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Outbound Sales As A Service: Is This The Better Way To Prospect? with Conor Lee [Episode 91]

In this episode, Conor Lee, founder and CEO of HipLead, talks about the emerging Outbound Sales As A Service (OBSaaS) model for prospecting and generating sales leads via outbound strategy. Combining expertise in big data and targeted email marketing, enterprises of all sizes are using Outbound Sales As A Service to scale their sales by taking over the top of the sales funnel. Among the many topics we discuss are:

  • How OBSaaS is different than outsourced lead generation
  • The situations where it makes sense to use Outbound Sales As A Service
  • The sales processes you need in place to leverage the prospects generated by an OBSaas company like HipLead
  • What HipLead can do that your SDRs can’t.
  • How OBSaaS supports the specialization of SDRs and (delays their early burnout)

If you’re in sales or sales management, then you definitely need to listen to this episode.

Episode Transcript


Andy Paul: Joining me today is Conner Lee the founder and CEO of HipLead. An outbounds sales as a service company based in San Francisco. Growing your business and zero time demands that you have a steady flow of qualified prospects streaming through your pipeline. But how are you going to get those leads? There’s ongoing war of words, between factions in the sales industry about where that responsibility rests for generating prospects, is that cold calling or is it marketing? Perhaps there’s a better way to do that because really what you hire your salespeople do actually sell right as opposed to generating leads. So my guest today believes is pioneering a better way to prospect and generate leads, and he’s going to sort it all out for us. Connor, welcome to the show.

Conor Lee: Thanks, Andy. Glad to be here.

Andy Paul: So just take a short minute, provide a real introduction to yourself other than what I said.

Conor Lee: Yeah, absolutely. So at HipLead we help companies scale their outbound sales and we do that by taking over the top of the outbound funnel. So we work with companies to basically, we have massive amounts of data that we get from crawling the web. We’re a data first company, and then we use that data to target very specific cohorts of segments, using information that, it’s very hard to get, doing it at scale, unless you use a lot of labor to do it.

We create these very targeted groups and then we work with our clients at a consultant basis to run outbound cold email  campaigns. W we get, we’re known for getting a very high rate of response and interested rates. And we do that because of the combination of using, the data and pairing that with various specific messages that are focused on pain points and value propositions to each one of these very tight audiences.

So yeah, so we help companies scale top of the funnel. We don’t do selling, we’re just focused. We’re a one trick pony in a certain way in that we’re just focused on lead generation and outbound email campaigns, but we’re very good at it.

Andy Paul: So would you say that without jumping too much into the buzzwords, so the leads you generate, then typically you say top of the funnel, they typically then entered into some sort of marketing, nurture campaign, or they actually turned over to sales force’s is to follow up.

Conor Lee: So yeah. So we’ll run the initial, that initial activation campaign oftentimes we’ll run the nurture campaign and then we’ll coordinate that with the company sales team. If you’re running outbound email campaign for AndyPaul.com. We would send those emails from you or from a member of your sales team. So folks who work with us there’s, the recipients of the message. I have no idea. There’s a third party involved, it’s coming from your sales team at all.

Andy Paul: Okay. But the question is then do leads then, in terms of how your clients then act with, act upon the leads once they receive them, did they consider them sales qualified leads at that point? Or, where in that spectrum typically?

Conor Lee: Sure. Yeah. So when someone, when, when an email or whatever respondent respond, once, when it responds to email campaign, then our team goes in, qualifies them, and we either qualify them as being, as have responded as interested, saying they actually want a meeting, responded as if they asked a question about the product Engaged.

If they asked more for me or they handed you off to the correct individual in the organization  and those are what we call interested, which we also call hand raises. That then goes to the sales team and the sales team then depending on their qualification process goes and actually qualifies them.

The goal of course, is to get them on the phone. It’s somewhere between similar to a marketing qualified lead, they demonstrated intent by responding interested. So usually, yeah, these are marketing qualified leads. Our clients get the marketing qualified leads that respond and they also own all the leads we source for them in the process of running an email campaign.

So they have, data qualified leads, and then they have the marketing qualified leads to respond. And then, usually the, then their sales team we’d coordinate with their sales team and the calling process. Sometimes clients call sometimes they don’t, it depends, obviously it depends on their processed.

Andy Paul: Okay. So if we take a step back and look back at the genesis of HipLead, where did the idea come from and what did you see in the market based on experiences you had that said, okay, we’ve got a need for this.

Conor Lee: Yeah. So this is my third company , I founded a company in 2011. Oh, there was a telephony, B2B telephony startup, and we were part of the Y Combinator accelerator. And then, it was, unfortunately he wasn’t, we got a little funny ran it, but it didn’t last too long. It was a short lived company, then joined another company that was a B2B marketplace, for, for buyers and sellers of consumer packaged goods at the wholesale level, and eventually founded HipLead later on.

But after I left my second company, as the second company wrapped up, what we did, we realized that a lot of my other friends who were founders started asking me to do the same thing for them, that we did to grow both those companies. And at the time that we were just being scrappy, we’re doing like you would say whatever it is. But we are running out on email campaigns. It’d be got to be very good at that. And that’s, that was responsible for almost all the growth of those last two companies. We always in between things, looking for things to do, and all of a sudden, my, all my other friends that were founders started coming to me and I’d eventually, we started scaling the company up that way. So we started, we grew word of mouth, and then added a lot of, of really great technology and technologists on as we grew. But we started out as a consultancy effectively.

Andy Paul: So yeah, that’s very interesting. So how has using Hiplead, let’s say. different than running your own up on marketing campaign, email campaign.

What do you do differently that sets you apart from what somebody could do? If so he’s got Marketo or HubSpot or any of those systems, what are you doing? That’s the cm incrementally better than what they’re doing?

Conor Lee: Sure. There’s two ways in which we reason why folks work with us. One is that, this is all we do, as I mentioned, we’re a one trick pony. But as a result, we’re very good at it. So we can get companies up to a level of getting 3-6% interested rates on our outbound campaigns in a month. And usually if you’re a new company, or if you haven’t run out bound yourself for this existing organization, it takes a quarter or more, sometimes even longer than that to get it to the point where outbound is running as a machine.

And so we get this machine running very quickly and because we’ve done it all. we’ve worked with every almost every single audience that’s out there. And we know the audience went know, admits to just resonate. We measure and test everything. we’ve got a team that just does that.

So A, we get it going faster and B we scale. We’re doing, we have our own lead generation system do every thing end to end. We’ve got a 130 million contacts in our system, 20 million companies around the world. And we’re regenerating for some of our larger clients, 50 to a hundred thousand new prospects per month. With some of the very large companies we work with so we could really scale that system up in a way, just because of our technology and expertise that our folks can. But to get back to your question about using Marketo and other systems, we also use specialized tools that we’ve tested and honed over the years.

I’ve gotten me very good at using them. so we can, do that up. And usually we recommend folks use a solution like Outreach, or there’s a number of other ones that detect responses. So responses are really the key, is a key metric that we look at responses and then interest responses.

And those are the two metrics that we focus on. Not as much as interested, not as much open rate or click through rate, we really want to focus on, you know, people actually taking real action expressing actual interests.

Andy Paul: So you’ve talked about this product outreach. I want you to explain what that is for people that are listening.

Conor Lee: Sure, Outreach is effectively a email sales automation tool. Good friends with the company of the founders there and, basically Outreach allows your sales reps, a competitor to Yesware and Tout, a number of other ones and hey send the emails that look like personalized emails. and they come from your, from your email center. So you’d would plug into a real person’s inbox. My inbox. And for say, and then it would look like it was sent. It doesn’t have necessarily have a big footer and the responses, the system tracks the actual response. So you set up a series of emails, four or five touches set over time. And if someone engages at a certain touch that they respond, that stops that sequence, that they don’t sequence continues. So it’s automating the followup part of sales prospecting, of outbound. So it’s automated the email part of that.

Andy Paul: So go back to your saying the referenced Outreach then is so if someone’s subscribed to your service you provide them leads, they, if they’re going to feed them into a sequence, they’ve set up in in Outreach.

Conor Lee: Yeah. Outreach oftentimes is the one we usually recommend we work with them to do.

Andy Paul: Got it. Got it. Okay. so now one of the trade offs, and then we talked about the beginning is okay. Cost trade off between using your service versus what most companies do, especially small businesses is having to get somebody on the phone and bang some phone calls. So what have you seen in terms of, telling people at the cost rate of between your service versus theirs in terms of generating leads?

Conor Lee: Yeah. Ut depends on your market, so if you’re going only after enterprise, let’s say you’ve got an ecosystem of total contacts that are like under 3000. It’s probably best to actually hit the phone. And that’s what we tell clients that they come to us. Because you could dial with one or two people, everyone, and have a great personalized discussion. As long as you have sales reps that are trained and, and you have a process set up for doing that. And usually companies that have only a thousand or 2000 total prospects that they could reach at all, we actually usually tell them to do that. So if those scenarios I’d definitely go along and say look, hit the phones yourself. That’s probably the best thing to go.

If you’re dealing with, if you’re dealing with companies that are, if you’re dealing with the ecosystem of 5,000, 10,000, 50,000, your reaching out to SMBs or mid market, areas that it’s just, it becomes very difficult to scale very quickly this outbound process. I’m sure you can get 500 people into a room, but the overhead, the management of all that.

It’s just slow. It’ll just take a while to do. And in my other companies we did that and at Hiplead we have outbound phone calling team as well, but we work that in conjunction with outbound email campaigns. And so we run an outbound campaign first. We then coordinate the calling once the campaign is finished.

The whole adage about, one out of 10 people are ready to buy, right? One out of 10 are never gonna buy. So the outbound campaign picks up that one out of 10 immediately. And you activate those and those go away and you’ve got a nice steady supply. Then for the other ones that are already in there, you act, and you can call them down and they’re familiar with your brand and know who you are, and then you gave them into a nice nurturing campaign and manage it. Those are two different, those are ways that we do ourselves internally. And, so that’s basically to answer your question, hopefully they answered it.

Andy Paul: Yeah, it did. How are you different than other outbound, outsourced lead generation services? So somebody is, and I’m thinking this from the context of the people are listening to this, CEO of an SMB or a midsize company. How did they  identify okay this is the service for me versus some other service. So may start with who’s the ideal customer profile for you, and then we’ll segue into that second part.

Conor Lee: Yeah. so a lot of our clients are our SAS businesses. And what we find are the folks that tend to work with best hula us with us or our companies that are oriented to work best for cold outbound.

Companies that do work well will have a clear and concise way of describing their product that, somebody can instantly get what the benefit could be in a second, in a single sentence or two, where their solution solves a clear and defined problem. And that the, and that we can identify, or they can identify, potential prospects that have that problem that have that pain point.

And it’s. So SAS companies are oftentimes good targets for that because they’re very, oftentimes it’d be very specific pain points that arise out of.

Andy Paul: Point solutions oftentimes, right?

Conor Lee: Yeah, exactly. Yeah and their consultancies will work as well. As long as they’re very specialized and things that tend to be a little harder to sell over outbound like IP phone solutions, things like that are, that every single person needs, but the vendors themselves are hard to differentiate. Those tend to not work as well because it involves that have to involve a true relationship sale or pressure sales enviorment, outbound isn’t necessarily the best solution for those. But there’s a, a humongous market that rest of the market where they’ve got to input a lot of labor and a lot of management overhead to to get to market and we can help them get to market much faster. and to really scale outbound in the, the whole, predictable revenue sort of way.

And do your customersAndy Paul: primarily have fairly established content marketing presence as well?

Conor Lee: It really depends. So we have customers, in 2-3 different flavors. One, are companies that are relatively A round stage, raised a couple of million dollars or they have product market fit and they have a small sales team. That’s sort of one end.

On the other end we have some clients that are very large companies that have only done content and inbound, and now they’re ready to attack enterprise and mid-market. Some companies that, that have had, that have, or even have growing out a B2B team within a consumer company. That’s another example.

And then you have kind of companies in the middle, that are the sort of th that are basically have a sales team have run outbound. And either they want to try new things and test it out. They want to scale it up really fast or, they want to refresh the list they already have.

And those are things that we specialize in doing. Cause if they’ve got to, they want to say, look, we have other data sources. we have, our Salesforce has 20,000 leads in it but gosh, we don’t, it’s just a huge mess. And, so we’ll go in there and we could pull out, we could find net new contacts that could be companies all in an automated fashion, and refresh a list on a regular basis. And in a way that’s very easy for us to do and very difficult to other folks too, because the technology that’s behind our platform.

Andy Paul: So you could refresh the list or for a customer that doesn’t have a list you can go out. And so are you source that through your own database? You sort the 130 million contacts, you can do a slice and dice on that and target to help a specific customer need.

Conor Lee: Exactly. Gor example, we could figure out, if a company has, let’s say you’re looking to only sell a couple, what is the have offices in two different countries?

Figure out that. Let’s say so you’re selling to companies with offices, two countries, but need to have a certain number of sales reps. So you can figure out how many sales reps that company has using a certain technology. And then we can only target people that have. Talked about or possess a specific skill set so we can get very granular, like granular to the point where, you’d have to have a team of a large team of people spend a lot of time shifting through data.

And the issue that it’s hard to train, it’s hard to train SDRs and folks to shift through all this data at a way that’s.

Andy Paul: It’s impossible. It’s not hard. It’s impossible. You have a hard enough time training them to sell, let alone.

Conor Lee: Exactly. Cause it, cause honestly, it’s one of the hardest, it’s one of the more painful jobs in sales. That’s why SDRs in San Francisco area we’re finding that the at the average company SDR’s ;ast around one year. That’s what we’re finding. And in other areas of the United States, about two to three years on average.

Andy Paul: Before the break I posed this question. You’re a new sales manager need to do a sales turnaround on a company it’s urgent where the first two things you do in the first week, they could have the biggest impact.

Conor Lee: Sure. So the first one I’ll I have to say, we have an unfair advantage, and I’m gonna assume that, I would assume you have some of the data that we have. And then I’ll give you a nice second answer will be so that anyone can do it.

The first one would be basically what we’ll do with we’ll analyze all the companies, all their clients over time. And then opportunities that have, that have gone pretty far to have others. And then we’re going to model, we create a model, and look for a company that you wouldn’t think would fit it, but match all the criteria.

And we do that because we have the ability to just look at so many different companies, the United States. So we’d go in and say, okay, let’s look at the opportunity. You guys are close with this period of time, Even if they came in from a, a friend or a longterm referral or whatever else, what is that?

What internally at that company made them buy, and then we’ll go and try to find a model, other companies that look like that. And we could, and usually what we’ll do is then we’ll, we didn’t go and run outbound campaigns to test these hypotheses and that very quickly, I’d say that the second way, which is one that I’ve done numerous times at other companies is, again, I go back to old opportunities and old leads and dive in there. Understand really quickly, try to get a good understanding of why they didn’t close. Get an understanding of if they’re existing pain points still exists or within that area and then basically run an outbound campaign to reengage those folks. It’s going to be that, obviously your old opps, very likely going to be the fastest things to close depending on your sales cycle. So if you want to get some quick revenue and get some quick momentum in the bank, that’s gonna likely going to be the first thing that you should do.

Cause then you just have a lot of conversations. You get a good understanding of the company, as an outsider coming in, of course they will know the flaws of the sales process because they didn’t close. So you’ll understand why they enclosed very quickly, rather than having to spend a lot of time with new inbound prospects.

Andy Paul: Yeah. No, I think that’s very clever about going to the opportunities that didn’t close because yeah. Statistics range anywhere from, I’ve seen recently just from 50 to 70% of opportunities in a pipeline never closed. So if that’s the case, If they didn’t close, chances are they probably haven’t made a decision. If that was in a relatively recent timeframe, go and hitting them up more effectively with a better value proposition messaging and so on, could be a good way to reignite and revise some of those opportunities. Excellent.

Conor Lee: Thanks.

Andy Paul: Good job. You pass. Okay. So onto the next. So we were talking about before the break, we’re talking about SDR longevity, you say in San Francisco, and I presume that’s true for the Valley in general, that it’s a year for SDRs, as average longevity on the job. Isn’t part of the issue there though, that they’re having so few conversations that these people are basically are bored. Part of the deal is that they don’t get a chance to get better at what they’re doing, because they’ve been making 50 calls a day.

I think the statistics I would make about 50 on average, maybe have five real conversations, sales conversations in a day. It wouldn’t have, perhaps if they’re using hiplead and they’re putting more opportunities. And the top of the funnel that filter down that maybe over a period of time, these guys actually have a greater likelihood of making a call, but they should connect.

Conor Lee: Yeah, absolutely. it’s incredibly easy to get burned out just in that, that boiler room environment, where you’re just hitting the phones and dialing. And, honestly, if you’re going to hear, you’re a young kid and, or not even a young kid, he’d go come in to that environment. You’re going to want to see a light at the end of the tunnel or get rewarded very well for your position life in comparatively, to keep that going. And I, myself, in a high school, worked in a boiler room call center, for a couple summers, and got started on sales that way. So I definitely know, I didn’t last, I lasted two months. It was also Phoenix. It was a hundred, 110 outside. There was nothing else that summer, but I definitely know that. The good thing is now I think a lot of companies are dividing up. There are. Are further for better or worse or further specializing, their SDR.

So they’re doing inbound SDRs and outbound SDRs. And for the outbound SDRs, they are segmenting their leads into, and this is what we usually encourage our clients to do is to segment, your leads into A, B and C and only call the A’s, hand email, the A’s, the B’s and C’s, which should be 90% of your leads. Of course it depends on how we are market is and all that, but take that 10%, call them down, handwrite them. Sure. Use a template, but personalize the heck out of it. Tesearch then do all that. And the rest of it run the outbound campaign for the rest. Cause then you’re going to get, you’re going to get that 5-10% that respond, is a good time. We would get a five to 10%. You’d start a conversation, just pick their interests. And then you can also spend the rest of the time, dialing, running, outbound email, dialing those A targets. and of course, after you run through all those, you can go down the good on, go down to B and go down to C and call them but you’re gonna, you’re gonna find your plates a lot more full with good prospects that spend your time qualifying instead of just, spending all your time in this stuff.

Andy Paul: Well, especially spending your time dialing, right? Because if someone’s making 50 calls a day, they’re basically dialing right. 80% of the time you’re going to get voicemail. So to me, it seems like part of the problem for SDR, especially if you find someone that’s good and worth investing, which presumably is the case. Cause you wouldn’t have hired them in the first place. Is that, what, if you could fill their day with 50 conversations instead of five.

Conor Lee: Exactly. And then you maybe would change the

Andy Paul: dynamic in terms of job satisfaction, how long they would stay and getting a better return on your investment. That’s why I’m fascinated by tools like yours and tools like ConnectAndDell. For instance, that’s, giving the reps opportunity where they making a thousand dollars a day for a rep and they can generate 40 50 conversations. You see the job satisfaction, really skyrockets longevity, skyrockets goes, they’re actually getting good at what they’re doing because they’re practicing it more often. And I think that’s part of the key to keeping people is that they just have to practicing.

Conor Lee: Yeah. And unlike any job, the more time you have doing it, the better you are, the better sales becomes, the better relationship is. SDRs are incredibly important part of any company. And it’s your first introduction to your organization. And if it’s someone who’s really green and isn’t satisfied. The chances of a closing down the road are going to be lows or are going to be a lower.

Andy Paul: Yeah. And if you look at it from a numbers standpoint, if you get somebody that’s literally, as the industry standard statistics are, SDRs may be having five sales conversations a day out of yield of 50 to 60 calls. So over, 20 days, 25 business days, may they make a hundred conversations in a month. Whereas if again, if you use a tool, some of these power dollars and so on that enable you to have 40 50 conversations a day. you got the practice in two days that you would normally get in a month. it seems like their effectiveness for a company it’s just going to skyrocket. And I think it demonstrates it does actually, I think the companies that are doing it. So anyway, without getting too sidetracked, I think HipLead obviously it could feed into environment. And for people that are listening to this and saying, gosh, we need look at new solution to help us accelerate the pace of our lead generation. And keep our SDRs busier. This is a good tool to do that. I just gave you an advertisement.

Conor Lee: Okay, great. thanks. There you go. Yeah. and I guess the thing that we do that we like to say is that we don’t re try to reinvent your sales process. We try to fit into the existing process and augment it.

Save your SDRs time, allow you guys to have more conversations. and then once that conversation starts, get out of your way and let you close. So your reps are spending less time closing and more time closing and less time doing everything else.

Andy Paul: I think even if you’re an environment, as a lot of companies just haven’t done the specialized sales role, especially in smaller companies, midsize companies, they still might have a hybrids force where people are combination inbound or, inside, outside the fact is you still have the same basic challenge.

You need to get leads into the system, into the funnel. And this is, you got to find a tool that’s going to help you do that, to accelerate the pace of your growth otherwise you’ll be left behind. So glad we had you on the show today. It was good. Good information. So in the last segment to show it got some rapid fire questions to ask you can give me one word answers or you can elaborate, however you wish you’re ready?

Conor Lee: I’m ready.

Andy Paul: And these are really serious questions as you’ll see it here. So what’s the most powerful sales tool in your personal sales arsenal?

Conor Lee: Expertise.

Andy Paul: Okay, great. Okay. So what’s the one tool you use for managing sales at HipLead that you can’t live without?

Conor Lee: Right now, our current sales team is one on ones with all the reps themselves. So a really quick 10 to 15 minute meeting that I have every week with, really everyone in my team to just get an idea. It’s a nice way to get a pulse of what’s going on in the company and to keep me involved. And my VP of Sales does it as well. Those are I find to be very helpful, of course, that doesn’t work forever as the organization scales but, but right now it’s a right tool for our company size.

Andy Paul: Okay. Who’s your sales role model?

Conor Lee: Gosh, a sales role model. Okay. Huh. It’s funny. I never received, I haven’t received any formal sales training at any point. So I don’t know if I can say I have one sales role model. but I have worked in the past, interestingly for, this is going to be an interesting answer, but I worked for politicians for, I was a Politico and I learned a lot about selling as leading as selling, essentially that I learned a lot from them. So I worked for a number of different politicians and at the California state level and national level. And, I thought from the politicians from a number of them, a lot of they had it, a lot of their other issues, but, they were all incredible sales people, but you didn’t call it sales. It was called leadership, political acumen, personality. all those sort of things were wrapped into, really, a presentation of their idea that direction, and then getting this, team of constituents to go this direction of belief that so

Andy Paul: Great. So who’s the politician you worked for?

Conor Lee: I worked for Gavin Newsome, when I was pretty young, who was the San Francisco governor and he’s Lieutenant governor right now. and he was, he was very skilled speaker, especially,

Andy Paul: What’s your, what’s the one book that every sales person should read? It doesn’t have to be a sales book, but one book, every sales person should read.

Conor Lee: I really, as someone who’s, as a CEO and a sales person is being a CEO is a certain type of sales person. I really enjoyed, Brad Horowitz’s book. and, at Andreessen Horowitz, Ben Horvitz rather. Yeah. So his book, I’m trying to think of the name of it right here. Pulled up. The Hard Thing About Hard Things which I really enjoyed, quite a great deal.

I’ve just started the Challenger Sales. I’m enjoying so far, but just started it. come back to me really, really interesting and relevant, but I guess Ben’s book, Ben Horowitz’s book isn’t necessarily about sales, in the traditional way of thinking about sales, but it’s about considering your audiences and how to talk to them, how to message to them and how to, how to work with every audience as their own audience and how to deal with things. And when things go bad, basically. Which is good.

Andy Paul: Hey, it’s good for every business. So tough question, what’s your favorite music to listen to psych yourself up for an important call or meeting?

Conor Lee: Ooh. I have a Spotify playlist. I’ve got a, my brother is a, is, he’s quite musical. And so I usually follow his playlist. so it’s usually in indie and electronic media somewhere in between that. So between a lot rock and electronic. And so I usually just turn on his playlist and, And listen to that.

Andy Paul: Indie rock. Okay. So last question. What’s the one question you get asked most frequently by salespeople?

Most frequentConor Lee: question. I guess the question is, are they qualified by my sales people? My sales staff with the, does, are these qualified? What do you think? or, I guess there are one is, it’s a. Really what, do we have any here? I guess the one thing is that because we have, we serve so many different audiences, right? Always trying to find clients, current clients or past clients that have reached the same audience, going after the same audience or selling to the same audience that new, that our new sales, would be selling to. So always try. And my sales team is always asking me to, to understand how this client is similar to other clients. So we’ve actually put together docs and a lot of other things to break down, which of our clients sold to what audience and how this is it’s different from the others.

So usually it’s something along those lines like, is this prospect qualified,A. And B if they’re qualified, have we sold other companies like them in the past. And if so, what happened and how did they, how were their results? but hopefully we’re doing a little bit, hopefully we’re doing a little less that lately. Cause we put together a sort of a system to manage that.