A Startup Founder’s Crash Course In Customer Support With Douglas Hanna of Help.com

Like most founders, you are probably looking to secure more customers, so you scale revenue. While this should be a top priority, it’s also important to think about how you are going to support your growing customer base before you face customer retention issues.

With this in mind, I sought out the help of Douglas Hanna. Douglas is a member of INC Magazine’s 30 Under 30, helped run customer support at HostGator, and sold his last company for millions. Currently, Douglas is the CEO of Help.com.

I sat down with Douglas to help you think more holistically about your customer support strategy and give you the tools, resources, and methodologies you need to be successful.


Have comments, questions, ideas, or feedback? I want to hear it. Tweet me at william_griggs.


Topics Covered In This Episode


  • How important is customer support?
    • Can it make or break a startup?
      • Can you give examples where it has lead to a company’s downfall?
    • Can it be a competitive advantage?
      • How does this change based on the company’s business model?
  • What are the biggest misconceptions founders or CEOs have about support?
  • What are the biggest mistakes you see founders or CEOs make around support inside their company?


Early Stage Entrepreneurs Doing It Themselves

  • How much time should they expect to commit?
    • How do they set themselves up for success?
      • Tools, methodologies, best practices, etc.
  • What do founders need to think about in this phase?
    • Learning from their early customers?
      • Product problems?
        • Cold vs. Cancer
      • Product ideas?
        • How do you prioritize product findings?
  • How do you recommend our audience think about handling angry/frustrated customers?
    • How should they defuse the situation?


First Support Hire

  • What should you look for in that hire?
    • How should they pass everything off?
      • What expectations should you set?
      • What are they going to need to be successful?
  • How should they manage their initial support team?
    • What best practices out there should our audience subscribe to?
    • What types of KPIs should our listeners set for their companies regarding support?
      • What reports should they want to see?
  • How do we continue to ensure a feedback loop between support and the rest of the business?
    • How do you make sure the support team is plugged in?
    • How do you feed bug reports back to the dev / product team?
  • What should the founders in our audience think about as they scale beyond one person to a team or 4 or 5?
    • What changes?
    • What do they need to think about?
    • What’s a typical org structure for a support team?



Startup Slingshot Radio’s audio transcription is done by GMR Transcription

William Griggs: Like most [inaudible] [00:00:32] you’re probably looking to secure more customers, so you can scale revenue. While this should be a top priority, it’s also important to think about how you’re going to support your growing customer base, before you face customer retention issues. With this in mind, I sought the help of Douglas Hanna. Douglas is a member of EEK e-magazine’s 30 under 30; ultra customer supported HostGator, and sold his last company for millions of dollars.

Currently Douglas is the CEO of Help.com. I sat down with Douglas to help you think more holistically about your customers support strategy, and give you the tools, resources, and methodologies you need to be successful. Enjoy. Douglas, thanks for joining us today.

Douglas Hanna: Yeah, it’s my pleasure. At the very least it’s the highlight of my day, maybe even my month.

William Griggs: All right. We’re getting the day started, getting that capped off. We might take the championship for the week, and then we’re up in – we’re contender for best moment of the month, I think that’s – I think we’re headed in the right direction.

Douglas Hanna: Yeah, I’d say so.

William Griggs: Very cool. Well, I definitely appreciate your time, and the audience appreciates your time today. Our goal is pretty simple, we want you to help the founders in the audience think more holistically about their customer support strategy, and give them the tools resources, thought processes, methodologies, etc., so they can do that, so they can be successful. But before we kind of do that and dig into there, can we dig into your background? Can you kind of give us a 30 second overview of what you’ve been able to accomplish, and what you’re currently working on?

Douglas Hanna: Yeah, of course. I started working when I was about 13 in technical support in the hosting industry. And I was in the hosting industry for basically my entire career. I ran customer service at HostGator, from when they grew from about 150 to 400 people. And then I became CEO of another hosting company called A Small Orange. And we grew that from 10 to 100 people in a couple years. And then A Small Orange was inquired by a big company called Inter International Group.

They’re properly traded now as a $3 billion dollar market cap. I was an executive there for two years including during their IPO. And then in August I started Help.com.

William Griggs: Very cool. We’ll dig into a little bit about that later on in the interview. Now, HostGator, I feel like I’ve seen all their billboards. Can you tell me, does that actually work for them?

Douglas Hanna: I think it did. I don’t – do they still – I haven’t seen any billboards recently. When I was at HostGator, we started investing a lot into billboards to get job candidates. We were really limited. The company was growing extremely fast, and we were really limited by the number of support and technical people we could hire. Because we wanted to keep the customer service experience really really great, and it was very tough to hire, like literally hundreds. We would sometimes hire 30 people a week, customer service people to be able to help customers. So we had these, like now, I think, kind of infamous billboards of, like know LINE-X, or know what DNS is, apply for a job.

And I think it drove a lot of brand awareness, and it was – even though it was targeted towards recruiting, I think a lot of customers learned about HostGator that way. I definitely had a lot of people when I told them I worked at HostGator, “Oh, I’ve seen those billboards: do you know LINE-X? I don’t know even know what LINE-X is, but I know about HostGator now.”

William Griggs: That’s one of those funny things that people typically look at and say: oh, man, those idiots are running billboards. And when you take a step back and if you keep seeing more billboards, like you see trial injury lawyers running billboards, it’s not because they’re dumb, it’s because they figured something out that you don’t know. And so that’s kind of fun to peel behind the current – peek behind the curtain and understand a little bit about the approach there. But today’s goal is to talk about customer support, account management, all that good stuff. In your opinion, from HostGator’s experience, from your current company, how important is customer support and account management?

Douglas Hanna: I think it’s critical. I think the relationship that customers have with the people at the company, which is usually through support and account management, can really make a big difference in the experience. And there are lots of examples of companies that have differentiated themselves through customer service and support. HostGator and A Small Orange, just two that I was involved, but there are obviously kind of dozens or hundreds of other examples. It’s one of those things I think can make a big difference if it’s done particularly well or particularly poorly, because customers definitely notice it.

William Griggs: Yeah, it’s definitely one of those things that I feel like can make or break startups, make or break companies, one of those things that’s, you know, if you have a bad experience, then you’re spreading that word of mouth versus having a good experience and spreading that word of mouth, and obviously it affects the brand, affects the customer acquisition costs, all that good stuff, but it’s also one of the things that when I talk with a lot of entrepreneurs about, they know the least about.

They know about their function of – typically they know about their function of either sales, or marketing, or product management, or maybe they come from the engineering side, but most of the people that I’ve discussed startups with over coffee, over lunch; they don’t come from the customer support background, so they don’t really understand it. They see it’s important. But can you give maybe a few of the examples of some of those that maybe see this as a competitive advantage?

Douglas Hanna: Yeah, for sure. And it’s an interesting point, there are not many customer service leaders turned founders and CEOs. I think I’m an exception there. And even my last job I was not a customer service leader. I had kind of more general responsibility, but it is a less common background, but I think it’s a good one to have. Like, there are plenty of – to answer your question – there are plenty of sort of cliché examples. Zappos, I think is a classic one that lots of people reference. I think Amazon is less classic and probably a little bit less known for customer service, but very known for a great customer experience.

Like, doing business with Amazon as a consumer is super super easy, and that it’s very smooth, and they spend a lot of time and effort in doing that. And then there of course brands that I think really have kind of built their everything they’re about in customer service and luxury, like Ritz-Carlton and The Four Seasons, or Park Hyatt, and they just go to extreme lengths to really kind of offer incredible customer service and experiences. And then a brand that’s close to us here in Austin that I think does a really great job pretty consistently is Whole Foods.

They are very customer centric. I know people that have worked at Whole Foods, kind of at their retail level and corporate level, and it seems like they’re pretty genuine about their kind of customer centricity, if you want to call it that.

William Griggs: We got the entrepreneurs in the audience starting to think about it. They’re starting to think about their interactions with these different companies, like you said. Maybe they got to stay at Ritz-Carlton recently. Maybe they ordered some shoes from Zappos, or something from Amazon, or went to Whole Foods, and they’re thinking about that as a differentiating factor. And it’s starting to come into their mind as something that could be important, but again we need to start breaking it down and start to get a little bit more tactical. But before we do, are there any kind of misconceptions that founders and CEOs have that you work with or that you’ve mentored around support?

Douglas Hanna: I think the biggest one is that it’s this cost center hole, and kind of the PNL of that you don’t get back and it’s just a necessary evil. When founders or other people think about it that way, I usually like to ask them to look at their – like, if they’re looking at their PNL, like look at the percentage of marketing and support spend as a percent of revenue. And usually companies that have better service have kind of less marketing spend and vice versa. If you think of it as kind of an investment and just kind of customer experience, and marketing and support as kind of one combined line item, you tend to think about it very differently.

At A Small Orange, we have under invested in marketing relatively when I was there, but we really over invested in support, but we were still able to achieve our business objectives because we had so many customers doing our marketing for us.

William Griggs: And is there a standard rule of thumb or some type of approach they can think about when looking at that, like you said that PNL, that percentage that they’re looking to invest?

Douglas Hanna: I think it’s gonna depend on the business and the industry a lot. And hosting, like it might be 30 or 40 percent, but it really depends, like if a company is growing really fast, or it’s very support intensive, it’s gonna be very different. And that’s kind of one of those good times to talk to other founders and be like: hey, what do you guys – like, what percentage of revenue do you spend on these combined and how does it break out? Because I think it’s usually a pretty useful thought exercise.

William Griggs: Yeah, it’s interesting. So when people start to view it as a cost center it seems like you have to get the reps that maybe have a time quota, they can’t be on the phone longer than a certain time, so they’re either rushing you off chat, or they’re rushing you off the phone. Are there any other kind of downsides to viewing it as a cost center, like that actually the customers experience?

Douglas Hanna: Yeah, I think doing those sorts of things are very short sighted. I think if you’re really enforcing call quotas and things like that, you’re effectively signaling to your reps that customer experience is not a very large priority, and by doing that you’re certainly mot helping to motivate them, and you’re not helping them provide better customer service. It becomes like a self fulfilling prophecy, where companies that have crappy service because they’re not investing into it, and by not investing into it, like the outcomes are not good.

It’s very difficult to do that, but I think really – and this is very cliché, but it can make a huge difference – doing what works best for customers is really gonna make or break the business when it comes to customer service and experience.

William Griggs: Very cool. We’ve taken a step back. We’ve thought about the big brands, some of the household names that are doing it right. We’ve thought about support as a competitive advantage, gave some examples there. How do you think about it as an investment, bundling it with marketing and support. But let’s start to drill down a little bit more to where most of the people in the audience are today, which they’re early stage entrepreneurs. They’re probably doing it themselves.

So as people are getting their business off the ground, maybe a lot of the time investment, or maybe the investment is gonna be more focused on their time rather than dollars out hiring people or anything like that. Do you have an expectation for them around how much time they should be committing to support?

Douglas Hanna: I don’t think there’s a rule of thumb. It’s gonna depend on the type of company. Like for example at Help, we’re in a private beta right now, and I am our support person. If our beta customers emailed us, I would respond. I don’t spend all that much time on it because we don’t have a ton of support volume. We only have like 10, 15 customers in our beta, which is what we wanted. Obviously, if you have thousands of customers it can be very different. I think in addition to just viewing it as emails that need to get an answered, as an early stage entrepreneur, like you’re also seeing a lot of customer feedback, and you’re hearing about how people use the product, and what’s going well and what isn’t, and what’s important.

And I think that sort of feedback is super valuable, and you can definitely get that through support interaction. I think it’s worth spending time on, just like it’s worth spending time talking to customers about their experiences.

William Griggs: So instead of thinking about a percentage of time, kind of the – the question was phrased it’s more like make it a priority and then think through and react and based on your business model.

Douglas Hanna: Right. It’s not just like: oh, my God I need to spend 10 percent of my time doing support. It’s all right, well, I need to spend some large percentage of my time getting customer feedback and hearing about customer opinions, and thinking about the roadmap in those terms, so let me – one of the ways I can do that is through support. Like, there’s in my opinion if people have support questions, like that’s just as good as picking up the phone to call someone and ask them how it’s going, if not better.

William Griggs: And as far as just getting up and running, is it as simple as having just a support email address, or maybe one of the founder’s email addresses on a support page on the website?

Douglas Hanna: I think that’s not a bad start as someone who has a vesting interest in people using complicated tooling; of course more tools are better, right? But I think for really small companies and just one or two person support teams, like keeping it simple is good, and making it feel authentic and personal is even better. The experience your customers will have by knowing they can just email the founder for support, or that the founder will reply, I think, is really valuable. And we talk about that when we’re talking to potential customers, particular for our beta. Like, hey, our founder, me, is doing the customer service and is your account manager.

And he’s doing this because he wants – we’re really obsessed with what our early customers, and all customers in the future, but particularly our early customers think about our product.

William Griggs: And as you’re working with those early customers, those beta customers, in your experience, how are you thinking through the feedback that they are providing you? You know, there’s kind of this old mantra of cold versus cancer, cold is gonna go away, cancer is gonna be there and progress and probably get worse, how do you think about looking at their feedback? Do you think about your long term product vision? How does that kind of come together?

Douglas Hanna: What we say a lot is that our customers can help us for the most part reorder our roadmap. They don’t need to, and don’t – we haven’t really seen this – or they’re not dictating it per say. Like, we hear very few things that I would consider out of left field, but we do let our customers help us determine what the priorities should be. Because we’re not – like I have a pretty good idea of what we need to do, and our customers have a much better idea of how important each step of that is to them. And we’ve definitely done things that customers were like: oh, that’s cool, but I don’t really need it.

And we’ve definitely not done things and they’re like: oh, my God, we need this today. So we defer to our customers really to help us order the roadmap, and then we have to prioritize things based on the effort versus, kind of impact sort of ratio. And if it’s kind of low effort, pretty much whatever it is, if we think it’s consistent with the roadmap, we want to do it, just kind of give that early customer delight. Like, there’s nothing I think that makes a customer of an early stage company more excited than hearing from, in my case – in our case, like the founder saying, “Hey, we got your feedback yesterday. Thanks.”

And of course you reply right away. And then like the next day it’s like, “Hey, this is live, try it out.” And we can be super responsive to our customers and really say – and really make them feel valued and their feedback feel valued, where as the reality it might have been on the next sprint or something, and we just like: this takes 20 minutes let’s do it, to make them happy. And we do that all the time.

William Griggs: Yeah, definitely a cool opportunity to kind of delight those early customers, those early beta customers in your case. What about as far as, maybe not in your current company, but in other companies you worked with, how do you deal with angry or frustrated customers when you’re handling the support? You know, sometimes it seems like bigger companies they got kind of these, maybe jaded, maybe just super experienced customer support people that have handled thousands or tens of thousands of angry probably, but for these people where this is their baby, and someone comes in and kind of rains on their parade, how should they kind of handle that type of interaction?

Douglas Hanna: That’s a really interesting way to look at. Because I think at A Small Orange and HostGator we had pissed off customers all the time. And it’s not because either company is bad at really anything, it’s just when you have tens or even hundreds of thousands of customers, like even if a very small percentage of them are upset, you’re gonna have a lot of upset people. But I think what’s nice about being at bigger company, it’s not just that you’re hardened and you’re tough and scary and you have a thick sin, it’s also that you have the experience of knowing, like okay, this guy is unhappy, but there are so many thousands of nice customers.

And we have seven or eight or more years of operating history of super happy customers, like this guy is an exception. It’s not us, it’s him or her. That’s like a really valuable perspective. If we had a customer like now at our small stage that was super pissed, I’d be like: oh, God it’s 100 percent our fault, even if maybe that wasn’t the case. So it’s probably important to step back and think about: all right, how does this person’s feedback kind of – does it seem consistent with other feedback we’re getting? Is it just like a more emotional version of feedback that we’ve already received, or is this just like totally out of left field, maybe they have unrealistic expectations.

Like, not every product and company is a great fit for every customer, and I think that’s important to think about. And depending on your model, if you’re kind of consumer SMB mid market, likely every individual is not super material for your revenue, so hopefully you can step back and think about: all right, maybe we’re just not a good fit for them. Obviously, if your stuff goes down all the time and it crashes and I lose all my data, that’s probably an issue on your end, not on the customer’s end. But if they’re like: well, I’ve had so many problems, and there are persons talk about problems that don’t exist, or don’t exist elsewhere, I think that’s really important context to have.

Like, we even see, like occasionally customers will report issues, and we will always try to give them context like: hey, this is something we’ve heard about before, or hey, you’re the first person to report this. And we just leave that out there to help them think about maybe it’s not an issue with Help.com, maybe it’s an issue with our own website, or just something like that. And I think that context is helpful for customers. Because most customers are pretty reasonable, they’re rarely like – they’re rarely – they don’t wake up in the morning being like I want to make company X’s life difficult today.

William Griggs: Right. Let’s hope not at least. So it sounds like they need to take a step back. They get that angry email, they get that frustrated customer, take a step back, don’t automatically respond off the top of your head. Take a step back and think about where they’re coming from. So it sounds like you said you could look at some demographic and psychographic information around what the concerns are, who they work for, their position, to see are they the right fit, maybe they’re trying to put a round peg in a square hole.

And therefore you can come back and provide context that way. Or if it’s kind of like you said the first piece of feedback of that kind, giving it context and saying: oh, that’s interesting, acknowledging their feedback, but then also saying that you’re going to be asking other people, or looking for other similar people saying similar things. And then it sounds like I’ve heard other people say don’t necessarily promise, right? So acknowledge the feedback, but don’t necessarily promise you’re going to fix something, unless I guess 100 percent you are.

Douglas Hanna: Yeah. I think that’s true, like that’s one advantage as an early stage entrepreneur, like when you’re responding to customers you make those decisions on the spot, which is a lot of times why founders make such great sales people is because they can promise – they can change the roadmap on the fly in a way that a sales person, even a VP sales can’t. And like I do that, I talk to prospects and they have an idea, I’m like that’s a good idea. We can do that. Whereas, if our sales person did that I would be very upset because he shouldn’t be promising things that we don’t have or that we don’t have clear plans to have in the near future.

The same can work in support too, where if you’re kind of – if you’re the founder or the co-founder or whatever, and you’re involved in the weeds at this stage, like it’s a really great time to be able to be super responsive to customer feedback. And I agree, don’t promise something unless you plan on doing it, and you’re sure you’re gonna do it. But definitely, if you think it’s a good idea I would share that, and I wouldn’t try and hedge it.

William Griggs: Before we kind of transition to talking about hiring that first support people, or first support hire, is there anything on this thing in that early stage that entrepreneurs should be thinking about?

Douglas Hanna: I think probably the number one tip is – or this is number one and number two, probably tied for one – is be very responsive and do things that you would probably not do at scale. I don’t know, when HostGator was just started, or when A Small Orange was just started, like they definitely did things for customers that we could not have done with tens or hundreds of thousands of customers. But when you’re small, like who cares? Like, deliver that great experience to customers. There’s a great story of the founders of Stripe, how they would like – people would email them with errors and they would like fix it in the middle of the night, and then go on the customer’s website and fix it , too.

Some like way above and beyond anything that Stripe would do today even as a very good company. And we do that already with our company. People will ask us to do things that at scale we won’t be able to do, and it just won’t be economically feasible, and it’s probably not even expected, but this is the point where we can over deliver, and I think it’s – if you can do it, then you should do it as an early stage company, it’s so critical. Because again, you want to make your first ten or a hundred, or a thousand customers such enthusiasts for everything you do. And if you’re really good in those areas, they’ll be more forgiving when your product inevitably is broken or has some sort of bug or something like that.

William Griggs: That kind of moment like you said, it seems like most entrepreneurs that I meet with, or lots of them, they’re always thinking about: how do I scale, how do I scale, how do I scale? Where lots of times it’s take that step back, you got to get that first ten customers, you got to make them super happy like you’re saying, so don’t worry about scaling initially. Figure out your solution, figure out your model, figure out your target market, and then worry about scaling. But it sounds like again, taking that step back and thinking through those wow moments.

You have the opportunity like you said as a small company to wow some people’s socks off very easily, because their expectations are already pretty low, just because either you’re a new company, or they’re new to your product and they haven’t been wowed before. And it seems like some examples that people could emulate is an example of something like MaleChimp, right? After you send your first campaign with them, I know for a long time – I haven’t sent a first campaign in awhile on an account – but for a long time they would say: hey, tell us your size and address, we’d love to send you something.

And then they’d have a T-shirt that’s sent to you. And I know there are APIs nowadays that can do handwritten notes. There’s an Austin company, I think that’s called MailLift that you can integrate. So once you get them signed up, you can send a hand written note, and it all looks like it coming from your zip code and all that good stuff. T-shirts, fruit baskets, whatever they want to send. Maybe it’s something that’s aligned with their specific theme or their specific brand. But that’s definitely something cool to drive home for customers. Have you seen any kind of interesting examples of ways people have wowed their customers?

Douglas Hanna: I think like all those things you listed are definitely a great idea, and I think they’re gonna set you apart. It’s like this is very6 – a company that’s on the receiving end of one of those is gonna be like: huh, this is really different than doing business with generic big Co. but I think just in the tactical delivery of the service, like being really responsive, being very informed, like as an early employee, just have such an information and empowerment advantage over like what someone at HostGator when we had 500 people would. When you’re 1 of 500 support reps, like it’s very different than being the first support rep, or the co-founder, or something like that.

Even if you’re – even if the 500th support rep is super great, like there’s only so much they can do, and there’s only so much they can impact. So I think beyond kind of the niceties of like sending a handwritten card or a T-shirt and things like that, all of which I don’t think would ever hurt, like just having really high quality support. Like, fundamentally when people contact support, they’re contacting it with an issue to get solved. And I think if you can kind of laser focus on that and just going above and beyond, like instead of asking someone to, I don’t know say reset your password, and – or whatever, pick a hypothetical situation, like anything you can do to deal with some of those steps for them, even if that is not typical, I think is really helpful.

Like, we had a customer who wanted us to help install our app on their website. And at scale we’d probably be like: here’s our guide on how to do that with your CMS. But instead we were like: hey, can we have a login and we’ll install this for you. And she wasn’t expecting that and it worked out really well, but at scale for a variety of reasons that wouldn’t be doable. As someone who as scaled customer service organizations pretty large before, like I am not at all concerned about what we’re doing now. Like, I’m positive a lot of what we do now will not scale, particularly me doing ht support, but I am also positive that it’s exactly the right thing to do at this time.

William Griggs: Perfect. That’s a good transition as we talk a little bit about scaling from, maybe the initial founder or co-founder to a first support hire, what should the entrepreneurs, people in the audience, think about and look for when trying to get that first support hire.

Douglas Hanna: We’re actually trying to make that hire now. So we’re looking for someone who is pretty technical and very much a self starter, and just totally kind of on top of everything. Like, this is one of those times where when you’re hiring, you should have all kinds of instructions in the process, and make sure that the attention to detail is incredible. Because they – like, any non founder is probably not gonna pay as much attention – or will probably not pay as much attention as someone with such a huge vested interest in the company. So you’re looking for people who really really care, and are really capable, and can learn and figure stuff out.

And can do so very naturally because things are gonna change, and like your first support hire needs to interact with product management, and engineering, and customers, and all these random people that your 50th support hire probably won’t have to deal with. It’s really important to look for a self starter. I think things like background and experience and all of that are probably a little bit less relevant than a lot of those soft skills.

William Griggs: That’s a good direction to start going down. You know, you touched on it a little bit, but I wanted to clarify, do you think that the entrepreneurs in the audience should start documenting some of the ways that they’re handling support to better position and give this first hire the things they need to succeed?

Douglas Hanna: I don’t think you can ever go wrong by documenting things, like the reality is probably for the most part they will not have a ton of documentation, and the support person is gonna have to figure a lot out anyway, so I definitely look for that in the hiring process, like what is this person’s comfort level with dealing with ambiguity? And I think that’s important, but yeah, you should definitely write some things down. And if you’re not writing out like full pretty guides, at the very least kind of have your scratch pad of here are the commands I use, or here are the secret URLs I have, or things like that because all that will be needed.

But for the most part, particular if you’re just hiring your first person, like I would – if you hire someone good within a month or two, like they’re probably gonna be just as good or better at support than you are, and they can help train the next person. And they’re probably gonna be the type of personality who would want to write it down in explicit detail anyway.

William Griggs: So getting that self starter, so someone that can, like you said deal with that ambiguity, figure it out; go above and beyond even what your initial support efforts have been. And then as the team grows kind of transition that knowledge. But it seems like as well, like you touched on it a little bit earlier, getting that self starter, getting that person that’s gonna put their own unique twist on it and bring some character and some wow to the support.

Douglas Hanna: Yeah, you’re definitely looking for, like I want to say a strong personality, which probably isn’t the perfect description, but you’re looking f or someone who is just like so on top of it. Like, you would just want to – if you could, you would want to outsource your entire life to this person because they would just handle it so much better than you would. Particularly for like most entrepreneurs, which tend to be like easily distracted and a little scatter brained.

You want the opposite of that. you want someone who is just so organized an disciplined because they’re gonna bring so much good stuff, for lack of a more articulate phrase, to your early support organization, and set such a strong cultural precedent that you’ll have good support by virtue of hiring someone like that.

William Griggs: And then what type of tools are they gonna need to succeed? Are we gonna expand beyond email? Imagine if we are expanded beyond email, what kind of tools would they need?

Douglas Hanna: Yeah, I think if you’re now in like there is two plus people dealing with support on a regular basis, it’s time to invest in a basic helpdesk. Like, you might want to explore other channels like phone support or chat or social depending on kind of your target customer and your availability. And there are lots of tools that are appropriate for small businesses or small teams at that level, but it’s definitely the time, I think, at that point to get it out of the email inbox in case someone is away or on vacation, it can be handled, it can be tracked, it can be monitored and reported on. I think all that’s important.

And then I’m sure the support person too will over time just kind of want all these sorts of internal tools to help troubleshoot issues and get visibility into what customers are seeing. And all that like custom tool suite is gonna be super valuable as companies get larger, too.

William Griggs: On the tool suite that you were talking about a little bit earlier, what do you recommend if anything on kind of some of these tools around maybe let’s say phone?

Douglas Hanna: Yeah, phone, there are a couple of options. Like, on that’s pretty common and super basic is called Grasshopper, and it’s fine. There’s a new one that the name is escaping me, but they work in Google Apps. I might be able to find what it’s called real quickly. But it’s a phone system in Google Apps and it’s pretty cool, and it works well with that. So those are some of the good phone systems one I think.

William Griggs: And then as far as social, if people are fielding support from social accounts?

Douglas Hanna: I don’t think you need to get too complicated. The phone system is called Switch – Switch Dotco.

William Griggs: I’ll put a link to the show notes.

Douglas Hanna: I think socially you can probably keep it pretty basic. Like, we just have social notifications show up in our slack channel and that’s fine for us at our volume. But over time you can totally do something like Buffer – or what is it called, Sprout Social and some of those tools. And then, like HelpDesk, you’re probably gonna want something like that. And Zendesk is the facto one. I think there are probably other ones that appropriate for small teams. HelpSkat is pretty good. And then for chat, like Ovark is probably the effective for super small teams and is a good product for small teams as well.

William Griggs: I’m just writing those down, so I can put those in the show notes for everybody to check out. Let me finish that. and then as far as you’re starting to expand – the audience is starting to expand their support team because they’re getting so many customers, their evaluation is going through the roof, it’s fantastic, are there certain KPIs or anything that people should start to monitor as they grow their organization?

Douglas Hanna: Yeah, I think you want to keep it simple. But I would start with some sort of customer satisfaction tracking like MPS, or see customer efforts’ score or something like that. I would definitely track response time and resolution time, and then just availability, so like what hours are we available and does that match to when customers seem to want to contact us?

William Griggs: That’s a good check list for the audience to think about. Let’s see what else? Any other kind of best practices that people should be thinking about as they start to scale from just themselves to a bigger team?

Douglas Hanna: I would also start thinking about like some sort of self service center and resource. So how can customers start solving some of their own issues? Like, guides and tutorials, and video walk through, like all that sort of stuff is super useful, not only for customers to be able to reduce contacts and let customers solve it themselves, but a lot of times that content ends up being really useful for when customers do contact you. And you can just send them like: hey, here’s this really great in-depth article that we wrote about how to do X. And then you don’t have to type it out every time, and customers kind of become aware that there’s a resource online for that.

William Griggs: Yeah, that’s interesting. I had an experience early today with Infusionsoft, and they did just that. I think that what made it unique, or what made it okay is you – I think you can handle that in the wrong way, like you say: oh, here it is. As in like: hey, you didn’t find it? Versus, hey, let me find something for you. Oh, yeah, here it is. So one of those kind of small tweaks to how you’re answering it. Because it seems like in a way the customer support person is kind of outsourcing it, and driving to drive you to the knowledge base, but sometimes you can’t just find it.

Douglas Hanna: Yeah. I think the perfect way to handle that is you mentioned both – you mentioned both what you kind of what the solution is, so you include basically the text of the article in the contact itself, but you also say: hey, we also have this here in case you want to take a look at it.

William Griggs: As the audience is building up their support team, they can think through some of these interactions, and more frequent interactions, but definitely gonna link up all these. You know, for that last example where you start building up the guides, is that when they need a knowledge based solution, or can they just do that internally?

Douglas Hanna: A lot of times it will come with your helpdesk. I would imagine companies at this size don’t need a specific knowledge based product. I’d be surprised if they do.

William Griggs: So just built into something like Zendesk or a few of the other ones.

Douglas Hanna: Yep.

William Griggs: And as they continue to grow, if they continue to grow to say four or five people from two to three, does anything start to change there?

Douglas Hanna: I don’t think there are huge differences between three and six people, or three and eight people, like once you start getting bigger than that, you’re gonna wanna start thinking about kind of like team structure and things like that. Are you gonna have supervisors, or is it gonna be by shift? I would say probably the biggest change that most company tend to go through as they start expanding the team size, call it from a handful of people to an actual kind of real team, as they start looking at expanding hours and availability, for some businesses this doesn’t matter, but for a lot of companies it does.

And they’re gonna at least try and do like 9:00 to 9:00 or 6:00 to 6:00, or something like that depending on where they are geographically, and that’s probably one of the things depending on customer demand that I would look at pretty early as I was expanding a team.

William Griggs: And then as far as are there typical ORG structures that come with account management and support teams?

Douglas Hanna: Account management will often sit under sales, depending on like if they have a revenue quota or something like that, sometimes it will be under support. I think usually you’re gonna want, like at scale a support supervisor might have 12 to 15 direct reports, but a smaller company, you’re probably gonna wanna like some sort of manager probably for like every seven or eight people at most I would guess, depending how senior they are and how much coaching they need and what their day to day looks like.

And then a lot of companies too at this stage start thinking about: do we want our support people to also be engaged in projects and things that are kind of outside normal key work, or do we want them to actually – or do we want them to be 100 percent focused on just handling interactions from customers.

William Griggs: And as you scale this group to maybe four or five it seems like one or two the answer is a little bit easier, but as you scale to four or five, how are you suggesting the founders kind of continue to feed some of these bug reports, or support requests, or product requests back into the respective teams?

Douglas Hanna: I think it’s important once you get to kind of a scale where presumably if you have five or six support people, like the founder is busy doing a thousand things beyond support at that point, and I think that’s when it gets important to kind of establish formal lines of communication between support and product or support and engineering. And one of the best ways to do that, and what we tell a lot of our customers to do is in your helpdesk or your chat system, like use some sort of tagging feature to keep a fairly quantitative view of this how many issues, questions and issues we’re getting about this part of our product, or this feature, or this bug, and take that to the engineering team on a very regular basis and say: hey, 412 people last week asked about resetting their passwords, like there’s clearly issues here.

Usually, support will have identified the bug, like support tends to be like a second line of QA defense. And this is a real issue. And I think having that data from as close to day one as possible will be so valuable because you will be able to really get trends and insights into where volume is coming from, and where it’s going.

William Griggs: That’s a good example of the password because it’s like you said kind of a symptom of a bigger problem, and having those direct lines of communication I can definitely tell will be super beneficial to all parties, right? And then help you overarching prioritize what is to be built. What do you think about some of these companies that have engineers or product managers or even sometimes sales people kind of serve as customer service reps at least, I don’t know like some people do it once a month, some people do it once a quarter, what are your thoughts around that?

Douglas Hanna: We did that at A Small Orange, all of our new employees, everyone we hired direct from marketing, and he was in support for three weeks. If your organization is setup to an extent where you can do that, like where you have some sort of training process and maybe you have some segment of your support that is like not super complex, where you can get up to speed in a week or two, I think it’s really really valuable. Like, Zappos, I think, trains all of their employees in customer service, so like during the holidays anyone, like the VP of HR can pick up the phone theoretically and start helping customers.

So for companies with a lot of seasonality I think that’s an awesome idea. And I think it really sets a very strong cultural precedent. The question is just like making it work. Like, you don’t want to – just because someone is senior and makes a lot of money, doesn’t mean they know everything about the product. Like, I would do support at A Small Orange pretty regularly. Like, I’d log into the phone system or take some chats. And honestly, like besides the fact that I could instant message or CTO and get an answer to a technical question, like I was not a great support rep because I was pretty far removed from the day to day technical issues.

So you definitely want to make sure that you are in a type of organization where you can do that, and the type of role that you’re putting this person in, like maybe it’s a less technical billing support or something like that. I think it’s important to talk to customers and hear what they’re saying and how excited they are and all that. So if you can do it I think it’s definitely worth the time, and I think it sets a tremendous cultural precedent and will get people very familiar with your products super quick.

William Griggs: That starts to be a good place to wrap up. Partly the goal, you know, obviously for the audience is to set them up for success, and the other part is to make sure that they don’t reinvent the wheel. So don’t reinvent the wheel, listen to what Doug is saying here, and start to implement some of that and figure out – and evolve with it and figure out what works best for their business and their business model. As we start to wrap up is there anything else you want to drive home for the audience about support or things that maybe I missed?

Douglas Hanna: I think you covered a lot of it. Like, a lot of the things, like setting up some simple metrics, getting your support out of an individual’s email, getting self service set up. These are things where if at an early stage company can do them, they’re gonna be like way ahead of the curve, and it’s gonna get a lot easier as they get larger.

William Griggs: Cool. Can you tell us a little bit about what you’re working on over at Help.com?

Douglas Hanna: Yeah. We’re working on building customer service software for growing startups and companies. So as they start outgrowing a lot of these small business tools, and they’re thinking about: all right, now we do have like five or ten people, like how do we take this to the next level? We want to provide software that really helps make that easier. We’re in our private beta now with our first product, and we’ll have our general release this summer.

William Griggs: And if people want to connect with you or learn more about your company, how can they do that?

Douglas Hanna: Yeah, so we’re at Help.com. It’s pretty straight forward. My Twitter account is just Douglas Hanna. And anyone can feel free to shoot me an email, just doug@help.com.

William Griggs: Cool. I’ll put the links to your website in the show notes. Douglas, thanks for joining us today.

Douglas Hanna: Yeah, it’s my pleasure. Thanks for having me and for asking some good questions.


Douglas Hanna’s Bio

doglus_hannah_potraitDouglas Hanna is the founder and CEO of Help.com, a next generation provider of customer service software. Before Help.com, he was the CEO of A Small Orange, the homegrown hosting company. A Small Orange, which Douglas joined in 2010, was acquired by Endurance International Group (NASDAQ: EIGI) in 2012 and Douglas continued running the company as the SVP and Brand CEO, A Small Orange at Endurance for nearly two years following the acquisition. Under his leadership, A Small Orange grew from 9 to 90 employees and revenue increased by more than 1200%. Before that, Douglas ran customer service strategy and operations at HostGator, one of the world’s largest web hosting companies. He also founded Service Untitled, a leading blog on customer service and the customer service experience and has done customer service consulting for companies such as Dell. Douglas earned a bachelor’s degree in sociology from Duke University.


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About William Griggs

William Griggs

William Griggs is a product and customer acquisition strategist who has helped numerous startups including companies backed by Andreessen Horowitz, FLOODGATE, & 500 Startups. In addition to his consulting work, he has written for Mashable, VentureBeat, & ReadWrite. You can check out his podcast on iTunes (The Startup Slingshot TV) or follow him on Twitter @william_griggs for Tweets chock-full of delicious knowledge nuggets.

In addition to everything tech startups, William loves breakfast tacos, dogs, short emails, and Amazon Prime. He currently resides in Austin, Texas with his beautiful wife Elizabeth.

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