Inside the Ohana

Inside the Ohana: The Value of a Beginner’s Mindset

Episode Summary

Meet Jim Sinai, CMO at Vanilla and former marketing leader at Salesforce. During his 8 years at Salesforce, Jim worked on various businesses including Salesforce Einstein, Salesforce Platform, AppExchange,, and Salesforce Industries. In this episode, Jim shares the lessons he’s learned from his biggest projects at Salesforce and how keeping a beginner’s mindset has helped him succeed.

Episode Notes

Meet Jim Sinai, CMO at Vanilla and former marketing leader at Salesforce. During his 8 years at Salesforce, Jim worked on various businesses including Salesforce Einstein, Salesforce Platform, AppExchange,, and Salesforce Industries. In this episode, Jim shares the lessons he’s learned from his biggest projects at Salesforce and how keeping a beginner’s mindset has helped him succeed.


“If you’re not rooted in the concept of a beginner’s mind, your projects will fail.”

Episode Timestamps:

*(1:56) - Ohana Origins: Meet Jim Sinai 

*(7:29) -  What Does the Ohana mean to Jim?

*(11:53) - What’s Cooking: Jim’s Current Role at Vanilla

*(19:45) - Future Forecast: What’s in Store for the Salesforce ecosystem?

*(19:07) - Advice for Aspiring Marketing Leaders

*(22:22) - Lightning Round!


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Episode Transcription

[00:01:35] Dan: Welcome to Inside the Ohana. I'm Dan Darcy, Chief Customer Officer at Qualified, and today I'm joined by my great friend Jim Sinai. Jim, how are you doing today? 

Jim:  Great, Dan. Good to see you too, man. 

[00:01:56] Dan: I want to dive right into our first segment, Ohana Origins. Jim, how did you discover Salesforce and start your journey? 

[00:01:59] Jim: I had known about Salesforce as a company, but I didn't really know much about why I would wanna work there. And two of my classmates from business school, Dave King, Sarah Patterson, both of them were in versions of product marketing at the time, and, uh, I was looking for something to do. I had just left EventBright, and Sarah had convinced me that the role of product marketing at Salesforce. Was the coolest job I could ever have. On top of that, like another friend of mine who's now a big sales executive at Salesforce, was trying to convince me to go to Salesforce. So I had a bunch of friends that were in the Ohana trying to pull me in and that's, that's, that's how I got interested in started interviewing.

[00:02:38] Dan: What year was that? Gimme the details. 

[00:02:38] Jim: Yeah. What was 2011? End of 2010. And Trisha Galman was hiring for a product marketing manager on the jigsaw team. And Jigsaw was the product that eventually became Data dot. You know, I was like, Trisha, you know, I've never done marketing, never done product marketing, but I think this job is something I could do. And I think I interviewed with everybody except you to get that job. I talked to Al Fti, Oriel Kelman, who went on to Amazon, Oracle, and uh, Craig Sw through Trisha made me do like. For assignments together, they, I think everybody was really pulling on it, on it. And another friend of mine who was at Salesforce at the time, Scott Holder was in the background putting the pressure on Craig to be like, You just gotta hire Jim.

[00:03:21] In the meantime, I got an offer from admins group in sales, basically turned back to Craig and Trisha was like, Hey guys, I have this job offer in sales and if you want me a product marketing, you gotta gimme an offer. There was one guy, everyone told me, Take the job in sales and one. Call Tran who's not at Salesforce, He's a venture capitalist, give you the best piece of advice. He's like, Jim, you can always go back to sales. But it's so rare that the door hit, a new department is gonna open and you should walk through that door and see what happens. 

[00:03:48] Dan: And here we are today. So, I mean, it sounds like we've made you run through the gamut. That's pretty awesome. It doesn't surprise me. So marketing manager for jigsaw, What was your initial impression? Like how big was the company at the time? The group? 

[00:04:01] Jim: So yeah, we joined, I joined, it was like 4,500 people, maybe just under, just at a billionaire revenue public. I, you know, I had just left Event Bright where I was employed, number 50, and in my mind I was like, I'm just gonna come to Salesforce for like three years, just hang out, get some, learn something, and then I'll go back to startup.

[00:04:19] And you know, in my mind I was like, it'll be like nine to five job easy. I had no idea what I was signing up for. I think I started week one and flew off to sales kickoff. Week two, I was in New York for a world tour. Week three I was in sales meetings in Spokane and like, I think the best way to describe it is like, Trisha fired me out of a cannon and I have never landed like it. I think I worked harder at Salesforce than at any point in my career and, you know, loved every minute of it. But it was one of those things where like I came in and I, I thought I was just coming in to like, Oh, cuz this, this will be out. Big stodgy corporate job and I'll just, you know, play a role and I didn't realize how fast the company moved and how much it was up to us to keep the pace to drive the base.

[00:05:04] Dan: And how much fun we had too.

[00:05:05] Jim: Oh yeah. Yeah. I mean, like candidly, the reason you stick, I was there total eight and a half years. The reason you, you come back every years because you looked at what you did, You said that was freaking awesome. Where else am I gonna get to do that? 

[00:05:18] Dan: Pulling on that thread, I want you to brag a little, because I know, like you just said, eight and a half years of incredible success during your time at Salesforce, what is the biggest success that you've had while working with Salesforce or really just something that you're proud of?

[00:05:31] Jim: I've done done some launches. I'm proud of launching, Salesforce platform a few times, including Salesforce One platform, the Salesforce Lightning platform. Uh, launch, launch and relaunch. And then of course, I got to be the, I got to lead the team, the launch Einstein, which was, uh, huge feather of my cap. I, you know, all those things were awesome, but the thing that I think I'm proudest about is like the leaders that. Groomed and grew on teams. So if I look at the current, like some of the people that work for me who are now off running, they're, they're running business lines way bigger than anything I've ever managed. People like Ally Witherspoon, those are the, those are the type of people that really like jump out as like the things I'm proud about.

[00:06:13] Dan: I love it. On the opposite side of the spectrum, what would you say your biggest lesson learned is? 

[00:06:18] Jim: I think the two things I, I learned along the way, and I think I learned it the hard way, is like, you gotta, you gotta pay attention to how you leave people. Not just, it's not just about getting the job done. I think early on Salesforce had this cut through cultures like, just get the job done. Don't really like, you know, don't care if you leave bodies. And I learned, you know, the hard way that like, that that doesn't scale and that's not actually not the best way to, to work.

[00:06:41] It is an effective way, but it's not the best way to work. And then I think the other thing is like, if you're not rooted in, in the concept of a beginner of mine, your projects will fail. And I, I, I think I once spent $250,000 on a video that was 86, never saw the light a day. And part of that was, it just wasn't a, like, we just, it was a very traditional approach to video and I did step back and say, Okay, this is a new thing. How would we do this differently? 

[00:07:07] Dan: Just pulling on also on that thread like, You know, the beginner's mind. If you could go back to, you know, Jim, that's just starting out with, as the marketing manager or you know, jigsaw at the time, what advice would you give yourself? 

[00:07:19] Jim: The best advice that I could give myself or, and really anyone who's who's starting at Salesforce is pay attention to the people you work with and really realize that you can't do it alone. I think that the young Jim tried to hero everything, put everything on his shoulders, and just get it done as cheesy as multipliers. Is, it really is true. If you could multiply people, you're gonna get so much more than you think.

[00:07:44] Dan: So I wanna ask you something cuz I asked this of every one of my guests, and that is, what is the meaning of Ohana to you? Because everyone describes a little bit differently, but how would you describe the ohana?

[00:07:55] Jim: Yeah. You know, I don't have like a pithy one word answer. I think of the Ohana as as employees, partners, customers, and even prospects. It was a word that was born outta necessity because you can't say those four things and actually have it mean anything because everyone can say, Oh, our employees or customers are prospects.We needed something that was like, these are our people, not more people. This may not be a politically correct thing to say, but I'll say it anyway. We just finished the high holidays. I'm, I'm Jewish. And we talk a lot about the tribe of Judaism, which is more than just the people that are religious and Judaism.

[00:08:29] It's the people that have all sort of descended from the people that were lost in the desert. Every group and every organization needs a name for their people, you know? And Mark really said, We need a way to name our people so that our people are, our people can identify our people, and. I think that's why Ohana stuck.

[00:08:48] Dan: What does being part of the Ohana mean to you?

[00:08:50] Jim: I mean, for me it's, it really does feel like of family, like very practically speaking, I am in touch with most of the people that I've worked with. I actually run a Slack group for alumni of Salesforce marketing and we're, you know, we're at like constantly sharing tidbits with each other. And to me it really is that family, those people that always be there for you when you have a question or you need help.

[00:09:12] Dan: So, before we get into our next segment, Jim, are there any special stories or oh Hana moments that are a little behind the scenes that you would wanna share?

[00:09:19] Jim: There's, there's a few, but I think the one that like, that's forefront and most relevant to everyone is like what it took to actually to introduce a character, which is Salesforce Einstein. 

[00:09:31] Dan: What do you mean by a character? Tell, tell everyone.

[00:09:34] Jim: Salesforce is unique in that it has mascots and you know, all credits to Adam Salman, Sarah Franklin, and Chris Warte, and Dominique the designer who invented these characters. So the four had ever really brought the Trailhead characters to life. And the year or two later when we were launching the Einstein platform, we not only had to figure out what Einstein meant, like what does it mean to launch AI in Salesforce? What it, what is it, what does it not, but then how do we talk about it?

[00:10:03] And then how do we. Brief light skin to this. You know, this person who, unlike the other Salesforce characters, is, is not a person, you know, a pastor and Cody the Bear. They're not historical people. That here is Einstein, who actually has a whole organization that manages his licenses, his rights, and so we had to like birth a character, but then we also had to manage this broad behind the scenes of like everything we were doing, we had to get rights clearance on, we had to make sure that it works for our brand, but also work for the brand of, of the organization managing Einstein brand globally. I spoke to lawyers, marketers, designers really took it to partners. It took a true aha to actually bring Einstein to life.

[00:10:46] Dan: Um, I mean, I I mean that is a true Ohana moment cuz if you think about it… you had to basically match up the persona – and I'm just gonna summarize – the persona of like AI in technology to actually Albert Einstein's true brand and kind of mesh those two things together in a way that was, that met both, both needs.

[00:11:08] Jim: Just so the record states that it's actually out in public record, this is Mark's idea. I actually, I actually had to unfortunate job of like presenting some third party research We did that like it wasn't a great name and got kicked outta the meeting. ? Yeah, . I came back next week and pitched it like it was my idea and he like, see, isn't that a great idea? So, I mean, look at that. That's awesome. I, I think, you know, part of that too is, Understanding when customers are actually right and wrong. And Mark had a vision for like how to personify what was AI and how to make it fun and playful. And he left it to us to, to bring it to we. But yeah, I'd, I would be lying if I had the answers if it wasn't that entire Ohana.

[00:11:53] Dan: Let’s get into our next segment. What's cooking? So Jim, you're now the CMO at Vanilla. I want you to talk a little bit about vanilla, but also talk about how you got to where you are now and what your journey has been like to get to the current role.

[00:12:14] Jim: Leaving Salesforce is, is a hard decision. I think everybody has to wrestle with when's the right time and, and, and why are you leaving? For me, it was really much about wanting to learn. I felt like my learning opportunities were getting less and less based on the paths in front. And this amazing company outta Santa Barbara that did construction software came along and they said, Hey, we have an opportunity for you to run our global marketing.

[00:12:39] It's a hundred person team. We're gonna go public in a year or two. And I really wanted the experience of leading a large team at scale globally and taking them public. And I got to do that at Procore. And then when I stepped out of pro. I started doing some inventory on what I had accomplished in my career, what I wanted to accomplish, and I really realized that I, I wanted to go and seal what it's like to build at a startup.

[00:13:04] I don't think that, you know, part of me is like, I had to think about did I wanna start a company and I thought about that, but I didn't have a great idea and so, I started talking to companies and Villa Emerges a really interesting company because I had just finished doing some estate planning with my, for my family. I have three kids and like I found out one of them wasn't even in my trust documents and to go get all that stuff in order. And as I was going through it, I just realized like this whole process is so broken and I go talk to these lawyers that. Legal documents that nobody understands and it's not integrated with my financials.

[00:13:36] And so how do I know, how do I think about how my estate actually looks and how, you know, what I should be leaving to my kids and what I should be leaving their charitable causes that I care about. You know, I think Covid also compounded on that this need to like, for everyone to think about what happens if, if something happens to. And furthermore, the, the leadership team that had come together was like a rockstar leadership team. So I, that's what threw me to vanilla and I really like wanted to step in and build a marketing team and culture from scratch. 

[00:14:05] Dan: Yeah. So tell us a little bit more about Vanilla. 

[00:14:05] Jim: Vanilla is a estate planning as a service software. Uh, see that's the SaaS mentality. Really what we're doing is we're selling software to financial advisors to help them facilitate and simplify the conversation of estate planning. Everyone goes through phases in their life. When things change, they, they get married, they have kids. They hopefully never divorce, but sometimes they divorce. It's a really hard thing to talk about because all this stuff gets buried in legal documents. So we're actually using the power of, of design and software to bring all of that information into a single place where you can talk about, you know, how your estate should look like with your advisor and with your estate attorneys and tax tax professionals.

[00:14:47] So we think this is a huge market. We think that it's only gonna get more important. As tax laws change, and quite frankly it's, it's a category creation market cuz no one's actually doing this right now. Advisors are basically doing it on PowerPoint and a little bit of Excel spreadsheet and some of them aren't doing it that well.

[00:15:06] Dan: Or they refer you to some estate planning lawyer.

[00:15:09] Jim: Yeah. Then it's like, then you're paying $1,500 in legal fees and you get back a document that gets buried in your file cabinet. Yeah. Yeah. You know? Anyone who's ever had a, a parent or a loved one and pass away knows how hard it is to figure out what is where, what, what their letter of wishes are. And candidly, it shouldn't be that hard. And that's why we call it vanillas. We, we think that it could be simplified. 

[00:15:32] Dan: So you spoke about beginner's mind earlier, and Jim, I want you to talk about, you know, what challenges are you seeing now at vanilla that you're applying what you've learned from Salesforce to these challenges?

[00:15:40] Jim: The number one thing I learned at Salesforce is a bias to action and urgency. Right? And a lot of that is that, you know, Salesforce, as large as it ever was, could always just rest and say, Hey, we're Salesforce. This is how we do it. But. There was always this need to reinvent and this need to step back and kind of like looking at yourself with that beginner's mind and say, Nope, we're gonna change this. We're gonna, we're gonna throw that out, or we're gonna evolve and, and give yourself permission to walk away from the past. I think when you're building a, you know, we're a very early stage startup right now, and part of what we need to do is be able to move forward at pace and a velocity and not get too weighed down to any one thing. The other thing that Salesforce instills in you is a bias – what was the term, Dan? It was tactics, not strategy. 

[00:16:31] Dan: Tactics dictate strategy.

[00:16:32] Jim: Tactics dictate strategy. Exactly. And part of that is, you know, I can spend my entire time thinking about what to do, but the reality is you just gotta go do stuff. It's gotta be, you know, it's like, I love the book ‘Thinking in Bets’ because you want to know what your expected return on your tactics should be, but you, you have to go do tactics and figure end. Those tactics turn into the strategy once they start working. But it's, it's for every minute you spend doing strategy. You're wasting minutes doing tactics. And if you're, you know, directionally right, and you do the right tactics, you're, you're gonna get to the right answer.

[00:17:06] Dan: And so what challenges at vanilla are you applying these strategies to? 

[00:17:09] Jim: We're trying to create an a category, which means go out and, and build demand for something that doesn't really, where demand doesn't exist. And so part of that, we have to go out and tell a narrative about a problem state that people may not be aware of. And I think if you think about the, the method of how Salesforce did this is they just went on a road show and they just took the message to the people. And so one of the things that we're working on right now, we're sort of like in the, the genesis of, of building and testing the message.

[00:17:40] And then next year our plan is really to take it to the road and just, just deliver it to as many people as we can and really evangelize the problem, knowing that if we do stellar job of evangelizing the problem, we're gonna win. And, and that's really something we learned from Salesforce. The other thing that I think we're applying, we're startups. So we really, you know, this is also something I adapt from Craig, the founder, have qualified is you really wanna look bigger than you. And there's a lot of things that you could do as a smaller company to look like a bigger company, whether it's content on your website, the way you, you know, create and deliver videos. And even the, the way you show up in your, sort of, your customer conversations. All those things are things you can definitely do to level how you appear. So those are a handful of things, but I, I really think that it all comes back down to just being curious about the ecosystem you play. Not being too wet to any one thing and moving quick.

[00:18:35] Dan: So what is next for you and how are you shaping the future?

[00:18:39] Jim: We've rebuilt the product that we're relaunching this month, so you can imagine that like when you relaunch a product, you've gotta step back and shed all your old marketing literature and all your old sales habits and launch it out and because we're an early company, we have a, you know, just a handful of sellers, you know, we have an opportunity to really step back and say, How do we wanna build a go to market potion that's gonna scale the way we want to versus inheriting one that's like status quo. I think a lot of marketers, a lot of people walk into companies and they think things are the way they are and it's hard to change that. And I think that, you know, when we look at building how vanilla, the product, vanilla and how we actually bring it to customers, one of the things that I am asking literally every day is like, if we were buyers of this software, What would we want to know before we talk to the company?

[00:19:28] What would we want to know? What would we want to experience and, and believe to be true before we even engaged? And I think that that is so much of the future of how software is being built and sold is, is building it where the, the go to market team is there to serve the buyer, not just to sell.

[00:19:45] Dan: So let's get into our final segment, The Future Forecast. What do you envision as the future of the Salesforce ecosystem? 

[00:20:02] Jim: I think it's all, I get bigger. I mean, Salesforce is a runaway train. I don't see how it stops. I don't see how it stops growing. The ecosystem could probably best be described now and forever as an ecosystem of ecosystems. Mm-hmm. , because you're gonna have an ecosystem around sales technology, service, technology, and ecosystem around marketing technology, an app dev ecosystem.

[00:20:25] Dan: Yeah, I mean we just had, we just had Dreamforce, you know, a week ago, and what's interesting about that, just noticing that, is that there were many other sub conferences that happened around Dreamforce so that the people who were at Dreamforce could attend those sub conferences. 

[00:20:42] Jim: Yeah, I think the ecosystems are gonna keep growing. I also think it's gonna continue to be more and more democratic. I. In the past, you've seen ecosystems where there's like five or six, five or six winners in the ecosystem. And I think the one thing, I've worked on app exchange for two years at Salesforce, and the one thing that it's so cool to see is how somebody does little companies like Own Backup that started as little things on the app exchange are now, you know, A hundred million plus businesses.

[00:21:07] Dan: Can you give us a prediction of what Salesforce looks like in the future? 

[00:21:11] Jim: I mean, the only comparable prediction would be like friendly version of Microsoft . Like, you know, you're getting bigger and bigger, bigger, and the need for growth is insatiable. And the need for, you know, serving the customer is insatiable. As long as the world exists to sell things to customers, sales forces can exist to sell crm. 

[00:21:33] Dan: What advice do you have for any aspiring marketing leaders out there? 

[00:21:35] Jim: It all begins and starts with the message. And ends with the message. Honestly, there's, there's so much talk right now about how data is transforming marketing. True. There's so much talk about how technology is transforming marketing. True, but these cycles always happen. And I think the people that are the best marketers and the, and the people that have really been able to grow their careers are the ones that know what the message is and not just know what it is, but they know how to communicate, they know how to communicate it internally.

[00:22:04] They know how to communicate it externally, and they know how to get everyone fired up about what the oh, about, what to say and when. And that's, to me, I think that that's, any marketer that wants to go beyond a sort of a director level at any company has to be stellar. Being outside, leading on what? What is the message?

[00:22:22] Dan: You know, you're speaking to my heart, Jim, so before letting you go, let's have fun with a quick lightning round. You ready for this? 

[00:22:29] Jim: Oh yeah.

[00:22:38] Dan: What's your favorite Salesforce product?

[00:22:40] Jim: I would call it, but it's probably lightning now. Cause , we've rebranded it. Yeah.

[00:22:46] Dan: Favorite Salesforce character?

[00:22:48] Jim: Einstein. That's an easy on. Come on. 

[00:22:51] Dan: Yeah, totally. Favorite brand of anything besides Salesforce? 

[00:22:53] Jim: You know, we used to ask this question when we interviewed people, like you know, who's doing good positioning and you're not allowed to say Apple? Yeah, I'm pretty, I'm pretty into Apple right now. I don't know favorite brand. I think Topo Chito has like nailed bubbled water.

[00:23:09] Dan: I don't know how that has come up, but you're absolutely right. What about a favorite brand for your kids?

[00:23:14] Jim: I mean, I am living in Pokemon right now, like head to toe Pokemon. Is it bit like Pokemon? Go Pokemon? You know the game, you name it. Like they've done a good job of building something that boys and girls latch on to. 

[00:23:28] Dan: Yeah. Secret skill not on the resume.

[00:23:32] Jim: Cooking. Anytime you guys wanna come for dinner, love to cook for you.

[00:23:35] Dan: I'm in. You just won front row seat tickets to your dream event. What is it?

[00:23:40] Jim: I'm gonna underline the word dream cuz I don't know if this is ever gonna happen again. Oakland Bay and Game seven for the World Series. I mean, first of all, Are they even gonna be in Oakland? Yeah. And then second of all, like, you know, can you get to game seven without the, without the, the payroll budget to compete with?

[00:23:59] Dan: I love that answer cuz that's the most creative answer I've heard since, so that's awesome. So Jim, this has been so much fun, but before I let you go, will you let the listeners know where they can find you? And is there anything else you'd like to plug today?

[00:24:10] Jim: Best way to find me. I'm on linked. Feel free to reach out. What would I wanna plug? Let's plug this podcast because I am honored to be on this, on this lineup with so many greats that you've lined up, Dan. So thank you for thinking of me. Thank you for having me. I'll leave this. Everybody should, you know, regardless of whether you have $10 to your name or a hundred million dollars your name, like go write down a will. Like what's gonna happen to you if something happens? We just got through a scary three years in the country and everyone learned that they weren't invisible. Do yourself saver and go, Go. Make sure your loved ones know what to do in case of emergency.

[00:24:45] Dan: That's so true. Thanks, Jim, and thanks for coming on the podcast. It's an honor to have you. 

[00:24:50] Jim: Yeah. Thanks for having me, Dan. Thank you.