Lynn Chen in "Caring"

“I like a really calm set,” says Maggie Kiley, something that may have been difficult to come by during her latest production “Caring,” given that the driving force of the show – toddlers – aren’t known for being the most cooperative collaborators. Then again, she had a crew, including cinematographer Ava Berkofsky, who were.

“[Ava] has a very similar energy to mine and even when we were like trying to keep a two-year-olds from crying in the crib, I was like, ‘We’re in this together, babe,’” said Kiley, making her web series debut with the comedy, which debuted this morning on Vimeo.

It’s a patience and a love for teamwork that Kiley has leaned on after becoming incredibly busy herself in recent years, having made the features “Brightest Star,” “Dial-A-Prayer” and “Caught” in just the last three. And while “Caring,” created by Erin Wagoner, may be shorter form, it is no less substantial. Over the course of its five eight-minute episodes, the show charts the travails of Amy (Mickey Sumner) and Vicky (Lynn Chen), two LA mommies making the adjustment to life with young children, and Kate (Hannah Dunne) and Carla (Diana DeLaCruz), the women that work for them as nannies. Careful to give equal focus to each of the quartet, “Caring” comes across as both satisfying vignettes and an overarching whole that covers a surprising amount of ground as it relays the experience of women living at different ends of the social strata, some separated by generation, by race and by financial class, while making light of the full-time occupation of being a mom.

Fittingly, “Caring” will be screening on the big screen at the Los Angeles Film Festival this weekend with a presentation of its third episode simultaneous with its online release, and shortly before its big screen bow, Kiley spoke about the learning experience of wrangling two-year-olds for a TV shoot, filming around L.A. and getting such a strong cast.

While “Caring” is episodic, it has a complete arc, so was it different for you approaching it as a series rather than a feature or is it all just storytelling?

W‎hat I loved about it – and I always like it – if there’s something just a little bit off. This series was already created and it was sent to me to consider and I just loved the world. It as something that I knew but hadn’t really seen them before, so it felt like a good way to get my feet wet [in an episodic storytelling format] and see what it was like for me and I loved that it was a multi-POV story and each episode belonged to a different perspective. I came on early enough where I was able to give some feedback on things and Erin Wagoner, the writer, was really wonderful and open. Because I have two kids, there were things I brought from my own experience that she was always so graciously willing to try.

There’s almost this confrontational visual style, at least in the first episode between the adults and the toddlers, that’s both intimidating and comic. Was that a foundational idea?

All of the episodes opened on this centerpiece moment with this toddler that was super challenging, and‎ Ava [Berkofsky, the cinematographer] and I talked a lot about shooting those opens in all the same way so you really understood, this is what being in a like confined relationship with a young child is like. I don’t know if you spend much time with two-year-olds, but a great descriptor which I’ve heard before is that they’re like your drunk boss. They’re very, very clear in their demands but they’re completely unreasonable. We really wanted to that punch and to throw you into that. We didn’t stick with it for every single one because some of the [episodes] required a little more hand held stuff [like] when [Lynn Chen’s character Vicky] is on the ground with her two boys, but that was one of the early conversations we had.

Also, you really have limited time to shoot children of that age, not only because of the legal guidelines but also because they’re only going to keep their attention with you for so long, so we knew when we did have them on set, we were doing everything we could to capitalize on the time and get the most coverage and the most interesting shots that we could, because a lot of the series, they’re not even scripted to be seen.

Were the toddlers as much of a handful as they looked or just really good actors?

Any two-year-old is going to be a little challenging, but they were all pretty wonderful. I don’t know why I didn’t think about it ahead of time, but I learned very quickly it was never going to exactly what was written on the page. There’d always be some other version of them not doing the thing you needed them to do, so it wouldn’t be beat by beat how it was broken down on the page and‎ once we locked it, it was what it was. But we didn’t have to rewrite a bunch of stuff to make it work.

In general, was there a fair amount of improv?

A bunch of it was scripted but not all of it.‎ My favorite episode is episode two, which is when the moms get drunk and go dancing. A lot of that was improv, with Mickey and Lynn just being hilarious and awesome, coming up with stuff.

Before that point in the episode, there’s actually a great scene where‎ Mickey’s character Amy is trying to figure out what to do with her day, leading to a montage of her finding all manner of unique ways to goof off. How did that scene come about?

That was one of those great moments in indie filmmaking where we were really running out of time and we only had the locations for certain number of hours and days. I had originally conceived of that in a very different way where we were moving the camera to all these different sections of the kitchen, but I loved that cutout window and I thought, wait a minute, let’s put the camera over here and let’s just do the whole thing in this one shot, which called back to my short, where it like keeps the camera still and then jumps through action but keeps it locked off. I just loved the way that turned out.

Were the locations already established in the script or were those things you had to go out and find?

They were pretty clearly defined in the script – you understood that Amy’s house was hip Silver Lake and Vicky’s house was described as Hancock Park and I had hands down the best location manager I’ve ever worked with, which was amazing because we didn’t have a huge budget. I think the houses were Airbnbs at the end of the day, which is what’s happening now in Los Angeles for locations. They worked really well but there was a lot of dressing. It’s my same production designer from both “Caught” and “Dial-A-Prayer” who came on to do this for me and she brought so much character to each of those environments that those homes didn’t actually have. What she did in those nurseries was incredible.

Then we were in Echo Park [for the park scenes], which is awesome because that’s where it was meant to be. I just loved being there and I’ve used the movie “Little Children” for reference before – there’s a great shot, a raking shot of the moms on the bench, and I was so excited to actually get to do a bench shot of the nannies in here.

The cast is great, but Mickey Sumner in particular seems like an inspired choice since since she hasn’t really played a mom before. How did she get involved?

Mickey was a suggestion of Heidi Levitt, who cast this for me. I had never worked with [Heidi] before, but I was so impressed with her and I had actually just seen Mickey, because I just participated in the Film Independent Directing Lab for a movie that I’m putting together and she spoke at the Director’s Closeup [screening of] “The End of Tour.” James Ponsoldt was saying how she’s like his favorite actress and he’d do anything to work with her again. Then [coincidentally] the next day Heidi Levitt said, “What about Mickey?” I was like,”Yes, but would she ever do this tiny web series?” What’s so wonderful is that Mickey and I have some shared connections. She did a play at the Atlantic Theater Company, where I’m a member and she really responded to this script, so we met and hit it off instantly and it was just great to get to work with her.

For both of you, it seems like a bit of departure in that it’s more overtly comic. Was that fun to do that?

Yeah, it’s a little wackier comedy than I’ve done before, but it’s great for me to have a more straight up comedic piece to be able to kind of go out with. I also loved [the opportunity to] make sure that the female characters are fully fleshed out and really meaty. I loved how messy Amy was and that Lynn’s character Vicky, you might initially write her off as one thing — this uptight mom who has her shit together — but then I love how raw she gets in her episode and owns up to like how she’s brought to her knees by the whole issue of being a mom. That was really exciting to me and then to get to work with these four amazing actresses who are all so accomplished in their own right was really great.

“Caring” will play at the Los Angeles Film Fest as part of the Episodes: Indie Series from the Web program on June 4 at 9 pm, June 5 at 5:15 pm and 9 pm at the Arclight Culver City. It can be watched online here.