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Podcast Pit Stop: Hiro Rodriguez on the Power of Mentorship

Posted by Arielle Walsh on May 20, 2022
Arielle Walsh
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There will be moments in your life where you will need to ask for help, and when those moments come, it’s time to mentor up! Building meaningful mentorship relationships can lead you to exciting new experiences. In episode 47 of the B2B podcast, Pit Stops to Podium, Hiro Rodriguez shares his journey and experiences as both a mentor and a mentee. Hiro is the CRO at Prefect, a dataflow automation platform. In his words, “lending my experience to somebody is certainly what it’s all about.” So don’t go at it alone. Ready to become a mentor or a mentee? 

Take 20 minutes to listen and digest and then head back to the races! 🏁🏆

Pitstop Highlights

Finding a Mentor

Hiro’s recommendation for finding a mentor: using the hybrid leadership matrix. Find all the characteristics that are important to you–maybe humility, strategic thinking, leadership–and look towards people that possess those qualities. It’s also important to know what kind of leader you don’t want to be like. These will be the people who will ultimately guide you to where you want to be in your personal and professional lives.

Being a mentee is universal and should be timeless.”

Paying it Forward: Becoming a Mentor

Becoming a mentor is more than a transactional conversation each month. It should be organic and leads towards building a natural relationship. It may take some time to initially develop a relationship, but having a trusting relationship on both sides will lead to a more meaningful experience between the mentor and the mentee. 

Expectations of a Mentorship Relationship

A key expectation for a mentee is having the characteristic of being coachable–willing to learn, ask questions, and seek advice from a mentor. Mentees should also be willing to have room for improvement, room to be able to learn more than they already may know. Having enough humility to admit you don’t know everything is okay!

Mentors should focus on building a relationship with their mentees. This will greatly help with the relationship in the long term and prevent it from becoming a transactional conversation each month. Mentors need to be intentional with their actions, truly be willing to answer questions, give advice, and offer support to their mentees. 

Connect With Hiro:

Full Transcript

Brendan: Hey everyone, welcome to Pit Stops to Podium, the RevPartners podcast where we talked to execs who competed and won, taking their companies from high growth to high scale. My name is Brendan Tolleson. I am the co-founder and CEO of RevPartners, and I'm delighted to have you with me today, Hiro Rodriguez for this episode of Pit Stops to Podium. Welcome, Hiro. 

Hiro: Thanks so much for having me, Brendan. It's an honor.

Brendan: I'm honored to have you here. You and I have gotten to know each other, I guess probably over the last few years through Mike, who was on the podcast last year. So it's fun to kind of see us come full circle. But Hiro currently serves as the CRO of Prefect. And so here, if our audience just to get to know who you are and who Prefect is, have you give us that elevator pitch on prefect and maybe a little bit about your background because candidly, you have a pretty unorthodox ride, which I think our audience would enjoy hearing about. 

Hiro: Certainly, it's been a lot of fun. So Prefect, what we do today is a data flow automation platform and we help our users build, run and monitor their data pipelines. It's what that means is very simple terms is these engineers, data scientists, they have code that needs to run inevitably. Sometimes it breaks. And so what we do is we make sure that they can identify when that code was broken and also very quickly identify and pinpoint what broke so that they can immediately address it. And so we work with customers from small to big. Our first ever customer was Cisco. We work with mom and pop shops. We have just released a case study with the Washington nationals, which, by the way, they started using prefect in 2019, the year they won their World Series. So maybe it was coincidence on immigration. We were actually the reigning champions. I want to make sure that's noted in this recording. Maybe they're perfect customers. I just don't know it because we also do have an open source component of our tool. And so there are a lot of people and customers who are companies that are using pre fact that are just on a free tier, and then eventually come talk to us. So that's what we do it for effect. So that's Cisco's not a bad first customer, by the way. So if you're getting your company started, that's a good logo to have in terms of a reference will client. It certainly really woke us up to the opportunity that we had had ahead of us. And today, you know, from there, we've been very fortunate that a lot of other Fortune 500 companies have adopted prefix, so it's been really exciting. We're just growing really, really fast and it's been just an incredible ride, but it's only been a short part of that ride. So to answer your other question about what brought me to this point is, you know, I started my very early sales career actually with Mike Arrieta. And what are your other guests, Mike casita selling costco? So that is where I learned that it's Costco. Tree just keeps growing. I tell you, we're everywhere. So that is where I learned just the basic fundamentals of selling. And so that's where I spent sort of my very early part of my career. But then I transitioned to my first part of my tech career in Salesforce and moved to San Francisco. I had this great opportunity to see how tech was being sold and live in sort of the Mecca of technology. And then I had this really unusual and just the most great, the greatest blessing and opportunity to meet with both Mike Arrieta and Keith kroc, the chairman, CEO of DocuSign. And so then I spent the next four or five years working alongside the two of them and helping build DocuSign into what is now a publicly traded company. I joined them when there were a series C company, and it was just an absolute joy. And then from there, Keith Kroc ended up going over to the federal government. So that is one of the reasons why I'm today. Based in Washington, DC I had a chance to serve as the chief business officer at the US Department of state, and that was the honor of a lifetime to serve our country. So now really had a chance to do that once. It was time to find the new thing. I knew I needed to be back in tech and here we are in effect building this wonderful data company. 

Brendan: Well, that's an awesome story and one to be very proud of. And I think it's a, you know, we'll dive in a little bit further as it relates to our big idea in light of your experience and you mentioned Keith, so we'll get to that in just a second. And I'm also reminded the flag in the background. I remember when I first met, you had no idea outside that being cool, but now I have a clear context as to what that's in reference to. But here, before we get into our big idea, we do have a tradition here at the podium and it's to get to know our guests outside of work. So what are three fun facts that our audience should know about you outside of your unorthodox career journey? 

Hiro: I love this. So the first one I'll give you is so I'm a concert pianist. So ever since I was a young boy to two years old, my mom had me sitting on her lap and started lessons of 4 and was very blessed that a chance to come. The US Open a couple of times, so it was very, very serious part of my life. Now as a father, I sort of just get to play with my kids on the piano, and that's where I find the joy. So playing the piano is a always a fun fact thrown out there. There's a US Open for. That's fascinating. We don't time for that, but I'm curious to know more about that when we grab a drink next time. Oh my goodness, there are some serious piano players, many families that their kids are homeschooled so that they can play the piano. So it seems to be a new Netflix series. Yeah, right? Thankfully, my mother really believed to me to balance individual, so I had to mix in some football and and sports with my piano too. So the second fun fact, which is always funny because, you know, by day, I'm in front of this computer screen on video calls and building tech. And so it's tech by day. And then funny enough, this a kid and lived in San Francisco right outside of DC now I'm a cowboy by night, I guess, I, you know, outside of work, if I'm not with my kids or I literally grew up knowing nothing about horses, and here I am on the weekends trying to figure out what it means to actually be the person that's on a horse. That's my hobby outside of tech, in my family. 

Brendan: That's awesome. 

Hiro: Yeah and then the third one I'll give you, you know, and it sort of is the inspiration behind this flag that you had mentioned here is I had this wonderful opportunity a couple of years ago where the Department of Defense selected 40 leaders from around the country and I joined what's called the jsoc, the joint civilian operations conference. And what they did was they spent a week starting at the Pentagon. And then you go every single day to a new base. So we went to Fort Carson, Colorado. We went to Las Vegas for the Air Force base. We went to Coronado and San Diego to watch the seals. And every day I had a chance to meet a different military branch and meet the men and women who serve and protect our country. And that was a unique experience. And I also share that because it was really a catalyst to what ultimately drove me to serve our country at the Department of State and partially where a big part of, you know, my patriotism. And I have an American flag behind me is I'm just so darn proud of how we just live in this great free country. And Jake really gave that blessing to me. 

Brendan: That's really cool. Thank you for sharing a little bit more about you and the piano side and the hobby. That's a post-covid hobby with the horse riding, but that's always fun to hear what people pick up and then experience serving our country. So thank you for that. Well, let's transition to the big idea, and you talked a little bit about it in your career is how people influence the trajectory of your career. And so I think the big idea for us today, let's park on this concept of really don't do it alone and how the power of mentorship and how important that is as it relates to your trajectory, not only from a professional standpoint, but what it means from a relational side. And so let's start, you know, as we think through how to break this down, let's unpack a little bit more about your experience being mentored and specifically with Keith at DocuSign. So let's share a little bit more in terms of what that was like for you and some of the takeaways that you receive from that. 

Hiro: Absolutely. You know, I feel very blessed that I've had a lot of mentors and I would include someone, you know, like my parents that but one of them that was certainly influential from a business perspective. As Keith Kroc, the former chairman, CEO of DocuSign and I was as his chief of staff for many years. And you know, one of the things I'll never recall I'll never forget, excuse me, was when one day Keith and I were walking in his garden and I said, Keith, you know, who's the greatest leader that you can think of? And I thought he was going to say to me, John chambers, the former and revered CEO of Cisco, who was Keith's true mentor. He met him once a month when he was building Ariba. And he goes, here, it's not one person. See, the thing is, you have to have what's called a hybrid leadership matrix. You want to figure out all the different characteristics that are important to you. So whether it's courage, fidelity to principle, kindness, public speaking, strategic thinking and then on the different access, you put all the different leaders that have and sort of carry those characteristics. And so you might say, OK, you know, like my father's really patient, I look up to him for that. Keith is very strategic when it comes to building businesses. OK, I'm going to come up to that. And so one of that really inspired me to do is to seek a lot of mentors, but not just mentors that I would, you know, call once a month and ask, hey, can you give me some advice about x, y and z? But the just sort of build this whole plethora of folks that I truly call friends first. And then they would ultimately the ones that drove a lot of the wisdom that when I was sort of facing a moment, I try to think about, OK, who might have a who might have a good perspective on this one? So Keith, in a lot of ways, really inspired that. But mentorship is such a big part of why I think what got me to where I am today. 

Brendan: I like that concept of it's not an individual, it's multiple people and we all have like it just reminds me we all have strengths. And so it's understanding what are the things you aspire to be and based off of that characteristic? You're kind of matching that competency with that person and building that relationship. 

Hiro: You know whats funny Brendan too, is that sometimes you find things that are where someone might not be very good at math. In fact, you might say, actually, that person is someone I don't want to follow, and that's just as valuable to because you go, OK, that's the kind of leader. I'm not going to be one day when I'm in that position, for example. 

Brendan: I think it's also it's probably also freeing for the mentor knowing that like the weight of expectations. You know, if someone's coming to me and saying, I want you to serve all these different functions for me as opposed to like, hey, I know you're really great at this, and so I love to just focus on that area. I think that allows a lot of freedom and comfort to really understand what the expectations are from that mentor-mentee relationship. 

Hiro: You're so right, Brendan. I mean, nobody, ever nobody out there in this world knows everything about everything. And the likelihood that you, you know that you're going to find somebody that can answer every one of your questions when you face a fork in the road is just zero. And so when you have all these different people that you can look up to, and that's what it's all about. And by the way, sometimes it's people that you don't ever personally know. It might be someone that you write about or you have seen in the news and you go, man, you know, that's I really have heard a lot about their leadership style. That's something I look up to. You know, Steve Jobs is someone, right? His ability to just be innovative. My goodness, I would love that thinking. But from what I've read is, you know, maybe his leadership style is a little bit more abrasive than I might choose to live. And so it doesn't always have to be necessarily somebody that you personally know, although that's oftentimes a good one. But sometimes the public folks are just as valuable, too. 

Brendan: That's great. And so I think naturally, as you are being mentored by someone and you mentioned there's multiple people, but I know Keith has been instrumental to you. There's probably a natural desire to want to pay that forward. And so how in light of what you've experienced and how that's benefited you professionally and personally, what are you doing now as it relates to giving back as on that paradigm? 

Hiro: You know, funny enough, Brendan, I had this conversation about a week ago with one of our salespeople here at prefect who's getting ready to be promoted. You know, prefect, we firmly believe about giving people a chance to get promoted from within. It's oftentimes where we'll look. And one of the questions he asked is, hey, you know, I really get ready for this next role in my life as a sales leader. You know, I'm really trying to find some mentors, you know? Do you have any suggestions and, you know, sort of goes, would you be OK being a mentor? Like, Oh man, I hope I'm on your list. You got it. You know, you can count on me being a mentor. One of the pieces of advice I gave him was that it's not about making sure that, you have this transactional once a month check in. Now I do have some folks that I do have the blessed opportunity where they do want to hear what I, you know, my opinion and advice, and we do have scheduled calls and I love that. And it's been great and to see them flourish in their career. But if I had one of them actually just became a chief of staff, so we had a lot to talk about. So as much as I can, lending my experience to somebody is certainly what it's all about time willing, but also, you know, when it's other ceos, SROs that are building their company, trying to go international and saying, hey, what do you think about this? I am all for that. But I only ask, is that, hey, sometimes it's tough to stick to this like once a month or once a quarter schedule. Just if you have a question, feel free to ping. I would love to help out, and that's one of the things that's really been transformative. So that it's not just this one way know. Once a month I have to prepare and they have to come up with questions, but it's very organic, and that is what's made these mentorships today that then I have the blessing to be a mentor on really blossom and very meaningful. 

Branden: Yeah, I think it's a good segue way to into we talk about what makes a characteristic of a good mentee. And you talked a little bit about earlier, the friends first mentorship, second, you've already tried to unpack that a little bit, but let's talk about a little bit further in terms of what should the expectations be going into these type of days or relationships? So like, what should the expectations be on both sides in your mind? Who's driving that and how do you kind of agree upon this like you told me, even cadence? This is an interesting topic of what the expectation should be. 

Hiro: Absolutely And I love that, right? I think I'm going to come out with a blog that's called friends first, mentorship second. It really is all about having to build this just natural relationship. And then when the time is needed, then you have somebody a friend that you can. Call in and ask for advice. I will say, though, at the end of the day, one of the things that's really important to me as a mentor is that I truly, really believe the common denominator behind every single mentee is that they're coachable. If someone's willing to say, hey, I have room for improvement, hey man, any mentor would love to take them on. But it's when somebody thinks that they know everything well, then they don't need mentorship, apparently. But I will also add that being able to have somebody you can call on is just the greatest. I'll give you an example. When I was in tech and I was contemplating whether or not to join the State Department other than JCC being really inspirational. At the time, I said, man, who can I call? And I ended up calling two of these very well established ones, and executive and one is former very high ranking military general. And I said, hey, both of you have served in the government and in the private sector. I'm contemplating going into the public sector. Do you mind if I just pick your brain? It was funny because the general goes, well, here, I'm obviously going to tell you to go serve your country. But yes, let's have a conversation. But it was helpful because at the time they were the, you know, I knew, OK, I can call on somebody that would have a very specific perspective on this very unique moment in my career. And I was able to do that because, you know, I built relationships, a friendship with them. And so I really would. Just my advice to anybody who's out there looking for a mentor is certainly, you know, be very intentional about it, but make sure that it's not a transactional relationship that you really are just building a relationship first. And then ultimately, when the time comes, you have a, you know, you can ask someone when it makes sense and as much as you can, it's sometimes hard and see if you can make it a two way street. How can I help you? Most of the time the mentor is going to go, hey, just helping you is enough for me, but just throwing it out there proves to them that this is not just I take and you give kind of relationship. And I think that's really important when it comes to this kind of stuff. 

Brendan: Yeah, I love that when you talk about coaching ability, I think about humility. And then there's also the component like there is, I think to your point, there's an authenticity when you talk about intentionality of like, what is your what is your true desire of this? Is it for the relationship and building a friendship? Or is it to get something from somebody? And that's a very different dynamic. It sounds like there's also an aspect of being like you mentioned in that general example when you're signing the government or tech like you also, you also had to be proactive and make the ask like meaning the mentor is not going to likely solicit, hey, do you want to be a mentee of mine? So like, how do you what would you encourage our audience as it relates to that in terms of how and when to make the ask? 

Hiro: Absolutely it's this idea of being intentional about it. You have to sort of make the decision that, hey, I'm not going to be afraid or I have enough humility to know that I don't know everything and I'm going to be OK with that. And then I think that carries a lot of weight when someone comes up to you and goes, hey, I'm really need some help on this question. I don't know enough about it. I tell you that carries itself. So highly, you know, in my eyes, when somebody asks, you know, for mentorship. So, you know, I think that humility is going to be key. The intentionality of saying, hey, I'm going to try to seek somebody that might have that answer. And you know, what's so great is that people are most of the time willing to help out. So, you know, don't be afraid to ask. As you said, there's really the key piece here. 

Brendan: Yeah, I think there's also this paradigm or paradox rather of weakness can be viewed as a strength. And to what you were just explaining is if you are coachable and you're humble, people gravitate to that. 

Hiro: So when I was at the state department, you know, I was joining into a world that I had nothing. I knew very little about. And there are Foreign Service officers over there and diplomats that have made a career out of this. And while I might have come in and Keith and I have came into this role that we were very blessed to do, the only way that you survive in this major bureaucracy is you have to be OK with understanding, hey, how do I get things done around here? You got to shake up feathers a little bit, but not being afraid to ask and really solicit advice from every single rank from the top. And, you know, in the White House all the way down to sort of the very early, you know, sort of earlier in the career diplomats, if you will like man asking everybody some questions and advice, that's another way that somebody could be a mentee, no matter how highly ranked you are in your role or at your company. Being a mentee is universal and should be timeless.

Brendan: I love that it's a final thought. It's not exclusive. It's really available to everybody, regardless of what stage you're at. And it's funny when I was doing actually on somebody else's podcast and they were asking me about those inflection points for my career. And it wasn't the role. It was the people that I was a part of and like what I immediately thought I was individuals. And I think that's probably pretty consistent with as just that. That's what you think about. And as it relates to what's helped you and propelled you as a people surround yourself with and those are your learning from. So here, thank you for sharing your experience and the value of mentorship, both as a recipient and as a giver, I guess is the right word there. So but here, as we wrap up, what are some practical ways that our audience can engage with you or with Prefect, for that matter? 

Hiro: Yeah, absolutely. So, you know, we're always looking for great, coachable individuals. So if you're interested in learning, you know, for us, we definitely have a culture of not just this idea of mentorship, but learning. Learning is literally one of our core values, so much so that we actually give our employees $1,000 a year to dedicate just to learning. And so whether it's a formal mentorship kind of thing or just reading a book. So here at Prefect, if you're interested, you can always come check us out. We're hiring in a big way. We're scaling up and a fast at a fast rate right now. So check us out there. And then also on LinkedIn, I'd love to hear from folks and, you know, drop a little message. I'd love to connect and support anybody that I possibly can. 

Brendan: All right, Hiro, I really appreciate you stopping by. Thanks for sharing your experience. And if those are folks who are looking for mentorship and a great company, that sounds like we've got a good fit here, so we'll be in touch. Thanks a lot. 

Hiro: Thanks so much, Brendan. 


Pit Stops to Podium: A RevPartners Podcast

On the RevPartners Podcast, we talk to executives who have competed and won, accelerating their companies from High Growth to High Scale. Hosted by RevPartners Co-founder and CEO, Brendan Tolleson. Take some quick notes from each week's "Crew Chief" and then head back to the races!

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