Cold Outreach in recruiting and digital marketing with Andy Cabasso of Postaga

Maren Kate
I'm so glad to have Andy Cabasso the founder of Postaga, a cold outreach platform for digital marketers and agencies, and also the former founder of JurisPage. Did I say that right, Andy?

Andy Cabasso
Yep, that’s right.

Maren Kate
Which is a digital marketing agency. And we are going to talk about remote culture, building remote teams, and hiring in fully remote environments. So I'm really glad to have you on the show. Thank you so much.

Andy Cabasso
Yeah. Thanks for having me. Excited to be here.

Maren Kate
Absolutely. So my first question is, what was your first job?

Andy Cabasso
My first job was selling ice cream at Carvel.

Maren Kate
I actually know what Carvel is. And what was your first professional job?

Andy Cabasso
I guess my first professional job was, I was a summer intern and a financial advisor and I spent my days filing things which was super exciting.

Maren Kate
Super fun. How did you go from there to what you do now?

Andy Cabasso
I guess, long story short,I studied business in undergrad and graduated during the great recession and some mentors suggested that I would be a good fit for law school. And that seemed like a good idea and so I went to law school. I was studying at Fordham in New York City. And then, as I was applying to work at different firms, I realized I wasn't so sure I wanted to be a lawyer. But the firms I was applying to, they all had really bad websites and a friend of mine at the time was a freelancer and we talked about doing web design and marketing for law firms. And so we started JurisPage, which was originally kind of like a side hustle. And I graduated law school, passed the bar, and I'm still licensed to practice in New York, but it hasn't really come in handy all that much lately. We did a good enough job with our own marketing that the agency kind of took off and so we built this agency focusing on marketing for lawyers and law firms. And three years later, we were acquired by a larger legal tech company. And from there, some experiences that we had with doing marketing for our clients, we wish we had a better way to do cold outreach so that we could do link building. So for anyone who's not familiar, to help you rank better in Google one of the big most important things in Google's algorithm is the quantity and quality of links from other websites to your website, which signal to Google that your site is relevant and has good content. But doing it for an agency we didn't really see that there were many scalable ways to do that. So we built our startup Postaga to help with cold outreach. And it was originally geared towards link building but since has expanded to also be for people doing PR, sales, lead generation, and really any other sort of cold outreach.

Maren Kate
What about recruiting? How have you or have you seen any companies that are, you know, in such a competitive hiring market, are you seeing companies start to realize that they need to not only make their sights qualify for sales leads but also for potential hires?

Andy Cabasso
For sure. So yeah, for kind of like what our process is, in terms of our software is, it starts with prospecting, how to find the right people, and then from there finding their email addresses and then pitching them. If you're on the receiving end, I'm sure you get dozens if not potentially hundreds of cold emails per week, everything from, you should hire us for mobile app development, or outsource IT, or some generic pitch like that, to some things that are more targeted, let’s say and relevant to you.

Maren Kate
I guess that's the, kind of, the vague question is how? How does one differentiate in that cold game because it is very similar with when you're recruiting passive candidates. Now in such a crazy market, especially in the States, especially in technology, candidates, great candidates, especially the ones that are working at known companies or that have had enough experience, they are getting outbound reach out to see “hey, can I hire you, would you be able to get on a call”, like dozens of times a week. And I'm just curious, you know, how you think about that even in an existential way? And then how are companies or individuals thinking about doing authentic outbound?

Andy Cabasso
So the most important thing, as a lesson for anyone thinking about doing cold email, think about the recipient’s perspective first. So let's say you're checking your email inbox and you have an email now from someone that you don't know. You look at the subject line. Is it interesting, irrelevant to you? Maybe. If so, you'll open the email or check out the preview and it's very important, in a very short period of time, that you establish that the contents of the message are relevant for you; that they're not generic and looks like it was copy-pasted and sent to a million people and that its specifically relevant to what you do or what your potential needs are. And this is really what I've seen separates people who get a low open and response rate to a very high, comparatively, open rate and response rate is really how appealing the pitch is and personalized it is for the recipient. So one tip that I personally found works well is humor. So everyone, so many people, as I mentioned before, and as everyone knows, everyone gets cold email pitches all the time, and a lot of them look something like, “Dear Sir/Madam, here is what I have for to offer for you. I can offer it at a great price or something. Can you schedule a call with me so we can discuss this further?” First, it's a generic offer. Second, it doesn't really appeal. And then third, usually, the close that they go for is, “let's schedule a meeting, and here's the scheduling link”. That's not how people have conversations over email. Usually, I try and make it so that my first email in a cold email sequence is really just to start a conversation. I don't want someone to click my scheduling link or whatever, because they're probably not going to. And so my real takeaway question-asking in a cold email is, you know, is this relevant for you? Is it something that you might be interested in? If so, email me back, and let's see about it and talk further. But in terms of humor, I find that humor is disarming, like, if someone sees, alright, I've got this cold email, like on autopilot, effectively, the recipient’s gonna be like, alright, this was a cold email, this is a cold email, send it to trash or archive or whatever. But if you can get the recipient to stop that mental workflow of being like, alright send it to the trash, archive it, whatever, ignore it, delete it, just to pause for a second to read what you have to say that'll significantly increase the likelihood that you get a response. So for example, that I was included, and I still am to this day, including in some cold pitches is a picture of me sitting next to my cat staring at the webcam or the camera, basically, and the caption is, “we are awaiting your reply”. If you open the email and you see this, you're like, “What the heck is this? Who is this person?” and if it's the first thing that you're gonna see, it's gonna, at the very least, make you curious to see what this is all about. Because I've shared a picture of myself now. It's not a headshot. It's not a professional picture. It's me sitting next to a cat and we're just strangely staring at the camera lens and it throws you off your rhythm. So I've found that tends to work well and stuff like that, basically.

Maren Kate
You know, it's interesting at Avra, at our agency, we've actually found similar with targeting outbound candidates for recruiting campaigns is humor really tends to open the door a lot better. So shifting gears a little bit? How is your company structured? Are you remote-first or remote-friendly? Do you guys have offices?

Andy Cabasso
We have never had offices. We've been remote-first since Postaga started in 2019 or 18. What year is it? 2019…we've been remote first. And I guess that kind of helped us from the beginning of knowing what the business was we wanted to create. In my last business, in the agency, we had an office and when I left, we still had an office. And we had actually, the company that acquired us had an office in one city and we had our office in another city and I was, kind of like, coming from the perspective of this wasn't all that necessary. There are some benefits to being able to collaborate in person in real-time. But it just, for me, just didn't seem 100% necessary. I felt, personally, just as productive working from home. And I didn't think, I just felt that people that I wanted to work with could also be self-starters and able to manage their own projects. And as long as we would have the right environment that could foster that we would be able to do it well. And so that's why, from the beginning of this business, we really put a lot of procedures and things in place to make sure that we would be successful working remote because we don't have, I don't see any other way forward.

Maren Kate
How did that look like? How have you structured the company and the team to thrive in that remote work environment?

Andy Cabasso
Yeah, so from, I guess, a few different things. So big picture in terms of, like, operating system, that's one thing that's been important to us. So I follow the Traction framework. And there are a bunch of other business frameworks as well, a business operating system. There's the Rockefeller Habits or scaling up or whatever their branding now. There's, I think, EOS and some other things. And really, it doesn't matter but I found that just having a business operating system works. And so what that looks like is, you have certain big picture five-year horizon goals, and one-year goals, and quarterly goals and projects, as well as regular KPIs and metrics that everyone across the team has and some that are unique to different roles. And so these are the things that we are accountable to, and beyond that, really into these will have regular check-ins, weekly check-ins, but not just for the sake of doing it, but specifically to get updated on project statuses and things like that. And everything is very specific and regimented. So we know we can stay on task and nothing falls behind. And there, you know, been some things that we've learned along the way. Like, in particular, not biting off more than we can chew. As a founder, in particular, there are a million projects that I want to do and before we started using, a business operating system, I could say for sure that I would have some big projects that will be my goals for the next few months. And then there would be a shiny object. And I'd be like, “Oh, that looks interesting, let me add that to my to-do list”. And then none of them would ever get done. Because I just kept adding more and more things to my plate. But by having your quarterly goals and projects, that keeps you accountable to those and making sure that these are the things that you have to get done. And as far as your own KPIs and metrics and things like that to keep you accountable to these are your personal numbers and this way your managers and your team members can know how on track you are and if we're hitting all these numbers then we're doing something right.

Maren Kate
It's funny, we actually use EOS from Traction as well and I have totally noticed that, and kind of a version of OKRs, I've totally noticed in the last year rolling that out it makes everything so much more clear. Even personally, when I'm thinking, “Okay, what do I need to do this week? Or what is the goal this month?” just going to one source of truth is pretty game-changing. And going forward, if I was ever starting something from scratch, I would build that into day one. Another part of that is the hiring part. And so, how do you all approach recruiting and onboarding for a fully remote team? Especially in today's market.

Andy Cabasso
Yeah. So I guess there are a few things. Before I get to finding candidates, in terms of onboarding candidates, onboarding the hire, one thing that I found that works particularly well is I have basically an onboarding curriculum for their first day, first weeks. If it's a role that I have hired for before I already have the training materials ready to go because the first time I hire for a particular role, I'm building out certain materials. I'm also, if it's the first time onboarding someone for a role, I or someone else might be training that person and in the training sessions recording them. So if we're doing this over zoom, I’ll record the sessions, I'll save that, we'll have that. And now I've created effectively a library of training materials that I can use for future hires in the same role. And what I've done is I'll take those materials and I'll create an e-learning course for onboarding for one big picture team. Like, here are our procedures, here's how to schedule time off, here are paid holidays, and all the team handbook kind of stuff like that, how to communicate on Slack and Clickup and all those things, and then have a separate course specifically geared towards their role that they can do asynchronously in their own time zone on their own schedule to get trained up for the role.

Maren Kate
So I like that. Yeah. So asynchronous is a big part of how you guys operate, I'm assuming?

Andy Cabasso
Yeah, because we have team members all over in different time zones. Yeah, I'm in New York and Eastern time, but I have people on my team who are 10 or 13 hours ahead, and if the person I’m training is directly subordinate to me there's only so much overlap of my waking hours, at least that I'm comfortable being awake, to do that training and onboarding. So creating those materials has been really helpful to do that.

Maren Kate
Walk me through your recruiting process, you know, how that looks.

Andy Cabasso
So, in general, I will say that the best people I've ever hired in the last, I don't know, 10 years I've been hiring people, have come from referrals. If I'm ready to hire for a new position, the first thing I'll do is I will ask my team ‘we're hiring for a new role, Is there anyone that you would recommend for the position?’ And if anyone has someone, great, they move to the top of the pile and I'll give them an interview. After that, if there's no one else that recommended, then I'll ask my networks if there is someone that they'd recommend. And once I've exhausted that, then I'll go with a posting on a job board or something like that. The reason I like referrals, in particular, I've found they work out the best is because when you get a referral, the person that you're getting a referral from is vouching for that person that that person is going to be able to do a good job in the role. Because no one wants to recommend someone who's gonna do a terrible job and, you know, hopefully, that won't affect your relationship. Someone's not going to want to recommend someone unless they're going to be able to do well in that position. And so over the last years, consistently, I'd say that the people that I had recommended to me have been the best performing people in their roles.

Maren Kate
Do you do any kind of outbound with passive candidates or you know, cold outbound in your recruiting process thus far?

Andy Cabasso
I have not. Typically, what I've done is, so if I'm ready to hire someone and I don't have a recommendation, I'll post on a job board. And from there, what I'll do is I, so if I'm in a position where I'm going to get a lot of candidates for a particular role, and I guess lately the roles that I've been looking to fill have had a lot of applicants, but might not all be the right fit for the role, I will add some automatic qualification to it. So a few things that I’ll do, so first, if someone is looking to apply they'll get redirected to a Google form or questionnaire or something like that asking about specific relevant experience with if it's a role that calls for certain software or certain software languages or something like that. And if they don't meet the threshold that we're looking for then I'll automatically send them an email, you know, “sorry that I don't think you'd be a good fit for this role but we'll keep you in mind for the future”. If the candidate passes the screening through that I'll set up a zoom interview. And usually, I'll end up with a few, like three to five candidates, I think are great candidates, but I still have no idea how it's gonna be working with them until we are actually working together. So, for every position that I hire for I create a test project, effectively. I will hire these candidates, three to five of them or so, all for this one particular project. And it has a fixed scope. It'll take a few hours to do. I pay the candidates for completing the project. After the project is completed, I'll review and see how they did and whichever one was the best and looks like the best fit, I will make the full-time offer to that person. And this way I have a better sense of what it's like working with this person. And I'm not going to just hire this person and then find out months later that this wasn't a good fit. And, you know, we both spent that time working together when it wasn't working out.

Maren Kate
I agree that's super important. What is your stack for managing your fully remote team?

Andy Cabasso
I guess a few of the main things are, for team communication/internal communication, we use Slack, no surprise there. For team management, project management, and everything like that I will use Clickup. In particular, one thing I like about Clickup is its dashboards. So what you can do is, if you want to better get a sense of your team members project and progress and everything like that, you can create dashboards and have them related to your team members workload, their work, you can plug in different things, there are a lot of integrations available. And so, for example, I have writers on my team and if some of their metrics are related to output in terms of content, I can see here's how many articles they have created this week, or this month, or anything like that. And I have an easy-to-view dashboard that I could compare. I can see their progress and I can compare it with others, see their historicals and everything like that. And so I have an easy dashboard that gives me the most important numbers that I need for them and for their role, which has been super, super helpful for management. Before we had this we were using other project management software but I didn't have a really great way to, as a manager, get a high-level view of how individual team members were doing. It was very much like going into their work product and manually reviewing and it took a lot of time. But once we can nail down our KPIs for our roles we were able to get it so those KPIs were really easily viewable from a manager's perspective. And so I get real-time view on those numbers.

Maren Kate
Yeah, that makes a huge difference. So I have some other kind of little more ‘out there’ questions. Not ‘out there’ but they're just, I always love asking these and they're so interesting when it comes to different people's perspectives. First of all, I understand that you are a Guinness World Record holder, what was the record that you hold or held?

Andy Cabasso
So in 2011 or 2012, the website Reddit was having an online Secret Santa and they had participants from all around the world. Basically, you'd get matched up with someone and you sent them a gift for the holidays and then someone else elsewhere in the world would mail you a gift for the holidays. I participated in that. I was one of like 11,000 or 12,000 people and, after it was all said and done, they found out that this was the largest Secret Santa ever and they got a Guinness World Record. And so I have a Guinness World Record plaque in my office now, which really fulfilled a lifelong dream I had since I was a kid of being a Guinness world record holder. You know, it wasn't like for feats of strength or some particular skill, I signed up on a form and I mailed someone a gift so it's probably one of the laziest.

Maren Kate
What was the gift?

Andy Cabasso
I think the person I got was really into (like it was a while ago) but they were into a certain video game or something, and so I went to Etsy and got them some handcrafted item that was relevant to whatever that product was or something like that. I really, I'm not sure on that. Oh gosh…

Maren Kate
Do you remember what the one you got was?

Andy Cabasso
Yes, the person who got me was in Alaska and they sent me canned salmon, smoked salmon, just a few different varieties of salmon, and a knife-like thing to cut salmon.

Maren Kate
Huh, wow. I would like to know what like the strangest ones people sent. I wonder if they documented that anywhere.

Andy Cabasso
I’m sure there must be somewhere. But the real sad thing was the very next year Reddit ran this again and it blew the previous record out of the water. I didn't take part in it that next year because I figured well they're going to just beat the record every year, but they beat the record, and then they never tried it again and so now, I say I'm a former Guinness World Record holder.

Maren Kate
Former. Oh my gosh. But you still keep the plaque.

Andy Cabasso
I don't know, should I throw it out?

Maren Kate
I think it's good. It's aspirational. Maybe you can always restart it yourself. That's really funny. That's a good one. If you weren't working in this industry doing what you're doing right now if you had to start fresh doing something completely different, what do you think it would be?

Andy Cabasso
I would love to be a water-ski instructor. That’s probably the dream for someday after I’m done doing this. But I've got a young child and we live in New York and we have family around us and so moving to Florida or a warmer climate is not really in the cards right now. But one can dream.

Maren Kate
I think you can water ski on the Hudson or maybe you can't. Maybe you skido on the Hudson. It's pretty dirty water, though.

Andy Cabasso
There is water around us, but it's, you know…

Maren Kate
Not water you want to get in.

Andy Cabasso
No one wants to. Well, no one wants to be in it from, like, you know, unless it's July and August. So two months out of the year.

Maren Kate
That's true. Very short season. So what would you say is your favorite podcast from the last year, if you're a podcast listener, and then what has been your favorite book from the last year?

Andy Cabasso
Favorite podcast for fun has probably been the Office Ladies Podcast. I was a big Office fan and just like hearing the inside details of different episodes that I might not otherwise know about so that's been fun. Business-related podcast, I like Startups For the Rest of Us. That one's also really interesting. All about startups and has a lot of great insights for anyone looking to have a startup or trying to scale or exit or anything like that.

Maren Kate
I like that one too. And then what about book-wise?

Andy Cabasso
Most of the books I've been reading last year have been related to raising a two-year-old so I'm going to go with Toddler 411.

Maren Kate
That's amazing. I love it. I love that name. Awesome. Andy, it was so great chatting with you. Thank you for sharing your knowledge and the time. How can people find more about you and Postaga online?

Andy Cabasso
Thank you so much. I'm pretty easy to find online. On Twitter I'm @AndyCabasso, LinkedIn is Andrew Cabasso, website is Postaga.com, and if you want to try our cold outreach software if you use the coupon code podcast50 that'll get you three months at 50% off. And we also have a Facebook group all about cold outreach and digital marketing called Grow Together SEO and that's on Facebook.

Maren Kate
Awesome. We’ll create links in the show notes for all this too. All right Andy, thank you so much.

Andy Cabasso
Thank you. This was so much fun.