The Support Automation Show: Episode 10

Jared Sklar, Sr. Manager of Customer Operations at HOVER joins The Support Automation Show

In this episode of The Support Automation Show, a podcast by Capacity, Justin Schmidt is joined by Jared Sklar, Sr. Manager of Customer Operations at HOVER. They discuss how HOVER helps clients develop their businesses and careers, why implementing automation inside a support function benefits both the clients and employees and the relationship between product engineering and customer support. 

Listen now!

Justin: Welcome to The Support Automation Show, a podcast by Capacity. Join us for conversations with leaders in customer or employee support who are using technology to answer questions, automate processes, and build innovative solutions to any business challenge. I’m your host, Justin Schmidt. Good morning, Jared. How are you doing?

Jared: Justin, I’m doing well. It’s a pleasure to be here today.

Justin: Pleasure to have you. Where does this podcast find you?

Jared: I’m out here in the San Francisco Bay Area. Looking nice out today, but just got through a couple of months of fog. Feeling good.

Justin: I spent two years in San Francisco. I lived at Golden Gate Avenue, effectively the corner of Turk and Stanyan.

Jared: No way. I lived in Baker.

Justin: Love that town. It definitely has a piece of my heart. It’s been a while since I’ve been back, though, but if the world ever makes travel easy again and I’m out there, we should go grab a coffee or something. Jared, tell me a little bit about HOVER and your role there.

Jared: I’d be happy to. HOVER is a smartphone app where essentially you take eight photos of an exterior of your home, and we provide the full exterior measurements and a customizable 3D model of that property. The primary customers being people like external home improvement contractors, insurance carriers and adjusters, and homeowners.

Justin: Very cool. You are the senior manager of customer operations there, correct?

Jared: That is correct.

Justin: How did you first get into customer ops?

Jared: I’ve been doing this type of work for about a decade now. When I first moved here, I quite honestly just wanted a job to be able to pay my own rent and make my own way. I found this job as a customer service representative very entry-level. This company is called SquareTrade, which is an external warranty service. I realized quickly that there were two different ways that you could take this type of role. This was an org with hundreds of representatives, and it was difficult to separate yourself.

You could take support in two ways. You could be someone who clocks in and clocks out and answers emails, chats, phone calls, things like that, or you can look at it as this opportunity to use the insights in front of you where customers are literally telling you exactly what you want to help drive the company forward. When I was a representative, I realized, how do I separate myself?

The first thing that I liked about customer support is your leader usually tell you exactly how you’re going to be measured. I would give that advice to anyone. Know what you’re being evaluated about because they did it in the old-fashioned contact center way where it was l stack rankings and things like that. I was like, if I can get my metrics into a place that will separate myself, it’ll allow me to take on projects to show my skill-set and I eventually became the number one stack ranked representative, which allowed me to take my first shot as a manager.

I was managing a team of 10 representatives there. I did that for about a year. Then I moved onto this company, Zenefits, which is an HR platform for small, medium-sized businesses. That is a whole different story, it is about a three-year epilogue there. There’s definitely been a bunch of interesting stories about that place in my career, but it definitely changed my trajectory. It was an MBA on the job. I was probably the 150th employee there. Within 18 months, there were over 1500 people there, and then 15 months later, there were 750 people there.

It was hypergrowth to the maximum, for sure. There were a lot of different learnings there. That was my first opportunity to manage managers and lead my own organization. After that, I wanted to see if I could do it from scratch. Went to some small startups where I found how difficult it is to find a product market fit in this arena. Did some cool work there, but the companies weren’t moving as fast as I would like them to. That’s when I found HOVER. Been here for about two and a half years. It’s an awesome place with an awesome culture, great group of people. We’re solving some really cool problems.

Justin: In solving those cool problems, you get a really good opportunity to do what you mentioned earlier, which I loved as a piece of advice for people, which is customer support doesn’t have to just be this burdensome, do it because you have to function in an organization. It’s a revenue driver. It’s all the market research and all the– it’s a wealth of inspiration for sales enablement, product marketing, et cetera, et cetera. Being able to identify that and leverage it is a great way to get your career started.

What’s really interesting about what you guys are doing over there is that you’re using technology to enable the customer of HOVER to leverage that technology with their customers to then drive more value for themselves. It’s like this flywheel of value there is apparent, and it’s very neat.

Jared: To piggyback on that too, I’ve worked at a bunch of different types of customer service organizations. The interesting thing about HOVER, just like you said, is like the use of our product directly correlates to someone else making more money. If I’m a contractor and I’m able to book more jobs because of this software, I’m going to use it more and more and more. I’m going to places where it’s more of an exchange of services and things like that, but this product actually helps them develop their business and their career. It’s completely different.

Justin: It’s fascinating stuff. Here on The Support Automation Show, one of the early questions I always like to ask everybody is, when you hear the word “support automation,” what does that mean to you?

Jared: That’s an interesting question. I guess I see it from two angles. One, as a support leader, to me, the automation piece is all about improving the impact my team can make and also giving customers what they want. We’re only going to implement solutions that actually improve the user experience and the business as a whole. We can go into some details of things that we’ve tried and found out that didn’t work, where we actually had to enable humans much more than we tried self-service bots and things like that.

Justin: We’ll absolutely have to get into that, but let’s put a pin on it and then continue your thought here. This is interesting.

Jared: Yes. When I hear that question, the other lens is through the eye of a consumer. We are all consumers. When I get some automated voice system or chatbot, I just think to myself, this better work, that experience of going around in a circle on a bot is so much more memorable than the few times that it does solve your problem. I think when we’re looking at it, it’s like, how do I want to be treated in this experience? Time is so sensitive to the consumer. It’s like, I want to be in, I want to get the information accurately. Hopefully, it’ll be representative as courteous, but really it’s like, I want this to be done quickly. This is a fast-moving environment. I think about it from both of those angles.

Justin: It’s also interesting to look at it from the internal life of the support rep themselves too because you touched on this a little bit too. When you are able to get the easy stuff done, if you’re able to deflect enough calls so that you don’t have an overrun support center of very simple requests, your agents are then enabled to really do more value creative activities and work to more of their best potential. Implementing automation inside a support function benefits not only your customers for getting accurate in and out fast information, but it also enables and augments the agents to do their best work.

When we think of some of those things you’ve tried to automate and the learnings from– I’d love to come back on that because it sounds like you’ve got some stories there, and I’d love to hear them. I think you mentioned specifically there are certain things you thought would work that you tried that didn’t and the lessons you learned. I think that’d be really valuable for the listeners.

Jared: Absolutely. About a year ago, we tried to implement a chatbot. We set it all up with all of these different answers. It would deflect some things. I think the main thing that we realized was that customers hated it. It’s just skipping through this bot, trying to get to a person. We’ve all been there jamming through or clicking next, next, next, next, next. We stripped it and we made it like, let’s connect you with someone that can solve your problem immediately.

You mentioned this earlier, where it’s like automation should be used to help people do their jobs better, not replace them. When we’re thinking of automating process workflows, it’s like, how do we take something that takes five steps now and maybe get it to only take two steps. It doesn’t have to be completely replacing the opportunity.

There’s a framework that our internal director, Dave Young, actually used that I really liked. He thinks of things through the lens of rubber-glove service, leather-glove service, and white-glove service. Where it’s like the rubber glove is the service where it’s like we’re cleaning up messes that we know we make for ourselves internally where it’s like, we know this is a hole, we’re trying to fix it. The leather glove is like we’re doing things on behalf of the user where maybe we have to reset their password or provide them an ETA when their product will be delivered or something like that.

Getting to that level of white-glove service just adds value to the business by improving the customer experience and brand reputation. I think it’s all about getting to that level where it’s like these monotonous tasks where it’s not something that we should look to automate through self-service bot, it’s like that should be included in the product.

Something that I’ve seen that is super valuable everywhere is this confluence that– excuse me, is the value of a relationship between products engineering and support. It’s like if you can make it where your insights are powerful enough on the support side, the way I see it is like we and support orgs are driving the car and pulling it into the driveway while product and engineering take the issue into the garage. It’s like we have to make sure that you know in detail what these problems are. We can’t just say the model’s not loading or something like that in terms of our product, it has to be much more specific than that.

I think working together on all those fronts, it’s not just about automating the support org or support experience, it’s like, should this even be an issue at all? Should this be in the product?

Justin: Yes, it’s like the precognition, if you will, of product design to avoid an issue that would potentially need to be solved by support, therefore automated by support in the first place. You facilitate that by getting to that. I love that rubber glove, leather glove, white-glove example. That is awesome. That belongs on a t-shirt or something at one of these support vendor conferences or something. I love that.

Jared: Definitely.

Justin: You guys went through the learning experience of a bot that caused frustration amongst users. We live in a world where we expect information to be instantly available, readily available in the format or medium that we’re choosing, or we prefer rather. Sometimes I wonder, and people in your position are a good person to ask this question too, how do you manage making sure the information, or the steps, or whatever your customer needs to solve their issue, how do you manage making sure that that’s available in all the different channels and formats that it’s expected to be in?

Jared: It’s a good question. For the most part, I think each customer service org has some general rules and things that they try to do like automating workflows to get the right case to the right person on the first try. That’s a classic thing that people try to automate, but then you have to customize it to your customer base. Whereas, for instance, for example here, we have general contractors who are onsite with a homeowner. They’re using our app, they’re taking photos of a property to generate measurements in a 3D model.

Now, if that fails, because they didn’t take the right photos or something of that sort, they don’t have time to look through a help center article to generate business for themselves. They need that problem solved immediately because it’s a nuanced question. It’s like, I need you to look at this specific property and tell me what to do. Now there’s tons of things you can add in products to help guide people. To me, it’s just diagnosing your customer base and understanding what their needs are. Maybe there are some issues where it doesn’t need to be responded to immediately even if it feels that all customer inquiries are created equal.

It’s like some are actually going to be make or break for this person. I view it that way where it’s all about allowing customers to get to the right person for your type of business. At SquareTrade, it’s like if someone needs a warranty for a TV, get them to a TV specialist on the first try. I think to me it’s all about what people want. Our user base told us loud and clear we need to talk to someone immediately.

Justin: Is the path to support built directly into the app where if the photos don’t create the right model, there’s a distant and work button that then bat phones to you guys, or have you built something that’s more like intermediary hop to a quick these are the most common issues sort of thing? How do you make that immediate connection? Because that’s really interesting because you’re right. When that problem comes up, it needs to be solved instantly.

You don’t want to create noise inside your support organization by people hitting a button when they necessarily shouldn’t. You want to do some bit of prequalification I assume. I’m just curious how you handle that. It’s a really interesting stance there that we need to be there when it matters most. Will that require some operational burden to be able to do that, right?

Jared: Absolutely. For instance, we do this thing called Wacky Wednesday at HOVER where every Wednesday we trial something new. We take a problem, we try to brainstorm solutions, and we implement something. We’re willing to have it fail, but we’re also hopeful that it will bring success and we’ll maybe adopt it as a full-time process going forward. One of our core values is to be different. For the longest time, we were dealing with the same problems that a lot of support orgs do, just understaffed, dealing with the problem, dealing with catching up, and being reactive.

We finally have figured that out in terms of forecasting and scheduling and all that sort of things. Now we’re trying to be proactive. In this specific example, we’re taking the issues that matter most when a payment fails or a job fails. We’re automating a task directly from our system into our support org to trial reaching out proactively before they even get an automated notification. What we found is that that touchpoint has a large conversion factor on people, not only converting that job but continued usage. The idea that when someone completes their first inquiry with HOVER, they’re much more likely to do a second, third, and fourth.

Once you do your fourth or fifth with HOVER, you– I forget what exactly– I think it’s something like 90% of customers don’t leave. That first experience if you have it and it doesn’t work for you, it can be really detrimental to your continued usage of the product. It’s not just something where it’s important to them at that moment. It’s important to you for the lifetime of your site while you’re here with HOVER. I think that’s how I think about that specific inquiry. Can’t deal with all of your inquiries, but if there’s $50 on the table every time you reach out on a personal connection, help someone through one problem, then they know that they can trust support going forward when they need help, can really change the game.

Justin: There’s a great lesson in there, and it’s different for every business. It’s not something that I can flippantly say on a podcast here, but there is a connection between support and the LTV of your customer base or your users. However, you define it. Understanding that relationship and being able to understand the knobs that you can turn to optimize that LTV is extremely valuable. It’s very cool that you guys take the time. I think that’s a good thing, maybe less than for people to bring back their own organizations, it’s you have that specified time, the Wacky Wednesdays as you call it, to fire drill these concepts and innovation comes from that stuff.

I think a lot of times, especially growing companies, you get into the– you’re just trying to keep the boat afloat while you’re– or the rocket ship together on its way to the moon, so to speak. To be able to have those Black Hat exercises and use that to drive innovation is really neat.

Jared: I also think there’s a lesson in terms of we were talking about the communication between product engineering and support and all of those different things. There’s a certain level where support or backend operations are making up for too many holes in your product where you’re over-hiring to fill these gaps that you know will eventually be automated. That’s something that I saw when I was at Zenefits. It’s like sales is selling products that potentially aren’t ready for the masses. They’re awesome products, but there’s these manual inputs on the backend that require people to do them that are going to be automated in 6 to 12 months. It’s measured growth at scale is super important, and definitely a lesson that I’ve learned through the different experiences I’ve had.

Justin: That’s an interesting one. I just think about this even internally here at Capacity. We’ve got product features and use case stuff where you get your lighthouse account in a particular segment, or whatever it is, and you have to– There’s a tacit understanding between the support and product teams. Look, this is the first cohort of customers that are going to use X, Y, Z. There will be issues here. This is one of those like let’s all sit down. Remember, we’re on the same team moments where we can come into this with the right attitude where we’re measuring the right data to be able to feedback into the development cycle.

All the learnings from this gets spun into the sales enablement materials, that sales then goes in, all the N+1 accounts that they bring in, a lot of this stuff is covered and fixed from those trials with their early lighthouse accounts. It touches on another piece that we’ve danced around a little bit in this conversation, which comes up a lot in these conversations. That is, you’re not going to be able to have that effective feedback loop with support products and sales on new initiatives and these bleeding-edge type things if your support agents are eyeballs deep in resetting passwords and showing people how to update their username or whatever it is.

This is exactly why the value prop that automation companies, Capacity, Zendesk, pick who it is, this is why we’re doing this, is to really open up that bandwidth so those meaningful conversations between support leaders and product or a support agent and a customer, the bandwidth is available for the meaningful ones. That’s really interesting stuff. In general, do you feel like the average company understands how powerful that relationship between support and product actually is? Or do you think this is an underappreciated thing?

Jared: I think it’s an underappreciated thing for the most part because sometimes the insights aren’t created properly, where they’re too general, and then it allows product folks to talk to three customers and make their own decisions on what they think they should do next. If there’s thousands upon thousands of people that are driving for the same solution, it’s a completely different ballgame when you’re talking about that development. We created this thing where there’s tags and subtags. Basically, these case summaries so product managers can go to one of our 100 tags and swipe through a little Twitter feed to understand exactly what the issues are without having to go through these long case threads and things of that nature.

We created an index where the frequency of the case combined with the C side of the case together in a matrix shows, what really is our most difficult issue? Some of them don’t need to be fixed by automation, some of them are just looking at it with good old-fashioned process workflows, or even just changing language or empathy. You’ve learned a lot from that stuff.

Justin: It’s interesting you’ve said something in there that we say often too, and that is, wherever you go into this mindset of I’ve got X, Y, Z. There has to be some solution out there that can automate this for me. Just as a marketer, there’s tons of– marketing automation platforms are actually a really interesting thing to look at in terms of a long-running and well-established “knowledge work” automation because this has been around for a while. Something like Marchetto, it’s a very mature product category.

What we tell people and what I’ve experienced myself too, is when you get to that point where there’s got to be a way to automate this, you really need to sit down and actually map out just good old-fashioned business process design. Because in your diligence of understanding the process and where there’s a failure of handoff, whether it’s one app passing data to another, or it’s one human passing responsibility to another, when you map out the process and really actually do the work, you might find that you just have a process design problem.

Bringing in an automation solution and spending all the money and going through the onboarding and doing all that isn’t going to help your issues. It’s just going to make it worse in a lot of ways. You need to do some job design or some process design.

Jared: You said something there where it’s like the cost or– Basically, it’s like, how do we solve a problem? The first thing is that people always tend to do and support is like, we need more people, we need new tools, or we need engineering to build something. All of which come at a large cost. The best way to make the case for that cost is to first try to solve the problem without those three things. I’m totally with you there on process management and trying to figure things out first before you make that leap. Because maybe you implement the tool and you’re like, “Ah, we were actually solving the wrong problem because we rushed into this.”

Justin: Exactly. When you think about the future of support automation, what excites you and what worries you?

Jared: I think the exciting thing is just enabling people to work on the right problems, the high-level things that bring value to your customers. In terms of what worries me is the over automation of things like voice systems and chatbots to a level where you lose that personal connection and it’s actually not that helpful. I know both of us have probably gone through a variety of different experiences, some good, some bad, but the most memorable bad ones are when you spend 30 minutes just trying to get someone.

Justin: Talk to an agent?

Jared: Yes.

Justin: Talk to an agent.

Jared: Exactly. Maybe there’s a world in the future where the robots take all our jobs and we’ll sit back and watch the sunset and R2-D2 brings me a piña colada. I think, for the most part, this is about enabling people to use their interest and skill set to make the company better, to make consumers happier. I don’t want to deal with this computer that doesn’t know what I’m talking about right now. I’m looking at this. There’s a variety of different ways to look at it. To me, it comes back to just automating. Automation will help people do their jobs better.

Justin: It’s important to know. I don’t think we directly covered this in our chat today, but you hinted at it. It’s important to remember too that automation should be brought in to augment and help people do their work better, not to replace necessarily. Just for all the support leaders out there, keeping that in mind, you’re going to get much better buy-in on whatever automation you do bring in from your team. If you go in under the auspice of, hey, we’re bringing this in to make X, Y, Z problems easier to solve so you can do you A, B, C with more attention and with more care towards it.

When you think about the– Imagine you’re sitting down, and you’re at a coffee shop or something and someone comes up and says, “Oh, Jared Sklar from HOVER. Big fan.” If there is a piece of advice you could give to someone who’s just getting started in their customer operations journey, what would it be?

Jared: I think the main thing is to make sure that you’re looking at a problem from a bunch of different angles. I learned recently that sometimes support folks only ask other support folks or other operations leaders or other customer-facing people how to solve their problems. I was working with an engineer recently, and instead of asking them to build something technically, I asked for a different mindset on our manual process workflow. It was a completely different view that I hadn’t thought of. Collaborate with different people around your company to solve the problem that you have. To me, it’s just all about looking at everything from every different angle to make sure you’re solving the right problem.

Justin: That is fantastic advice, especially when you look at people who are not just tangentially related to what you do, but potentially entirely different departments or industries or whatever it is, a variety of perspectives and an inclusive mental attitude towards those additional perspectives is incredibly powerful, and it’s easy to forget. We’ll wrap up our conversation today, and this has been fantastic Jared. I really can’t thank you enough. You’ve dropped some amazing nuggets here. Rubber gloves, leather gloves, and white gloves are going to go down in The Support Automation Show in history as one of the better little nuggets.

Jared: Even mine [laughs]

Justin: You get to take credit for it in my book. Whenever I repeat that, it’s going to be attributed to you. Let’s end with our quickfire round here. What is the book that you most often recommend to people?

Jared: I think the main one that I’ve read multiple times, not just at HOVER, but has been recommended to me by HOVER and I recommend to others is Delivering Happiness by Tony Hsieh. When customer service is this general thing, but when everyone’s trying to replicate “the Zappos model,” there’s a reason for that. It’s just flipping stuff on its head and making sure that company culture is tied to the overall success of the company. I think the main thing I learned from that, too, is just to always be learning and prioritize the learning of your employees. That’ll make it good for you and trust you.

Justin: What a great mind in a tragic loss that was.

Jared: Absolutely.

Justin: It is amazing how often you hear about the Zappos way. It’s actually to, I think Amazon’s credit, after they swallowed Zappos up– Amazon’s got very good customer support. For the scale and the size that they are, their support’s actually phenomenal. You do wonder how much of that is part of what Bezos bought. That’s a great one. In terms of your own workflows and habits on being productive and being the best self you can be, what’s the best productivity hack or productivity tip that you’ve implemented into your daily work that you’d recommend?

Jared: It’s simple, but creating and aligning on shared goals within your team. Anything that you’re working on, you can always point back like, “Is this really important for what we’re trying to solve? That’s a really cool idea, but maybe we should focus on our goals first.” Whenever I’m doing work, or I’m in a meeting, you have to ask yourself why you’re there and if you’re using your time wisely to meet your goals. I think that’s a big one for us and for me personally.

Justin: Yes, that is really good because, especially at startups, it’s very easy to get distracted by imagineering, if you will, or, “Oh, that is cool. We should test that,” and then the next thing you know, you’ve spent two weeks designing something that, to your point, might run anathema to the actual goals you’re trying to achieve. Keeping those in mind. That is very, very good. It’s one of those things too that is going to drive all the sub-layers of thinking and being productive that you have just always keeping that Northstar, love it.

If you could recommend one website, blogs, Slack community, LinkedIn group, Facebook group, pick your networking hub of choice here, but if you could recommend one community for support leaders to join and participate in, which one would it be?

Jared: I guess I’m biased because currently, we use Intercom. They have some solid support content, but quite honestly, I’m an old-fashioned type of person. When it comes to this, I like meeting people face to face or call to call, if you will. The best way I’ve learned about support by far is to ask my network or colleagues about their own past experiences and scaling organizations by far. Picking people’s brains, what worked, what didn’t, telling them a little bit about your organization. I think you can’t leverage your own network enough when it comes to building out your current organization.

Justin: You really can’t. Related to that is something I tell people all the time, and that is there’s a reason the phrase no such thing as a stupid question exists, right? It’s exceptionally easy for people to fall into this trap of not just asking, you know what I mean? It’s amazing what you get out of life when you just ask and it’s amazing what you get out of your network when you just ask, meeting people and just striking up these conversations.

Jared: I remember one of my first leadership opportunities I called my old boss, and we created this whole RFP for finding the right way to hire, if we should outsource or do this thing, and she was like, “You don’t want to do any of that. Here’s what you want to do.” I looked at it, and I was like, “We completely missed it. She’s right.” It’s funny how another person can make you look at something differently.

Justin: Yes, 100%. Last question. If you were to be able to take out one person in this field for coffee, or a cocktail, depending on the time of the day and the vibe, to just pick their brain, who would it be?

Jared: Quite honestly, it would have to be personal mentors of mine. Laura Kreitler and Sarah Blanchard who I worked under at Zenefits, they were VPs there, were just these super-powerful leaders who gave me my first shot to lead and manage managers. It gave me the confidence that I needed to not live as two separate versions of myself. I didn’t need to be a professional version and a personal version. I could be myself and find and navigate my own style, which I’m still working on to this day, but it’s been a while since I’ve gotten to see them, so make it a cocktail.

Justin: [laughs] That was the best answer to that question I’ve had yet on the show. Love that. You don’t need to be two versions of yourself, you just need to be yourself. Love it. Jared, I can’t thank you enough for your time today. This has been great. Lots of good stuff in here for our listeners and anyone looking into either getting into or advancing their career in support or looking to bring in any automation into their organization. A lot was covered today. All of it is good. Where can people find HOVER, or yourself, if they wanted to throw you a follow?

Jared: I’m on LinkedIn. That’s the only social media I have currently. In terms of HOVER–

Justin: Good for you.

Jared: [laughs] Yes. You can go to, our website. I also just recommend downloading the app, snapping photos of your house, it’ll walk you through it. As a homeowner, you can do it for free and we’ll send you a 3D model and be something pretty cool.

Justin: As we were preparing to have this conversation, I downloaded it and you can share apps and shared it to my wife and was like, “Hey, can you download this really quick and scan our house. I’m very interested in what comes up?” Super, super cool, great conversation. Thank you so much, Jared, and I hope your day is wonderful and your weekend’s even better.

The Support Automation Show is brought to you by Capacity. Visit to find everything you need for automating support and business processes in one powerful platform. You can find the show by searching for “Support Automation” in your favorite podcast app. Please subscribe so you don’t miss any future episodes. On behalf of the team here at Capacity, thanks for listening.

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