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Building an Outbound Demand Generation Machine with Russell Taylor CEO & Founder of Hello Outbound


Russell Taylor

How to Use Outbound Marketing to Boost Your Business

How do you get leads to your business?

Probably through an inbound marketing strategy—you put out content to the world and see who comes in.

And while this can be effective in many ways, there is a way to take things up a level and bring in specific, highly-targeted warm leads in a streamlined manner—outbound marketing.

Russell Taylor, CEO and Founder of Hello Outbound, joined us on a recent episode of the Stride to Freedom podcast to discuss the magic of outbound marketing.

Here’s what you need to know.

What is Outbound Marketing?

If inbound marketing is a one-to-many strategy, outbound marketing is a one-to-one strategy.

That means all of your marketing materials, copy, or communication channels are targeted to a specific customer or company instead of multiple.

Cold calling and door-to-door sales may be the original outbound marketing strategy, but today you can use any regular platform to do it, including social media, email, or LinkedIn.

The key component to outbound marketing is an emphasis on personal connection and one-to-one conversation. It’s intentionally bringing in leads that are best suited to your business rather than throwing your message out to the world and hoping people receive it.

In a sense, it’s a quality over quantity type of strategy.

Balancing Automation and Personalization

The key to a successful outbound marketing strategy is balancing automation and personalization. You may be able to make a few personalized calls, emails, or campaigns, but once the leads start pouring in, it’s easy to get overwhelmed.

So, there’s a need to automate some of the initial tasks that get you to in-person contact. But if you automate things too much, you lose the personal touch and things start to look a bit like spam.

Russell’s approach with his clients is this:

  • Hello Outbound focuses on data prospecting, campaign execution, and copywriting—the backend systems and processes to bring in leads.
  • Once there’s interest from a lead, the client takes all the personal calls, emails, or other form of communication.

It’s automation on the backend, and personalization where it matters.

Hello Outbound’s ability to set up a robust system in the backend is due to their emphasis on data collection.

They data-scrape job boards, funding events, technology stacks, Yelp reviews, team demographics, and more. By doing so, they can identify specific pain points from potential clients.

For example, a job posting of a potential client may say “I need bookkeeping help.” That’s information of a specific pain point that you can then address in an outbound marketing strategy.

This data serves as signals—signals about what the client needs, where there pain points are, and how you can help.

And, through that signaling, you can design a specific outbound marketing strategy that will speak to exactly what they need.

How to Get Started with Outbound Marketing

Anyone interested in outbound marketing simply needs to get started and prove it’s possible. Find some potential clients who fit your niche and compose the best, most personalized email you’ve ever crafted.

And you’ll start getting results. Genuine and honest one-to-one communication is effective.

The great thing with outbound marketing, too, is that you can always play around and try new things. You might not find your “golden script” right away, but trial and error helps you figure out what works and what doesn’t.

Once you have confidence in this outbound approach, you can start thinking about how to scale. You can automate some of your processes and systems in place to get things rolling on a consistent basis.

And, of course, you can work with Russell and Hello Outbound to show you the ropes! If you want to learn more from Russell, make sure you listen to his full episode on the Stride to Freedom podcast or follow him on LinkedIn.

The Stride for Freedom podcast is hosted by Stride Services. Contact us today We offer back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth.

You’ll enjoy this Podcast episode with Russell

Listen Now

We are fortunate to have Russell available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, click here and let us know. Stay well. Stay safe. Stay healthy.

Show Notes and Links From Episode:

Russell Taylor: LinkedIn

Hello Outbound: Website/LinkedIn

Russell Taylor: Top 10 Takeaways

Russell Taylor: russell@hellooutbound.com

And if you want to know more about us at Stride Services, contact us today. We offer back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth.

Episode Transcript:

Russell Benaroya: Hello, everybody. Welcome back to another episode of the Stride 2 Freedom podcast. I am your host, Russell Benaroya. The Stride 2 Freedom podcast is targeted to business owners to help them get and stay in their zone of genius.

What is your zone of genius? Your zone of genius is your superpower. It’s that thing that you do that you don’t really think it’s all that but people look at you and say, “How did you do that thing?” It feels effortless, and you’re in flow. You lose track of time. Our genius zone at Stride, which is the sponsor of this podcast, is to help business owners use data to make better business decisions.

As you’re listening to this podcast today and as you’re reflecting on where you’re spending time, think about, “Am I maximizing my time in my genius zone?” Well, we have an awesome guest today who is going to help us help you spend more time doing what you do best, which is probably growing your business. I am pleased to welcome Russell Taylor, the CEO and founder of Hello Outbound. Hey, Russell.

Russell Taylor: How are you doing? Thanks for having me.

Russell Benaroya: Oh, it’s great to have you here. The fact that we have two Russells on a podcast is going to throw everything into disarray.

Russell Taylor: Have you had that happen before?

Russell Benaroya: I know a lot of Russells out there. There are a lot of Russells. On a relative basis, I haven’t run into that many. But you’re a special one. How about that?

Russell Taylor: What’s the title of the podcast? Russell V. Russell, Russell on Russell?

Russell Benaroya: Probably not Russell on Russell. That might change the dynamic but open up a new market audience for us. We’ll see what happens. What I am excited about today is to clarify for listeners and for myself, what is outbound marketing? What is the power of outbound marketing and building a machine in your business that ultimately can transcend you?

As you know, because we’ve been working together for a long time, I’ve always used the term, I’ll talk about the me Russell for a second, the Russell hustle. The Russell hustle is business owner is out there, pimping leads is not the right word, driving leads. Whatever it takes.

Russell Taylor: Whipping leads.

Russell Benaroya: Whipping leads. Oh, okay. I was thinking now it’s the R on R podcast.

Russell Taylor: Yeah. We might have a new segment here, too.

Russell Benaroya: We might have a new segment. I’m out there hustling leads, and that’s only as good as I am out there hustling leads. But I haven’t really built a machine and an engine. What I’m excited for listeners to hear about today is what you have built at Hello Outbound, which is really a machine to create a method of efficient outreach, experiment, and iteration to figure out the right message to get to the right audience and drive inbound interest in meeting.

Boom, boom, boom. With that, I want to jump in and really just get people connected to what Hello Outbound is, why you started the business. What’s the problem you’re trying to solve for business owners?

Russell Taylor: Maybe do you want to start with defining what outbound is versus inbound and marketing? I think that’s maybe an important distinction.

Russell Benaroya: Yes, I love you guiding me on the agenda of my podcast. Yes, do it. I’m into it.

Russell Taylor: Awesome. For us, outbound is a very intentional one to one style of communication. If you think about traditional marketing and inbound, you’re putting out content blog posts, you’re getting stuff out there, and it’s interacting with lots of different people. They’re interpreting it in their own way, and then they come back to you. So that’s where you get your inbound leads.

That’s great because the work’s in the front end, and then you have leads coming in. You’re less in control of who those people are and how qualified they are. And it’s a one to many type of approach. Most marketing is one thing, and it’s going out to lots of people.

For us, when we think about doing outbound, it’s a very intentional one to one way to communicate with somebody. You are choosing a single individual or a single company, and you are targeting them with your sales copy. So it’s a lot more intentional. You have a lot more control over what you’re doing. It allows you to move into new markets, test new ideas, set new leads.

That’s an important distinction when we talk to people because the channels are all the same: LinkedIn, email, Facebook, whatever you want to do. But the idea of doing outbound one to one communication is a little bit different.

Russell Benaroya: What is the history of outbound marketing? What’s old school outbound marketing from 20 years ago? What is it? Five years ago? What is it today? Where’s it going?

Russell Taylor: The traditional stuff people are not going to cringe when they hear it is cold calling. What it’s been for decades or door to door salesman, one person knocking on your door. Cold calling still works. I think for some industries, we run into it every once in a while. But I think, overall, people are moving away from that.

The new way to think about this is really your channels that you do marketing on. We work in email and LinkedIn, those are our two main channels. But there’s a way to do it with Twitter. Think about any network that your target market is a piece of, you can do your one to one communication with them there.

Russell Benaroya: Why couldn’t I just take my understanding of what outbound marketing is and start emailing one to one people that I uncover through a database or otherwise? What is it that Hello Outbound’s solved to make this more efficient?

Russell Taylor: That’s where we talk to people, they’ll say, “Hey, I have 10 target accounts.” We tell them, “Automation is not going to do you much good at that point.” lt’s a great way to start to figure out, “Hey, do one to one emails. Find somebody you’re interested in and write them the most customized over the top message. And you’re going to get the best results if you had time to sit down and look at every prospect and do that.”

That’s a really great starting point for a lot of people. It gets some results, especially if you have a really small list. That falls apart when you’re trying to get the most of your time. When you want to start going after hundreds or thousands of people, you’ve got to figure out, and this is the line we walk with clients, what is the line between super high quality, customized outreach, and automation?

Usually, the more automated you get and if you automate too much and you’re not paying attention to the messaging and the quality, you start getting into lower quality type of outreach, some people might consider it spam. So that’s where we’re saying the best results is if you sat down and custom wrote a single script to everybody.

As a founder or a small team, that only gets you so far before you burn out. And you realize it’s not the best use of your time. So that’s where we come in, where we’ve been building our system to help people still keep that high quality of the outreach they want to do but then start to chip away at the automation and say, “Okay, look. This never changes. Let’s keep doing this every month and just keep taking away the tedious parts of the tasks for them.”

Russell Benaroya: Okay. To bring this down to, say, fifth grade level, let’s take a client that you have that wants to serve a particular market segment. Heck, you could even use Stride as an example. But maybe walk through what that journey looks like. I come to you and I say what?

Russell Taylor: You say, “We’re really relying on inbound leads, and we would like to be more intentional about going after new markets.” To that, I would say we are really good at the infrastructure of outbound sales, making sure the system’s running, campaigns are executing, people are reading what you want.

You still need to be responsible for the human part of the sales. Taking the phone calls, nurturing them, doing anything that requires human creativity. We’re enabling you to do more of that while we’re handling the data and the prospecting side of it.

Russell Benaroya: Got it. If I come to you and I say, “Hey, Russell. We really want to make a move into the outsourced IT services market.” And you say, “Oh, great. Well, boy, there are like thousands of them out there. We know this is a highly fragmented market. Here’s what we’re going to do at Hello Outbound for you.” This is my experience with you. “We’re going to build your database.”

I’m going to let you parse these all in a minute. “We’re going to figure out your targets. We’re going to put them into our database. Through our system, we’re going to help you build campaigns that are email and LinkedIn. We’re then going to distribute those campaigns. We’re going to measure responses or response get me off your list or neutral, and then we’re going to pass that information or give you visibility to that information so that your sales team can reach out to that interested party and engage them in a personalized way, hopefully with the intent of setting up a meeting.”

Russell Taylor: I think an important part of us and figuring out our business is where to draw the line in what we’re doing and then what we enable our clients to do. And so we break it down into three pillars: data and prospecting, why are we targeting somebody? You just came up with an example, “Hey, we want to move into the MSP target market.”

The second part of that is campaign execution, making sure your messaging is getting out, people are reading it, people are opening it. Third part of that is copywriting. Are we saying the right thing to the right people? Now the line in the sand for us that we feel is the best setup, at least for our clients, is that when there’s a human response to outreach, that’s when you want to get a human in.

When someone says, “Hey, that sounds really interesting. I’d love to learn more.” That’s when our clients are plugging in a human to say, “Hey, great. Here’s a white paper. Here’s an example. Here’s our pricing. Tell me more about your business. Let’s get you into the pipeline.”

Everything before that could have been automated and set up and taken off the plate of founders and small businesses trying to get outbound set up. Again, we’re enabling that human side of sales so that you can spend more time there.

Russell Benaroya: There are a number of companies in the market that say, “Oh, well, we do outbound for you in a variety of different ways.” Some companies will cold-call outbound on your behalf. Some companies will seemingly do what you do. But what I found interesting about Hello Outbound is you’ve really built a technology platform around it. What has that technology designed to do for the customer that makes it compelling to use you?

Russell Taylor: Really how I describe us, the core of our company and the platform, we’re a data company. We happen to help people do outbound sales on top of that data. But effective outreach comes from understanding the pain points and what your prospects are struggling with. And so using data, that’s what we’re helping people do.

An example of this is we scrape a lot of job posting boards. If a potential client of yours has a job posting up saying, “Hey, I need bookkeeping help.” or “I need an accountant.” That might be a good lead for you guys. They have the budget, they have a pain point, they put up a job posting, they’re showing need, they’re giving off indicators that now is the right time for you to reach out to them.

We think about it in terms of signaling. And that’s our buzzword in data signals. Job postings is one of these. You can think about funding events, technology stacks, team demographics, Yelp reviews. You start getting into SEO, we’re looking at listings and Google results. Team demographics are really powerful. What is the internal makeup of a company?

There’s just tons of signaling. What we’ve built and realized is half of your success doing outreach is your right timing and the data, and then the other half is what you’re saying. So if you can figure out the timing and the data and the right contact using signaling, which is what our platform revolves around, your messaging becomes way easier. You just sit down, and it’s super obvious.

To us, the best type of sales outreach is asking questions and providing value. People know it’s automated. Smart people understand how sales and marketing work. They don’t care. If you get in front of them with the right question at the right time, they say, “Yeah, sounds great. Let’s talk.” And that’s really what we’re striving to do.

Russell Benaroya: I love your comment about asking questions and providing value. Outbound marketing is not just trying to hawk your wares, sell your service, “Want to buy?” What I’m hearing you say is whether or not somebody is in the buying cycle, we don’t know that. But what is most important is can you build a relationship? Can you build a rapport? Can you talk a little bit more about what you mean by adding value and what some examples of that are?

Russell Taylor: Definitely. When we talk with clients internally, especially in writing copy, we put it in the realm of hard selling versus soft selling. Hard selling is, “Hey, we do X, Y, and Z. Do you want to buy now?” Soft selling is, “Hey, we just created this free resource. I think it’ll help you. I’d love to send it to you. Are you interested?” Providing value versus hard selling.

Now hard selling has its place. At the end of the day, you have to have the ask. You got to be asking for something, a meeting. And so you need to get there eventually. We’re just finding, even the longer we’ve been in business, softer you can go, “The more value you can provide somebody, you got brand recognition.” They’re saying yes, you’re getting your brand in front of them.

If they’re interested in all of the soft things, the value provided, they’re going to say yes to the meeting eventually. So it might take a little more work in terms of, “You got to have some content.” It helps to have things to share and value to provide people. But every company, whether they’ve written it down formally or not, they have internal knowledge that they could be sharing. And this is a great way to get it out there as a way to generate leads in meetings.

Russell Benaroya: That’s one type of messaging, the soft messaging. You talked a little bit about the hard messaging. What I appreciate about Hello Outbound, and you can talk a bit more about your technology, is that if we want to try a soft selling campaign this month, great, let’s see what happens. Then next month, we can easily write new copy and distribute more of a hard sell and see what works and what doesn’t. Can you talk about the environment that you’ve created for rapid learning and why it matters?

Russell Taylor: At the end of the day, there’s no golden script that works. We’ve been doing this four years now, and we’re testing 10 different strategies every month. We’re pretty ramped up at this point for outbound. 90% of our business comes from outbound. But we encourage our clients to constantly be testing new things. New ideas, new pitches, new verticals.

Most of our clients come to us and they want to set meetings as quick as possible, which is understandable. Once they see how it works, they start to open horizons to say, “Hey, we can test product ideas. We can test regional ideas.” I remember, an example, for you guys was testing webinars, providing value to people and getting your webinar out in front of them. So lots of opportunity in terms of segmenting and getting ideas out there outside of the, “Hey, we do X, Y, and Z. Do you want to meet with me?”

Russell Benaroya: What I’m hearing you say is outbound can also be a path of customer development?

Russell Taylor: Yeah, definitely. I’ve had many businesses in the past, and one of the mantras that I feel like I’ve developed is sell it before you build it. There’s a lot of ways to test the market. That’s part of the reason I started this company. I’ve done this type of outreach long before this business. Getting your ideas out there and testing the market and if you can sell it first, and then building it comes second.

I think a lot of people have ideas about what they need to be building, when they should be talking to people and getting confirmation of those ideas before they invest lots of money into actually developing it.

Russell Benaroya: Could you distinguish the data set that you build by identifying these signals versus say, data list companies like ZoomInfo? I don’t know if that’s exactly the right name, ZoomInfo.

Russell Taylor: ZoomInfo comes up a lot, Seamless. We’re just in a different business model. These guys have a static database. They’re huge companies. If their database happens to have what you want in it and it’s a fit, that’s great. It works for a while. Their business model is to resell as much data to as many people as possible, and they’re pretty good at it. These are big companies.

It’s not as custom and high quality as we’ve set the standard for what we do. Our clients come to us with requests, we help them understand what are the pain points and triggers that are going to make someone a good lead. And then most of what we’re doing is based on web scraping. Going out, identifying these events, pulling stuff in.

We’re fairly a small company. If clients have requests, for example, somebody wanted to target B Corporations. We can build signals like this pretty quickly, we just have an infrastructure to go out. Maybe we’ll never scale up to the size of ZoomInfo. But I think that’s okay with us. I think we’re in a spot where we’re just providing a little bit of a different value and service than some of these bulk data providers.

That’s what’s interesting about the business. It’s old, this industry has been around forever. Everybody’s had a bad experience with an outsourced service, a data provider, a sequencing tool, pieces of the puzzle. And so our challenge when we talk to people is like, “What are the bad experiences you’ve had?” Everybody’s had one. Then helping them say, “Okay, cool. How are we different? What are we doing that’s a little bit higher quality than that?”

The one that comes up quite a bit is appointment setting services. I’m sure you’ve had some experience of this before. And again, value props are always kind of the same in our industry. But the process is a little different. Appointment setting services, they’re selling you human capital. It’s almost a staffing service.

They’re saying, “Hey, we’re going to assign you the sales guy. He’s going to click around LinkedIn, he’s going to bring you leads, he’ll represent your companies, he’ll set the meeting. So qualify him. He’s going to bring you a lead that’s ready to buy.” It sounds great in theory, and I think there is some scenarios where this works. I would say most of our clients have tried some of these services, and they get burnt.

You’re basically paying another company to represent you. Our theory is you want that capital inside your business. If somebody has learned about your business enough to effectively communicate and sell it and do that creative work, you probably want that person on your payroll and not necessarily on somebody else’s payroll.

Russell Benaroya: But there’s also a bigger difference which is, it’s not just that you’re not doing the appointment setting whereas other companies are doing the appointment setting. What else in the core infrastructure sets you apart from the appointment setters? Do the appointment setters have similar technology around list building, scripting, etc?

Russell Taylor: I’m sure some do write it. There’s so many of them. But traditionally, appointment setters are just assigning human capital to the problem. Clicking around, they have no sense of automation or signaling or getting things set up in a way. A big part of the way we’ve set up, and this was extremely unique to us, I think, and what sets us apart, once we develop a signal or a strategy and it’s based on events coming in every month and we know that it works, our goal is to automate it.

Say, there’s 100 job postings that get posted looking for bookkeeping help every month. Our goal is that when we find the copy that works with that, we’re just going to keep it running month over month and the people we work with can say, “Hey, I can count on five leads coming in from the signal. Let’s move on to new signals, new ideas.” And we’re just helping them build as time goes on.

You get back to the predictable side of what we’re doing. We should have our bread and butter campaigns running that are producing leads, allowing our clients to think a little bigger about new verticals, new industries, new ideas that they actually want to go out and test.

Russell Benaroya: I really see Hello Outbound as a system builder. You build the factory, and then you allow cars to run through the factory based on what color models that client wants to roll off the assembly line that month. But once that factory is built, once those inputs all get in place, the universe of possible outputs is really quite broad. And so a client can use Hello Outbound in a variety of different ways to test a variety of different messages, to take action using a variety of different resources.

Russell Taylor: Yeah, exactly. One of our challenges we talk about internally now at the team meetings is we’ll get the system set up and a lot of clients they’re like, “Hey, there’s a lot here to respond to. Now what?” And everybody has a different level of, “Do they have their CRM setup properly? Do they have sales reps to actually handle the low level stuff? Do they have the nurturing and the automation?”

Our challenge as a company is, again, figuring out where do we draw the line of like, “Okay, we’re going to bring you to here. And then it’s your job to take it from there.” I think that’s where a lot of trial and error is on our packaging. We tried appointment setting for a while, and we just didn’t feel like it was the best relationships for the types of clients we work with.

That’s the interesting part where you get them to a certain point, and then everybody’s in a different maturity level as to what their pipeline looks like. Some people don’t even have a CRM setup yet.

Russell Benaroya: What advice would you give to a business owner that may be listening to this podcast so that they are set up to take or extract maximum value from an outbound marketing strategy? What do they need to have in place?

Russell Taylor: It starts with the data and understanding why you’re reaching out to somebody. There’s the old mantra in startups, do what doesn’t scale to figure things out and then figure out how to scale. And I think that holds true here. Obviously, we built a system and there’s a million tools out there. But put together a high quality list of 100 companies, get a script that works for them.

You don’t need any special automation to get going, but show yourself that you can get responses. I think the biggest thing for us is showing people that it’s possible, showing people that they can, “Hey, wow, a warm lead just came out of me emailing them but at random.” Usually, one warm lead really turns people’s minds. They start getting ideas about what’s possible.

I think segmentation, too. A lot of people will come to us and they’ll say, “We work with hospitality companies, we work with food brands, we work with tech companies, we work with finance companies.” For us, it’s breaking that down into a really specific segment. Choose one. The more segmented and the more specific you can be to a specific company, the better your chances of getting a response from them.

We work with a lot of agencies, a lot of marketing agencies. Some of them will come to us and say, “Hey, we do all marketing for all types of people.” And we’re like, “That’s great from maybe a business strategy. But in terms of a sales and marketing message, that’s really bad. You want to present yourself as an expert in one really specific problem or segment.”

I think that’s what outbound allows you to do. No matter what your internal structure is, you can present yourself as the expert in financial services, marketing. And you can have case studies and content around that allows you to test those types of things.

Russell Benaroya: What I heard is one, test it for yourself first. Make a list of 100 companies. Build a script. Show that you can sink a putt every once in a while. As a non golfer, I just want to call that out.

Second, I heard have a segment. The more targeted you are in the customer segment, the more you look like you’re an industry partner, that you know what that customer segment is dealing with, the issues that they have, and so you don’t look like you’re just selling a generic thing.

Then if I decide, “Hey, I want to run with this outbound marketing machine.” What systems or resources do I need to have in place at my business to make sure that I can make the most out of partnering with a company like you?

Russell Taylor: A clear idea of your segmentations. We’re relying on our clients to come with us to that. And a big part of that segmentation is the copy becomes a lot easier to write. What are you going to do with the warm leads as they come in?

Again, 80-90% of our clients right now are agencies. And they’re really used to inbound and referrals and people that are just ready to buy because a friend of a friend told them, “Hey, go work with these people.”

I think the biggest thing people can do is have the mindset that, “Hey, I’m going to have to nurture these people. I’m going to have a meeting. I need to stay in contact, and I need to have the people or systems in place to continually stay in front of them.”

If you have newsletters and nurturing opportunities, that’s great. Those are automated. But it could just be as simple as in your CRM, having a monthly task checked back in. The amount of times we’ve been like, “Oh, those leads are old.” Then you just send an email, “Hey, how are you doing? How are things going?” And then they’re reengaged.

Part of doing that type of outreach is once someone expressed interests, knowing how you want to move them through your pipeline and what you want to do with them.

Russell Benaroya: So have a CRM with stages, have a vehicle where you can nurture those contacts because as I heard you say, listen, not everybody’s necessarily ready to go into the buying funnel or the sales funnel. But that doesn’t mean that they aren’t a relationship that you can continue to cultivate. Okay, got it.

Somebody in my organization, ideally, is cultivating that relationship. Somebody in my organization is responding to the warm response. Who is that? Is that a sales development representative? You can talk about what that is. Is it somebody else? Shoot, is it me? Oh, heavens. Is this my highest and best use? Talk to me.

Russell Taylor: Most of our clients are under 50 headcount. A lot of times we’re talking to CEOs and founders or a single head of sales type person. And a lot of what I tell them is like, “Look, you’re the most strategic person in the company to make this work. Get it up and going. Prove to yourself that it works, baby steps.”

We’ll work with a founder or a solo head of sales. We’ll start getting them the warm responses like, “Hey, this is great.” Pretty quickly, they get burnt out with answering 20 emails a day of people saying, “Yeah, send pricing. Send this”. So there’s gold in there.

That’s when we talk to them about, “Hey, look. Let’s get an entry level salesperson or a sales rep in here to start actually handling this.” And that’s another part of this. We prove to them that it’s reliable, and then it allows them to make that internal hire in then, “Yes, that’s exactly what you want to do.”

Most of the time, a founder or the original person we started working with is still closing deals. They want to be the face of it. But pretty much, the way we have it set up, we can automate everything up until that call. We’ve got a system in place we can do outreaches, we can answer all the questions, schedule meetings. I can look at a client, research them 15 minutes before, hop on a call, answer all their questions.

To me, that’s a huge time saver. Before the initial discovery call is automated away, we’re pretty transparent. Everybody comes on board, we show them everything we have set up in the CRM. And most people are like, “Yeah, that’s a pretty cool setup. How do we do that for us?”

Again, our perspective is not we don’t work with enterprise clients. We don’t have huge sales teams. We are working with less than 50 headcount usually consulting and professional services, lots of agencies who maybe they have experience with it. But they’re really relying on us to drive most of their outbound efforts.

Russell Benaroya: We use the term sales development representative or business development representative. Not everybody knows exactly what that is. Can you just explain what that role is for a company?

Russell Taylor: There’s lots of different words that mean the same thing. But we think about BDRs and SDRs as being your entry level guys. They’re the meeting setters. If you were to give these guys a commission structure, it would be on number of qualified meetings set. So they’re communicating with leads, maybe they’re answering questions. But their goal is to get a meeting set that then a closer can then come in and communicate with.

A big organization, you’re going to run into account executives. Those are SDRs that have graduated into account executive roles. Most of the companies we work with, that’s going to the director of business development, head of sales, or the founder or CEO themselves. I will stop there. Did that answer the question?

Russell Benaroya: Yeah, that helps. I don’t think people always understand from a structural standpoint, oftentimes for smaller businesses. I’ll say smaller businesses call it under 10 million. You think, “Oh, my salesperson’s my salesperson.” but haven’t teased out, “Well, what are all the functions of sales? Is there a technical part of sales? Is there a meeting setting part of sales? Is there a closing setting part of sales?”

It’s a way to think different about the machine of sales. I think Hello Outbound can be a good complement to the entry point of the machine, which is qualifying leads that are worth the closer’s time to work.

Russell Taylor: Again, it can save you money. If you didn’t segment any of that, you’re like, “Okay, I need a guy that can close and represent the company. I need someone who’ll click around LinkedIn. I need someone who can verify emails.” Usually, the closers want to close. And the prospectors want to press.

Again, for a lot of our clients, it’s still a founder, a CEO, or a senior salesperson. They’re the closer. If all they had to do was hop on and talk to qualified prospects and get them into the pipeline, they’re ecstatic. If everything up into that point just falls in their lap,  that’s a really good setup for, like you said, smaller companies.

Russell Benaroya: Yeah. You said a couple of times, “We work with a lot of agencies, we work with a lot of agencies.” Why is that? Is that just the segment that you’ve chosen? Or what is it about agencies?

Russell Taylor: I used to run a marketing agency before this. So that might have something to do with it, I guess. Origin story for us was, I was working with a partner on an agency. We’re trying to do a tech-enabled growth agency. Long story short, I think we’re just trying to do too much. But I was doing all the engineering and prospecting and scraping.

We were scraping AngelList and job posting boards trying to find leads. It was working really well for us, we were getting a lot of leads coming in. We weren’t offering this type of service, but our clients kept asking for it. And so I tried to convince my partner to pivot, didn’t work out. So I pursued this idea, knowing that we were doing it internally.

A marketing agency falls under professional services, and I think this works well for professional services. Because the pitch is usually, “Hey. Before you hire internally, work with us. We’ll help show you how to do it properly. Potentially, you’ll make an internal hire down the road. But it’s going to be a lot cheaper and less risky to work with us in the short term.” And so I think that just pitch lends itself to outbound really well.

Russell Benaroya: I’m sure some people may be listening and saying, “Oh my gosh, I get all of these invites on LinkedIn every day for people that say, ‘Hey. I was just on LinkedIn. Your profile looks very interesting. I’d like to connect.’” I’m just curious, how do you separate the wheat from the chaff a little bit and differentiate in a world that seems to be becoming more and more automated on LinkedIn?

Russell Taylor: It’s funny. Me and one of our account managers, Maggie, we save all these responses that we get because we’re going to make a scrapbook one of these days on Table Reader. People tell us to get lost or not so nice words. But the other ones we like, it’s, “Hey, I don’t normally respond to these. And I don’t know why I’m responding to these. But this one was really good.”

What’s cool about my business is we use what we build every day. I’ll get on a call with somebody and they’ll be like, “Well, I don’t understand the value prop.” And I’m like, “Well, you’re here talking to me. Yeah, that’s the value prop. You were in a campaign, you got outreach.”

I think back to your original question of how you stand out, you have to be intentional. You have to put the work in to understand, put yourself in their shoes and understand what they’re struggling with. Again, it comes down to the most effective sales outreach is asking a question. If you’re talking about, “You, me, me, me, we do this, we do this, I’d love to talk to you.” you’re falling flat.

You need to say, “Are you struggling with this? It looks like your big segment for us is ecommerce agencies. Hey, it looks like you’re running Shopify. I’m curious, are you struggling with ecommerce abandonment rate?”

The thing is, sometimes I think we need to take horoscope writing classes. You write copy that can’t apply to anybody in that segment. But when they read the question, they internalize it. And it’s super personal to them. So again, when you create a really segmented list of prospects, which is what our technology does, the signaling. And then you just look at that, your copy almost writes itself because you don’t have to think about every scenario and everybody and everybody’s pains.

Usually, have one segment that has a really clear pain point. And the copy is super short and sweet. Some of our copies is just one question, “Hey, wonder if you’re struggling with this. We built a solution. If you’re interested, I’d love to talk to you about it.” That’s all you got to say sometimes, if you’ve put in the work on the front end.

Russell Benaroya: Good call. Are there any regulations that companies need to be aware of in working with companies like yours that are doing targeted outbound email?

Russell Taylor: Yeah. There’s CAN-SPAM here in the States, GDPR in Europe. Most of what we’re doing is here in the States. So that’s what we stick to and talk about. At the end of the day, it comes down to, do you have a reason to reach out to somebody? Is it business related? And do you give them a way to unsubscribe?

Now, unsubscribe can come in a couple forms. It could be a link. But we like to make it a little more personal in that we put it in the script like, “Hey, I think this about you. Curious if you struggle with this. I could be wrong. Just let me know, I won’t follow up.”

The more authentic you can be with your script, you’re going to get no, thank yous. But if you get people who are, “Hey. No, thanks. Not relevant.” That still means that you wrote a script that was authentic and relevant enough that they said, “Hey. No, thanks. Maybe later.” So for us, respecting people’s inboxes, understanding that it might not be the right time and giving them a really clear way to say, “Hey. No, thank you.” or the unsubscribe link. And that usually satisfies most of it.

Russell Benaroya: One of the features I appreciate you building is the ability to use Zapier as connectivity from Hello Outbound software into the CRM. Can you talk a little bit about what that allows?

Russell Taylor: Yeah. Again, that comes back to that handoff line. Our job for clients is to get them to the interested response. When someone says, “Hey, I’m interested. I want to learn more.” then our client has to decide, “What do I do with this? Do I push them to a meeting? Do I put them in a newsletter?” So we’ll have triggered events, and we’re building native integrations for HubSpot and Salesforce. But Zap opens up a whole new world of possibilities.

We send text messages, Slack notifications. We’ll populate a CRM, we’ll add people to a newsletter. Zapier is a really powerful tool. I think it’s fortunate a lot of people have experienced with it. But basically, a lot of our strategy sessions in month one or two with clients is, “Okay, we got these warm responses. What do you want to do with them? Do you want to get them to a specific rep? Do you want to auto enroll them in something?”

At minimum, you want your CRM populated with all the information. So yeah, that was a pretty big win for people. And it just came from people asking from it, so we built it.

Russell Benaroya: Yeah. Well, that’s what happens when you’re a technical founder of a small, nimble company. Oh, you want that?

Russell Taylor: Yeah. Maggie, our account manager, was on vacation last week or two. So I just took the opportunity to sit down and talk to all the clients and just be like, “Hey, what sucks about the platform?” And just a laundry list of things came out, and now we have our prioritized-

Russell Benaroya: Roadmap.

Russell Taylor: Yeah, a roadmap for the next month of what we’re going to do.

Russell Benaroya: What I love is your willingness to ask, “Hey, what sucks about the platform for you?” and being candid yourself inviting them to be candid and just getting raw, authentic feedback and not fooling yourself that you’ve got something figured out when you don’t yet. So good on you for continuing customer development.

Russell Taylor: Yeah. We’re just all using software all day long. Every time something doesn’t work in somebody else’s software, you’re like, “Argh!” And those build up subconsciously, no matter how much you like the software. I think the worst are the ones you hate a lot of pieces of but you feel reliant on for certain ways. So it’s like they’re still getting your money, but you begrudgingly give it to them because you don’t want it.

I think it’s just realizing I have those feelings every day using other people’s software. People are definitely having that about our software at some aspect in like, “How do you tease those out?” Because for every person that tells you, there’s probably nine that didn’t say anything and eventually want to churn or have issues down the road. So I think you have to put the 10x multiplier. On every honest complaint you get about your software, there’s probably nine more that agree with them.

Russell Benaroya: It’s a great takeaway. Tell me a little bit about your pricing structure, how you sell the service.

Russell Taylor: I would describe it as a four-year test to find the right structure. We’re bootstrapped, I started solo by myself. Yes, I have a software engineering background. So I’m able to build a lot of that. And that is a great asset to the company in terms of budgeting. But we just have to start as almost consulting. High ticket item, pay us to do everything. We’ll take care of it. Don’t worry.

It was really simple, back in the day. As we’ve matured, the goal has always been to get down to zero, no contracts, month to month SaaS options that people can come in at a lower level, especially smaller companies and then use us as they see fit.

I think this year, our biggest thing is figuring out those month to month options that allow people to say, “Hey, does everybody think we’re different and want to try us?” It’s usually just a function of cost. And so we are constantly testing. Our team meeting this morning was like, “Hey, these packages are great. They’ve got us to this point. What’s the next version? Do we need to be adding more volume? Do we need a cheaper price?”

I almost feel like we built five businesses in one with all the different solutions. We have deliverability solutions, prospecting solutions, sequencing. It’s all one big suite. And how do you package them in the perfect way that people get the most value?

I don’t think we’ll ever get to the point where we are like, “Yes, this is the perfect pricing structure.” I think we’re just going to keep getting better and better. And as the technology gets better, it allows us to have more entry level packaging, which we’re pretty excited about.

Russell Benaroya: I’ve been on that journey with you, and I appreciate how hard pricing strategy is. So, thank you for being candid about it.

Russell Taylor: Yeah, I think it’s the ultimate question. It’s hard to change because all your current clients see it. And if it’s too different than what they had, then they’re going to come. So it’s always got to be a better deal than what they saw before. But also, we’re not selling a $10 product that has hundreds or thousands of customers a month.

You don’t get this really statistical significance on those types of analysis. It’s more swing for the fences, put something out there. And then your team has to say, “Yeah, this is working better.” You might change your prices. It’s not till six months later, you say, “Yeah, that really affected churn or that really affected this.”

I think it comes down to founders. Those are the decisions they have to make. There are definitely ones that have kept me up like how do we package this? And what do we price it at?

Russell Benaroya: What is the biggest challenge before you right now coming into 2023?

Russell Taylor: Oh my god, I don’t even know how to pick the biggest one. I think for us, we’re getting to a point where we have to figure out how to scale. We’ve done a lot of things. We’ll bring people on on the SaaS month to month offerings, but we’re still giving them tons of value outside of the software. There isn’t a package anybody buys where we’re not giving them feedback on copy, feedback on strategy.

I think the question for us is, how do we scale that? Are we getting content out there so people can learn themselves and then it’s more of a SaaS offering? What’s the balance of an account manager helping run? You’ve been part of the process. Our account managers are fairly involved in the strategy of things that go on. And so I think that’s our biggest challenge moving forward.

Again, this comes back to packaging and pricing and setting expectations. How do we 10x what we’re doing? How do we even double our client load right now? I don’t think we could 2x our client load right now, with the current structures we have in place. I think things would fall apart. And so again, with scale, how do you maintain the quality of what we’re doing? So I think that’s what keeps me up, the bigger questions I try to find time to work on.

Russell Benaroya: Yeah, appreciate it. My takeaway is that, as a business owner, it’s super important to commit to having a culture that embraces outbound marketing as a vehicle to customer acquisition because outbound marketing is a certain energy, it’s a certain velocity, it’s a certain level of responsiveness and action and engagement and sales. And it is cultural.

I think about, say, friends of mine that are in the commercial real estate industry that are say, selling buildings or selling apartment buildings. Literally, they have a team of people that are cold calling property owners like 100 a week or 400 a week or some crazy number.

It yields amazing results. But you’ve got to have a culture that says outbound marketing matters. And I think the bridge across for a business owner and where you’re helping them is to get a taste of what is possible so they’re confident enough to build the infrastructure to start supporting that at scale.

Russell Taylor: Yeah, definitely. That’s our goal. We talk about every client, and we’ve realized this is the make or break. The quicker we can get a warm response in somebody’s inbox, the easier their relationship is. Usually, closed deals take 3, 6, 12 months for people. Just the nature of their business.

For us, if we can show them in a very short amount of time, “Hey. You had no idea this person existed, and now they’re interested in your business.” then they become hooked. And you’re like, “You said it’s an investment. There’s very few B2B companies out there that I don’t think this would work for.”

The question is, how many tests are you going to have to go through? How long is it going to take you to figure out how to do it? I don’t think the question is, will it work? It’s just, how long is it going to take you to figure out how it will work?

Russell Benaroya: Challenging your clients on being clear about their customer segment is so important. In fact, you end up becoming a bit of a guide, as much as a service provider, because the message is, “Listen, we could do this all day long for you. No problem. But the more specific you are, the more confident you are in the message to that specific business function in that specific industry, the higher likelihood you’ll get a response. And if you’re not clear on that, I’d back it up and revisit your strategy.”

Russell Taylor: I think it comes back to the you versus me. If you’re approaching this and thinking, “These are all the things we do, who wants to buy it?” Flip it around, “Here’s our best clients, how can I provide extra value to them?” And that is relevant to the people who need outbound sales, “How can I provide value? What can I put out there that is going to be a value to other people?”

Sometimes it’s a really hard question, if you haven’t invested in content or your marketing is not quite there. But that’s where you’re going to get the best results. And you talk about people just getting hit up all the time. Go look in your spam folder, you’ll find a million really shitty outbound sales emails. And it’s like, “Hey, we do X, Y, and Z. Here’s the menu, what do you want to buy?” And it’s like, “No, that’s just not going to work.” So yeah, put yourself in their shoes. What would they want to hear? What are they struggling with?

Russell Benaroya: Russell, thank you so much. I know I planted some questions for you, which I consistently share that I asked none of them because I really just want to follow the conversation and figure out where there’s energy and curiosity and putting myself and you into the shoes of the people listening like, “Gosh, what would it look like if I wanted to launch an outbound marketing effort?”

I do believe that this segment is so important because it’s one that is not well understood, from a tactical standpoint. It’s also not well understood from a cultural standpoint inside the organization. But I would say that if you’re a business owner and you want to transcend your business, you want this business to survive you being out of it on a day to day basis, having a machine that allows for a consistent and confident stream of inbound leads or leads coming from your outbound marketing effort, that is an engine. And that’s worth the investment.

Thank you, Russell, R on R, for sharing with us a bit more about Hello Outbound and outbound marketing in general. So everybody, if you want to learn about Hello Outbound, go to hellooutbound.com. We’ll put information for you in the show notes. Russell, thank you so much. I’m sure people will be reaching out and appreciate your generosity today.

Russell Taylor: Yeah, thanks for having me on. This was fun.

Russell Benaroya: All right. Thanks, everybody. See you on the next episode of the Stride 2 Freedom podcast. Bye.

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