant keywords and topics to target using those platforms.
Depending on where you are in the world, look for events on meetup.com and/or Yelp. There are almost certainly going to be groups and events related to your target demographic. Think book clubs, wine clubs, sports, theatre etc.
Digital signposting - e.g. screens at medical establishments, local public transport, gas stations.
Lastly, perhaps advertise at night-schools or venues that host a lot of evening classes.
If I were you, I'd try a mixture of Facebook (based on demographic features) and AdWords (based on search intent).
Additionally, you might accomplish a fair bit simply by networking with people in the right LinkedIn groups. If you can identify blogs with the right audience, then publishing an interview or advertorial might help raise awareness.
Curious what your brand is ...