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New Ways to Hire & Get Hired - Mindset of a Remote CTO w/ Janelle Tiulentino

Tim Marting

In this episode, I’m excited to talk to Janelle Tiulentino, a Stanford graduate and early Snapchat engineer, and currently a co-founder and CTO of Talentdrop, a company that is changing how other companies recruit their employees.


You recently just spent a large amount of time in Switzerland. Starting a company that began and still is in California. What was it like being a CTO based in another country, and then how did you manage that?


We did have a couple of people say, that's a bit crazy. You're kinda signing up for all of these things at once. The nice thing about working with my co-founder Maddy, is that we've been through the slog of selling our souls to startups.



But this time around we said, our lives come first. Yes, starting a company is hard, but we want to build something that we can structure around our lives. And so she's currently on maternity leave with her first baby. I knew that the move to Switzerland was coming up and so we said, we're going to try it. The world is moving towards more remote work. We're going to use ourselves as guinea pigs and just take it step by step.


How do you manage a team from abroad?


Even within the US we are scattered. We've got some people PST. Well, they're only four of us total, including Maddy and I, but we range from PST to EST and then there was me out on Swiss time. I think the first step is learning how to manage yourself before you even try to start building bridges with everyone else.

So for me, it was about setting up a routine that I wanted for myself. For example, what are the hours that I'm going to reliably be online? When do I think the best? When does working make me the happiest? That has worked pretty well for us. And not only applying that to myself, but to everyone on our team as well.

If you want to take a two-hour lunch break, but you want to spend more time working in the evening, by all means do that. We'll figure it out. We'll just make our meetings more efficient and pack more things in there.


It’s hard to say what'll happen when we grow our team, but we're hoping that that kind of philosophy can stick.


What are the pros and cons of living in Switzerland?


Basically, it was like heaven on Earth. I think there are pros and cons to any place. Yes, it is absolutely beautiful. Yes, it is clean, and it is efficient. Public transportation is the prime example that comes to mind. But as with any place you live in, they're always going to be pros and cons. Some of them are as annoying as grocery stores are closed on Sundays. So if you want to cook something, you have to plan ahead.


Another one is social things like social dynamics, class, race, and all of those things. It's not just a US problem, it's everywhere, Switzerland included. So it's not like this utopia where everything is magically figured out. You've still got those kinds of problems. And so it's comforting to know that it’s not that the US is so dysfunctional


and it's alone in that. I mean, you do have a lot of beautiful places, scenery, the national parks... It's easy to forget about when you're here and then when you leave it, you're like, actually, it's pretty good.


What’s your one must-see or must-do recommendation for someone visiting Switzerland?



My favorite place that I've been to so far there was this area called Lauterbrunnen - it's in the Alps. We went in March, and so there was still skiing going on. But you take this tram, it actually looks pretty precarious when you're looking up. But you ride the tram up and then it's just basically like a little snow globe town set in the hillside. You can hike up it. It's a pretty rough hike if you're not in shape but it's adorable. You can take the lifts there and just hit all these points up the mountain and then just ski all the way back down. So I would highly recommend that, whether it's for skiing or hiking, any time of year, winter, or summer, it's beautiful.


You worked at an AI medical lab before. What was your experience? How do you see AI and the medical field mixing in the future?


So how did I end up there? I had left Snap. It was a much bigger company at that point than when I had joined and I spent some time off. I knew I didn't want to go back to a more traditional big tech company. And so I was interested in new areas of tech. Tech is all-encompassing seemingly these days.


It was a mix of opportunities both personally and professionally. I got that role through colleagues of mine. But basically, what I was interested in was that because it's a university setting, they are more experimental with things that they're willing to try. And the benefit of this lab was in close partnership with Stanford Hospital. They were okay with putting things like sensors and cameras into more sensitive areas like ICU or ER.


But I personally think that it's not as simple as just replacing a human being. It's not like, you know, here's a doctor, here's a nurse, now here's a robot. It's not that at all. It's more heading in the direction of how can AI augment what the medical staff can do. So in this particular lab, one experiment that we were working on was hand hygiene in hospitals. Obviously, you have to wash your hands, but it's actually quite the source of secondary infections and a lot of problems can stem from it. And so it's not practical to station someone at the door and watch everyone wash their hands.


Is there some kind of low overhead sensor that you can put over the hand washing stations just to kind of make sure our people following the protocol? How often are people not following the protocols? Then use that holistically to improve behavior in general and extend it outward.


So, there are a lot of promising applications. Of course, it's not without problems. You have a lot of concerns about it because ultimately, the thing with all of this AI stuff is there's a lot of data involved and data becomes the name of the game where, you know, now it's like who owns the data? How do you collect the data? Is it OK to have this data? Are people OK with having this data? So you get into these uncharted territories, and I just thought that the intersection of all of that stuff is very interesting, not just, oh, wouldn't it be cool if we applied AI to this thing? But also like, how is it going to affect our lives?


If I'm in the ICU, am I OK with this sensor hanging over me, recording me, even if it's kind of blacked out? So, I thought it was an interesting environment. Was it for me, ultimately? No. And that was more to do with it being an academic environment than the subject matter.


I will say though, it's hard to do tech in healthcare because it's a lot more sensitive. Things move a lot more slowly. I think in order to be there, you've gotta have a lot of patience and you need to get a lot of stakeholders on the same page, which is hard to do.


It is going to sound a little cynical, but my view is that data is very valuable to a lot of different parties in a classic, economic sense. You follow the money and you can do a lot with that data. So yes, AI can be used to do amazing things, but you need the data first. That's kind of how you see things being developed, like GPT-3. It had to basically ingest the entire internet before it can do what it does. So, it’s the same idea with these devices working in hospitals.


You met your co-founder in Talentdrop, CEO Maddy Nguyen, at Snapchat. How did you know that you were ready for a startup of your own?


When we were at Snap together, we had some overlap, but the way the company was structured, they kept us pretty separate. She was on recruiting and I was on engineering, and fortunately, because I was there a little bit earlier, I had friends on these other teams and so that was how we got to know each other. I think we always just had mutual respect for each other.


Fast forward to 2019 is when we synced up again. She knew what I could do and I knew what she could do. I was on the tail end of my lab job and looking for something else. I just knew that academia was not the right environment for me. I wanted something a little bit faster than healthcare. And that's when a mutual friend of ours said, oh, Maddy is looking for another person to work on this thing with her. She had incubated it first, and then we met for coffee and the rest is history. And it grew because one amazing thing about us is we don't actually have very overlapping skill sets, and so what that's translated to is just trust in each other. And that's worked out amazingly well where she trusts in me to handle the tech stuff, the product, and I trust in her to handle the business and the people aspects.


And when you have that kind of trust, things just happen. Things just fall into place. We can focus on what our strengths are and then leave our weaknesses to the other person.


What are the responsibilities of a CTO?


At our stage, I think either CEO or CTO primarily to me means that you have to be willing to put on whatever hat you need to put on. I don't get to sit pretty and say, well, I'm only going to manage my team and tell them what to do and have my coffee.


No, it's none of that. Sometimes it's like, oh, a bug came in, or, oh, someone wants to talk to me about website stuff, or, oh, I need to do a quick design spec. Am I good at any of these things? Am I a professional at any of these things? Not necessarily, but I just gotta do it and figure it out. And so it's kind of more in the startup realm than anything. But all that to say is that you have to just be a flexible person, you have to keep an open mind. You kind of have to anticipate, like did I expect this problem? No. But is it going to happen? Yes. And do I need to just be ready to tackle it? Yes. For us, a CTO is not just building the website, which is what I do, but it's also thinking about how it should work, how it should look, what should happen when a person wants to do action A or B on the site. And if you look at more traditional engineering, that's way beyond the scope of what your standard engineering manager will do.


And also communication, learning how to talk about these things with people who are coming from different backgrounds, and different contexts. I can't just go off into my own, you know, blabbery about, oh, well here's the code et cetera, et cetera. I need to be able to translate that for people like Maddy, or third parties that we're working with in a way that everyone can understand.


What does Talentdrop do?


At its core, Talentdrop is a talent marketplace where we open up hiring opportunities to everybody. The more traditional model that you see are okay - they're head hunters, recruiters floating around. You have to go through them to get access to a job. We thought, why not just open it up to everybody? If you have good people in your network, if it's yourself, if it's your friend and you see a job and you say, hey, I can actually connect my friend or myself to this opportunity, why should you not get rewarded for it? Why should it only go to a select number of people? Why should only they have access? So, that's the idea.

I mean, basically, you have companies posting bounties. They can set their own bounties cause it's a marketplace. And for example, they'll say if you know of a good marketing expert, I will pay this person 5K or 10K to refer someone to me. And if that person gets hired, then the referrer will get paid. So that's what it is in its purest form.



There's a lot of tech stuff in there. Hopefully, if we get bigger, we want it to represent more industries across more areas because Maddy and I were from the Bay Area and our circles are tech.


What are clients saying about their experiences with Talentdrop?


We’re in the muck stages right now where in order to test an idea, you have to put it out there. And you get the good, the bad, the ugly, and where we see the value is the ugly.


Companies want quality hires. So then it becomes a question of, you know, what are the hotspots for the kind of hires that they're looking for? And so within this talent marketplace, you have different groups of talent. There are parties who want super-experienced engineers with 5 or 10 years of experience. Those are hard to find already. And then there's a lot of demand for them. Then you have really smart people who are looking to make a career change. Maybe they don't have experience in coding. Maybe they've never worked at a tech company. But they’ve got a ton of potential. So, you create opportunities for that pocket of talent. But an interesting matching problem appears. Maybe the people who only want the super experienced people should be in their own pocket. Crypto's another one. Maybe the people who only want crypto people, you put them in their own pocket. That's what we're trying to sort out right now, and that's what we've had a lot of feedback on. For example, companies who want someone with a ton of experience are wondering why they’re getting a candidate that has one or two years of experience. Maybe they shouldn't be matched together, but you also don't want either party to walk away with a bad experience. That's the main problem that we're hitting these days.


Where are most hiring recommendations coming from in Talentdrop?


That's a really good question. One of our earlier hypotheses was to hit up indie recruiters - these recruiters who have devoted their careers to building up these relationships with good candidates. I mean, you can't hire everyone if you're representing a company. They've only got a finite number of roles. You can only take the gold medal winners. What do you do with everyone else? And so we thought, well, what if we were to focus on them? But actually where I have been seeing a lot of promise lately are these career switch people or these individuals who are kind of in these lesser-focused pockets.


I'm going to say Nigeria has actually been an amazing example for us where they've got a very vibrant tech community. There are a lot of motivated self-learners out there who are pouring through stuff on the internet and creating their own projects. Yet, because they're in Nigeria and you have all of these more Western companies, they're not looking there. However, those people are really motivated and they just want a foot in the door.


So, if it were just me personally speaking, I think that's a really exciting pocket we could really unlock. What if we could get more people to look at them? There have been efforts to do more of this, but maybe all of us as a collective force in the name of moving towards a truly remote global workplace.


Why has Talentdrop had 90% organic growth? And what are your plans for the future of Talendrop?


Back in May, June of last year, we got into Y Combinator last minute. And at that time we didn't even have Talentdrop built at all. We had just landed on the idea and said we were going to run with this. The name of the game was to put something out there on the internet and see what happens. And I think somehow, either under the Y Combinator umbrella or people just kind of searching for jobs, people found us. We have been really bad about doing analytics and stats. We're just so stretched thin that I just haven't built anything like that. But we looked at it after a couple of weeks and found out people have been finding us organically.


One hypothesis I have too is that it's all about your network. When you pull people into the system, they pull other people into the system. Hiring is a big need right now. And so, when one company hires, they've got other friends who are hiring, and they tell their friends about it. So I think that has really helped. And also because the core idea is pretty simple.


Some have tried different flavors of this in the past, and actually, not to name names, but we've found a couple of copycats floating around on the internet. So we take that as flattery. This is a good idea, people are paying attention, but yes, people have tried it before and one thing that's stuck with me is that a lot of it is like an endurance race.


You’re going to hit all kinds of problems and it's super easy to just have moments where you want to give up, like the example I mentioned earlier where maybe you have a company who wants someone super experienced and they're getting a not super experienced candidate. So I think it's stuff like that, that has probably caused the earlier players to drop out of it. It's not as simple as selling on eBay. You're dealing with people. People are investing their time and their energy. You have to put more nurturing and care into it. You can't just throw it to the wind and say, I don’t know, deal with the website, it's all there.


How is Talentrop incorporating AI while keeping the human aspect of things?


I love this question cause I think it hits on the core of who we are. Maddy is a recruiter. While it's easy to pitch this as we're replacing recruiters, we actually don't want to replace recruiters and put them all out of jobs. We want to make their jobs easier. We want to do something for them. So you can think of it as maybe you have these recruiters who wanted to go freelance. Maybe they want to become indie recruiters, but they don't know where to get the clients. They don't know what to do with their networks they've already spent a lot of time building up. What if they could just all go to Talentdrop and freelance there? So that's one aspect where you do need the human. I mean, the human is the one who's walking these candidates through the process - being their advocate. Like, I will go to bat for you. That is super important when it comes to hiring. Being hired, whether you're the candidate or the company, you want to have a human being there to represent your interests and be able to bridge all of that.



And we just don't think that AI alone can solve that. It can help with these matching problems that we're talking about. But ultimately, you're still dealing with sensitive things here. I know that recruiters also sometimes get a bad rap, but honestly, the good recruiters out there will go to bat for you. And we've heard this from people who are making career switches or just breaking into the industry. In fact, Nick, who is our resident talent partner, was super important that while Maddy was out. We had an in-house talent expert because again, you're dealing with people. He's had people reach out to him and say they want to break into the tech industry and ask for his help. So, he becomes their advocate. That's something that you just cannot replace with code or robots.


So we always want to have that ethos in there where we know you're a human being. We're not going to throw you to the wind.


Can AI recognize a good candidate for a job?


One can hit all these like checkboxes on paper, but what if it's just really hard to communicate with this person? What if you just butt heads over something that's not at all related to the tech or the job? Whereas what if you have someone who maybe doesn't tick all of those boxes? You see the potential there, and you see that this person can grow really quickly. Maybe someday they can build an AI for this, but until then, it's going to be really hard to do it and to have one that people can trust.


Who uses Talentrop to hire people?


It's been primarily smaller companies and that's because a lot of our earlier companies have been YC companies. We do have more of a range. There are some that I think are series A or B, but we have really liked working with the smaller companies in these earlier stages because they're easier allies for us. We can get the CEO on the phone and ask what they're looking for beyond what they wrote in the job description. We can extract all of these things that you can't really get on paper. While if you're dealing with a ginormous company, you have to go through several layers of executives. So the smaller companies have just been an amazing help to us. They're flexible, they're nimble, and they're a lot more understanding.


The goal is hopefully we can expand this model to fit any kind of company, not just the small ones, but in these stages, they've been our best ally so far.

What have been the major developmental changes or failed attempts that you've had to pivot from with Talentdrop?


Maddy and I have been building a couple of prototypes since we joined forces. Talentdrop, as you see it today, is our fourth or fifth iteration. So it's been a lot of building up something quickly and testing it on a couple of people. Do we like it? Does it feel good to move with as a business? If not, be ready to throw it out the window. And that's another thing that she and I line

Last summer, heading into Y Combinator, we had just thrown our last thing out the window. I forgot what the exact reasons were. I think it was more enterprise software oriented, and then we came up with this idea. We interviewed with YC, and they loved the idea, but they were not going to let us in until we build it for them. So that was actually the big kick in the pants. So, we built the first MVP in two weeks.


It wasn’t pretty. You basically just need it to work and you need it to function in some way and just get it out there and hope for the best. And that's what we did all throughout YC is just adding onto it little by little, or a lot by lot rather.

Fast forwarding to how we got to where we're today... because we're a marketplace for people, the turnaround time for transactions is not as fast as selling an item that's inanimate. With the job process, you have to interview. People need time to make decisions, they need to talk. So there is naturally just a longer lead time there. And we knew that and we accepted it. It's going to take a couple of months for us to study a couple of cycles of that just to see where people's pain points are. And by now, we've got like a thousand referrals on the site.


But we've been able to see different cycles happen whether they get through one interview, two interviews, all the way to offer… There have been people who have gotten offers through Talentdrop and we've been able to study those and get a better understanding of the risk points. These are where people kind of get a little bit lost and they're like, what do I do now? This is where our strengths are. In 2022, we just got a much clearer idea of all the ways that the MVP lacked really. And here's what we need to do a 2.0.


Do we wish the lead time was shorter? Absolutely. But not to sound cheesy, I think it's also budgeting in our own lives into this picture. After YC, we were really tired, and then, you know, Maddy went on mat leave and I went to Switzerland. We knew that we're not going to be able to go, go, go all the time, even though that's very much the startup mentality. We have our own natural cadences, just our personalities and we can utilize those go times and slower times and make it all fit.


Let’s talk about the scalability mindset. What’s the best way to scale a company?


So coming from this very classic Silicon Valley mentality of fundraise, kill yourself for a year, and then Series A, and then hire 500 people, Maddy and I hate that model. We actually have friends who are doing it quite well, but it's not at all like, oh, you've raised a series A, you've made it. Your stresses multiply. And so Maddy and I are taking more of a slow self-sustaining, bootstrapping (if you want to call it) approach. We wanted to build a base that works really well and we know it'll work really well if it's the kind of service that we can just have on the internet. We've been having people find it, people decide to use it on their own, and then have it grow organically from there.


Also, we keep our team lean. And our team really likes that because they have more freedom, more ownership to make these decisions and not have to deal with bumping into more people. So we said let's go from there and if that means we grow much more slowly but steadily, we will 100% take that over the kill yourself for a year and do Series A.


Because we went through that incubator. I mean, you can put the gas on, but it's not sustainable. Ultimately too, we end up overworking for someone else. It's our company and we should enjoy it. We should be the ones building it to be what we want it to be, not just according to some gospel that exists out there. So I'm sure there are people who disagree, but I'm very much in this camp of there's not one way to do it. And, there are always risks to any approach. People can come out and overtake us. But again, going back to what our brand is, we're about people. We're not trying to replace people. We understand that these things are sensitive and we're kind of relying on that. Like, hey, we're real people too. We're going to stick to our philosophy and kind of present ourselves to the world in that way, even in the way that we want to grow our company.


If you've got a core that's falling apart, you can only disguise it for so long. We'd rather have one that we are proud of, but we can build on top of and feel good about that and live our lives in the meantime.


To wrap up, if you could take all of your life experiences, turn around, and give somebody one piece of advice, what would that piece of advice be?

Don't sweat the small stuff. Think: I'm still alive, still moving, right? If you're alive, you've got good health, and good people around you, it'll be okay. I think sometimes life is too short not to laugh at things, and that's very much what Maddy and I try to do. Like, oh, we had a bad day, we're just going to laugh at it together. It just makes everything so much better.


Where can people reach out to you? Where can they get onto your platform and all that?


So talentdrop.com is our platform, but I'm Janelle at Talentdrop. I mean, anyone can figure that one out, but it's amazing the kinds of people you meet when you are working on these things and I've met a lot of really cool people that I never would've expected to meet or chat with. I'm also on LinkedIn. Feel free to shoot me a message there. Happy to chat about any and all things related to Talentdrop or even if there's just anything periphery that I can help with.


Janelle, thank you so much. I appreciate the time.


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