Career Changes from Salesforce to Twilio to CockroachDB

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CTO advisor podcast I have with me Kevin swab swab. Oh, who's a good friend and actually, you know, we're Related to the same person which is a weird thing to say But he is a really great person and I've known Kevin for years and he's not on the podcast as an account executive for cockroach DB because we're Close not just because we're close but because he has a really interesting career story that I think offers a really Simon Worley esque Perspective to when you're close to value and you transition into a role That's a little bit further away from the value and what does it mean to still bring value to your customers?

That's today's conversation Kevin welcome to the podcast Excellent Keith. Thanks so much for having me as you mentioned, you know, we've been you know tight for a while and it's a pleasure to speak with you today and Share my story and I hope it's of interest all your listeners So we're not going to start the story at cockroach DB. We're going to start the story at A More of the business value end of your career. I've enjoyed watching you for years You know, you've I've watched you, you know go from high school to college and now into your career you're a seasoned professional and You know just be thinking about that journey is really impressive But you you didn't start your career on the infrastructure side of the equation No, you're you're right.

You know, it took me I bounced around career wise a lot after college I did some stuff in politics I did some things that investment banking during the Great Recession right when banks were falling apart So my timing for a lot of things was was unique I was doing some public relations work and my wife was working in at sales at Salesforce at the time In San Francisco, this is actually before we were married and she said you should you should go into software sales there's a lot of transferable skills that that makes sense and You know, it was a brilliant suggestion I I definitely followed it and went into Salesforce and In in San Francisco in the Bay Area.

They are a huge employer. Everybody knows somebody who works at Salesforce and You can tell I think working there that Mark Benioff the CEO of Salesforce is a former salesperson in addition to being an engineer and Someone who's worked in the technical space. He understands sales he understands go-to-market and the product was really built for go-to-market teams, so a lot of Conversations were being had with business executives and leaders sales leaders Marketing leaders customer service a lot of people who own the lines of business that were that had a customer touch point and in some cases particularly being a cloud-based solution and Working not just with big enterprises, but with a lot of small businesses.

There were a lot of business leaders making decisions independently of IT in some cases Or or in conjunction with them in some other cases depending on what you know products they were using and how things were being implemented But it was a very much a business value focused conversation like you you had it at a lot of Sandler sales methodology I'm not sure if people are familiar with that. You know, I know command of the message is kind of the new in vogue training but a lot of Sandler stuff and and and and command of the message are similar in the sense that you're trying to find business pains You're trying to find you know, are the conversion rates on your sales a little low Are you not getting enough leads our leads falling through the cracks?

what's the business impact of that and You can start to build an ROI case and quantify the potential value of making a change or investing in a new solution And so a lot of the conversations were focused on kind of being like a consultant but really for the business not digging into the weeds of The technical side of things and so that's why I started started things out Yeah, if this was a different podcast, I'd love to go into like the sales methodology of Salesforce and how they use the platform to you know, tracking and Monitor sales and the whole sales pipeline.

I spent a little bit of time In enterprise software sales in which I had to use Salesforce and the data was just horrible inside You know Salesforce is gonna fix bad data if you have bad data in It's not magical and Salesforce is going to solve that problem, but I love your description of what Simon Worley does with his basically essentially with his maps, which is to show where the value of a object is or a theme is relation to the Capabilities that you bring so if the value or object of value is, you know driving sales or Having a higher close rate, etc Salesforce is about as close to From a software or technology perspective Salesforce is about as close to that That object or value equation as you can get and you've described it like, you know, you're not necessarily selling into IT you may be selling into the sales director or sales VP or the customer service group, but not necessarily IT That's exactly right.

Yeah in many cases and there are there are a couple Salesforce is a huge platform now They own slack they own Heroku, which is a building platform. So there's some other products that might touch IT but they are CRM company first and that was definitely the case where you're you're engaging the business leaders traditionally way more often than than the technical the technical leaders and as kind of a You know an application that you could quickly, you know customize maybe with a small consulting contract You know small consulting contract or small expert services compared to other projects that may be going on you could kind of do these workarounds where you didn't need a ton of approvals and other things that you would for you know a Database or core infrastructure the other types of things that are much bigger projects.

So that was that was certainly the experience there and it's a good a good viewpoint to Start and that's why I thought would be interesting to have you on because you have this Outside in perspective it will reach the cockroach DB part of your story. So after you left Salesforce What did you know? Did you go directly from Salesforce the cockroach DB or was there a stop in between? there was there's a stop in between I was at Salesforce for a few years and then I went over to Twilio and Twilio is Similar in some sense to Salesforce and that it's a lot of customer engagement conversations, but there are API's You're not calling out-of-the-box applications They are communications API's or API's that are Designed to improve that engagement in some way whether it's with data whether if it's improving a communication A lot of people use Twilio without even knowing it if you're you know speaking to your uber driver That's not their actual phone number.

It's not your actual phone number that information is protected All that stuff is happening through Twilio on the back end whether it's a text message voice call email contact center stuff and I think it was an interesting to move into that realm because Our first points of contact leveraging Twilio and this was part of their Their marketing strategy was we're not going after business leaders first. We're actually or technical executives We're going after developers the the larger, you know, the broader software development community and that was the marketing approach of the company and So a lot of the leads and a lot of the people that you initially talked to or people Who want to just test build something really quick incorporate, you know that SMS or voice API into their application?

See how it goes and that's generally the first point of contact Within Twilio, so all of a sudden I'm in a position where I have to be much more intelligent technically I can't just go in and and do a business value conversation because a lot of those folks That's not what they're thinking about first. They're not thinking about the why they're thinking about the how how do I build this? How does it work? And so I realized that my key to being successful there was I'd still have to have those business value conversations, but I couldn't lead with it I would have to build some expertise and how these API's were kind of some unique things about telecom I worked in Latin America a little bit with Twilio and helped them break into that market so I learned a lot about how telecom works in that market and through that you build a little bit of trust and With with developers with the customers, they may introduce you to more people you help them build things actually, that's a really fun experience is that work with somebody to help them build something build a POC together and so it was a transition to a more technical sale it still had business value, but that wasn't the lead and it was a New skill set that I needed to have and I I really enjoyed that that technical sale.

Yes. I'm liking to projection or progression to your role at Cockroach DB, you know you purely business level conversation You know, it's in your wheelhouse, you know coming from investment banking background political Science background you're dealing with people you're dealing with problems and you're at these, you know big intractable parts of either social issues or Business issues that you're just using your transferable skills and saying hey, here's You know people don't care if it's software or if it's a Bunch of you know Gorillas in the background doing some type of automation to make to solve the problem being the conduit to solve the problem they just want the problem solved and now you're transitioning to Now people care at Twilio about how the problem is solved still similar conversations Like there's these big outcomes.

And again, if we're looking at a worldly map, we're seeing You know kind of a value move a little bit to the right instead of the left closer to the business value But still really important Competition is starting to thicken up a little bit because there's more people in the infrastructure layer Thinking about these API level problems. They may be a little bit more tactical in their approach They could be a little bit more strategic but overall Competition and there's a little bit more noise Now that brings us all the way to the right and now you're at cockroach DB.

This is the platform that folks like Twilio or Salesforce as You're looking at it at the stack. You want them to build their platforms on top of cockroach DB So now the business value conversation Completely changes. So talk to me about that experience Yeah, it's a great point, right? I'd love to have Shout out the Twilio if you want, you know, if you if you need a new resilient database, I think Some companies out there that are working with us that I don't want to you know I don't know that we have legal rights to talk through all the customers that we have at this point in time But I do think that you're absolutely right.

Those companies are perfect fits for what we do And I think it's really interesting to go from you know Out-of-the-box applications to API is working with developers then to the database Right the database where the engineers and folks who've been part of building the core of a company For a long time have been are you know are working and it's a very different type of conversation It's very very technical I'll admit I'm still learning a lot in the role I'm very fortunate to work with the solution engineer who has in decades of experience working with databases because You know the the ins and outs of how people have been able to you know Scale their systems with an Oracle or Microsoft SQL Server these other platforms have been out there for four years you know, it's a challenging sale because if you're building something that is so core to the business of how an application performs that may be the core product that performs You're very very careful about making changes.

And so it's a it's it's challenging for sure. And I'm definitely Learning a ton about how to make the most of that But I think it's it's really fun too because what I learned from Twilio is That it's really fun to be in a sales cycle where you're helping to have another company build it Right, you're helping you're in the process of building together. You can't just hire Consultant put something together really quick. You need to be involved in the process for how it works right, and so I think that's very much the case with with the database as well in terms of People really want to prove out the solution.

They really want to test it for different scenarios It's almost like if you know, I was used to kind of if you were to make an analogy of selling cars, right? I was used to kind of going in there the one day getting a feel for this person who really wants the car kind of Using that emotional intelligence to kind of get their confidence up and sign in the dotted line And now all of a sudden I'm selling this huge huge Engine within a jet and explaining how the RPMs work and really getting nuts and bolts of how how it all happens and so it's a it's a very fun, but different conversation and I think it's fun to be a part of something.

That's so core to so many applications It's so central, you know these these sequel databases, you know, there's different types of databases out there There's no sequel stuff in the sequel stuff, you know cockroach DB is more focused on distributed sequel. So Data that has to be consistent and correct, you know applications that involve a ledger Pricing information if you're a bank, maybe it's the deposits or loans that data has to be correct It has to be consistent across and so these are core applications But it can be a variety of tier zero or tier one applications that it touches Identity access management metadata about a product if you're talking about Salesforce and Twilio the SAS companies Metadata is critical to how everything works with those products So those are the types of use cases that are interesting that you can touch all those different things With a core database and that's why I'm I'm excited about the work.

So if we zoom out in this Quintin This is ultimately coming down to a question of business value, but business value from different lenses you know What has to happen, you know, we may look at that initial worldly map and say oh if the business if the business outcome is the thing that we're aligning to and Then we have the database which is right of Salesforce. It's right of Twilio We may look at and say hey, you know what was we're selling the wrong thing I'd argue you're probably looking at the wrong worldly map You're looking the worldly map now adjust to kind of that value that Twilio brings that in value that Twilio Twilio brings or Whatever Twilio is and then the database is just right of that It is right next to its essential to the value.

So while the sales Manager looking up the performance for last quarter pipeline versus Closing may not care What database is running? Salesforce the team at Salesforce Absolutely cares to your perspective and you have to adjust your mindset in your purview so talk to me about that process that you've gone over the past few months if you've Adjusted from having the business value conversation with that Far end user to having that conversation with the teams that's building products Yeah, it's an interesting transition And like you said, it's business value, but the lens is very different.

And so it's interesting to see there are still compelling events and aspects that you want to ask about that come back to the core engine of that jet or that Car, right? How often does it break down? What do you need to do to get more workloads out of it and scale it and go faster? So those are interesting conversations. I'll give you an example would be if your product has an outage Right and every most companies most, you know software applications at some point in time have an outage of some sort You know, they haven't been able to scale their applications.

Maybe they're running globally It's hard to get everything to go through one database with in a cluster in Virginia if you're running a global business It's very difficult If you're doing everything on AWS and AWS happens to have an outage for example for a brief amount of time You want to be multi cloud? There could be efforts to shard so you're trying to scale your database But when you shard and you do those manual types of things it makes the builders jobs harder because every time they have to do A release every time they want to build a new feature application They're having to add more work because of the sharded database.

So those types of hints are interesting They tell you how somebody has built something and how it will impact the future Outages are obviously a key issue You know all I won't say the name of the customer because I don't know if I'm a liberty to say it But you know, there was a gaming company out there that had an outage for a certain key period of time When let's just say they were a very popular online virtual gaming platform And it was a popular time for when a lot of people gonna play and they had an outage You know, that was very very expensive if you're thinking of it from a business value perspective How does it impact your brand your brand?

How many transactions did you lose that certain data? Issues come up. Did you have an SLA tied to the service being available? And then you kind of tie it back to well, how can I fix this, you know I think that's where a distributed sequel what cockroach has to offer is interesting Obviously, I'm biased because I work there and I'm offering the solution but those are those are core things and I think it's interesting to see how you can You can do that and how you know tends to be with a lot of these kind of newer companies You're gonna be able to just build things a little bit better often Because it's it's been built in a more in a newer way, right?

But I think of it kind of like house renovation projects There may be a lot that you want to do to renovate your house Right and you want to you want to build it maybe from the foundation up and redo a lot It can be expensive and hard to do that a little risky to do that And I think that's kind of similar sometimes to databases particularly for tier 0 and tier 1 apps So oftentimes a lot of people are thinking how do we test this out with a smaller ancillary app?

Maybe it's not customer facing you validate it You see how it works and then all of a sudden you start to use it for more critical applications And and you can go so there's a lot of risk tolerant Types of conversations within it that just weren't there, you know If sales first didn't work you had your old CRM or you can move stuff around You can test API's out you can plug and play with other ones But database is not like that this is like there's a lot more of a risk tolerant type of thing that I have to manage and It's been interesting to learn about that.

It's definitely a key challenge and I respect Engineers who have to work with these things because they have a lot of pressure on them You know if somebody's testing and deploying a quick API or quick app, that's one thing But when you start moving stuff around with databases You know these site reliability engineers these core heads of infrastructure platform directors Architects, they have a lot of people looking at them to make sure that everything works right when they release so I have a lot of respect for what they do and You know, those are interesting conversations that have well Kevin.

I really appreciate you taking the time out to Talk to me about this. I'm gonna borrow a term from my buddy in Menlo Park Jeff Frick turning the lens on business value and selling Software to three completely different groups and as you walk through the value Chain of ultimately adding business value seeing how you're able to connect the dots You're not looking for a new job. So don't take this way as a way, but I'm going to I'm looking forward to again watching your career progress from a kid in high school to as you motor around after college to selling software and now selling different types of enterprise software to when you're Leading the sales organization with one of the enterprise software vendors I know it's gonna happen one day because you have this unique view you're going you're getting you know, you're getting the darts in the back so to speak to Get the skill to understand how to tell this value proposition from different lenses in it And I think it's an extremely valuable skill for you in the long term For those of you want to learn more about the CTO advisor, you can follow us on the web the CTO advisor calm I'm on Twitter Kevin isn't so if you have a question for Kevin you want to reach out to him You can reach out to him on my behalf.

He's on LinkedIn. I will have his LinkedIn bio on The show notes talk to you next CTO advisor podcast. Thanks Kevin. Thanks Keith. Take care