00:00.60
Niraj Ranjan Rout
So, welcome, Chloe Shill. Great to have you with us — really looking forward to this conversation on customer service, your leadership of remote customer support teams, and your deep experience. It’ll be exciting for us to continue.
00:17.41
Niraj Ranjan Rout
I’d love to start these conversations from the beginning. How did you start your career, and how did customer service happen to you? How did you end up making this your career and investing in it?
00:37.01
Chloe Shill
Awesome, thank you for having me. I’ve always had a passion for traveling and experiencing different cultures.
00:50.61
Chloe Shill
I studied abroad in college, which led me back to Argentina, where I had studied. I started my career there, working for a small boutique language company.
01:03.09
Chloe Shill
It was remote, and I consider myself pretty lucky to have worked remotely almost my entire career — except for a short time. That was back when Skype was the main tool, and now it’s long gone.
01:17.99
Niraj Ranjan Rout
Mm-hmm.
01:19.92
Chloe Shill
I was working as an account manager in operations with a very diverse team. Then I pivoted into international teaching in China.
01:30.77
Chloe Shill
I worked at a British international school for quite some time, teaching history. It was a really cool experience, and I thought that was going to be my career path — international teaching.
01:44.55
Chloe Shill
I had even accepted another job in Dubai, and then the pandemic happened. I found myself in Spain, getting married.
01:56.05
Chloe Shill
International teaching here is a bit challenging, so I had the opportunity to join Flight. I found a lot of transferable skills and experiences that transitioned really well.
02:13.48
Niraj Ranjan Rout
Mm-hmm.
02:15.80
Chloe Shill
My role at Flight has evolved over the years. I’m currently the Director of Operations, responsible for several things — company strategy, day-to-day operations across teams, and supporting cross-functional growth initiatives.
02:33.20
Chloe Shill
I also manage payroll and compliance, working with different teams and processes to make sure they scale and function properly for our fully remote setup.
02:54.88
Chloe Shill
I’m a huge advocate of remote work. It’s been a big passion of mine — it’s opened many opportunities for me and for others I’ve met.
03:07.80
Chloe Shill
I’ve met very few people who’ve worked remotely and later said they didn’t like it. It happens, but overall, remote work and support are incredibly empowering and important in today’s fast-paced world.
03:32.92
Niraj Ranjan Rout
Makes sense. I’d love to get deeper into what you do day to day at Flight CX. What does your team look like? Are they in the same time zone or distributed? And how do you manage them in a remote framework?
03:49.48
Chloe Shill
Absolutely. I manage operations on the Flight side. Flight CX, in a nutshell, is a customer-support outsourcing agency.
04:01.92
Chloe Shill
We work with various clients and plug into their systems. What makes us unique is that we manage our support teams in collaboration with clients.
04:13.68
Niraj Ranjan Rout
Right.
04:15.44
Chloe Shill
An agent is part of Flight but also part of the client’s team. We integrate based on whatever the client needs — some have fully outsourced support, but most take a more integrated or hybrid approach.
04:33.44
Chloe Shill
Initially, most of our team was in East Coast and Pacific time zones, but we’ve expanded since then.
04:49.65
Chloe Shill
We’re strong advocates for creating community across our teams — it’s a powerful way to keep people connected, especially when remote.
05:04.70
Chloe Shill
I’ve been part of many teams, and the community component often seems like it should just happen naturally. But I really believe you have to build it — you have to put the opportunities and systems in place and encourage people to connect.
05:26.83
Niraj Ranjan Rout
Mm-hmm.
05:26.95
Chloe Shill
That’s something we do really well — creating ways for teammates to connect and buy into our systems and processes. It ensures we can deliver the best service possible, regardless of where we are.
05:43.61
Chloe Shill
It’s about connecting teammates and keeping everyone on the same page, which is incredibly important.
05:57.09
Chloe Shill
You can build community in an office, but in remote work, it’s even more essential.
06:02.18
Niraj Ranjan Rout
Yeah. I’d love to get into your specific activities and ideas for building community. As you said, many assume it happens organically, which might be true in an offline setting — but online, it requires more deliberate effort.
06:24.54
Niraj Ranjan Rout
So, I’d love to know how you go about it at Flight.
06:27.90
Chloe Shill
Yeah, absolutely. When you’re in an office, it kind of happens organically — excuse me — which yes, but also no. I worked in a school for several years, and you naturally fall into groups, right?
06:37.61
Niraj Ranjan Rout
Thank you.
06:44.76
Chloe Shill
For example, I used to hang out with the other history teachers or those who were closer to my age — that’s natural. The same thing can happen online. But what we do, and I think we do really well, is create intentional opportunities: frequent happy hours, Slack challenges, wellness activities, and kudos shoutouts.
07:06.33
Chloe Shill
We have tons of community Slack channels focused on different interests.
07:19.47
Chloe Shill
We also make sure to maintain them properly so it doesn’t become overwhelming. If a channel stops serving its purpose, we archive it or tweak it.
07:27.49
Niraj Ranjan Rout
Thank you.
07:29.76
Chloe Shill
That’s something we’re very intentional about. We want our communities to stay relevant and easy to engage with.
07:42.57
Chloe Shill
We also try to build connections through our happy hours — not just within Flight, but also with clients who are interested in joining. It helps build stronger relationships between our internal teams and client teams.
08:02.16
Chloe Shill
What we do really well is build personal connections with our clients and team members. It’s not just about offering great service; it’s also about creating a sense of belonging. When people feel welcomed and connected, they do their best work.
08:28.14
Niraj Ranjan Rout
Makes sense. And that’s very interesting because, as you said, it requires much more intention than we usually give it.
08:39.14
Niraj Ranjan Rout
So whose job do you think it is? At Flight CX, and in general — who should own this? Because in a company with dozens or hundreds of people, it’s everyone’s responsibility, but that can also mean it’s no one’s.
08:54.11
Chloe Shill
Right, yeah, that’s a great point. We have a People Ops team, and their responsibilities span several areas.
09:06.81
Chloe Shill
One of their key roles is building community — and that ties into training. We have something called Flight School, which is part of our onboarding program. It covers the basics of support, how things are done at Flight, and a bit about the client before the agent starts working with them.
09:33.81
Chloe Shill
During onboarding and in Flight School, we also introduce new hires to our community.
09:38.20
Niraj Ranjan Rout
Thank you.
09:39.29
Chloe Shill
Of course, you can’t force anyone to participate, but I’m a big believer in encouragement — and it starts from the top. Team leads and leaders must be equally invested in the community.
09:56.70
Chloe Shill
That can be hard — everyone has different roles and busy schedules. It’s easy to say, “I don’t have time for a 20-minute happy hour,” but showing up makes a difference.
10:07.77
Chloe Shill
Our happy hours are short, but when leaders attend and encourage participation, it really impacts engagement.
10:18.38
Chloe Shill
Being active in Slack channels you’re interested in also helps. When leaders see their teams engaging, they can mention it in one-on-ones — it shows that they notice and value participation, which motivates people to keep contributing.
10:44.99
Chloe Shill
And again, participation isn’t just ticking a box — it genuinely improves well-being. I can confidently say that team members who are involved in the community have the best experience because they build connections. Remote work can feel isolating otherwise.
11:09.52
Chloe Shill
We’ve all felt that way when working remotely.
11:09.82
Niraj Ranjan Rout
Yeah.
11:12.42
Niraj Ranjan Rout
And that becomes even more important when you have a multicultural team spread across time zones and continents.
11:24.12
Niraj Ranjan Rout
So any insights on that? I understand your team is fairly multicultural and distributed — what have you learned about managing and ensuring such a team works well together?
11:39.63
Chloe Shill
You mean across different time zones?
11:42.05
Niraj Ranjan Rout
Yeah.
11:43.29
Chloe Shill
One thing that’s been really impactful is rotating the times of our happy hours and team events. That way, it’s not always optimal for just East Coast or West Coast folks — everyone gets a chance to participate.
11:56.73
Chloe Shill
Also, for those who can’t attend live sessions, our Slack challenges and “Question of the Week” are designed to be relevant to everyone — across cultures and regions.
12:15.38
Niraj Ranjan Rout
Oh.
12:21.16
Chloe Shill
We make sure the prompts are things everyone can connect with. For example, a couple of months ago, we had “the ultimate debate” — should pineapple be on pizza?
12:37.79
Chloe Shill
It was really fun to see how it evolved. We had folks from the Philippines share their favorite pizza toppings, and others from Chile chimed in. It was fascinating to see the cultural differences.
12:56.76
Chloe Shill
Those small interactions matter — you start remembering things like, “Oh yeah, that person likes this,” and it helps build connections. Keeping the community approachable, light, and fun makes it easier for people to engage.
13:01.47
Niraj Ranjan Rout
I agree.
13:06.45
Chloe Shill
We’re not asking people to spend hours every week on community activities — it’s about small, meaningful moments that help people feel included.
13:14.11
Niraj Ranjan Rout
Agreed. Great. So, as I understand it, community is a huge part of what you do. The other important aspect is accountability.
13:23.00
Chloe Shill
Yep.
13:23.19
Niraj Ranjan Rout
Let’s talk about that — how do you make sure people take accountability seriously, and what have you built into your processes to ensure it?
13:34.41
Chloe Shill
Absolutely. When it comes to accountability, the most important thing is to focus on your processes and documentation early on.
13:54.92
Chloe Shill
You have to define what you expect your remote teams to do — the how and the why. How do we do things at our company, and why do we do them that way? These need to be clearly documented, and key stakeholders should have input.
14:17.04
Chloe Shill
Then, it’s about giving your team the right tools to succeed — tools for communication, documentation, and accessibility. Everyone needs to know where to find information and how to engage with it.
14:35.10
Chloe Shill
It has to be accessible, over-communicated, and easy to engage with.
14:39.42
Niraj Ranjan Rout
Mm-hmm.
14:42.57
Chloe Shill
And it’s important to set expectations early on. You can have a fun, engaging culture, but at the end of the day, this is still a job. People are working across multiple time zones — micromanagement isn’t possible or realistic.
15:02.45
Chloe Shill
So, you have to give people the tools and autonomy to be successful.
15:13.08
Chloe Shill
That means choosing the right tools and leaning into them. Some organizations struggle because they introduce a bunch of tools but never implement them properly or consistently across teams. That creates confusion and weakens accountability.
15:38.43
Chloe Shill
When done right, though, teams can be successful, accountable, and empowered to do their best work.
15:49.14
Niraj Ranjan Rout
Interesting. Another thing I’d love to get into is your teaching experience — how that’s influenced what you do now at Flight CX.
16:07.23
Chloe Shill
Yeah, that was an interesting pivot. I went to China to visit family and got an opportunity to work on curriculum development at an international school. That eventually led to a teaching position.
16:25.62
Chloe Shill
I went on to get my master’s in teaching and stayed there for almost four years. It was a great experience — very challenging, working in a completely different environment and culture, managing students, parents, and staff.
16:38.80
Chloe Shill
I also ran the Model United Nations program, which was a cool experience. It involved working with stakeholders from all over China and internationally, which taught me a lot.
17:08.64
Chloe Shill
As a whole, I think there are a lot of transferable skills between teaching and support.
17:20.07
Chloe Shill
When I transitioned into Flight and operations, it wasn’t planned — I expected to teach long-term — but it turned out to be a natural transition because so many of the skills overlapped.
17:38.94
Chloe Shill
It was a natural transition because there are so many transferable skills and experiences you can bring from teaching into support.
17:51.31
Chloe Shill
In teaching, every single day is different — you never have the same class twice. It’s the same with support teams and customers.
18:02.05
Chloe Shill
Education is an ever-changing industry, no matter where you are in the world.
18:02.25
Niraj Ranjan Rout
Yeah.
18:07.24
Chloe Shill
There’s always a new teaching method or philosophy, and managing children is challenging in itself.
18:11.09
Niraj Ranjan Rout
Hmm.
18:18.22
Chloe Shill
Working with colleagues from multiple backgrounds adds another layer of learning. So, when I transitioned into operations, a lot of those skills came with me — especially communication and creating clear systems early on.
18:40.26
Chloe Shill
In teaching, you think carefully about how you want your classroom to function — particularly in an international setting, where students come from all over the world.
18:54.73
Chloe Shill
How do you bring these children together to connect and learn? It’s the same with remote teams.
19:06.01
Chloe Shill
You have people from all over the world, and you’re bringing them together to collaborate and deliver great service for clients.
19:20.42
Chloe Shill
So really thinking about those systems and processes upfront is key to ensuring everyone can succeed.
19:20.75
Niraj Ranjan Rout
Makes sense.
19:32.72
Niraj Ranjan Rout
Very interesting. One thing I’d like to go back to is how you’ve built your team and how you recruit. Of course, some roles require subject-matter expertise — those are the hard skills. But support also demands softer skills, like handling conflict and managing difficult situations.
19:50.12
Niraj Ranjan Rout
How do you balance those, and how do you test for both when recruiting?
20:09.01
Chloe Shill
That’s a great question. I’ve been fortunate to be involved in our recruiting process from time to time, and we involve several stakeholders — which I think is really important.
20:25.63
Chloe Shill
We always start by understanding the client’s profile and pairing that with Flight’s ethos — what kind of agent we want representing both brands.
20:38.81
Niraj Ranjan Rout
Thank you.
20:42.57
Chloe Shill
It’s not just about prior experience or education — it’s about connection. Do you have a genuine passion for helping others?
20:56.13
Chloe Shill
Do you communicate clearly? How do you handle feedback? Because especially in remote work, feedback is everything.
21:09.61
Chloe Shill
If a candidate seems resistant to feedback, that’s a red flag — it’ll be hard for them to grow in this environment.
21:22.48
Niraj Ranjan Rout
Thank you.
21:27.98
Chloe Shill
We also evaluate conflict management and communication skills. Those are things we emphasize heavily.
21:45.76
Chloe Shill
It’s not just about background — it’s about how you carry yourself throughout the interview and how you respond to different scenarios.
21:58.79
Chloe Shill
We do a mock support exercise with candidates, and we look closely at how they handle conflict resolution.
22:16.04
Niraj Ranjan Rout
I think the key takeaway for me is that two things matter most: how someone handles conflict and how open they are to feedback.
22:26.73
Chloe Shill
Absolutely, I couldn’t agree more. Feedback — from peers, leaders, and customers — is so important.
22:37.82
Chloe Shill
It’s one of those things that often gets underrated, but it’s how we grow. Of course, we’ve all been in situations where we received feedback we didn’t love or weren’t ready for.
23:02.02
Chloe Shill
At Flight, we focus on how to give constructive feedback, because that’s how improvement happens. Especially in remote environments, where you might only get feedback once a week.
23:27.81
Chloe Shill
In an office, feedback happens naturally — you’re constantly crossing paths with colleagues. In remote work, you have to be deliberate about it.
23:47.36
Niraj Ranjan Rout
Absolutely. Great point. My last question, Chloe Shill — I’d love to hear your thoughts on AI. How do you see AI and automation impacting how support and remote teams work?
23:47.36
Chloe Shill
Yeah, absolutely. AI is definitely the hot topic right now. There’s a lot of discussion around what it means for customer support and how it’ll affect the industry.
24:04.64
Chloe Shill
I see it as an incredibly powerful tool — especially for remote and multicultural teams. Real-time translation and transcription tools make global collaboration much easier.
24:28.80
Chloe Shill
Before, these things were more time-consuming or complex. Now, AI helps us bridge those gaps seamlessly.
24:47.25
Chloe Shill
Even scheduling has become smarter — AI tools can find optimal meeting times across time zones and preferences, helping teams sync up more effectively.
25:00.80
Chloe Shill
It’s also really powerful in project management. Most support teams aren’t just handling tickets — they’re managing projects, too. AI features within project management tools help streamline workflows and improve efficiency.
25:35.14
Chloe Shill
And then there’s collaboration. Tools like Slack and Microsoft Teams now offer smart suggestions, while Zoom has great AI note-taking features.
25:37.23
Niraj Ranjan Rout
Absolutely.
25:53.89
Chloe Shill
I’m a big note-taker, but I’ll admit I’m not always great at capturing everything. The AI-generated meeting summaries have been a game-changer for me.
26:09.31
Niraj Ranjan Rout
Absolutely. Great, Chloe Shill. That was really insightful. I’m sure there’s a lot in here for people running remote teams — especially support teams.
26:21.37
Niraj Ranjan Rout
Thank you for the conversation.
26:23.54
Chloe Shill
Thank you so much. It’s been a pleasure.
26:26.51
Niraj Ranjan Rout
Thank you.
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