With a new year comes--you guessed it--a new set of healthcare-related deadlines to keep track of. The good news: with extensions and exemptions, you may have more time than you realize to implement a plan and get a handle on new paperwork requirements. Here are some of the dates entrepreneurs should jot in their calendars.

For small businesses:

Enrolling in SHOP-based plans for 2014
When: Ongoing

If you’re a small employer who missed the deadline to enroll employees in a SHOP-based health plan starting on January 1 this year, don’t fret. While the open enrollment period for individuals to buy exchange-based health plans for 2014 ends on March 31 this year, employers can start offering coverage through the small-business SHOP marketplace at any point during the year--and potentially qualify for a Small Business Health Care Tax Credit for up to 50 percent of employer-paid premiums in 2014.

If your employee enrollments are submitted before the 15th day of the month, your group coverage will begin the first day of the next month. So, if the enrollments are submitted on, say, February 10, 2014, your group coverage would begin on March 1, 2014. For enrollments submitted after February 15th, coverage would begin April 1. Note that online enrollment for SHOP plans is not yet available through the federally run Healthcare.gov site or many of the state marketplaces. You’ll have to do a paper application, go through an agent or broker, or deal directly with the insurer you select.

Enrolling in 2015 health coverage
When: November 2014
Open enrollment for 2015 health plans will start on November 15, 2014--a month later than originally planned. By this time, the federally run online SHOP marketplace should be fully functional, with key added features including the option to offer employees a choice of health plans. And we’ll be able to see how insurers adjust rates up or down based on their first-year Obamacare experience.

For larger businesses:

Noting health care costs on W-2s
When: Now
Most companies will be sending W-2 forms to employees soon--and, if you’re a larger employer, you’ll need to report, in Box 12, the cost of any health care coverage that you provided in 2013. This is essentially the same rule as last year--and the same exemptions apply. Specifically, if you’re filing fewer than 250 W-2 forms for the 2013 calendar year, you don’t have to comply with this requirement. 

Complying with the employer mandate
When: January 2015
On January 1, 2015, the employer “shared responsibility” mandate takes effect. After a one-year delay, businesses with 50 or more "full-time equivalent" employees will have to begin offering subsidized health coverage for full-timers--or else pay penalties on each uncovered worker, excluding the first 30. Firms with fewer than 50 people will continue to be exempt from the requirement to offer health insurance. Make sure you know which category you fall into by starting to carefully track employee hours now. Read our guide for more information about calculating your headcount under Obamacare.

Keeping a record of your compliance
When: January 2016
You’ll have another year to start worrying about another Obamacare-related reporting requirement--section 6056 of the Internal Revenue Code, which requires large employers to report to the IRS (and employees) information about how they are complying with the employer mandate. The first 6056 notices don’t need to be filed until January 2016, but to do that you’ll need to start tracking your company’s benefits details starting in 2015.