My thoughts are that Jesus is referring to the 144,000. I believe they are described as the New Jerusalem(Kingdom of heaven) coming down from heaven in Revelations prepared as a bride for Jesus which is the kingdom coming down to earth. That kingdom dwells with the rest of the people on the new earth which is the great multitude. Jesus says he who is least is greater than John, meaning John isn't a part of this group in the kingdom of heaven. If john isn't, then this group must be some really special people. The only group that I can find in the Bible that matches up to this is the 144,000.
The 144,00 are described as being kings with Jesus which would place them in the Kingdom of heaven. They are also described as the only ones being able to learn the new song which puts them in a class of their own.
Revelation:
""Now the dwelling of God(Kingdom of Heaven/144,000) is with men(Great multitude), and he will live with them. They will be his people(great multitude), and God himself will be with them and be their God. He will wipe every tear from their eyes...(which is description of the great multitude, also shown again here...)"
Revelation 8:3 (great multitude) "...For the Lamb at the center of the throne will be their shepherd; he will lead them to springs of living water. And God will wipe away every tear form their eyes."
The 144,000 isn't ever described as having every tear wiped from their eyes, instead they are described as being redeemed from the earth and learning a new song that no one else could learn(which I'd assume is from the overflowing joy from being redeemed).
I also believe the 144,000 is who Paul is referring to when he says this...
I am jealous for you with a godly jealousy. I promised you to one husband(144,000 being the bride), to Christ, so that I might present you as a pure virgin to him.
One of the descriptions of the 144,000 is that they are not defiled with women, for they are virgins.
I also believe this is referring to the 144k referring to the kingdom of heaven.
"For there are some eunuchs, which were so born from their mother's womb: and there are some eunuchs, which were made eunuchs of men: and there be eunuchs, which have made themselves eunuchs(celibate) for the kingdom of heaven's sake. He that is able to receive it, let him receive it."
I hope I didn't side step too much here to make my point. If there's any other ideas from others on this subject I'd be open to hear them.
I'd also like to add this...
"but he who is least in the kingdom of heaven is greater than he.
NKJV
Since the word "he" is singular could it be that Jesus is looking ahead to the mission of Paul?"
Jesus says "he", but it doesn't mean singular as he mentions he who is "least". Meaning there is more than one of them that Jesus is describing being greater than John. You would also think that John would be greater than Paul, as Paul persecuted the people of Christ at one point in his life-time.
I'd like to end with that I'm one who truly believes that the 144,00 is a literal number. You can see throughout the Bible that God used groups of twelve to continue out his ministry. The 144,000 being a factor of 12, as well as there being twelves tribes with 12,000 from each.
The 144,000 is also in contrast to the great multitude that no one can number.
Yes, Revelation is symbolic, but the numbers are literal. There may be 11 horns, horns being symbolic, but there being 11 is literal. So if 144,000 were to be taken symbolically than the other numbers in revelation couldn't be taken literal.
It's also clear that the 144,000 are separate from the great-multitude as they are wearing fine-linen opposed to white robes and holding palm branches. They also learn a new song that no one else can but them.
I thought I should add that in there to strengthen my whole view point on your question.
Like I said, I'm open to hear other thoughts on this subject. I need to get back into fully studying the Bible as it's been a little while.