While I have an admittedly limited exposure to things Chan (as my practice is centered around Vajrayana), I always found my Chan teacher, Guo Gu, to be very helpful. Since you asked about contemporary and progressive teachers, I can't think of anyone better.
Guo Gu was the long-time attendant of Master Sheng Yen of Dharma Drum Mountain, as well as his monastery's disciplinarian, before he became a family man and lay teacher within the lineage. He currently teaches as a professor at Florida State University, leads the Tallahassee chapter of Dharma Drum (a.k.a. the Tallahassee Chan Group), and is a pillar of the local Buddhist community as a whole. In the relatively conservative Florida panhandle area, Guo Gu has managed to attract many students---of all different ages and from all walks of life---which I assure you is no small feat, and speaks to the effectiveness and realization behind his teaching style.
In my humble opinion, you'd do well to check him out. Here's a short bio from his website (which also includes a bio of Master Sheng Yen and several of his teachings, too):
Guo Gu is one of Master Sheng Yen's senior and closest disciples, and assisted the master in leading activities at the Chan Meditation Center, Dharma Drum Retreat Center, and Dharma Drum Mountain in Taiwan, and other parts of Europe and Asia.
Guo Gu first learned meditation when he was four years old in 1972. He studied with one of the most respected Chinese meditation masters and ascetics living in Taiwan, Master Guangqin (1892-1986). In 1981, due to his family's relocation, Guo Gu moved to the United States.
In 1982, he began learning meditation from Master Sheng Yen, who was residing in New York at the time. Beginning in 1989, Guo Gu began to attend intensive Chan retreats with him. After the first retreat Master Sheng Yen gave him the Dharma name, Guo Gu, which means, "results from being the valley." In 1991, after college, Guo Gu was ordained as a monk and became the Sheng Yen's first personal attendant who traveled with the master. In 1995, he received inka (the seal of approval) for his first Chan experience, and was given permission by the master to teach Chan independently. He has subsequently received several affirmations of his experience in 1996, 1997, and 2007. In a chance meeting in June 2007 his experience was verified by the Rinzai Zen master, Roshi Noritake Shunan, of the Myoshin-ji Zen lineage.
In 2000, Guo Gu left monasticism and re-entered the world. In 2008, he received his Ph.D. in Buddhist Studies from Princeton University and began teaching Buddhism and East Asian religions academically as an Assistant Professor at Florida State University. In 2009, he founded the Tallahassee Chan Center. He is the guiding teacher for the Western Dharma Teachers Training course at the Chan Meditation Center in New York and the Dharma Drum Lineage.
More info, teachings, and texts can be found on the following websites:http://www.tallahasseechan.com/https://www.youtube.com/user/Tallahasseechanhttp://www.facebook.com/home.php?sk=group_473937640500
Hope this helps!
"The Sutras, Tantras, and Philosophical Scriptures are great in number. However life is short, and intelligence is limited, so it's hard to cover them completely. You may know a lot, but if you don't put it into practice, it's like dying of thirst on the shore of a great lake. Likewise, it happens that a common corpse is found in the bed of a great scholar." ~ Karma Chagme དྲིན་ཆེན་རྗེ་བཙུན་བླ་མ་རཱ་ག་ཨ་སྱ་མཁྱེན་ནོ།