The Value of a Beginner's Mindset
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, Data.com, and Salesforce Industries.
(upbeat music)
- Welcome to Inside the O'Hanna.
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?
- Great to have you.
Good to see you.
- Good to see you too, man.
I wanna dive right into our first segment, O'Hanna Origins.
Jim, how did you discover Salesforce and start your journey?
- 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,
I believe Sarah's been on the show,
has actually took jobs there,
doing both of them were in versions
of product marketing at the time.
And I was looking for something to do.
I had just left Eventbrite and Sarah convinced me
that the role of product marketing at Salesforce
was the coolest job I could ever have.
On top of that, another friend of mine,
Adnan Chodry, who's now a big sales executive at Salesforce,
was trying to convince me to go to Sales.
So I had a bunch of friends that were in the O'Hanna
trying to pull me in.
And that's how I got interested in starting an interview.
- Well, what year was that?
Give me the details.
- That was 2011,
end of 2010, and Tricia Gilman was hiring
for a product marketing manager on the Jigsaw team.
And Jigsaw was a product that eventually became Data.com.
And I was like, Tricia,
I don't think I've never done marketing,
never done product marketing,
but I think this job is something I could do.
And man, she must've made,
I think I interviewed with everybody,
except you, to get that job.
I talked to Al Faustione,
Ariel Kellman, who went on to Amazon,
Oracle, and Craig Swensrude,
Tricia made me do like four assignments together.
I think everybody was really pulling on it.
And another friend of mine,
who was at Salesforce at the time,
Scott Holden was in the background,
putting the pressure on Craig to be like,
"You just got to hire Jim."
In the meantime, I got an offer from Adnan's group in Sales.
And so I basically turned back to Craig and Tricia.
I was like, "Hey guys, I have this job offer in Sales.
"And if you want me in product marketing,
"you got to give me an offer."
And there was one guy,
everyone told me to take the job in Sales.
And one guy, Kelly Tran, who's not at Salesforce,
he's a venture capitalist,
giving the best piece of advice,
he's like, "Jim, you can always go back to Sales,
"but it's so rare that the door into a new department
"is going to open and you should walk through that door
"and see what happens."
And here we are today.
So it sounds like we made you run through the gamut.
That's pretty awesome.
It doesn't surprise me.
But what, so marketing manager for jigsawdata.com,
what was your initial impression?
How big was the company at the time, the group?
- So yeah, I joined, I joined those like 4,500 people,
maybe just under just a billion in revenue, public.
And I had just left if I'm bright
where I was employee number 50.
And in my mind, I was like,
"I'm just going to come to Salesforce for like three years.
"Just hang out, get some, learn something
"and then I'll go back to startups."
And 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 and spoken at.
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 loved every minute of it.
But it was one of those things where like,
I came in and I thought I was just coming in to like,
oh, this will be a big, stodgy corporate job
and I'll just play a role.
And I didn't realize how much,
like how fast the company moved
and how much it was up to us to keep the pace,
to drive the pace.
- And how much fun we had to.
- Oh yeah, yeah.
I mean, like candidly, the reason you stick,
I was there a total eight and a half years.
The reason you come back every year
is because you looked at what you did
and you said, that was freaking awesome.
Where else am I gonna get to do that?
- Yeah, exactly.
Well, like 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?
- I've done some launches I'm proud of,
launchdata.com, Salesforce platform a few times,
including Salesforce One platform,
the Salesforce Lightning platform.
- Launch, launch and relaunch.
- Yeah.
- And then of course, I got to lead the team
to LaunchDinestein, which was a huge feather in my cap.
All those things were awesome,
but the thing that I think I'm proudest about
is like the leaders that I groomed and grew on teams.
So if I look at the current, like some of the people
that worked for me who are now off running,
they're running business lines way bigger than anything
I've ever managed, people like Ali Witherspoon,
those are the type of people that really like
jump out as like the things I'm proud about.
- I love it.
On the opposite side of the spectrum,
what would you say your biggest lesson learned is?
- I think the two things I learned along the way,
and I think I learned it the hard way is like,
you got to pay attention to how you leave people,
not just about getting the job done.
I think early on, Salesforce had this cut through culture
was like, just get the job done,
don't really like, don't care if you leave bodies.
And I learned, you know, the hard way that like that
doesn't scale and that's not actually not the best way
to work.
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 the concept of a beginner's mind,
your projects will fail.
And I think I once spent $250,000 on a video
that was 86, never saw the light of day.
And part of that was it just wasn't a like,
we just, it was a very traditional approach to video,
and I didn't step back and say, okay,
this is a new thing, how would we do this differently?
- 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 data.com
as a marketing manager, or, you know, jigsaw at the time.
What advice would you give yourself?
- The best advice that I could give myself
or really anyone who's starting at Salesforce is,
you know, 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.
And you really, you know, like, as cheesy as multipliers
is, it really is true.
If you can multiply people,
you're gonna get so much more than you think.
- So I wanna ask you something,
'cause I asked this of every one of my guests,
and that is, what is the meaning of "Awhana" to you?
Because everyone describes it a little bit differently,
but how would you describe the "Awhana"?
- Yeah, you know, I don't have like a 51 word answer.
I think of the "Awhana" as employees, partners,
customers, and even prospects.
And, you know, I think it was a word
that was born out of necessity
because you can't say those four things
and actually haven't mean anything
because everyone can say, "Oh, our employees,
our customers, our prospects."
Like, and we needed something that was like,
"These are our people, not your people."
And so, you know, just in the same way,
this may not be a politically correct thing to say,
but I'll say it anyway.
You know, like, we just finished the "High Holidays"
on Jewish, and we talk a lot about the tribe of Judaism,
which is more than just the people
that are religious in Judaism.
It's the people that have all sort of descended
from the people that were lost in the desert.
And 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
and we can identify our people."
And that's, I think that's why O'Hanna stuck.
- What does being part of the O'Hanna mean to you?
- I mean, for me, it really does feel like a 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 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.
- So before we get into our next segment, Jim,
are there any special stories or O'Hanna moments
that are a little behind the scenes
that you would wanna share?
- There's a few, but I think the one that like,
it's forefront and probably most relevant to everyone
is like what it took to actually,
to introduce a character, which is Salesforce Einstein.
- What do you mean by a character?
- Salesforce is unique that it has mascots.
And all credit to Adam Selvin, Sarah Franklin
and Chris Duarte and Blinking on the designer's,
Dominique, the designer, who invented these characters.
So before that, I really brought the trailhead characters
to life and a 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 is it, what is it not?
But then how do we talk about it?
And then how do we breathe life into this
this person who, unlike the other Salesforce characters,
is not a person, Astro and Cody the Bear,
they're not historical people,
but here is Einstein, who actually has a whole organization
that manages his licenses and his rights.
And so we had to like, bur the character,
but then we also had to manage this broader,
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 works for the brand of the organization
managing the Einstein brand globally.
And it was, you know, I spoke to lawyers, marketers,
designers, really took a two,
the partners, took a true Ohana,
actually bring Einstein to life.
- I mean, that is a true Ohana moment,
'cause 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 met both needs.
I mean, that's definitely really--
- And like, just so the record states,
and it's actually out in public record,
this is Mark's idea.
I actually had the unfortunate job
of like presenting some third party research we did,
that like it wasn't a great name,
and got kicked out of the meeting.
And I came back next week and pitched it like it was my idea,
and he was like, "See, isn't that a great idea?"
- So I think that's awesome.
- I think, you know, part of that too,
is like understanding when customer,
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 bring it to life,
but yeah, I would be lying if I had the answers.
If it wasn't that entire Ojada,
it wouldn't have come out the way it did.
- 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 that current role.
- Leaving Salesforce is a hard decision.
I think everybody has to wrestle with
wins the right time, 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 of me.
And this amazing company out of Santa Barbara
that did construction software came along,
and they said, "Hey, we have an opportunity
"for you to run our global marketing.
"It's a 100 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 Procore,
I started doing some inventory
on what I had accomplished in my career
and what I wanted to accomplish.
And I really realized that I wanted to go
and feel what it's like to build at a startup.
I don't think that, you know, part of me is like,
I had to think about did I want to start a company,
and I thought about that, but I didn't have a great idea.
And so I started talking to companies,
and Vanilla Emerge is a really interesting company
because I had just finished doing some estate planning
from my family.
I have three kids, and like, I found out one of them
wasn't even in my trust documents.
And, you know, I had 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 do legal documents
that nobody understands,
and it's not integrated with my financials.
And so how do I know, how do I think about
how my estate actually looks and what I should be leaving
to my kids and what I should be leaving
to charitable causes that I care about?
And, you know, I think COVID also compounded on that,
this need to like, for everyone to think about
what happens if something happens to you.
And furthermore, the leadership team that had come together
was like a rockstar leadership team.
So that's what drew me to Vanilla,
and I really like wanted to step in
and build a marketing team and culture from scratch.
- Yeah, so tell us a little bit more about Vanilla.
- Vanilla is estate planning as a service software.
See, that's the SaaS mentality.
And 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 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.
And so we're actually using the power of design and software
to bring all that information into a single place
where you can talk about how your estate should look like
with your advisor and with the state attorneys
and even tax professionals.
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 a category creation market
'cause no one's actually doing this right now.
Advisors are basically doing a PowerPoint
and a little bit of Excel spreadsheet
and some of them aren't doing it that well.
- Or they refer you to some estate planning lawyer.
- Yeah, and then you're paying $1,500 in legal fees
and you get back a document that gets buried
in your file cabinet.
- You know, like anyone who's ever had a parent
or a loved one pass away knows how hard it is
to figure out what is where,
what their letter of wishes are.
And candidly, it shouldn't be hard.
And that's why we call it vanilla
is we think that it can be simplified.
- 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?
- So I think that the number one thing I learned
at Salesforce is a biased action and an 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 look at yourself
with that Beginner's Mind and say,
"No, we're gonna change this,
we're gonna throw that out or we're gonna evolve
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 velocity and not get too wed down
to like any one thing.
The other thing that Salesforce instills in you
is a bias, what was the term then?
Those tactics not strategy?
- Tactics take strategy.
- Tactics take 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 have to do it,
part of my French, you just gotta go do stuff.
It's gotta be, you know, it's like,
I love the book Thinking and Bets
because you wanna know what your expected return
on your tactics should be,
but you have to go do tactics and figure,
and those tactics then turn into the strategy
once they start working.
But it's for every minute you spend doing strategy,
you're wasting minutes doing tactics.
And if you're, you know, directionally right,
you're gonna be, and you do the right tactics,
you're gonna get to the right answer.
- And so what challenges at Vinala,
are you applying these strategies to?
Like how are you thinking about it?
- Well, right now we're trying to,
we're trying to create a category,
which means go out and build demand for something
that doesn't really, where demand doesn't exist.
And so part of that is, 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 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 genesis
of building and testing the message.
And then next year our plan is really to take it to the road
and just deliver it to as many people as we can,
and really evangelize the problem,
knowing that if we do a stellar job
of evangelizing the problem,
we're gonna win, and that's really something
we learned from Salesforce.
The other thing that I think we're applying,
we're startups, so really, this is also something
I got from Craig, the founder of Qualified,
is you really wanna look bigger than you are.
And there's a lot of things that you can do
as a smaller company to look like a bigger company,
whether it's content on your website,
the way you create and deliver videos,
and even the way you show up
in your customer conversations,
all those things are things you can definitely do
to up level how you appear.
So those are a handful of the things,
but I really think that
it all comes back down to just being curious
about the ecosystem you play in,
not being too wed to any one thing and moving quickly.
- So what is next for you,
and how are you shaping the future?
- We've rebuilt the products 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 just a handful of sellers.
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?
And I think a lot of marketers
and a lot of people walk into companies
and they things are the way they are,
and it's hard to change that.
And I think that when we look at building
how 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 wanna know before we talk to the company?
What would we wanna know?
What would we wanna experience and believe to be true
before we even engaged?
And I think that that is so much in the future
of how software is being built and sold
is building it where the go-to-market team
is there to serve the buyer,
not just there to sell.
- So let's get into our final segment, the future forecast.
What do you envision as the future
of the Salesforce ecosystem?
- I think it's only getting bigger.
I think, I mean, Salesforce is a runaway train.
I don't see how it stops.
I don't see how it stops growing.
I think the ecosystem could probably best be described
now and forever as an ecosystem of ecosystems
because you're gonna have an ecosystem around sales,
technology, service technology,
and ecosystem around marketing, technology,
an app dev ecosystem.
- Yeah, I mean, we just had Dreamforce 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.
- Yeah, I think the ecosystem's gonna keep growing.
I also think it's gonna continue to be more and more
democratic, I think in the past, you've seen ecosystems
where there's like five or six winners in the ecosystem.
And I think the one thing,
I worked on AppExchange 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 AppExchange are now $100 million plus businesses.
- Can you give us a prediction of what Salesforce
looks like in the future?
- I mean, the only comparable prediction
would be like a friendly version of Microsoft.
Like, you're getting bigger and bigger and bigger
and the need for growth is insatiable
and the need for serving the customer
is insatiable and as long as the world exists
to sell things to customers,
Salesforce is gonna exist to sell CRM software.
- What advice do you have for any aspiring
marketing leaders out there?
- I think it all begins and starts with the message
and ends with the message, honestly.
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 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 internally,
they know how to communicate externally
and they know how to get everyone fired up
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
at being out front leading on what is the message?
- 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?
- Oh yeah.
- Okay.
What's your favorite Salesforce product?
- I wouldn't call it force.com,
but it's probably lightning now.
- It's just, we've rebranded it.
- Yeah.
Favorite Salesforce character?
- Einstein, that's a key me.
- Yeah, totally.
Favorite brand of anything besides Salesforce?
- Ooh.
- You know, we used to ask this question
when we interviewed people, like who's doing Mark,
you know, who's doing good positioning
and you're not allowed to say Apple.
- Yeah.
- I'm pretty into Apple right now.
I don't know.
Favorite brand?
- I get, I think Toppo Chico has like nailed bubbled water.
- I don't know how that has come up,
but you're absolutely right.
What about a favorite brand for your kids?
- I mean, I am living in Pokemon right now.
Like head to toe Pokemon.
It is, 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.
- Yeah.
Secret skill, not on the resume.
- Cooking.
Okay.
Anytime you guys wanna come for dinner,
love to cook for you.
- I'm in.
You just won front row seat tickets to your dream event.
What is it?
- I'm gonna underline the word dream
'cause I don't know if this is ever gonna happen again.
Oakland days 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 payroll budget
to compete with like--
- I love that answer 'cause that's the most creative answer
I have 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?
- Best way to find me, I'm on LinkedIn.
Feel free to reach out.
And I think, what would I wanna plug?
I think, just let's plug this podcast
because I am honored to be on this lineup
with so many greats that you've lined up in.
So thank you for thanking me, thank you for having me.
And everybody should, you know,
regardless of whether you have $10 to your name
or $100 million to name, like go right 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 invincible.
So do yourself a favor and go make sure your loved ones
know what to do in case of emergency.
- That's so true, thanks Jim.
And thanks for coming on the podcast.
It's an honor to have you.
- Thanks for having me, Dan.
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)
(upbeat music)