Ep. 2: How to Win in Outbound Sales with Florin Tatulea

Anis Bennaceur (00:01.353)
Florin, how's it going today?

Florin Tatulea (00:03.246)
Hey, Anis, it's going well. How are you?

Anis Bennaceur (00:05.033)
I'm great, thank you. Super excited to have you on this show.

Florin Tatulea (00:08.91)
Yeah, I'm pumped to be here.

Anis Bennaceur (00:11.081)
So for everyone listening to us and watching this, Florin is one of the best at what he does at just very simply go to market, understanding how to acquire prospects, how to convert them, how to close them. He's one of the most influential voices in the sales and marketing space. So very excited to have you here.

Florin Tatulea (00:36.334)
Yeah, thank you. That's very kind of you to say.

Anis Bennaceur (00:40.137)
So let's get into it. I would love to know about the three pivotal moments in your life that got you to where you are today.

Florin Tatulea (00:50.734)
Yeah, it's nice to reflect back, but I do have like actually three pivotal moments exactly. So the first one started like pretty young for sure to like, or my parents were immigrants, I guess technically I am too, because I came when I was like one and a half to Canada, but we're Romanian by background. And, you know, it's a classic story where the family kind of decided to like pick up everything from Eastern Europe to give their kids a better life. So.

I think that was the first pivotal moment for me where, you know, the parents came here with pretty much nothing like built a life. So I think my whole like trajectory in life has been set up by that premise of like, you have to do something great because like your parents kind of sacrificed everything to get you to where you are. And then later on, so the second pivotal thing, I don't know if you know this, but I played tennis.

Well, not professionally, but I was like a nationally ranked tennis player in Canada. So I was training with some of the best players in the world and had a top national ranking. And I think that whole like part of my life was a super important part for me in terms of like discipline and understanding like what hard work actually is. And I think there's a lot of skillsets.

that get passed on from athletes in general to sales. And it's actually why a lot of athletes become very good sales people. So that's definitely the second big moment in my life. And then from a career perspective, I think it was the first startup that I joined when I got into tech sales. It was a company called Lupio. So I joined as the first salesperson there. And we had an epic seven year run. We had like a...

pretty substantial private equity exit, which was fantastic for the Canadian ecosystem and Toronto and overall. So just like seeing that company go from literally nothing to nine figures was like an epic journey that I think changed a lot of people's lives. And the craziest part about that story too is that we only raised one round of funding. So I think a lot of the employees and founders actually got most of that pie, which is awesome.

Anis Bennaceur (03:10.185)
That's pretty incredible. I had no idea about your tennis background. That's, well, now it checks out. I remember when I met you, I was like, this guy's actually taller than he looks on camera. And definitely bigger. But yeah, so that really checks out, right? So kind of like that quest for excellence throughout your tennis games and tennis kind of semi -pro.

journey. What really made you consider a startup as early as LuPio? Why did you join that one? Did you feel that it was going to be something big one day? Why did you join that?

Florin Tatulea (03:52.558)
I think a lot of people over attribute their decisions to like, I'm the genius or whatever. I definitely don't think that's the case for me. So I went to business school, I feel like everyone in business schools, you have like three career paths. You go into like accounting, investment banking, or management consulting. That's what was pushed to us, especially like in the, what, like 2010, 2011 era.

So I found out pretty quickly like in an internship that I did not like doing finance or consulting. So I was always pretty entrepreneurial from like selling paying jobs door to door in like grade nine, grade 10, or even the newspaper, I think even earlier in my life when I was like 13. I was like very extroverted and just entrepreneurial in general. So for me it was like, okay.

I want to be an entrepreneur one day. What's like the best way for me right now out of university to build that skill set. And everything kept leading me to like, okay, what are you good at and what's going to help you in the future? And sales was kind of like that thing where I think like things intersected for me. So I actually just found Lupio randomly on a job board. Uh, they sell RFP, request for proposal response software. So it's not like sexy or anything. It wasn't like, Oh, this company is going to be a billion dollar company or whatever, but.

I interviewed there and I just got this feeling from the three founders that they were onto something and they both had really good experiences in the past at other tech companies as well, although they were first time founders. So it was a bit of luck and a bit of, I think, trying to figure out where can my skillset really be used.

Anis Bennaceur (05:32.425)
That's super interesting, right? I like a lot of the fact that obviously you have this self -starting attitude when you were younger and you kind of index a lot on being a great salesperson to one day become a founder, right? What do you feel like today are the things that are missing for you in terms of skillsets and competencies that could make you one day a great founder?

Florin Tatulea (05:41.806)
Yeah.

Florin Tatulea (06:01.71)
Uh, this might be a nontraditional answer, but...

I think it's like a mental thing a little bit. I think there's the mental aspect of like making the jump to entrepreneurship and like a little bit of self -doubt I think comes into it and like, am I good enough? Like, is that something I really want to dedicate like 10, 15 years of like hardcore time to? And I think I've been lucky that I've been in the tech ecosystem long enough and like, especially working directly with founders where...

Like everybody just sees the unicorns and stuff, but like I can tell you right now that if anything, working at three startups in the last decade, it's probably turned me off from entrepreneurship more than anything, which you probably don't hear from a lot of people, right? And I think not having that safety net of like income, I think is a bit of a barrier. Now I'm definitely like, as I get older and you realize that nobody has things figured out.

I'm definitely at a point where I think I'm more comfortable potentially making that jump and I think it'll happen soon.

Anis Bennaceur (07:12.617)
I hope so, figures crossed. It is definitely a hell of a ride. That being said also, whenever you're missing out, you're missing some of the skill sets or competencies or even kind of the confidence too, right? As you're saying it very well, you always have kind of a co -founder or two co -founders that you can rely on and share kind of some of the doubts and.

Florin Tatulea (07:35.31)
Yeah, exactly. But I think people, and I'm curious to get your thoughts on this and how you made the jump, but I think people downplay how much of an emotional impact it has for you not to have a guaranteed paycheck. Like even if you have savings or whatever, because you're like, well, now you're eating into your savings, like for your retirement or whatever, what if it doesn't work out? Like that, that mental jump that you have to make, in my opinion, is actually pretty significant and why I respect entrepreneurs so much. Like it's not an easy thing to do.

Anis Bennaceur (08:02.729)
Yeah, it's really hard. At the first startup, I found that there were months where I was not paying myself. And obviously, it makes it extremely stressful. But also, that makes you, at the end of the day, double down on growth and make sure that you grow your revenue for the next month as fast as possible and also increase your profit line if you're kind of a bootstrap profitable business. And then, you know, on the other side of things, if you're running a

Florin Tatulea (08:27.086)
Yeah.

Anis Bennaceur (08:32.297)
venture -backed business, you have to kind of every single month try to get to a higher objective, you know, over 20 % growth month over month as they're saying. And so at that point, how do you, if you're able to do that, then you're gonna be able to get to the next funding ground or the next funding ground until at some point you end up being profitable, right? Or get acquired or IPO. But.

Florin Tatulea (08:56.59)
Yeah.

Anis Bennaceur (09:01.609)
And that in a way gives you kind of like visibility into how much runway you have and how much comfort you have getting your next paycheck. But getting back, switching back gears into you right now. So you've been doing outbound for a while now, right? I know a lot of people who try it and burn out pretty quickly. So tell me, what's your secret for staying so passionate about it?

Florin Tatulea (09:30.766)
Yeah, it's a good question. I don't know if there's like a secret necessarily. I think it's important that you love the work that you do generally speaking. I get a lot of energy from, again, being more naturally extroverted, talking with people. I like to solve problems and just talking to people to figure out like what kind of businesses they're running in the world. I think that that to me is one of the most interesting thing parts about sales. And maybe that's the entrepreneurial side in me, but it's like,

I've what? I've probably, I've closed about 150 or so deals in my career so far. And it's like, think about all the other companies, probably a thousand that I've actually like talked to, and I'm trying to figure out like how they're thinking about business, what ideas they have. So to me, that aspect of it is super interesting. And that's what kind of keeps me going. But I think the other thing too is like knowing that it's a bit more of a marathon than a sprint and detaching from the outcome a little bit like.

If you get too tied to putting your self -worth to your results, I think that's like a sure sign that you're likely gonna burn out very quickly. So I like to look at things, being consistent, but doing things in sprints a little bit. Like you don't have to go 120 % every single day. Like I don't think a lot of people are actually built like that.

Anis Bennaceur (10:51.433)
Yeah, that made sense, just back to back sprints, but don't over -sprint.

Florin Tatulea (10:58.574)
Yeah, I think like consistency and showing up and like doing the work every day, like using outbound as an example. Uh, sure. If one day if you're feeling and you want to make 200, 300 calls, go ahead. But maybe there's a day where like you're not, but the worst thing you can do is not pick up the phone and make like 10 20. Like you have to put in that the deposit, right? And this is actually where like training for tennis eight to 10 hours a day for like years of my life, it kind of builds that resilience, that muscle in you.

Anis Bennaceur (11:28.905)
Yeah, I could totally see that, right? You end up having kind of that organization and the mindset to keep doing the same things. And I wouldn't call it a routine, but just kind of that structure that makes you keep doing the same things and being as effective in your improvements. So when you do, let's say when you cold call, you just mentioned that, right? How?

Do you approach cold calling in general? What would you say is your best secret for conversion and for getting people to actually, A, want to talk to you and then B, end up at least taking a meeting?

Florin Tatulea (12:12.398)
I think for, well, the first thing is realizing that prospects don't want to talk to you. Like you're bothering them. Right. And I think being okay with that is important. One piece of advice that's actually pretty simple, uh, or actually two for cold calling one, it's generally going to be the most emotionally straining part of your day as like an SDR or sales rep. I like to do that first thing in the morning. So it's like, you get the hard things out of the way. The other thing I do is I actually like to.

pump myself up, so whether it's like listening to some, a couple of songs as if you're like, you're about to work out or whatever, it just like gets you in that rhythm. And then just actually getting to it and getting a few rejections, I think that's perfectly fine. But that's kind of like from the mental perspective, how I would set up for, for calls. And then I think in terms of actual getting conversions,

It comes down to a few different techniques. And this goes back to like Chris Voss has never split the difference. But I think a lot of people try to talk at prospects too much and like, you're not actually listening. And I think a lot of people, especially early in their career, you feel like obligated, like you have to like say as many words as possible and pitch them and whatever. But you actually have to open up the conversation and provide like just one insight, you know, whether it's like, Anice, I noticed from your job postings that,

you're hiring like a growth manager. So it looks like you're trying to do X, Y, and Z. So boom, now you've made a connection. This person knows that you've done your research. And then you open up the conversation and be like, you know, curious, since you have this strategy, how are you thinking about doing whatever you can, your solution can help with, right? So open ended questions and then labeling and mirroring so that you're getting that prospect a bit more comfortable with you.

and getting as much information as possible to make that conversion.

Anis Bennaceur (14:09.609)
So when VORs are using parallel dialers that call five people at the same time, and then one picks up and they end up being connected and routed to them, it's almost impossible at that point to get all the right data about your prospects. What do you think in general of parallel dialers? Is that something that VORs should be using if they want to maximize the final outcome, which is getting a meeting? What do you think about all of that?

Florin Tatulea (14:15.502)
Yeah.

Florin Tatulea (14:40.078)
I have no problem with parallel dialers. I've actually bought a few parallel dials for my team in the past. And I agree with you, it is difficult. The way that you can kind of counteract that is you have to be a bit thoughtful about how you're building your lists. So what I actually recommend for power dialers is upload a list where today you're only going to call VPs of sales that are hiring, let's say a growth manager.

So it's like you're running the same script in your head for those 200 people. I think that's the biggest thing, you have to segment.

Anis Bennaceur (15:12.809)
That's super smart. Do a lot of people do that?

Florin Tatulea (15:17.038)
Not enough, that's for sure.

Anis Bennaceur (15:18.281)
I mean, it seems so simple and basic, but yet you've just taught me something there, right? People do that for their email cadences. You should be also doing that for your cold calling lists. And so kind of jumping into automating just processes for lead generation, I'd love to know kind of a little more about your strategy in general when it comes to

comes to adding automation to what you're doing? What have you been prioritizing within automation? And what were some of the most recent things that you've learned around automating outbound?

Florin Tatulea (16:02.67)
Yeah. So I'm going to start with what I think a lot of people get really excited about automation and miss the fact that like there's some fundamental things that people need to like really get right before you scale and automate things. For example, a lot of people just take it for granted these days that like, oh, AI can just generate copy for you. It's like, okay, it can generate copy for you, but is it good copy? Generally the answer is no.

I saw a quote the other day. It was like, uh, everybody wants to create AI generated content, but nobody wants to consume AI generated content. Right. So for me, it's like, you have to, as a sales team, understand the fundamentals. First of all, what are, what is working for you? And only then do you automate that stuff. Right.

Anis Bennaceur (16:53.833)
Yeah. Yeah. I remember you said also kind of if you, if your messaging sucks, you're just using kind of these automation automations, you're just going to suck at scale.

Florin Tatulea (17:03.246)
Yeah. I need to trademark that. It's if, if your fundamentals suck, your automate or AI is just going to help you suck at scale. And that's exactly right. Right. So for me right now, I don't, I haven't seen AI get to the point yet where it's good enough to like without human supervision, send 400 emails. Like you still want people to look through that.

Where AI is getting better now because AI relies on data is if I can feed you a model. So you use Florin's email template or Kyle Coleman's email template and the AI can create it based off of that. That's where you want to automate, right? The other things that I think about like what takes a rep a ton of time that we can automate. So the first thing that comes to my mind is research. The problem today is that we actually have way too much information.

for a sales rep to consume about an account or a person. So what AI is very good at is being able to consolidate all that and give you like, okay, here are the three things you should focus on. So when I think about automation, like research is the first part where I'm like, that's what I'm using automation for right now. And then obviously like waterfall enrichment and all that stuff you can do in like clay and these different systems.

Anis Bennaceur (18:22.825)
Yeah, I absolutely agree with you. Whenever you're trying to send the perfect email to someone, you obviously spend a lot of time looking about what they posted on LinkedIn, what their background experience is going to say about them, and you're going to try to connect the dots and then say something that is interesting but also relevant to what you're offering and what you're trying to solve. And most people don't realize that. They just mention the university you went to or the city where you live, right?

Florin Tatulea (18:52.334)
Yeah. And I'll give you a specific insight there. What people, so I think I've probably trained over like five, 600 SDRs myself. I also have in my newsletter, I used to do a weekly email critique where people would submit their email and I would rewrite it for them. And you start to notice trends. The thing that people and AI still is not very good at is...

Anis Bennaceur (18:52.905)
And it's.

Florin Tatulea (19:17.134)
Okay, it's easy to find the insight. Like you're hiring a growth manager, you raised around the funding. I read this in your 10 K report. What people cannot do very well is how do you tie the insight or the trigger to why your solution is the right one for them now? Tying the context into your solution is like very difficult to do for most people. And that's what more people should focus on. And it goes back to the fundamentals of understanding like how to copyright and

The good thing about learning how to copyright is if you can write, you can think. It's like a very logical type of process, right? So that's one thing people should focus on.

Anis Bennaceur (19:55.785)
100%. When hiring her to new SBDRs, the first thing I told them was, hey, write all of your emails manually. I don't want to see one single automated emails, even though we're an AI for startup. I want you guys to do things that don't scale. Then save all the emails that get responses. And from there, we'll build a decision tree that takes the logic for each different email. All right, if this profile said this thing, then send out this tie to this value prop.

If this other profile or this company has, let's say, value -based pricing model, then you should actually tie it to this value prop in this use case. And if you're able to use AI to build those specific decision trees, then at that point, that can be very powerful, right? Because as you said it very well, the AI will not know your business as well as you do, and they will not know the use cases and the things that work as well as you do.

Florin Tatulea (20:50.126)
Yeah. And at the end of the day, like even with clay tables, like you can have AI generated messaging, but you need to, you need to understand the logic and how to prompt it in order to create a good message. So you still need someone that's thinking through that logic, right? Like AI is not going to do the thinking for you. It's pretty, it's just like a, it's a coding. It's like an if, and then else statement or whatever, right? Like that's, that's what it is.

Anis Bennaceur (21:08.649)
a set.

Anis Bennaceur (21:12.155)
Yeah. 100 % 100 % I love that. So speaking getting a little more into kind of like unique insights and and whatnot. I would love to know for you, Florian, what is the kind of unique insight, the secret on the world and more specifically the world of go to market that you think that you've cracked that most people do not get right?

Florin Tatulea (21:41.262)
I'd probably say like the, I don't know, focusing maybe on outbound here because like that's a lot of what I do. When you think about a general market of potential customers, you've probably seen like the triangle before, but roughly speaking, there's 3 % of people that are in market to buy your solution, about 7 % or so, which makes up a total 10 % that are open to it.

Anis Bennaceur (21:48.553)
Mm -hmm.

Florin Tatulea (22:09.71)
The rest of them are not in market. They don't know your solution. They're not interested in your solution or whatever. The thing that people are not doing right now or what they're doing too much of is they're focusing on the 90 % or maybe if we're being nice, 70 % of people that are never going to buy your solution right now. The job of outbound and what technology is helping us do right now is

because we have access to so many signals that we can now aggregate in one place, we can actually find that 10 % with a fair amount of accuracy and that's only gonna get better over time. Now, the big change that's happened, so in 2016, 17, 18 when I was like a SDR manager, what we were doing with platforms like Outreach and Sales locked in these SEPs, they enabled us.

to be able to send mass amounts of emails, hoping that we would hit the 10%. That's not working anymore because we've now spanned everyone's inboxes so much. And now we actually know with signals who the 10 % are. So that's what people need to focus on. Like how do you find the right signals for your business and looking through your historical data to know what signals mean someone's going to buy and hitting that person at the right time.

And 95 % of teams do not do this to this day.

Anis Bennaceur (23:36.937)
I love that. Absolutely. People will try to spray and pray their entire time instead of really focusing on those signals, right? This compelling event happened. And so this is why I'm going to reach out to this person now and I might have higher response rates. As a matter of fact, we tested that on a specific use case and we found out, believe it or not, 17 % meetings booked out of that test cadence.

Florin Tatulea (23:49.998)
Yeah.

Anis Bennaceur (24:06.313)
And so that's kind of like what got us back to the drawing board and said, hey, let's stop doing any of these cadences. We'll just try to figure out all the successful residues, all the successful use cases, the right copies. And then actually, once we're ready, we just roll those out. But yeah, everyone's talking about intent today. And I feel like a lot of people haven't really mastered it completely.

Florin Tatulea (24:34.51)
And then, so to take it a step further with intent, first of all, signal -led outbound is a hot topic right now. It's not anything new. We've had signals, right? Like a champion that's changed jobs. We know that the chances of them buying your software are going to increase. Or now you have access to like these systems that can find website visitors. We had that in the past, maybe not at the individual level. The thing that you can do now though is you don't rely on one or two signals. You can actually cross -reference across like,

your community across your product usage, across your sales team. And if people are opening your emails across marketing channels and you can now use AI or software to give you an idea of like, Hey, this is the right person at the right time in the right account. So there's more than just like a signal itself. It doesn't mean anything. It's you have to use many different signals.

Anis Bennaceur (25:27.049)
and you cross them together and then you kind of have a good idea who is kind of like the warmest lead, right?

Florin Tatulea (25:32.27)
Exactly, yeah.

Anis Bennaceur (25:34.601)
That's fascinating.

Anis Bennaceur (25:40.713)
I have another question now, kind of focusing more on just, you said earlier that you hired a lot of SDRs and trained a lot of SDRs. Today, if you had to make your dream team of sales reps, account executives, and SDRs, what do you think makes the best combination of reps in terms of profiles, in terms of types of characteristics? Let's say, all right, you have five people to pick.

within a smaller team, how you go about it.

Florin Tatulea (26:15.598)
Yeah, and I think the skill sets between like an SDR and AER are quite different. So I think they probably have different attributes. The first thing that comes to mind because I feel, especially for me as someone that likes to be at the forefront of technology, like things are changing pretty fast. There's tools that I did not know about in January that are coming out like in March. And it's like, it's difficult to keep up with them and things are changing very quickly. I think you need...

especially in the early days, a bit of a self starter mentality of someone like, hey, you probably don't have the skills you're going to need in three, six months, nine months, but I need to know that you can figure it out. Do you understand how to like learn? I think that's a very big thing for me. Another one is being very receptive, receptive to feedback. And I think this is actually something I learned from a few different sales leaders in my life that.

are much better at interviewing than me, but when you're running someone through like a scenario, like a mock cold call, I don't actually even care that much if you bombed the call, but I care about if I give you feedback and we run it back on the call, can we, are you listening in real time and applying it very quickly? So are you one, like do you have a starter mindset too? Are you receptive to feedback?

And three, I think another big one for me is resilience. Like have you proven in the past that you were able to get through difficult things and succeed?

Anis Bennaceur (27:50.313)
So speed of iteration and just, yeah, that amount of resilience is huge, right? Because every day you're going to go through ups and downs, especially in a startup. All the odds are against you. So how do you make sure that you're extremely dialed in and make sure that you're going to just be consistent in your efforts and make sure that you learn as much as you can from your past mistakes and the feedback that you receive, right?

Florin Tatulea (28:19.758)
Yeah, exactly.

Anis Bennaceur (28:21.481)
Great. Great. To finish the conversation here, so where do you want to be five years from now?

Florin Tatulea (28:36.11)
Yeah, it's definitely something I think about a lot that I'm not fully clear on, but I think there's a few different paths that I've thought about. There is the path for me of like going down the CRO path where, you know, owning like a full kind of revenue function, whether that's SDRs, AEs, customer success, marketing, or some combination of that. But probably really what my dream is either to like start a company and...

I actually used to be that person that wanted like this huge company, like, you know, you get more status, the more employees or teams you have under you and stuff. But I think my mindset shifted a little bit with AI where before I would be like, I want a hundred person sales team and like all these divisions and like multiple layers of management. Now I'm like, how can I get to or build a company to a hundred million ARR with like five people?

Anis Bennaceur (29:26.409)
Yeah, and that's going to be possible, right? Everyone's talking about the one person company where you have hundreds of AI agents that do all these things for you and you can be so much more efficient than anyone could be five years ago.

Florin Tatulea (29:30.158)
Yeah.

Florin Tatulea (29:40.654)
Yeah. So that's like my second avenue. And I think further down the road for me, like, because I have this entrepreneurial mindset, I love working with different companies and I do have a bit of like a finance background from a business school is maybe get into like venture capital and, you know, help build the ecosystem after I help myself.

Anis Bennaceur (30:01.897)
I feel like you'd be an amazing operating partner at a great VC and any good in market team would be incredibly lucky to benefit from you. All right, who are three sales or growth voices that you think deserve a shout out and should get a spot in this podcast?

Florin Tatulea (30:29.646)
Yeah, I think you definitely know some of them. One that comes to mind that I've recently had some conversations with Kyle Coleman. I think he is, we're aligned on a lot of things and he had a similar path where he started as an SDR and now is like a CMO that scaled, you know, clearly to a hundred million plus and likely going to do it again at his next company. Who else would be really good? This is someone that's kind of a little bit outside of sales, but Morgan J. Ingram.

I'm sure you're familiar with him. He was like the OG, like LinkedIn kind of guy, but the way that he's thinking about using influencers and brand to build pipeline and what he's doing with like his amp series is something that's been really inspiring to me and someone that, you know, I've been having some conversations with as well. And then maybe someone that's a bit lesser known, but Saad Khan, who's a good friend from Toronto as well.

I think he's a very tactical person, especially like in the PLG space, like really understands how to drive pipeline. And he's brilliant mind. He actually just did a great webinar for the GTM fund where they walk through like how to actually build pipeline with the PLG. And I think in the last quarter, they like double or triple their pipeline after he like joined. So really, really smart guy.

Anis Bennaceur (31:52.585)
Wow. Yeah, I actually interviewed him. His episode is going to come pretty soon after yours. But yeah, love sad also definitely Morgan and Graham is great too. Well, look, Florian, thank you so much for being here. This was awesome. And I'll see you soon. Bye.

Florin Tatulea (31:55.854)
Yeah.

Florin Tatulea (32:14.478)
Thanks, Anis. Pleasure.

‍