Amir Bormand: [00:00:00] On this episode of the podcast I had with me Tony Dong. He is the Senior Director of Engineering at Rippling. We’re gonna be talking about maintaining a startup mindset while scaling the team. He has seen some incredible growth from an engineering perspective. Two to, you know, close to 140 plus.

And, you know, going through that and seeing how to kind of keep yourself nimble, but, but allow people the right amount of autonomy. Allow them to be inventive. Definitely some challenges. And Tony’s here to, you know, talk us through how he has navigated that. Tony, thanks for being on 

Tony Dong: podcast. Yeah.

Thank you for having me. Excited to be, Absolutely. 

Amir Bormand: Let’s start off at the top and understand two things. One what does rippling do? And then secondly, as a senior director of engineering, what are some of those responsibilities that you have? Yeah, 

Tony Dong: so rippling, I think of it as like the first way for businesses to really manage all of their [00:01:00] hr, it, payroll, finance, everything, all in one unified platform.

Think about like how you’re running your company day to day, right? Every product that you’re using, every individual SaaS product has the sprinkling of employee data within it. It could be things like your. Simple like identity or email or your department team, work, location manager, et cetera, right?

Maintaining the fidelity of data across all these different systems, which are usually disconnected and essentially is like managing data across multiple databases. Right, and this is why like a lot of the companies have a very convoluted processes on making change, on change management, access management, and we’ll typically have armies of hr.

IT people kind of solves this problem by giving companies employees a single platform to manage everything and knows everything about your company and can orchestrate everything in a way that just makes sense. Great. My role right now is leading the HR products and platform here at the [00:02:00] company. The HR product centers around a lot of the core employee information.

Basically how all these different systems interconnect with each other and linking back to that core employee information. And platform side provides a lot of the underlying technologies and products that tie everything together, like unified permissions, approvals, workflows, reports, rq, et cetera.

Everything we kind of bundle under the idea idea of rip replacing unity. 

Amir Bormand: Awesome. All right, so, topic is, you know, maintaining that startup mindset as your team is scaling. I, I guess, you know, before we start, let’s, let’s talk. You mentioned growth I think it’s good to kind of just understand what that context means.

Like when we talk about scaling for you and your team, what does that look like over the last few years? 

Tony Dong: Yeah, so I joined September, 2019, so just over three years from when we’re recording this podcast here. So I think in that kind of three years has gone [00:03:00] through tons of different phases of growth, right?

And again, growing the team from. Like two other people when I started to now 140 plus. We’ve gone through phases initial. We’re just trying to basically kind of rebuild and get to the point of the team where we can build and actually live sustainably, right? So those first couple months we’re definitely just like, Hey, trying to catch up and make sure we’re not kind of like just.

Overwhelmed by the amount of like, you know, support tickets, amount of like operational work we need to do day to day, right? Kinda as we’ve continued to scale the team, we’ve started to be able to then define the individual sub-teams and the kind of like team structure long term, right? Start to define the vision behind the HR product area as well as the platform area and those.

Two areas kind of like continued to blossom there afterwards. And then we, we were able to get into a position of kind of being able to now look more ambitious and look at the kind of like bigger product roadmap and look at the things like, [00:04:00] you know, ripple unity, which I’ve just mentioned. Right. So during that period we’ve had to kind of like skill the team and scale the processes accordingly as well.

Absolutely. 

Amir Bormand: And, and I guess, you know, I think it’d be interesting to, to talk. You know, I, you, I hear a lot, and I think it’s talked about a lot about, you know, kind of staying agile, maintaining the startup mindset. I guess when you kind of think about maintaining a startup mindset, why is it important to you?

Like, what is it about that, that, that, that will help your team? Obviously, you know, no one wants bureaucracy and, and red tape, but, but what is some of that kernel of, oh, we gotta maintain, you know, this, this x. 

Tony Dong: Yeah. I think the startup mindset really has three different components that are like really core to kind of how we operate as rippling, right?

One is around kind of like bias to action, right? Not just waiting around for kinda like someone to tell you what to do or like, you know, waiting around, go through huge committees or, you know, [00:05:00] long, long design processes before actually getting something. Like, out into the world or getting something that you can kind of like prove out your ideas, right?

I think that has helped us kind of like build a lot of different ideas and products and build them very quickly and get to like, test that product and test with product with customers, right? Another component of kind of like that startup mindset is around thinking bigger, right? Being more ambitious.

I think a lot of times when you’re stuck in trying to optimize in one area or like trying to like really think about one very, very small specific problem, you kind of lose sight of. What is really possible if you kind of like step back and build something bigger and be able to maintain maintain a team that has that kind of like mindset of being ambitious, kind of really is really helpful going forward.

And then I think the last thing is around like kind of. Looser boundaries than lack of kind of like, lack of like, you know, tights or lack of like well-defined[00:06:00] team boundaries, right. So I think one of the things that you get as you kind like go into bigger companies, or I’m gonna establish companies they, there’s of like, oh, that’s not my responsibility, that’s someone else’s, Hey, I’m gonna bounce your tickets around until something gets done.

And that’s not really productive and never really helps. So I think we wanna find a way to help the team continue having that. Like, Hey, we’re in this together, we’re delivering together. How do we get this done? And not going to the, oh, this is really your team, or my team thing. Right? 

Amir Bormand: Absolutely. And, and I guess as you’re, you know, you’re high, you, you started with two, you, you have a lot more now 140 plus engineers and, and as you start hiring, And you’re bringing different people in different mindsets, different backgrounds, right.

You know, working at startups, big companies, things will start changing you know, to, to a degree. Obviously. That’s good. You know, bringing all those different perspectives to the table will help. How do you start picking and choosing [00:07:00] what becomes the culture ad, right? Because cuz you can’t have everyone wanting to do things their in own way.

Cuz obviously early days. There’s a lot less eyes on process. There might be minimal process, but how do you start paying attention to, hey, like these are the processes that we need to build upon. And, and obviously that, that’s gonna kind of help be the foundation. 

Tony Dong: Culture is kind of an interesting concept, right?

Because culture is not something you can like, Define and say, Hey, everyone acts this way. Right? Culture is really the people and what you observe as the cultural norms of the people, right? So that’s really why it’s so important to think carefully and deliberately about every single person that you’re hiring and thinking about who are the kind of like, Culture ads and making sure that you’re not finding people who go kind of like on the opposite spectrum of what you’re trying to define as your company culture, right?

Or what you’re looking to see as [00:08:00] your company culture. So again, like it’s not like we only hire startup. People and like we never hire from big companies. In fact, we have tons of people from all different backgrounds, all different kind of like, types of engineers. I think really it’s looking at the things that we want to be promoting, right?

The three ideas and tenants that we talked about previously. Right. Which is thinking bigger, being kind of like. Be able to break down team boundaries and bias to action, right? Those are things that we’re looking for in my hiring manager calls in our kind of like interview process throughout, and making sure that we find people who can attend to those three core tenants really helps.

Amir Bormand: Absolutely. I, I agree. I think, yeah, pe people, people are your culture, you know, the, the, the people, the processes, you know, what they embody becomes, What your company stands for. I guess as you start becoming further removed from, you know, hands-on, you know, watching, you know, you have managers that are reporting to you, [00:09:00] how, how do you stay in touch with that?

Tony Dong: Yeah, that’s a good question. I think it definitely gets harder and harder as the team skills, but one of the things. I’ve really tried to do is be hands-on in particular areas and really go, we have a concept within Brooklyn called Go and See. Right? Really just like, Hey, like I can try to hear from like three layers of indirection and game the telephone of like, Hey, they said this, and then it gets translated to some other version and finally makes it up to me.

Or I could just go and talk. The individual engineers or go look at the code or go look at the kind of like, or go sit in a meeting or et cetera, to be able to actually see what’s happening day to day. It doesn’t necessarily mean, hey, I’m gonna go and like code out the entire thing, or go and like, you know, solve every support ticket in that area.

But it means that I have sufficient kind of like, Sufficient context and capability in that area to be able to understand what’s happening and have a fuller picture and be able [00:10:00] to go and actually resolve those issues accordingly, or help the team resolve those issues accordingly. Okay. One of my favorite shows actually is is, you know, undercover Bosses.

Right. It’s kind of like that same idea, except I don’t have to like, you know, put on like a disguise to, to actually go see what’s. I like 

Amir Bormand: that, that that’s like, that’s, that’s, that’s a good way of that’s a good analogy. I think a lot of people probably will, will, will relate to that. I guess as you’re, you know, you’re talking, you, you know, go and see.

I guess on the flip side, you know, when, when a startup is early stage it’s very sales. Requirements driven, right? You know, we need to make a sale. Let’s go implement this, or somebody needs this to get something over the, the hump. Let’s go do it. As the matures, you know, product managers come in and there’s a roadmap and you know, they’re taking the feedback and prioritizing.

As you kind of start seeing the team grow and you guys start seeing some of those, you know, yeah. Some of the separations formalize. Right. What’s that impact to the engineering team? Because obviously when those [00:11:00] 2, 3, 4, 5, 6 engineers, you guys probably were getting dotted line feedback coming in pretty quick, pretty easy.

You start getting some of that insulation naturally just because you get formalized teams and processes. How, how was that? 

Tony Dong: I think this is, again, coming back to the go and see mentality, right? So the same way I might go and see like individual support tickets and stuff, that’s the expectation for the engineers as well, right?

It’s not just like, Hey, I’m gonna wait till the PM tells me this indirect feedback multiple from like, you know, multiple layers removed. I’m gonna go. Into Salesforce and look at the underlying kind of like customer communication so we can actually see what the customer is exactly saying. Right? And the expectation for people working on individual verticals or individual areas is that they start to become that not just technical expert, but kind of like a product expert in that area as well.

Again, like this is where I hire a lot of engineers with that mindset of like, you know, never, not my problem, right? These are things that like I need to be looking at, not just like [00:12:00] siloing myself into the pure technical side. So that gives people kind of like a more well-rounded picture of what’s happening on.

Like, you know, their product and decision. And this is why we trust a lot of people with kinda like giving that bottoms up feedback during roadmap and during like quarterly planning, right? Because they’ve been on the grounds that they’re like talking to customers, they’re seeing the feedback, they’re seeing the technical side, they’re seeing what the kind of like, what we actually should be doing going 

Amir Bormand: forward.

How did the team structures change, I guess as you were kind of, you know, going from a few engineers to a lot of engineer. Yeah. Did you guys start off, you know, full stack, were you specialized in and then you kind of grew that? What, what happened to the team’s? Apology? 

Tony Dong: Yeah, so it’s kind of interesting because we’ve started with.

A pure backend team reporting to myself. And then we had kind of like a centralized front-end team which kind of like had almost like a rotating front-end engineer. Kind of like more like a, almost like a consultancy kind of like [00:13:00] type, I think that. Didn’t quite work well for us. So we ended up doing is kind of like, having the engineer individual, like front engineers start to be basically vertically aligned to each individual product area.

So each team became more of a full stack team where you have back engineers, front engineers use, occasionally have QAs depending on the team. You have PMs that are like just dedicated purely into this area. Right. Again, like giving people. Like focus in that one area allows them to then, you know, be more understandable, understanding about the product, understanding about kind of what the customer is seeing.

Interesting. 

Amir Bormand: And yeah, actually, you know, that’s interesting. You start off with a team of backend developers that I, I wouldn’t have guessed that, but that’s, that’s interesting how you guys evolve from there. You mentioned you know, talking about bias to. You know, obviously you need some autonomy to do that.

You need people to go take initiative. As the team’s growing [00:14:00] and obviously process is being put in place and I like to go and see, you know, mindset, how do you start balancing, you know, obviously, This freedom to go and, and, and, and, you know, be, be a little bit on the forward foot of, of learning, understanding with accountability.

I mean, there’s gotta be some of both because obviously, you know, we need some, some form of accountability. How, how does the team accountability balance? The hardest 

Tony Dong: thing for us is balancing accountability with kind of like psychological safety, where you have the kind of like psychological safety to fail.

So I think a lot of people get scared about that level of accountability, thinking like, hey, I have to be right a hundred percent of the time. Right? No one’s right. A hundred percent of the time you’re allowed to make mistakes and as long as you course correct effectively and efficiently. Right? So I think a lot of times is setting that kind of like, setting the example, setting the kind of.

Direction that, [00:15:00] hey, your account for this area, like you need to take action. And since you are kind of like the domain expert in this particular area, have that like kind of, have that autonomy, you’re given that autonomy to actually execute. And kind of make those decisions. And again, like on the same side, like, hey, just because you’re making a decision, we’re not expecting you to be right a hundred percent of the time, but make decisions based on framework.

Thinking about like what is the, kind of like vert to that decision, right? What is the worst case scenario and how do we roll back a decision if needed, like. Making sure that you have as many functionalities with, for decisions as possible, but with those sets of like frameworks in place, like we try to empower people to make those decisions locally.

Right. Think about the, what is the terminology here? Like think locally at globally kind of situation? 

Amir Bormand: Yeah, definitely. I think, I think I think that’s, that’s definitely a balance cuz you’re asking people to take risks, but also they, they know with risk comes [00:16:00] you know, accountability and, and, and downside.

I was gonna ask you, I mean, you’ve, you’ve been at, at, at the company for a while. You’ve seen this growth. It’s a big question, so I don’t, I don’t need you. I, I, it’s more of a high level just outta curiosity, maybe if it’s a mindset thing. But when you’re looking back now, and obviously you’ve experienced, you know, the positive growth, would you go back and potentially apply any learnings to, you know, obviously trying to maintain this startup mindset?

Is there anything that you’d have gone, Hey, I could have potentially done something better 

Tony Dong: or improved it? I think one thing that I would’ve done a little bit earlier is to put, is to kind of like focus more on the recruiting process and think about the kind of like cultural interviews then, et cetera, earlier on in our kind of like team building.

I think a lot of these kind of like, ideas and like a lot of the kind of like, cultural value questions really kind of like were evolved a little bit later in our interview process. So I would say, you know, we’re not perfect at hiring. We definitely [00:17:00] had some false positives that Kind of like detracted us from our overall goal.

Right. So I think for our case, like if I had to go back, I would probably day one really think about the interview process and kind of like how do we make sure we are very adverse to false positives? Because like, I think, you know, false negatives, it’s gonna happen and like, you know, this could happen a lot with any interview process really.

It’s the false positives that really. 

Amir Bormand: That’s actually, I mean, that’s actually a really good one cuz I think as you’re in the heat and you’re of the moment, you’re, you’re looking to hire. It’s, it’s, it is, it is a challenge. I mean, you, you’re scaling, that’s a lot of engineers over a couple of years. Especially in the last couple years.

It’s been a super competitive market. So good for the team for being, you know, being able to, to hit those type of numbers. But I, I, I think, yeah, the, that cultural side, obviously as you mentioned, there’s a cultural ad and there’s an evolution to that. It definitely makes sense that the culture side would be something you’d go back [00:18:00] and maybe 

Tony Dong: look at.

Yeah, I would say this is probably one of the hardest part about kind of like this job is to make sure that you are maintaining that quality bar and cultural bar at the same time you’re trying to grow, right? You have on one side really pressure to like, Hey, we need to deliver more things. We need to hire, we need to get the team and scale up.

And I think on the other side, like you know personally that like you have to maintain this engineering quality bar and cultural bar. Otherwise, if you. You know, bringing in people who don’t quite fit at the fit that bar, it kind of like dictates your team really quick, quick, way, quicker than you think, right?

So in reality, hey, this team could have been 200 people or two 50 right at this point, but we kept our bar high and we make sure that like, we make sure that the team is growing in a way that sets up for long-term success. And I think that’s really the most important part of this job. 

Amir Bormand: Awesome. Tony, thank you for being on.

I’m cognizant of the time. I was gonna ask you that if you [00:19:00] had a, a question or, or a topic that you’d like a future guest to answer, what that would be? 

Tony Dong: I think one topic I would be really curious on future leader to cover is around kind of like navigating engineering team at this kind of like current economic situation, right?

You know, everyone has their opinions to how long this kind of like downturn will last. It may last a little bit longer, and we’re just trying to figure out like, hey, what are people doing to like, keep up morale? What are people to doing to make sure that they’re running a lean team that is effective and that is kind of like maximizing output.

Awesome. 

Amir Bormand: That’s a good one. I’m sure, I’m sure we’ll, we’ll hopefully find somebody to talk to that I’m sure people would like to hear about that one as well. And then if somebody does wanna reach out to you to talk about anything that you’ve covered on the podcast or just in general, what, what, what’s a good way of getting hold 

Tony Dong: of.

Yeah, I think LinkedIn is probably the easiest and very, should be very easy to find. And I’m well also on Twitter. Again, pretty easy to [00:20:00] find. Just Tony, Don, that’s it. 

Amir Bormand: Okay, well, we’ll make sure we include those in the show notes as people can find you. Tony, thanks for being on. Thanks for sharing. I appreciate it.

Tony Dong: All right, thanks. Have a good one, Absolut. 

Amir Bormand: That’s it for this episode. Be back again. Different guests, different topic until then. Two things. One I think the topic Tony mentioned navigating an engineering team in the current economic situation is, is, is interesting. I think a lot of people would be served well with a topic like that.

So if you know someone or you yourself wanna talk about that topic, reach out to me, let me know. I’d love to have you on. Secondly, if the podcast is useful share it give it a review. Couple of five star reviews never heard. That’s how the podcast has been growing and I appreciate everyone who does that.

Until next time, thank you and goodbye.