He absolutely needs more than 1 title to have any real shot.
If you look at the guys in the HOF that made it basically for GM/President type work there really are only 4 in the HOF Embry, Colangelo, Thorn, and Krause (I may have missed someone, but no one else stood out to me). Rod Thorn is in a fairly similar boat as Ainge, but he worked for the NBA and did Olympic stuff for 15-20 years in addition to being a player, coach, and GM. Colangelo has all of the Olympic stuff (as well as ownership) in addition to several different GM/President stints. Krause was the Bulls GM from the mid-80's to the early 00's (so he has 6 titles). Wayne Embry had a pretty prolific playing career and him being the first black GM in the NBA also helps that case. I don't think he makes it as a contributor but for him being the first though (he was also executive of the year twice).
So in sum, I don't think Ainge really makes it in without getting more titles or going to work for the NBA or Olympics. He has to make more of a mark than 1 title in 17 years.