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(Just to disclose my “bias” upfront, and not trying to argue with anyone, I'm not a believer in “cry-it-out” sleep training. The research seems to lean that way, too.)
My kids were very light sleepers, which led to many bleary-eyed days, but I was lucky enough to not go back to work until they were school-age. A couple of things come to mind with your son, but I always rule out anything health or pain-related first, such as teething (those molars hurt!) or an ear infection. It sounds to me like you've nailed the cause, though: He wants to be with you :) And that’s not a bad thing or something that should be discouraged: We want our kids to know we are there for them when they need us, so they will come to us later with the big stuff like dating, drinking and drugs. You just need to meet that need in a way that lets everyone get some sleep!
A good bedtime routine is invaluable:
* Early is better: It took me a long time to accept this, but the later a child stays up, the harder it is for him/her to fall asleep. That “second wind” can derail bedtime in a big way, so make sure you start your routine before he’s too tired. Same goes for naps.
* Snack: We found that a healthy, protein-based snack before bed helped the kids sleep longer through the night. (It’s important to brush teeth, too, and avoid carb or sugary snacks that are a banquet for the nasties that cause cavities.)
* Story/song: Reading or singing, even if just for a few minutes, can help mark the end of the day and the beginning of night. And if your child can sit in your lap while you read or sing, that helps meet the need for physical contact, which is extra-important now that you’re working outside the home again. A very popular book at this age is Goodnight Moon, which can be adapted for your family so Jack says “goodnight” to people and pets on his way to bed. We made up songs for each child and I’ve also used soothing music (and now that they’re older, books on CD) at bedtime. Return to Pooh Corner by Kenny Loggins is a lovely CD to fall asleep to.
* Bath/massage: My kids always got wired from time in the tub, but some kids find it relaxing. I used lavender-infused oil for belly rubs and leg rubs, which worked especially well with my high-strung daughter. Lavender is very soothing and relaxing for adults and kids, I’ve found.
* Consider ditching the crib: This can be a nightmare for some families, but a twin-size bed can allow you to cuddle with your son until he nods off, and then tiptoe away. Even though my kids are 8 and 10, taking a little time to cuddle with each of them before bed makes bedtime much easier for everyone, and lets us end the day on a happy note.
Above all, try to go slowly and don’t expect change overnight. Give him as much one-on-one or physical contact as you can, so you can meet that need and your need for sleep. If bedtime has to be handled by other people, make sure there is a consistent routine between all caregivers, so your son can get into the habit.
This got long, but I hope it helps!

Poor you and poor Jack.  We went through something similar during the night with my oldest daughter.  On the advice of a friend and some books we read, we decided to let her cry at night to get her on schedule.  The first night she cried for a few hours and the next night she cried *a little* less.  It took about 4 nights I think before she slept through.  It was so hard for us to lay there and listen to her.  Probably one of the hardest  things I have ever done.