Bearchats by Bearworks #2: From Philosophy to Sales: Cameron Souza’s Playbook for Building Winning BDR Teams

Bearchats by Bearworks #2: From Philosophy to Sales: Cameron Souza’s Playbook for Building Winning BDR Teams

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As we said before - sales isn’t just about closing deals.vIt’s about building teams, systems, and culture that scale. The best sales leaders know how to set the tone, coach talent, and create environments where reps succeed over the long haul.

In this episode of Bearchats by Bearworks, Albert Wang and Joshua Estes sit down with Cameron Souza, an industry leader who scaled sales orgs at Datadog and SPIF. They unpack:

• How to build a repeatable talent pipeline
• The crucial role of mentorship and goal-setting in career growth
• Why personalization in outreach creates a true competitive edge

From Philosophy Major to Sales Leader

Cameron Souza didn’t start out in sales. A philosophy major with plans for law school, he unexpectedly launched his career at Acquia as an intern. The experience gave him a new appreciation for tech sales and set him on a path to leadership.

Cameron rose from SDR to running Acquia’s SDR team, then joined Datadog as the first director of business development. There, he scaled the sales org from three small teams to a mature, enterprise-focused structure. Most recently, at SPIF (acquired by Salesforce), Cameron focused on commission automation, streamlining painful manual processes for sales teams.

Lessons in Leadership and Mentorship

For Cameron, great leadership starts with mentorship. “I had managers who gave me clear feedback and coaching early in my career. That defined my success.”

He stresses that leaders must be passionate about business development, not just holding a management title. The job of a BDR leader is unique: constant hiring, training, and creating a system where top talent can thrive—even knowing they’ll promote out quickly.

On building teams, Cameron is clear:

coachability, grit, adaptability, and curiosity are the DNA of great SDRs. Skills can be taught, but drive and mindset make the difference.

Personalization as a Sales Superpower

Cameron believes personalization is the ultimate differentiator. “The fastest way to lose deals is lazy outreach. The fastest way to win is showing you actually understand your prospect’s world.”

Examples range from sending tailored notes to highly creative outreach—like SDRs designing mock Pokémon cards themed around the prospect's business challenges.

Cameron also advocates for hand-written letters to executives, an old-school approach that cuts through the noise. “If you’re willing to go the extra mile to just get the meeting, that signals how you’ll show up for them as a partner.”

Key Takeaways from Episode #2:

• Leadership is about hiring people passionate about developing talent.
• The best BDR teams have clear career pathways and mentorship baked in.
• Personalization at scale is a competitive advantage.
• Sales success is about operating rhythm, structured prospecting, and constant iteration.

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[00:00:00.09] - Sarah
Good? Cool. Hi, and welcome to the Sales Leaders Pathway, presented by Bearworks. I'm your moderator, Sarah. Let's meet your hosts.

[00:00:07.18] - Albert Wang
Hi, I'm Albert Wang. I'm the co-founder and CEO of Bearworks.

[00:00:10.18] - Josh Westes
I'm Josh Westies, VP of Parameter Ventures and co-founder and Senior Partner at STES Media Marketing Agency.

[00:00:16.03] - Cameron Souza
I'm Cam Sousa. I'm the guest today. I've been in the tech sales space for about 12 years, specializing in business development. Super excited to be on the podcast.

[00:00:25.15] - Sarah
Thanks for being here, Cam. We're so excited to have you. I guess just kick us off a a little bit. Tell us a little bit more about your sales career and how you got to be where you are today.

[00:00:35.01] - Cameron Souza
Yeah. I feel like most sales folks, I fell into sales to begin with. I had a little bit of a strange background before I got into this space. I was a philosophy major in school who thought they were going to go to law school, but like many people graduating, I found that I needed money to pay for things. So I was fortunate enough to start my career at a company called Acquia, actually as an intern. And at that time, I probably had a pretty stereotypical understanding of what sales was. But through that internship, I got a much better sense of what that career path actually looks like, and I just fell in love with it. As soon as I graduated, I started full-time as an SDR. I did that for a while before eventually transitioning into an AE. Then I was super fortunate to run the SDR team there for about two and a half years or so. And then I joined Datadog, which in a lot of ways is how we all ended up here today. I met Albert there very early on, but I was super excited to join Datadog. I was brought on as the first director, really with two primary objectives, which was like scale the org out and create really career maps that were going to be clear and almost like the bench system for the broader sales org.

[00:01:37.09] - Cameron Souza
So when I joined, I think there was three teams in North America. It was really heavily commercial-specific at that point in time. Over the five and a half years or so that I was there, a little less. It ran the gamut in terms of what I was able to do and get exposure to. Helped scale the team to eight teams, and then I split off and focused really heavily on the enterprise segment, which was a lot of fun. Got to learn from a ton of great leaders there. That team ultimately scaled out to eight teams as well. And then a lot of passion projects worked really closely with the marketing team and the product team. Albert and I were ultimately able to stay in touch throughout that time period as well. And then about nine months ago or so, I joined a company called SPIF, which I was super excited about. One, because first and foremost, I was literally my own case study for the product in terms of spending time fixing team commission statements and things like that. But it was also just a really fun team, a lot of great people, amazing leadership.

[00:02:28.01] - Cameron Souza
It gave me the opportunity to actually report into marketing for the first time, which was a lot of fun as well. And that company was actually just acquired by Salesforce back in February. So that's the SparkNotes version of my career to date so far. I really joined Bearworks as an advisor last month as well.

[00:02:44.14] - Albert Wang
So Cam, congrats on a yet another exit with SPIF, sail to Salesforce. I think for the audience, they definitely interested, what does SPIF do? Super famous, but not everybody's aware.

[00:02:54.23] - Cameron Souza
Yeah. So SPIF is a commission automation platform. So effectively, the way of old A lot of teams would calculate commissions in Excel files, and it would take a lot of time, very laborious and prone to user error. So this really just streamlined that entire process, making it easier, faster, and allowing your teams to do more with their commission statements, whether that be by changing your quotas or goals on the fly, things that would otherwise be pretty challenging to pull off. Spif was able to streamline a lot of that. And it was a very natural marriage between SPIF and Salesforce, just because so much of our customer base were Salesforce users, but it really fit very nicely into their sales cloud as well. So, yeah, it was very excited for them and their customer base with the big news.

[00:03:37.09] - Josh Westes
That's super exciting. Look, you've really excelled through the ranks in sales cam, starting from an SDR, to quote You started from the bottom, now you're here. What was that? How did you climb out of that SDR role and move beyond just smiling, dialing, and setting up meetings?

[00:03:56.08] - Cameron Souza
I always love smiling, dialing. But candidly, I think it was probably just a ton and then learning from it. I'll never forget the first cold call that I ever made was probably the worst phone call in the history of telephones. Just got absolutely obliterated. I didn't do my research. I made a bunch of mistakes. But making all those mistakes, I learned a lot, and I was pretty self-aware of what my gaps were. I was just really, really lucky, frankly, and fortunate to have some great leaders and mentors in my career that cared about my development, but also were really good about giving me coaching and feedback, which ultimately led to me being able to pretty clearly define what it was that I wanted to do in my career. I've always been incredibly passionate about coaching people and helping almost pay it forward because I was so clueless when I started as an SDR. But through that, though, it was really just a combination of learning how to define what your goals were and then attacking them aggressively. And when you missed, look in the mirror and ask yourself why. What was the reason that maybe you didn't land on the mark that you wanted to?

[00:04:55.17] - Cameron Souza
And always trying to get better every single day. But ultimately, though, I give all my credit to just the people that I've been surrounded by. It's hiring great people, creating a great network, and a lot of that helps you be better in turn. You never want to be the smartest person in the room. I think I've been incredibly fortunate to be surrounded by so many smart people and just really hard workers as well.

[00:05:17.15] - Albert Wang
That's a super interesting point about people, right? I think there's this phrase where you want to be naturally gravitated towards people like you, but also having a diversity of thought, diversity of background in a room is also well known to be beneficial. And so I'm curious, when you chose to join a team in companies that you did, did you know going in, wow, there's something different, something unique about the people? Did you have a feeling or attribute? And how did you go about that process of thinking, oh, this is some place I want to learn from or some place that will push me? What was going through your head?

[00:05:50.06] - Cameron Souza
I would say that just transparently, my first job, I probably didn't appreciate that. But hindsight being, like I said, I almost locked into that. How I got into sales was ultimately, I was actually somebody's date to a birthday party. The individual whose daughter it was, was actually one of the leaders of sales at Aqia, a man by the name of Mike Stankis. He and I started talking and asked me a lot about what my goals were and things like that. I said, I wanted to go to law school. I'll never forget. He says, You don't want to do that. You want to get into sales. He told me to look up this company and this technology, Drupal. My senior year, I reached back out to him and I said, Hey, I would love to. That's how I ended up in that internship, which then was a slippery slope. But that was a person that obviously was somebody I could learn a ton from. I think that that was ultimately the same. When I think about evaluating new opportunities, I get this question a lot. It's like, what's the most important thing to you? I think who your boss is and your leadership team, basically who are the people that are going to be teaching you things, is one of the most important things.

[00:06:48.21] - Cameron Souza
I'll never forget, when I started my interview process at DATA, I met with Shant Vascanian, was one of the first people that I spoke to there. I had a really close friend that had already been working there, and he spoke super highly about him. He had a really impressive background and just clearly somebody that knew what they were doing. But obviously, Datadog was at this inflection point of doing something really special at that stage in time. Then that was a huge part of why I joined SPIF as well. My boss there, Anna Fisher, who's the CMO. She was somebody that had an incredible background, especially in the things that I'm really passionate about in marketing demand gen, in business development, having run those teams at ZoomInfo for, I want to say, about eight years or so. In terms of that, your network can help you learn of these things by back channeling. But through your conversations and really self-definition of what's important to you, you can learn to tease some of these things out as well. People always say, When you're in an interview, you should be interviewing them because they're interviewing you. And I think that that's one of the most important things that I try to do in that process.

[00:07:48.01] - Cameron Souza
Anytime I'm considering another opportunity.

[00:07:51.02] - Albert Wang
Super, super insightful.

[00:07:51.23] - Sarah
Your story about how you got into sales by being a date to a birthday party, I think, is just so typical sales. Like Most people that are in sales don't know that they want to be in sales, and you obviously went from wanting to be illegal to that. So I'm just curious, was that your experience? Did you have knowledge of sales as an industry prior to that birthday party? And when you did decide to test it out and pivot from legal into that, what did people think? Were your parents like, what are you doing? Was there any feedback there from your family?

[00:08:23.16] - Cameron Souza
Yeah, it's a great question. So I think it was... I totally had a stereotypical understanding of sales. I believed it was maybe the sleazy salesperson who's trying to take your money and run. That was all I knew because that's all you hear seeing TV and movies and things like that. But I was really inspired by Mike. I was like, This is clearly somebody who's incredibly successful, super smart, and just hard working. And through the internship, the first thing I realized is just how wrong I was. But the second thing I realized is I walked into this tech office. I was like, this is what people's 9: 00 to 5: 00 is. This is It's such a cool environment. There's a ping-pong table. Everyone's super friendly and laid back. And the idea of how hard you work is what you're going to get out of it was super attractive to me. And that's when I started to realize that, first off, the stereotypes are just wrong. Especially in tech sales, specifically, if you're that type of persona, you're going to lose deals very quickly because the people we sell to are really smart. It's a much more consultative approach these days compared to maybe what it might have been 30 or 40 years ago, so to speak.

[00:09:29.18] - Cameron Souza
But the philosophy, background, and the legal study side of things, my parents were always super supportive. They just saw success and were excited for me because they would see how excited I would come home when I'd get a promotion, close the deal or whatever that may be, or really the big one for me is when I had people on my team get promoted, you feel it. It's a different type of mentality when you're waking up and going to work, when you're actually doing something that you genuinely like to do. But there were some ongoing jokes early on, especially amongst my friends.

[00:10:00.00] - Cameron Souza
We were SDRs at Aqia as well around, I was the weird guy with the strange background, and how the heck does that translate to anything? I get that a lot. I think the one thing that my background taught me a lot to do is communication and specifically writing skills. I think those were things that helped me a lot, especially early on, because I also lacked in a lot of areas. I actually struggled a lot as an SDR right out of the gates because I had really poor organization skills, candidly. I could talk to people on the phone and I could write emails, but I had no structure or just didn't know how to walk and chew gum. But my manager at the time, Tom Murdoch, did a fantastic job of, one, helping me identify this is something you need to nail down because it's going to lead towards repeatability over time. And that was a big light bulb click moment that helped me take off from there.

[00:10:48.18] - Albert Wang
No, I appreciate that a lot. And for context, I think in sales, like I said, people stumble into it in really funny ways. And your story, I think, is big attribute for what I was looking for. It just makes sense to me. But I'm curious, you've mentioned your manager pointing out an area that was a light bulb moment for you. I know a lot of salespeople have that moment where it clicked or maybe a couple of memories where they're like, Wow, I got this. Do you have one? Is there one you look back on where you're like, That was a really good day. That was a really good call that defined how you see yourself as a salesperson? Yeah.

[00:11:21.02] - Cameron Souza
I mean, the concept of an operating rhythm was a big one, especially at the individual contributor level of just a lot. And this isn't necessarily a bad thing, but it makes your job harder. But what I see a lot with SDRs is that first three months or so, getting into that operating rhythm is the hardest aspect of the job is a lot of what they'll do is they'll work during the day to get to their goals that day, a. K. I have to make 60 calls to 60 prospects. I'm literally prospecting on Monday and making calls to those people on Monday, and it's just really hard to do that every single day at scale. When I started to learn the importance of planning a day out, two days, a week, a month, that was huge for me. I think that also helped me a lot when I transitioned into leadership because you can't just be looking at just what's directly in front of you. You have to be seeing around corners a little bit. I think I certainly made a lot of mistakes early on as a leader and even as a second-line leader at Datadog.

[00:12:18.08] - Cameron Souza
I think one of the big click moments for me at Datadog was like, I'm hiring managers now, and they're a very different skill set, and they have a very different background. I was really lucky because I had people in my network that were looking to break into this space that were great individuals and are still doing fantastic things in business development. What I started to realize, though, is when you're hiring for a business development leader, and this might not be universally true, but I found that it leads to an easier long term success metric with these folks is you want somebody who wants to be in business development leadership, not just leadership. And I think that this is not always the case, but I do think some people think that just being a manager or director is just the trajectory of what you're supposed to do to evolve in your career. And that's not true, I don't think. I think people who, especially, are leaders of business development professionals who are, generally speaking, usually earlier in their career, need to be in it for the right reasons. Because that feeling and motivation of growing and helping develop people, that gets felt both ways.

[00:13:22.01] - Cameron Souza
And you have to be super comfortable constantly getting rid of your best people and building really, really quickly. Whereas in a more enterprise motion, I think the expectation would usually be that you're in that seat for a little bit longer, comparative to maybe a year in an SDR role before you're making that jump. So being really passionate about building and having the right mentality was a really interesting inflection point to realize that's really the profile that I need to hire for, not just the best eight is automatically going to be the best manager because that might not actually be true.

[00:13:53.12] - Sarah
I'd love to hear a little bit more on how you think about that. So I'm sure we get that question a lot at Bearworks, right? What's the skill set to get promoted and that career path. A lot of times being an SDR, it's an entryway. They're also trying to figure out where they want to be. From the leader's perspective, how do you think about what's the attributes of somebody who you think has that potential, either in terms of a skill that they stand out on and are really exceptional, or it'd be interesting to see your concern about the negative, right? Is there something where you're willing to tolerate to generate somebody who's below average in a certain attribute, or they just need to at least not have any glaring red flags?

[00:14:36.15] - Cameron Souza
Yeah. So just in the context of SDRs or leaders. Either one. Yeah. So for SDRs, I think the biggest thing that I've learned is, and this is not to say that your resume isn't important. It obviously is. It tells a story of who you are and what you've done. But for an SDR, there's almost never one thing that's going to exist on a resume that magically makes them going to be a great fit. It's much more based on skills and attributes. So being really curious. Coachability is an obvious one. Hard work, grit, adaptability, especially in the tech space, you need to be comfortable with change all the time. If you have those attributes, you're generally going to be able to work with that person and it really effectively. The other one that's a little hidden, and this can be the negative that you want to watch out for is goal orientation. I'm comfortable if you don't have to tell me that you want to be a VP of sales to get this job, but I want to know why this job is going to help you achieve something greater than just being employed. Because one of the biggest reasons people, in my opinion, fail in this job is usually not aptitude, it's passion.

[00:15:40.01] - Cameron Souza
They are not actually excited about cold calling people every day or the product or the people that they're engaging with and the conversation type that they're having. I've seen a lot of people that maybe struggled at a DATA dog or an AQUIA that went on to be incredibly successful in sales. It just wasn't the right fit and mixture, but they had the right DNA Those are some of the things that really stand out to me for sales development. I also think it's very similar for leaders. It's just at a heightened level. And I do think the resume plays more of, I'd say, a crucial part in that process because, again, it's going to help me understand why do you want to do this and what is it that you've been doing to help you prep to do this? And again, it's always if I know what your goals are and there are things I can help you achieve, that's going to be really mutually beneficial for us because you have to know what motivates an individual to effectively help them, right? Because you can't just treat everybody like cookie cutters. So at the leadership level, I still do really want to understand, are they thinking about this as their next role, or are they thinking about this and how it's going to impact their role two or three roles from now?

[00:16:44.11] - Josh Westes
Kam, One common thread that you keep bringing up and that I want to pull on more is of leadership is of mentorship. To me, it sounds like those that you like to hire are those that are willing to be mentored. It sounds like you yourself have been mentored very well and have mentors that you work with. Envision, you're probably, just from the way you talk about this now and even the adjectives you're using to describe what you care about in someone, that you're currently mentoring others. How do you approach as an SDR or someone new in the field finding that mentor? I find that can be a challenge. Sometimes it happens naturally. I have mentors that I met at a party and started a conversation, and it's just evolved as a friendship can evolve. But I've also heard where people have straight up cold-emailed individuals that they respect and are like, Hey, game recognizes game. I think you're doing great. I would love for you to help mentor me because I want to walk in the same path that you do. What advice do you have for people that are seeking a mentor? And then on the flip side, what should you look for in a good sales mentor?

[00:17:49.12] - Cameron Souza
I think that's a fantastic question. I've definitely gotten that a few times. I think one of the first things you need to do is define what does mentorship even mean to you? Because I think it can look different. The example I give is a lot of natural mentorship comes in school when you have a coach that you really respect and there's somebody that has helped you either personally or obviously, athletically. It's not to say that this is not always the case, but that person might not be the person you need to go to around professional advice because they might not have the scope of what it is that you're trying to accomplish. To me, a mentor is somebody that is in some capacity doing or has done something that you're striving to achieve. And they're somebody that that wants to be a part of this. They're actually very passionate about coaching and developing people as well. They have the ability to basically take you as a person almost out of the equation and just objectively look at situations and give you concrete feedback on it. That could be on your abilities or decisions. It could be on a whole host of different things.

[00:18:50.05] - Cameron Souza
But I think defining what mentorship means to you is at its core, extremely important. Then when you think about the process of how do you actually That person's officially your mentor. I personally believe it comes naturally by virtue of how you engage with them and they engage with you back. There's almost like an unspoken agreement at times. But I refer to people like Mike Stankis or Tom Murdoch or Anna Fischer as mentors to me because I've worked with them directly. But I've also maintained these relationships far beyond. I haven't worked with some of them in six, seven years. So you have to be really intentional about how you're engaging with them and the value that you can also bring to them in their careers as well. It doesn't have to be a one-way street from that perspective. But I do think I've had people come to me and ask, Hey, would you be open to being a mentor to me? And I am always going to be jumping at the ability to help somebody else however I might be able to, whatever big or small contribution I can make. But I think you have to have a little bit of an EQ to recognize, is that something this person will do for me and wants to do for me genuinely?

[00:19:57.20] - Cameron Souza
And not just like, This is a box that I'm just going to check because I feel like I'm obligated to, so to speak.

[00:20:03.15] - Josh Westes
Yeah. I mean, you want them to be invested in your success, right? Otherwise, they're probably going to serve you platitudes, and it's not really going to help you go anywhere. But if they actually care about helping you succeed for whatever reason that might be.

[00:20:18.17] - Cameron Souza
And I mean, by virtue of that point, they actually know you, right? You're not just a face and a name or a professional. They know things about you personally, your ambitions, your goals, your failures, whatever those may be. That's an important aspect, I think.

[00:20:35.13] - Sarah
Super interesting point. Doing a startup means I get to meet all sorts of really random people I've never would have expected. And I've kept in touch with some of these random people for dozens of years. And it's unexpectedly paid off where one of our lead investors was through these connections. But you're absolutely right. You never know, right? Why do you choose to mentor somebody? Obviously, you want to help people and all this stuff. But sometimes you see something in this person They remind you of you or remind you of who you didn't want to be or something like that. You just want to help that person. But you never know. It ends up that person may be promoted faster than you, and you're super happy for them, and you'll help each other out. I think, especially in business, you never know your career will be so broad and so long. It's really fulfilling over time.

[00:21:18.15] - Cameron Souza
Totally agree. I think advice to people starting their career is find somebody like that because, again, I didn't in the moment maybe recognize it, but in hindsight, they were massively impactful to my success, but also how I defined my career path. And I think it's just it's such an interesting network that I'm selfishly and very much like beyond appreciate is the type of interaction that I tend to have with SDRs on my team naturally leads towards that mentorship type of path. And I have this really cool alumni network of hundreds of SDRs that I've worked with over the years, and you just never know where you're going to come back around with those people.

[00:21:58.06] - Sarah
So I guess going on that subject of mentorship, now that you're on the other side, you've been a leader, you've been that senior career, what are some common misconceptions you've seen about maybe being a leader or about enterprise sales that you've seen that you wouldn't have expected when you were first starting your sales journey?

[00:22:17.23] - Cameron Souza
It's a really good question. I might have to simmer on that one a little bit. But I think, again, I do think one of the biggest misconceptions is just the idea that you need to do this in order to grow your career. I mean, some of the most successful sales people I've ever met have been individual contributors their entire professional career. I think probably will continue to do so because, one, they make a lot of money and they're really good at what they do. But you really do have to be in that for the right reasons. And that was also a mistake that I made because I've hired leaders that maybe weren't good for reason. And that was something that made that job much harder for them in the long run. I think in terms of, like, misconceptions about leadership, and especially in an enterprise sales, I think there's You see it on memes, on Instagram and things like that, where it's like, leaders are just sitting here to crack the whip and really just try to ride you to the ground and they don't actually care about you. Choose the right places to work, that's not true.

[00:23:13.15] - Cameron Souza
You know what I mean? I think that's part of, I actually think, a really bad stigma with sales is that it's a chop shop in that you're literally just doing nothing but smiling, dialing all day. And if you don't, you're out the door immediately. There are absolutely places like that that are like Wolf of Wall Street or whatever. You got to look out for that. Or maybe that's the type of thing that you thrive in. It's different strokes for different folks. But I think that that's a really dangerous misconception around leadership is that, one, they don't actually care, and two, you're literally just a tool for them to achieve their goals.

[00:23:45.23] - Sarah
Yeah, I think that's well said. Big lesson for me is being in even an SDR or an AE, whatever, entry-level person in enterprise sales, it's so pivoted nowadays, right? Because relative to all the many things you could be doing. It's very intellectual. It's very challenging. Like you said, statistically, it is difficult to make it. But at the end of the day, finding good candidates is so hard. For me, on the other side, interviewing salespeople, a lot of founders tell me it's one of the hardest things people do. And so because you're being sold to.

[00:24:18.17] - Josh Westes
It's the toughest role, man. I mean, salespeople are selling to you. So even if they're halfway decent, they are trying to sell to you on the job to sell for you. It's- What a twist.

[00:24:27.18] - Sarah
It's to your point about not being a chop shop, I think at the end of the day, it's all people. There's an investment in finding the right person, investment in interviewing and in training that person. And so it's super fascinating the different sales cultures across different companies and how they treat their members and alumni.

[00:24:46.18] - Cameron Souza
Yeah. And you, as a candidate, you can weed some of that out. I mean, there's technology that will help you do that in class store and things like that. But I think we talked about the importance of diversity briefly earlier, and those are generally good signs. If you have a really diverse workforce as an example of something to keep an eye on, to tell you that that's probably not the environment that you're walking into. It's not going to be this type of one-way or the highway chop shop. Cool.

[00:25:12.17] - Sarah
So let's see, should we switch to a lightning round real fast?

[00:25:18.03] - Cameron Souza
I'm ready. All right.

[00:25:20.01] - Albert Wang
Let's do it. Cool. Am I taking it away?

[00:25:22.18] - Sarah
I'll let you try. Okay.

[00:25:24.03] - Albert Wang
Cam, question one. What is your favorite bear?

[00:25:27.19] - Cameron Souza
All right. What's your favorite bear? What's your favorite bear? This is the only one I did see. The answer is polar bear. The reason behind that is, very recently, I was reading something. I had no idea how absolutely massive they are. There was a scale breakdown of them versus black bear, grizzly bear. They're huge. I just think that's fascinating. They just lounge around in the cold weather all day, just hanging out. It's a good vibe to have.

[00:25:51.06] - Albert Wang
I love that answer. In particular, because Joshua, do you recall two weeks ago, three weeks ago, maybe, what you mentioned about polar bear and bearworks?

[00:25:59.11] - Josh Westes
I I do. Cold calling, baby. Let's go.

[00:26:02.01] - Cameron Souza
Exactly. The parallels are right there. Cold bear. Cold bear.

[00:26:05.09] - Josh Westes
Bear works. Cold bears are the best salesmen. They're ready, man. They can cold call like anybody's business, and they're the big man on campus. Eight feet tall, strike a little fear in their hearts, too.

[00:26:17.23] - Cameron Souza
That's good. If you can survive in the- Seal the deal. The dad puns are ready to go.

[00:26:24.08] - Albert Wang
This is marketing. We're in a marketing meeting now. That's a great answer. I love that answer, Sam. Next one, What is one sales tool you couldn't live without?

[00:26:32.09] - Cameron Souza
I feel like you could debate whether this is a purely sales tool, but I think Salesforce in and of itself is just crucial for tracking as a leader, as an individual contributor. You can get a lot of really good data out of that. I think sales navigator is probably my direct answer to that, though. I've always had that at every place I've ever been. I remember when we got that at Acquia when I was an individual contributor, it was a game changer. It was important skill sets as an IC that you can have is your ability to strategically research at scale. And that was a big challenge for me because when I started, I wanted to know the person's blood type, social security number, family tree before I would ever even pick up the phone. And I realized that's actually not always going to be the most efficient use of my time. And I would go down these research rat holes. But sales navigator really helped me lock in and actually research effectively.

[00:27:24.14] - Sarah
It is insane the quality product that LinkedIn has built. I think yesterday, there's an outage. When LinkedIn went down for half an hour. Cam had posted... Cam actually made a post right before the outage. When the product came back within 30 minutes, he had like 100 likes. I know Cam is super popular and has a million friends, but it was insane. Everybody was just It's literally itching to get back on to LinkedIn.

[00:27:47.12] - Cameron Souza
It is. Well, I was very, very, very everyone to interact with that. I really do appreciate that. But LinkedIn and all, I am admittedly very bad with social media in the sense that I'm constantly checking and engage. I have this OCD tick where if there's a notification, I have to look at it. So that one got me a little bit for that 10 minutes of stress that it was down yesterday.

[00:28:11.02] - Albert Wang
Typical, right? No, but that makes a lot of sense. I mean, from a sales rep's perspective, both of those tools that you mentioned are huge. Having a single source of truth and being able to access your data in a CRM and then being able to enrich that data with something like Sales Nav, they're both big wins. Absolutely. Totally. Okay, cool. I have one more that I think is my personal favorite, but there's five questions here. Should I ask them all or just one more?

[00:28:34.15] - Sarah
No, jump to your favorite.

[00:28:37.14] - Albert Wang
Cool. Okay. Cool. Okay, Cam, if you could sum up your sales philosophy in one word, what would it be?

[00:28:44.23] - Cameron Souza
Man, one word, I'd say probably personalization. I think the way you stand out in a crowd of thousands of people all trying to engage with the same individuals, selling competitive tools, selling different tools. It's really I mean, this is where the stigma of sales comes from is lazy sales, just blasting email indiscriminately with no value. It's just spray and pray effectively. I think the people who, and you see it, actually. I've seen this with people on my team is prospects will reach out and be like, That was a really good note. You personalized. People don't want to feel like they're being sold to. You're trying to create relationships with individuals. I think showing that you're not just a robot, basically, that can actually provide value based because you did homework, like you spent the time to try to get to know the person so that you could actually solve a problem for them rather than just try to shove a product down the throat. There's a concept called the seller deficit disorder, which basically states that any time we walk into a sales room or a meeting with a prospect, the prospect generally doesn't think that we actually care what their problems are, but rather we want to project what we know what problems we can solve for are.

[00:29:59.08] - Cameron Souza
I think that's a really quick way to differentiate yourself is to listen and actually care about what the person is dealing with and solve for their issues and not just whatever your product can solve for. Because I think that nobody's going to win in that circumstance if you just give somebody something that's not going to actually help them do something they're trying to achieve. I think that's personalization in a different way in the sense that you're personalizing almost like a prescription to somebody for the needs that they actually have. Totally.

[00:30:27.19] - Albert Wang
And it's that element of a pattern disrupt, right? Like you said, if you're walking into a meeting and they think they're going to get X, but you give them Y, all of a sudden they might be listening a little bit more to what you have to say and what you want from them. When did you... I'm curious, at what point in your sales career did personalization click for you? Have you just always been that way or was there a moment where you felt like it became more of a priority? Yeah.

[00:30:51.03] - Cameron Souza
Again, Tom Murdoch was my first manager as an SDR, and he hammered that into our heads that have to be different in that sense. And you're not going to... At all the companies I've worked with, I've sold to really smart buyers in the sense that these people know what they need. I don't need to tell them that. More so what I'm trying to do is help them understand, if they don't know us, what we could actually do for them in a lot of ways. So to say that that was, from a very early stage, hammered into me. I would say it wasn't easy to figure that out because, like I said, the half joking, I would go down these research rat holes and try to find every little thing on planet about somebody. That doesn't necessarily lead towards what we're talking about in terms of personalization. Sometimes it does. One of the examples we get a lot of is like, oh, this team. It's like, okay, I don't know what that does for me as a professional. But then the inverse is, oh, you research somebody did some hobby that they really enjoy, and you shared something about that that you read or did homework on that could maybe augment what they already enjoy about that thing.

[00:31:58.04] - Cameron Souza
It sounds Both are very similar, but they end up having pretty different results in the grand scheme of things.

[00:32:04.05] - Albert Wang
Yeah, it's like the approach and the thing that you pick to personalize makes the difference. Exactly. Yeah, totally. Just to follow this vein, sorry, I know these are supposed to be the lightning round, but I'm curious about this. Do you have any... I remember I had a sales manager do a cooking class one. He was giving me examples, and he literally went to the same cooking class that one of his prospects had posted about because they posted about it and then got it in that way. Have you come across any out of left field ones like that, whether it's you or a teammate of yours? I'm just curious to hear any wild ones if you have it.

[00:32:37.12] - Cameron Souza
Yeah. One of the ones that I thought was really creative and different was it actually worked two different places. But Pokémon, the company, our reps made Pokémon cards with what our products were and outlined what their power would be and what it would solve for. I'm now realizing because we did it two different places and it works, probably a few people are doing that, and maybe that's not strategy that's going to work today. But in the moment, I thought that that was pretty cool and unique from that perspective. That was one that I liked a lot. Tim Bertrand was our CRO for a period of time, and he really liked this strategy. It's going to sound very, maybe bizarre almost, but something that's referred to as a veto letter, it's very important top officer. But basically, it's a handwritten note that you like, snail mail to somebody. And because that's so different in these days, where you don't really get literal mail from prospects, you get emails up the wazoo. But it's changing your approach by virtue of knowing that your competition probably just isn't doing that. And it shows a hyper level of care and research because you literally took the time to do that, that the individual hopefully would see that as this person is different in that sense in a good way.

[00:33:47.04] - Cameron Souza
If they're going to put this level of effort just to speak to me, I'm sure down the line, if we have a more deep relationship, this is somebody that I can trust to work hard on my behalf.

[00:33:55.19] - Sarah
Cam, do you remember the ER or baby delivery story?

[00:34:00.22] - Cameron Souza
No.

[00:34:01.09] - Sarah
Oh, then. There's at least a few enterprise reps that have closed six and seven-figure deals by posting and sending messages to their prospects, either during or right after baby delivery.

[00:34:14.06] - Cameron Souza
Maybe not that extreme, but I remember one of the directors on the enterprise team, it was end of year, and I think I want to say it was Wayfair was the account. They showed up at the Wayfair headquarters dressed like Santa Claus with a gift bag that I think had some beer or something fun in it for their prospect, and this literal signing for the paperwork for them to actually close the deal before the holidays went through. So similar. I thought that one was pretty unique. And it worked.

[00:34:43.15] - Albert Wang
I love that. That's what's so cool about sales is that, sure, you have to have the grit and the grind and the creativity, but it's like you're given space to really break the pattern and break the mold of just sitting at your desk 9: 00 to 5: 00, right?

[00:34:56.22] - Cameron Souza
It's like, some people might feel like this is an overstatement, but you are like a little mini CEO of your business because there are best practices and there are a lot of things that will guide you to success. But how I find success versus any of you, it's always going to look a little bit different because we're people and people engage different ways. I've always found that creative side of things to be something that's just a fun part of this job that keeps it from being stale. But you can make the counterpoint that, Oh, you're just making a million dials every single day. How does that not bore you? The answer is, if you're doing it with something you're actually interested and passionate about, the conversations that you're having are going to be different every time. To me, it's fascinating because you learn about different industries, what their problems are, how we fit into those things. It's different. Even though you have a product that solves a specific use case, how it fits into those different industries and verticals is always going to be a little bit different. That's something I've always found to be just inherently very interesting.

[00:35:55.14] - Sarah
I'm relatively new to sales, but I've done product management for a long time, and I feel super strongly that there's just so much overlap of what you're talking about. You're about consulting, learning, objection handling, and really all about prioritizing what matters to a customer. All those skill sets translate fantastically to what you said, like Being a CEO, being a general manager of your own business, because of all the different activities you could be doing, you have to do what is going to move the needle. If it doesn't work, you have to cut it off. Yeah, absolutely. Super hard. Going back to, I guess, outside the lightning realm, back to regular scheduled programming, you've given me such great advice about how to build and scale out a BDR team. As much as I'd like to hoard it and keep it myself, we get this question a lot. It's just been so thoughtful. I love to hear... I think people would be really interested in your take. Maybe we'll start from the startup side and grow from there. I guess just to tee it up, a lot of questions people always ask, how do you pick, how do you start to build your first outsourced BDR team?

[00:36:56.04] - Sarah
Do you have any suggestions to people in terms of how do you pick an agency? What agency? How should you structure this?

[00:37:02.00] - Cameron Souza
To me, it always comes down to people in circumstances as well. The example that I would give is where I came on board at Datadog scaling versus get another opportunity might look different. We were in a hyper-growth mode. So one of the most important things that we really locked in on early was what's our most consistent talent funnel? And this was also the case at AQUIA as well. We had really tight relationships with local schools and universities that actually had sales majors and programs, which is a relatively new concept, even though sales is probably one of the oldest and most common professions on planet Earth. There hasn't been a discipline for it in the education space. It's always been business or marketing. And obviously, those things have a lot of tangential transfer skillsets. But actually having direct sales teaching, and good sales teaching, I would say, is something that I think was tremendously helpful for us because going back to that concept that I talked about in terms of Where I see people failing is very, very rarely aptitude and ability. They either realize that sales isn't just what they even want to do in the first place or it's something within the sub-industry itself.

[00:38:13.16] - Cameron Souza
But if you can have a talent pool of people, very, very few people at that stage of their career know that they want to get into sales. A lot of people think that they want to get into sales, and those are very different. If you can funnel through that group that knows that they want to, you're reducing a lot of the risk of that burnout higher that comes on board and really struggles because it's just not something they're actually passionate about. That was something that if you're in that hyper growth mode or just building out an org, defining your successful and repeatable funnels, I think is incredibly important. I think, similarly, if you're picking an agency and things like that, one of the challenges that I've experienced with agencies can sometimes be that you can naturally lead towards, are these people actually going to be interested in the convos that they're actually having on behalf of our organization? Do they have certain types of specialization? Tech sales, right? Okay, we're an agency that specializes in tech sales. What does that mean? There's technology that sells to salespeople, HR, marketing, IT, so on and so forth.

[00:39:14.06] - Cameron Souza
It keeps going. Those are all super different conversations. When you're thinking about your brand-Your ICP. I'm obviously very biased here, but the SDR, or that's the tip of the spear. That's the first interaction most people are going to have.

[00:39:29.12] - Josh Westes
You hit earlier, too, that personalization. If they're not used to selling to that ICP, it's not going to be personalized. It's going to feel forced, and it will hurt your brand, and it will be awkward. I also think it's hard to align agencies sometimes. To your point, you said it earlier. You said that part of what you really liked about sales is as hard as you worked is what you got out of it from a financial gain perspective. When you're interviewing internal, it's easy to set up those that are, A, excited by that and are driven and hungry and want that big carrot at the end of the stick, not just going to be comfortable off of their base. But then when it comes to an agency, how do you incentivize them the same way can be a different challenge Curious. Have you ever dealt with that?

[00:40:16.08] - Cameron Souza
I've seen different incentivization programs for sure. What I would say on behalf of the positives of an agency, they're usually... One of the things I think is really important is evaluating what is their sales philosophy. How are they teaching and onboarding their own individual people on their team? If that onboarding and training process is aligned to how you would think about doing it for your teams, that can actually be a good fit because they might have a very similar value-based approach, let's say, in terms of how they're going to go to market with your products. So it can be really hard to evaluate that, but I think the way that I've approached that in the past is really just you're interviewing them in terms of almost like, how are they leaders to their people, too? Like, these people up. I don't love scripts, sales scripts, I think, because the second you go off script, it can get really ugly, really quickly. But again, with what I've seen where it can be success, not going to say script is talk tracks. You know you're going to come up against these objectives. How are you training your people to handle those situationally?

[00:41:18.08] - Cameron Souza
Roi can be hard to judge, too, because it's obviously not a cheap resource, but some of them are incentive-based, so you'll pay them more based on their output. If you really define clearly what your outputs are, that ROI can actually be really strong. But again, it really comes down to, I think, what you're pointing out is like, alignment of vision of what you're trying to accomplish, what the agency can actually provide, and then how do you actually execute and go to market on it. I do think there's some level of inherent value of if you can be involved in them and through this, you'll see and hear and observe things that are going to be valuable to you as you either expand that relationship or don't.

[00:41:57.20] - Albert Wang
That's huge. I know at BearWorks, that's something that we're exploring currently. I can imagine there's lots of other teams out there doing the same. We really appreciate your insight on not only this camp, but absolutely everything that you've shared today. We just want to thank you so much. Thank you for your time and your wisdom and for being with us today.

[00:42:15.17] - Cameron Souza
Oh, of course, anytime. This is a blast. Again, I'm super excited about this company specifically because it's a sales tool for my people, the biz dev folks. Helping you do your job more efficiently and effectively, that's the name of the game, right? It's efficiency at scale. How is that going to help you grow? Getting more at Bats is only going to help you as a seller or continue to flourish and grow in your career. Role-playing is fantastic, but again, there's nothing like a live at Bats. Again, I've learned far more from my, frankly, failures of at-bats, but you don't get a lot. So the more that you can get, it's only going to help you.

[00:42:51.06] - Sarah
Thanks again, Cam. Going back to being a mentor, it's been so obvious. We've only just dabbled into the depths of how much knowledge and experience you have. So thank you again. Every time we chat, we always learn so much. I personally learn a ton every single time.

[00:43:04.14] - Cameron Souza
Just getting started.

[00:43:05.20] - Sarah
Exactly. It's going to be a journey. It's going to be a fun one. Absolutely. Cool.

[00:43:10.03] - Albert Wang
Thanks again. Thanks, Cam. See you. Thank you.

[00:43:11.22] - Cameron Souza
Have a good one. Thanks.

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