What we talked about
Join Dario de Santis as we delve into the transformative power of AI in reshaping how teams collaborate. Discover cutting-edge AI solutions that are breaking down barriers, enhancing communication, and fostering innovation across industries. From virtual assistants to intelligent project management tools, learn how AI is enabling seamless teamwork and driving productivity to new heights. Tune in to uncover how AI is not just a tool, but a game-changer in the world of collaboration.
Show notes
Dario de Santis watched colleagues at Cisco get seven back-to-back meetings booked in the same time slot and realized that AI-assisted calendar Tetris was solving exactly the wrong problem. Investing in optimization when a calendar is already overbooked just spreads conflicts onto evenings and weekends, the only real fix is fewer meetings, not better-arranged ones.
What we covered
- The insight behind Tweelin is deceptively simple: a workday has a hard ceiling of 8 one-hour or 16 half-hour slots, so no calendar optimization can increase productivity beyond that asymptote. Dario argues that the only way to increase resolution is to get people talking in the gaps between meetings, in five-minute bursts that currently require a week of scheduling overhead to arrange.
- Tweelin works by reading telemetry from users’ devices rather than just their calendars. Microphone and screen activity at the operating system level is a better proxy for real availability than calendar status, which is why someone can appear “free” on Outlook but be mid-conversation on WhatsApp. The system uses this cross-app signal to find a genuine available moment and then triggers the connection.
- The connection success rate of a standard phone call is around 12%. Tweelin achieves roughly 90% connection on the first attempt by waiting for the right moment rather than interrupting at a random one.
- Gartner named Tweelin a Cool Vendor in Digital Workplace Applications for 2024, one of only three companies worldwide in that category, without any external funding. Dario and his co-founders, all ex-Cisco and WebEx leaders, invested their own money and shipped a complete product before raising outside capital.
- He frames the problem historically: phone culture in the 1990s enabled fast, spontaneous collaboration, but the explosion of notification channels made interruptions feel rude. The response was to raise barriers, focus mode, asynchronous messaging, which solved the interruption problem but destroyed the spontaneous conversation that actually moves work forward.
- The next planned milestone is cross-platform bridging: a Slack user making a “wish” to talk to someone who uses Microsoft Teams, with the connection happening through whichever video tool makes sense. Dario also described a roadmap item where an LLM analyzes project context to identify who needs to talk to whom along the critical path, and proactively connects them before anyone realizes they’re blocking each other.
About Dario
Dario de Santis is the co-founder of Tweelin, an enterprise collaboration startup he built after more than 20 years in product and technical leadership roles at Cisco. He describes the pace of learning in four years of startup work as exceeding the learning from his previous 16 years in collaboration AI and product management combined.
- LinkedIn: https://www.linkedin.com/in/dariodesantis
- Website: https://tweelin.com
Episode 37 of the PreVetted Podcast.
Full transcript
Federico Ramallo (00:01) Welcome to the Prevetted Podcast, where we spotlight extraordinary talent, changing the world. On today’s episode, we are joined by Dario De Santis. He’s an innovator who has spent more than 20 years turning ideas into practical collaboration and AI products. Dario is worth listening to because he combines product and product vision and hands-on technical leadership.
So you should listen to what Dario has to say. Hello Dario, how are you doing today?
Dario De Santis (00:38) I’m great. Thank you, Federico. And thanks for having me and hello everyone who is listening or watching the podcast.
Federico Ramallo (00:45) Yes, yes, have people watching on the videos and then we have people listening on the podcast. Thank you for being here today.
Dario De Santis (00:55) pleasure.
Federico Ramallo (00:56) So I understand you have a lot of experience with corporate environments. You’ve been working many years at Cisco. And recently you launched ⁓ your own startup called Tweelin. ⁓ So let’s talk a little bit about Tweelin. ⁓ What gave you the idea to create Tweelin in the first place?
Dario De Santis (01:20) ⁓ that’s a great question. Thanks for asking that. Well, you know, I’ve been in product for many years and the more I went up in the hierarchy, I became more important within organizations, the more people wanted a piece of you for anything, You can become a central role in your calendar explodes. You’re always in back to back meetings and people pinging you and asking you for…
all sorts of things on email or through instant messaging at a certain point things starting falling through the cracks for example let’s say an account manager for a really large bank needed me to jump on a call for giving a demo of a product for this really important account and they would send me a message on teams and if i didn’t read that message within 10 minutes
it would bubble down because other unread channels would bubble up. And so a lot of things started falling through the cracks. And the solution for all of that was always scheduling a meeting. Let’s say this account manager couldn’t really get a hold of me. So what they did, they just open Outlook, schedule the meeting for the following day at lunchtime. And now there you have it. Now I…
I have to move things around to make room for this urgent meeting with an account team for a large customer. So this was my daily routine. And I I asked myself, is this the right way to collaborate? Because at a certain point I became a central role more and more, but what I was doing was coordinating availabilities and…
communicating back and forth with people to find time for meeting a week from today. Is that a good use of my time? So one day we said, look, what is the, if we had the magic wand, what would be the ideal experience, Federico? Well, I think about talking to you and then magically we get connected.
at everyone’s earliest convenience with no coordination needed, like bumping into each other on the street right at the right moment. So we built an AI, substantially, that does that. But that’s the inception. The reason why we started is because it was impossible to talk to people. In large organizations, especially key roles, are super busy. They are overbooked.
It’s incredible, Federico, talking to large enterprise customers. Some of them have four, five, I’ve seen up to seven meetings for each single slot. When companies are really big, I’m talking about a hundred thousand employees or above. That is unmanageable. Meetings have spiraled out of control. And a lot of companies out there are investing in AI.
to play calendar Tetris, you know, move things around automatically. But think about this. If a calendar is overbooked or you have multiple bookings for each single slot, what can you really resolve? What can you move? If anything, if there’s a conflict, it goes and spreads it on free slots and push people to work over time on the things that matter. So we took a different
stand and we say the only solution to too many meetings is less meetings. And so we designed a solution that allows workers to avoid meetings.
Federico Ramallo (05:22) Right, right. I mean, I think that the AI optimization on, you know, find, you know, like what you were saying, playing Tetris is the optimization in the wrong dimension or the wrong direction, right? Because you’re optimizing on, want this person to have a schedule fully booked, right? And that’s not necessarily increased productivity. It’s, you know, it could be the other way around, actually.
Dario De Santis (05:51) Absolutely. And look, very large companies are already rethinking the concept of productivity because they realize that. And I say, well, more meetings doesn’t mean you’re being more productive. Well, if think about it, you are incurring more coordination cost. And this is one mind blowing thing, Federico, that I’ve always thought is take your workday. You have…
8 slots of an hour or 16 slots of half an hour if you want to reason in a smaller resolution. If you fill them up there’s a limited amount of things you can do.
And so if you want to increase productivity, you have to change the playground for it. Because if you play with Calendar, you always have an asymptote. You have a limit to what you can achieve because of this 16 slots that you can exploit every day. And so we said, how can you increase the resolution and carve out every possible moment?
If I have to wait for a week to talk to someone for five minutes, really, and if I could do that today, then I could accelerate a deal with a customer, accelerate revenue. I could speed up the execution of a project. I could be more responsive to a customer request. And so that’s where we’re coming from.
Federico Ramallo (07:21) Right, right. I remember when I was doing IT support and it’s a similar thing. You have a team of technicians and then you have a team of people using whatever it is and then lots of issues come up and you have to fix them, right? ⁓ And then I realized a pattern that we will prioritize who screamed the most. That’s how I kind of… ⁓
the loudest, you know, because we could have a ticketing system, right? But then the most, ⁓ sometimes obnoxious, sometimes it was, you know, they would just show up at our, you know, at our space, right? A user will show up at our space saying, have this issue, right? And then we will prioritize that person because it’s the most obnoxious, it’s not the right word, but you know, you know.
that it would stand out out of the noise, right? ⁓ And then, you know, and you have them there, you cannot say no, right? So there was social pressure, there was, you know, so many things. And then adding that, that you have a junior inexperienced socially, you know, ⁓ green, you know, ⁓ engineer, right? And then, you know, we were prioritized who was the most…
Noisy right who was the most you know obnoxious I guess right so Yes, yes, well we had that as well right yeah, but usually was you know it was somebody that would come up with something that was very simple, but you know low priority But still you know they will push through everything and we’ll give priority to that right ⁓ So I understand what you’re saying that you have a lot of people coming up to you right it’s really hard to
Dario De Santis (08:53) most pissed off one. The angriest.
Federico Ramallo (09:19) prioritizing the right way, right? And if you optimize on having a book calendar, a fully booked calendar, then you don’t have enough time to actually follow up and prioritize correctly,
Dario De Santis (09:36) Right, right, absolutely. Plus, think about the slot itself. How many times you are in a meeting and it could have taken 10 minutes. It takes 15 minutes really, but your slot is still full. You still have 15 minutes left. You could be available to talk to someone and avoid the future meeting that way. Or you could…
make a decision faster, but you don’t know if somebody is available or somebody else’s meeting ended earlier. Or you don’t know the real people availability. I see Microsoft Teams reads my calendar and shows me red. But I’m online on WhatsApp.
And I have a different status on Zoom. And what is the right status? And it’s not consistent across. really, what, especially after the pandemic, what happened is we decided that creating meetings, scheduling meetings, it’s really the safest bet. And I’m scheduling a meeting and then I hope you show up.
40 to 70 percent of the meetings get rescheduled and then it lasts 30 minutes. At the end of those 30 minutes you haven’t done talking and now you have to schedule a follow-up maybe two weeks later and to finish that conversation and now half of the future slot is to remember what you discussed two weeks before and then move a little bit forward. All of that doesn’t make
doesn’t make sense. There must be a better way to collaborate. And that’s what we what we’ve built. And we’ve been lucky that also Gartner found out that what we’re doing and they decided that we are a cool vendor and they named us cool vendor in 2024 because of this.
Federico Ramallo (11:29) Right. Right.
Dario De Santis (11:50) innovative approach that kind of challenges the calendar paradigm. But the IT, just to tie back to your IT service management triage.
use case, that’s also very, you know, a classic use case where speed of interaction, especially internally, may make or break customer satisfaction. know, your customer comes with a problem. Now you as an IT service manager or an contact center agent or whatever, you have to go back and talk to four or five engineers trying to figure out.
what the problem is for the customer and going back to the customer. If you are able to talk for five minutes to all the engineers today and reply by this evening, it’s really good. If it takes a week and five meetings to talk to five engineers and get back to your customers, then it looks bad. And so we said…
We designed a solution to accelerate the conversations in these scenarios.
Federico Ramallo (13:05) Interesting. ⁓ I was going to ask you about Garner calling you guys cool vendor. Can you tell us a little bit more about that and why is that such a big deal?
Dario De Santis (13:20) Well, it’s such a big deal because, well, there are really three companies in the world in 2024 that became cool vendors in digital workplace applications. And we’ve been absolutely blessed and lucky to become one. If you think about our history, we are a startup of ex-Sysco, WebEx leaders. We invested our own money.
haven’t raised any external money until our solution was complete and we were named already Gartner Cool Vendor. So basically we started that from scratch without external funding became Gartner Cool Vendor. And the reasons, know, for me, I can’t speak for Gartner, but the way I see it is everybody else is investing.
in the current box, collaboration box. You have a calendar, it’s a base for your productivity, you have the usual tool, you’re applying AI to what you already have. You know, let me give an example. For example, you have multiple meetings right now, you have three meetings at the same time. Which one do you go to? Well, you go to the most important for you.
but the most important for you might not be the most important for another person you’re collaborating with who’s really hoping that you would join their meeting. And this creates a lot of friction. The way they are resolving, they’re investing a lot of money today is creating an AI that attends the other meetings for you, summarizes it. If there’s an action item to you, it assigns it to you. And basically,
you send your agent into that meeting that figure things out for you. The problem is if you’re a key person, you’re already back to back all day, you don’t have time to go and read the summary of those meetings. So people are not really doing it. And then if somebody assigned you…
Federico Ramallo (15:30) Right. So you have the false sensation
of attending a meeting, but if you don’t even have time to read the summary, what’s the point, right?
Dario De Santis (15:43) Right. And if they assign you an action items “in absentia”, when you’re not there, will you work on it? You don’t have enough context. You don’t really know. You you start accumulating requests anyway, and you don’t. So it’s really tough. The way we’ve solved that, said, We do not apply AI to handle multiple meetings. Just apply AI to avoid multiple
Federico Ramallo (15:52) Right.
Dario De Santis (16:12) meetings. so so we say if I today today I open Outlook the standard is I open outlook and schedule a meeting with someone I want to talk to with our solution to Tweelin you just make a wish to talk to the person “Un deseo”, if we want to talk Latino, a little bit to speak Spanish. you make a wish you say I want to talk to Federico
as soon as possible for 10 minutes about this topic and you receive a notification that says, hey, Dario wants to talk to you, expect a call. Then we look at a few telemetry data points securely from all our devices, phones and laptops. And it turns out that the telemetry of your operating system
is a good proxy of your real availability across all your devices, across all the apps. Because if I’m using the microphone on a phone, that’s a hard no, no, I’m not available. I’m already talking to someone. So we look at those things, which are absolutely agnostic to the application that you’re using. And then we cross that data with your calendar availability. Are you busy or free right now on your calendar?
and we are able to do all sorts of things. For example, you may be busy on a certain slot, but we see that through the telemetry that comes from your devices that a meeting ended earlier. And now there’s enough time before the next meeting and you want to talk to Dario for five minutes. Now Dario is meeting a customer and his phone is silent in his pocket, but he’s just about to board the
a plane so he turns on the he’s got a little a few minutes so he turns on the screen of the phone and starts catching up on the notifications so even if the phone is silent his attention is on that phone which is unlocked so he’s reachable from a notification and now we can say hey Federico call Dario right now on Microsoft Teams or make a phone call on this phone number so we go and carve out every possible moments
And that works very well, by the way, so people don’t have to schedule meetings to talk to other people. But they do it this way. Now I had to explain you how it works so you can, you could, you and the readers, maybe I did it too late already, you know, 20 minutes in the podcast or so, but you know, this is, this is what really differentiates us. So going back to Gartner, well, it’s the approach which is new, I believe.
Federico Ramallo (18:54) You
Dario De Santis (19:04) And also the telemetry, applying AI to telemetry, which is something that nobody has done in the context of enterprise collaboration. You see, we look at what’s going on in your devices and we infer your real availability across, instantaneously across all your apps. doesn’t matter whether you’re busy on Teams or green on Zoom.
We know if you’re really available because we look at the operating system.
Federico Ramallo (19:35) very interesting. You’re acting like a catalyst. You’re making the meeting happen without participating in it.
Dario De Santis (19:42) Yes, absolutely. we are absolutely, we don’t participate and we don’t want to participate. There’s plenty of AI that helps you in the meeting. That’s not our business. Our business is getting people in live conversations effortlessly at the right time without coordination whatsoever.
Federico Ramallo (19:43) Hahaha
Great.
Yes.
Right. Right.
Dario De Santis (20:05) What
happens in the meeting? That’s for other awesome AI companies that do summarization, speaker, the realization and attribution, action item extraction, et cetera, et cetera.
Federico Ramallo (20:21) Yes, yes. that’s why I’m thinking about the catalyst because the catalyst speed up a chemical reaction or make it happen sometimes. And then the other thing, ⁓ what you were talking and describing what twinning is doing, was also thinking about there’s this story where
the founder of Apple, Steve Jobs. He
He designed the loop to increase serendipity. ⁓ And then when he bought, ⁓ I think it was Dreamworks, I don’t remember the studio that he bought, right? After he left, Pixar, thank you, yeah, I was mixing it up. So when he bought Pixar, it turns out that he had ⁓ teams working on different buildings.
Dario De Santis (21:09) picture.
picture.
Federico Ramallo (21:20) And he basically moved them all together into a single building, right? And that increased serendipity, increased collaboration, that increased, you know, the quality of the products that they started to build up, And then the third one that I, you know, while you were talking about, that we’re thinking about. So I went to visit the Walt Disney Museum. It’s near the Bay Bridge, near the…
Golden Gate Bridge, right? ⁓ And basically they go through the history of the family of Disney and how he built ⁓ the company and how he built, how he innovated, right? ⁓ And it was a very quick ⁓ process, innovation process, right? ⁓ From going from, and I apologize I’m kind of going sideways, but. ⁓
going from ⁓ static pictures to motion pictures to then ⁓ cinematography movies ⁓ with animation. ⁓ Anyway, they had this studio where they had a small team working together and they were working as a family. And they would live nearby and they would spend a lot of time together there.
and the notes there, they would say that it was like a family, right? Hanging out together all the time. And that increased serendipity and that increased collaboration, right? So anyway, the reason I’m bringing this up is because you’re doing exactly the same thing, but on the virtual world, right? And that’s a very unique challenge that until now nobody has been able to fix. So that’s…
very interesting.
Dario De Santis (23:17) Thank you. I think you hit the nail on the head. What you say is very pertinent. In fact, we even call our solution digital serendipity. The whole idea is really stemmed also from the COVID times, where…
Federico Ramallo (23:32) interesting. Great.
Dario De Santis (23:47) Once upon a time, you could go to the coffee machine and have all the cross-pollination talks you wanted with everybody else in your organization. Now that doesn’t exist anymore. Now you are home. You are only collaborating with the people you’re supposed to collaborate. It’s really hard to have serendipitous conversations outside your direct collaborators and
And so we want to also bridge that gap. We want to make up for some of the water cooler conversations that you lost through the pandemic and the fact that people, even with mandate to return to office, they are not really going. Or if they go, they spend time in virtual meetings anyway. So why do we even bother going to the office? We could do that from home.
save gas and be more productive because of, well, we avoid commute. And, but that, that of course affects the ability to get used to the other folks, to more people in your organization and create ties with the organization. So send, so we, there are certain use cases that we are able to support that are very interesting for HR, for example. You know, imagine your company, you’re hiring
new hire and now this new hire has a mentor you assign a mentor to this new hire a busy you know mature engineer to teach to this to the younger engineer and now the younger engineer works from home and he has to collaborate and talk to the very busy or older engineer and you send messages that person responds you maybe at the end of the day
or when he can or you missed calls, not even, you know, you don’t even bother calling. Calling has 12 % success rate at most. And so what can you really do to get up to speed and learn about your organization if you’re a new hire? So one of the use cases is, I need to talk to the subject matter expert, you know, this older guy. I just make a wish. Hey, I want to talk to you five minutes.
And then he tells me, hey, get connected now. And that’s earlier than the slotting common you find on your calendar, maybe 10 days from today. It’s earlier. we’re accelerating conversation. And so you bring people up to speed faster. Same applies to, you know, sales or projects. You’re able to speed up projects more. You’re able to be more responsive to customers. Customer asks you for a quote.
Now you’re an account manager, you’re selling something really complex, a complex project to a large customer. And now before answering, you know, responding to that request for a quote, you have to go and talk to seven people in your organization. Those are seven 30 minutes meetings over two weeks. And you lose momentum with your customer. Imagine you could just go back and in
two or three days you talk to all of them. Now you’ve shortened the time to respond to customers by five times and you have a customer and you close the deal faster. You close the deals faster. So there’s a tangible value in doing all of that. ⁓
So, serendipity.
Federico Ramallo (27:32) Right,
right. Yeah, I mean, what I’ve been doing for the last 10 years is software development, stuff augmentation, near shore teams, building teams in Mexico for companies in the US. And one of the things that I encouraged before COVID was to spend time on site with
with the team in the US ⁓ so that we could generate that serendipity, right? ⁓ Because it’s different when you have a face, ⁓ an avatar, a photo, online, right? An email address versus we play mini golf together and I won or the product owner won, whoever, right?
you know, we had a great time together. Now it becomes a much more enriched relationship and a much more enriched collaboration, right? ⁓ And I saw that happen, you know, and it’s what you’re talking about. We will generate those moments where we would just hang out or we would just, you know, work together on site, right? ⁓ And talk about… ⁓
personal life, but also work, but also, you know, how can we do better? Right. And ⁓ we got to a point where, you know, people would say, you didn’t let me know that you were going to come because, you know, I wanted to take you to this restaurant or I wanted to, you know, plan this and that. Right. And ⁓ it was very interesting. Right. We had a lot of fun, but also it was great for the collaboration of the team. Right. ⁓ And it was
that serendipity that you’re talking about,
Dario De Santis (29:30) It’s about establishing trust. How can you establish trust with your coworkers? And ⁓ when you meet in person or you have interactions frequently and you accelerate the building of trust. since I’ve become more predictable, it’s a usual thing. ⁓
Federico Ramallo (29:35) Yes.
Dario De Santis (30:00) I go bike riding every day when I’m in the US. Not right now, I’m in Europe, as you know, for a period of time. When I’m home in the US, I I have to bike rides every day. And every day I see the same people doing the same routines. And you you do it 10 times and then they start waving their hands and say, hello. And then one day you stop and talk to them. And now…
And then you can talk because they see you, because they saw you five, 10 times and they trust you. You’re predictable. You’re always there. They know that you’re from their neighborhood. They know that they feel confident in being approached by you and they’re actually happy because now they’re talking to someone that they’re curious about because they see them every day. That, it’s a very interesting dynamic that…
It’s really lost if you just work remotely and you interact. Your interact was all lost. It’s very badly delayed. If every two weeks you talk to someone, you kind of almost start over every time. But if you’re able to interact faster, seven times in 10 days with quick conversations.
and you know maybe for seven five minutes conversations in 10 days rather than seven 30 minute meetings in seven months you’re gonna be you’re gonna establish a better relationship this is what i feel intuitively no
And this is, by the way, gold for a company that wants to promote certain culture, that wants to spread, you know, the example of certain successful people. want young, younger youngsters to be exposed to those people as much as possible, Federico. So you want them, those conversations to happen so they can learn from them. They can see what…
what success means in that organization and they can imitate them. so all of that has to, in the post-COVID world is really hard and we’re trying to facilitate that as much as possible.
Federico Ramallo (32:26) Very interesting. So I saw a product that would simulate an office, a layout of an office, and then you could see the avatars going from one place to another. So then you could see, you could nudge people and have little voice calls, which I was trying to solve the similar issue, a similar problem. ⁓ And I found refreshing.
compared to other solutions, right? You know, like kind of playing a game where you see ⁓ the avatars around, right? And you can interact with them. ⁓ But now that I’m learning more about what you’re doing with tweeting, I think they missed a mark on the serendipity part, right? Because, ⁓ yes, you can see the map of the people, but ⁓ what you’re doing is proactively…
creating the serendipity, right? And this solution that I saw was still a passive serendipity, right?
Dario De Santis (33:30) I mean, it’s a location, you go there and you’re expecting to see people. You don’t see them in the physical office, but you can see them in the virtual office. And probably they’re there also when they’re sick, but they’re an avatar. They’re not, they’re a little more than a chat.
Federico Ramallo (33:35) Right.
Yes.
Yeah, and the complexity of understanding where, when they could be available and when they could have, know, when they could be available for a quick talk, you don’t know, right? So I would be afraid to ping somebody, you know, because I could interrupt that person, right?
Dario De Santis (34:09) Yes, yes. And look, I think you and I are, I don’t know how old you are, I’m approaching 46. And I’ll tell you, when I was a kid, when I started working, everybody was just placing phone calls. Whenever you needed to talk to someone, you just dialed the number. And if they weren’t at their desk, okay, it’s a missed call, but if they were at their desk, they would always…
pick up the phone and talk to you, especially older, more skilled workers. So whenever you needed somebody from a subject matter expert, just dial the number. Hey, I’m the kid. I’d like to know how to do this. yeah, I’ll explain you. And you would drop everything, talking to someone say, ⁓ hold on, they’re calling me. And hey, and answer the phone call. Even with your cell phone, it was fancy.
Federico Ramallo (34:50) You
Dario De Santis (35:06) to have the cell phone ringing and then you just took that Nokia out of your pocket or that Motorola and say, hold on, one a second, somebody wants me. The flip phone, somebody wants me. Now, that calling habit.
Federico Ramallo (35:11) The flip phone, yeah.
Dario De Santis (35:25) had a drawback because if you are now focused and they’re calling you, they distract you. It’s an interruption because it’s not necessarily at the right moment. But you had that ringtone on or the vibration and you were waiting for, and it was cool that, somebody called me, must be important. You had that. But if you are, again, if you’re working on a team and somebody receives a call,
Federico Ramallo (35:35) Yes.
Yes.
Dario De Santis (35:54) and takes it, now you’re slowing down the team. It’s an interruption.
Then, then for some reason that I still can’t figure out, especially in the US, we started pivoting towards, let’s erase the barriers, maybe too many apps, maybe too many channels for communication, email messages, apps, various apps, messages related to specific apps, WhatsApp, Facebook Messenger, whatever.
there’s too much, too many notifications. So what you do is say, in order to be productive, we have to isolate ourselves as much as possible. Raise the barriers and isolate ourselves. And we say the real productivity is your personal productivity. Now, before we used to collaborate and do a team productivity with all those phone calls and those phone calls that were
that were really going on among people. Now is, no, I don’t want those phone calls anymore because to be successful, I have to focus myself. But now we are missing, that it’s so hard to talk to the other people that we’re missing that collaboration, collective collaboration that is happens maybe via messaging or via email, which is fine for certain things, but other things you have to talk.
Other things require discussion. You can’t send an email and then after three hours somebody answers and then after three hours somebody else’s chimes in. It’s too slow. For certain things you have to go back to that conversation. But that conversation happens only if you open Outlook and try to coordinate five people’s availability and you end up scheduling three weeks for today or start sending messages, hey, it’s too late.
three weeks, can you find any availability that day? You you start negotiating earlier slots. That’s so much, it’s so much coordination cost for doing something that one day was very easy to do. And so we said, before we collaborated fast among people through phone calls. And then we said, no, now we raise the barriers. We focus.
Federico Ramallo (38:01) You
Dario De Santis (38:21) and we don’t collaborate outside. Now with digital serendipity, we see that we’re kind of bridging the gap because I collaborate with the speed of a phone call, but that comes in the right moment when I’m not interrupting you. So it’s kind of the best of both worlds that we’re going after here that we have implemented.
Federico Ramallo (38:47) Right, right. I am.
So, yes, I have a similar age, I’m 42 now, so I kind of live the same, similar things, right? I live the flip phones and the non-smartphones, I guess, right? And what I’ve seen ⁓ in the last, I don’t know, 15 years, 20 years, whatever, when the smartphones became more popular, right? Is that…
Dario De Santis (38:56) Here you
Federico Ramallo (39:18) the level of notifications that we get increase and increase and increase. And now what happens to me is that if I’m working on code, I need to focus. So I don’t want to get interruptions. So I block as much as possible. And then what used to be a call, now people are used to send a message for it. Because it’s like,
If I call you, I’m interrupting whatever you’re doing and you have to stop everything just to pick up my call, right? Is this a real emergency? like you need an answer right now. You know, now you move towards that, right? What it used to be socially acceptable to make a phone call right now, it becomes a text message, right? Or an email, right? ⁓ And people are overwhelmed with notifications and messages here and there, right?
Dario De Santis (39:51) Yes.
Federico Ramallo (40:17) ⁓ which I agree with you, became a bad practice but because now we have so many messages and so many notifications that it becomes overwhelming, right? ⁓ So yeah, I am agreeing with you and I think that that is becoming an issue and the other issue that is happening with that is that the attention span for everybody is getting shorter and shorter.
Dario De Santis (40:46) Absolutely. Absolutely.
Federico Ramallo (40:47) Yeah, and that becomes
an issue. And that’s kind of one of the reasons I started doing podcasting because, you know, we can have this space to discuss ⁓ much more complex and rich concepts than a quick conversation on, you know, right.
Dario De Santis (41:11) Post of LinkedIn, Post on LinkedIn, is, right?
And then a few people chime in with a hundred characters and that’s it. You can’t really go deep into a subject.
Federico Ramallo (41:20) Yes, yes. And then the
Yeah, you cannot go deep
into any concept and, and, know, if you do a post on LinkedIn, if you meet at a conference, right, you’re, there’s so many people that I feel overwhelmed, you know, like I can meet like 10, 20 people in a single, you know, event, but then, you know, we never had a, it was like, ⁓ quick Q and A’s and that’s it, right? There’s no.
more meaningful conversation, right?
So, ⁓ go ahead, go ahead. Yes, I mean, this is so much fun. Yeah, I had really interesting conversations and very intriguing, you know, the thing is people have been changing my mind on topics, on things, Whereas on a quick conversation, it’s more of a information dump. It’s like, here it goes, blah, blah, blah, blah, blah.
Dario De Santis (41:55) Yeah, are fun.
Thank
Federico Ramallo (42:23) And that’s it, right? ⁓ So, yeah.
Dario De Santis (42:25) or
we agree on disagreeing. And we don’t open up to each other’s point of view much to enrich each other.
Federico Ramallo (42:28) Yes. Yes.
Yes, yes, that’s true. ⁓ So one question I was going to ask you about Tweelin is ⁓ how does it work for smaller teams, right? Like I can see that, you you’re probably working for corporations, bigger corporations. I’m wondering, you know, for smaller teams, what ⁓ effect do you see, have you seen happen?
Dario De Santis (42:38) and
Yeah.
So one statistic that is very important to understand the difference is in medium and large organizations, seven meetings out of eight are internal on average. So the majority of the meetings and the interactions happen internally within the organization rather than towards external people. Now, when you start
shrinking the size of a company that uses Tweelin, then the majority of the interactions start happening outside rather than inside. And for those companies, we have developed certain capabilities that help smaller companies as well.
Of course, if you want, may say it’s not our core business or the most impactful part of the story, which is saving a huge amount of money in terms of efficiencies for very large companies. But the small companies become much faster when coordinating with partners, ⁓ other organizations they talk to because Tweelin works cross-organization as well.
So I can make a wish to talk to somebody I know the email of and I know that that person belongs to a company that uses Twillen and now I’m able to get in contact with that person serendipitously in another organization. Now, if we are in the same organization, Federico, you don’t even have to accept. It’s, hey, Twillen, tell me when I can talk to Federico about this.
you receive a notification, hey, Dario wants to talk to you about this, expect a call at the right moment. And then when the right moment comes, I just press a button and talk to you. And it’s pretty accurate. About nine times out of 10 people talk at the first attempt. It’s just pretty impressive if you think about 12 % of a phone call.
Federico Ramallo (45:22) Wow.
Dario De Santis (45:22) 10 % probably do a
call, it’s a huge leap forward. Now across your game. Yeah, 12 to 9, 289.9 something. And at the first attempt. So people end up talking, but also, you sometimes at the second or third attempt. But the first is nine times out of 10, they talk immediately. So it’s really amazing. And then…
Federico Ramallo (45:26) You go from 12 to 90.
Dario De Santis (45:46) cross organizations is different, there’s an acceptance step because you don’t want to get a hold of somebody in another organization without that person agreeing on talking to you. So you say, you and I are in two different companies and I say, Federico, I want to talk to you. You say, hey, Dario wants to talk to you. Are you available today or not?
And you can say, no, sorry, I’m busy or yeah, okay, I’m available. If you say I’m available, then the telemetry starts flowing, Tweelin finds the right moment and you receive a card to join a meeting. So now it’s a meeting, it’s a meeting link and you both join the Microsoft Teams meeting, for example.
And then, yeah, so it becomes a meeting across two different companies.
Federico Ramallo (46:31) Right. Right.
Interesting. So you can have both intra and outer, across organization meetings.
Dario De Santis (46:42) Yep.
Yeah. So for a smaller company, imagine you have a series of partners and you all get Tweelin, now you’re able to quickly collaborate. If you have a cluster of companies working together, a district, ⁓ creating parts for a large auto manufacturer and you have to coordinate the efforts across the smaller companies, each one doing a certain part. Just an example.
then you can all have Tweelin and avoid scheduling two weeks from today, but say, want to talk to this guy, this guy, this guy. And then, if right moment happens, then everybody gets pulled into a meeting on the fly.
Federico Ramallo (47:30) Right, I see, interesting.
And what is the next big milestone for tweeting? What are you planning to do in the next year?
Dario De Santis (47:41) Ha, I’m to have to tell you some roadmap stuff. Okay. There’s some things that I can tell you. We are, we’re going to be integrating with Slack. Okay. So, and Bridge also companies that wouldn’t talk to each other today. across company today, finding a moment to talk, it’s really hard. And if they’re different companies on different platforms, it’s even harder.
Federico Ramallo (47:46) You
Dario De Santis (48:11) If you have a Microsoft Teams company and a Slack and Google company, they don’t have a lot of tools in common to organize a meeting. Maybe there’s a booking solution that they can use, or not the polling when you guys are available, but we can kind of bridge that gap. What we see is I’m a Slack user.
You are a Microsoft Teams user. We are in different organization. I make a wish through Slack to talk to you. You receive in Microsoft Teams the notification that says, Dario wants to talk to you. Do you accept? Yes. And now at the right moment, we use my Zoom link to talk. So bridging different platforms and putting them together in a cohesive experience.
Federico Ramallo (48:54) ⁓ I see.
Dario De Santis (49:04) which is a man in the middle facilitation AI that does not exist today and fills a very big gap, which is organizing meetings and interactions across organizations in an efficient way.
Federico Ramallo (49:24) Very interesting. There’ll be something unique. I don’t think anybody’s doing that yet.
Dario De Santis (49:29) Nope. Another thing I can give you, another bit of interesting thing that I mean. So we are not a large language model, obviously. We have our own proprietary AI that applies to the telemetry of your phone and laptop and calendar availability. But we can, you know, what we are going to exploring is, you know, using large language models to understand the context of your projects.
understand who has to talk to whom along the critical path of a certain project and putting these people together serendipitously to speed up project execution and time to delivery.
Federico Ramallo (50:14) so you can, you would be able to proactively ⁓ ask people, invite people to talk to each other before they even realize that they should talk to each other. Wow.
Dario De Santis (50:26) Yeah.
Along the critical path of a certain project. LLM can understand, LLMs can understand the context of your project and figure out certain critical path. now think about how you do projects today. Especially in larger organization. You have a calendar, you have tasks over time that are dictated by the calendar. And one day you do this, one day you do that.
people what they do, they do this and then they stop. They wait for the next day and they do that. And then they have to do another thing on the critical path and they need somebody who’s a subject matter expert divided across five different projects that decides to go on vacation. And now there’s a discussion along the critical path of a project that is delayed by the two weeks of vacation of that person. And
And just simply projects are laid by 40 % across the board.
And, but there’s gotta be a better way. If instead of having that, imagine you have a work breakdown that is not constrained on the calendar cadence, but you’re able to accelerate that because you can have people interact faster and make decisions faster. Then you have for the first time, it’s amazing.
Federico Ramallo (51:55) The value for that is amazing.
Dario De Santis (51:59) for the first time in history, you’ll be able to compress the timeline of a project. So we’re going to explore that.
Federico Ramallo (52:08) Wow. So ⁓ I remember like when they built a new highway on or a new road on, you know, in a city, right? The number of, know, you have all these crossings and then you have the number of notes grows exponentially, right? ⁓ So that complexity makes that, yeah, you make a bigger road, but then you have more traffic coming in and then, you know, that makes
you know, the final impact is going to make that it’s going to be slower than it was before, right? So it’s counterintuitive. You’re adding more bandwidth if you like, but then, you know, you have more delays, right? So I feel that something similar happening with large organizations, right? Because you have such a large, ⁓ you know, ⁓ group of people that have to interact with each other, right? ⁓ So
What you’re doing is optimizing that. You’re being able to take, optimize ⁓ that, those interactions, reduce the time to market and make the companies much more ⁓ competitive. Right?
Dario De Santis (53:25) Right. the more with size and more people in an organization, the coordination cost goes up. This goes up big time. My startup, maybe I spend 15 % of my time talking to people internally.
At Cisco I was talking to internal people 80 % of the time of my day.
Because with the large number of people to make things happen, there’s a huge amount of interactions needed to create consensus, grow exponentially.
Federico Ramallo (54:03) Yes.
Dario De Santis (54:03) And so if you are able to streamline those and reduce the impact of, reduce the timeline of all those interactions, you are delivering a tremendous amount of value.
Federico Ramallo (54:18) Yes, I agree. Very interesting. I will review twilling in more detail because I find it very fascinating.
Dario De Santis (54:26) Absolutely, absolutely. And if you want to try it, we offer really generous free trials. ⁓
Federico Ramallo (54:35) Oh really? Nice. We’ll put the links
for the product at the notes of this episode so people can reach out. So I have one last question before we wrap it up.
Dario De Santis (54:41) Absolutely. Thank you. Thank you.
Please.
Federico Ramallo (54:48) What is
biggest change you’ve seen from going from corporate to ⁓ working on a startup? What has been the biggest change you’ve seen or insights that you can share?
Dario De Santis (55:02) ⁓
Ha, the biggest is, that’s quite, let me try to elaborate that quickly. You know, being in medium and large and small companies, I’ve done them all. The difference between a small and a large company is the pace of learning, which is absolutely, probably in four years doing Tweelin initially part-time and then.
the last couple of years full-time I’ve learned more than the previous 16 years of collaboration AI product management. and I learned learn you learn at a so much faster pace anybody because your span of of control is not a slice of a large of a small slice of a large pie, but it’s a large
slice of a smaller pie. and you see all, I wore so many hats and I saw so many dependencies between different functions and I learned how to you know do more with less, optimize resources, go faster and and so the biggest difference is the pace at which you can learn and grow
Another difference: that is absolutely evident, but we already talked about it, is the lack of coordination cost that, you know, that you don’t have the huge coordination costs. you don’t, you don’t have to align the stars. Well, especially in my position, being a co-founder, I talk to people, I let them understand what we’re doing. They get excited. We execute, we execute fast. There have been companies that…
It took six months of discussions with another team to add a ⁓ link in the intranet of the company, change the link in the menu of the intranet. These are mind-blowing inefficiencies that you absolutely forget about. But the good news, I think, is…
I think that there’s, as an entrepreneur who is approaching a smaller startup, knowing, having seen larger companies and how not to manage them, it’s really helpful in shaping the future of your startup or the growth, the mechanism, the organization. So I think it’s really good that I’ve done all of them.
all the sizes and kinds.
Federico Ramallo (57:52) Yes, think that there is, know, some of, most of the processes that the big corporation built have a reason to be every single step, but then you can, you know, summarize them and compress them and do it, do it, you know, yourself or having one person on your team doing what will be four or five people on a bigger company, right? And you can move so much faster. Yeah.
Dario De Santis (58:17) Absolutely. You don’t have to ask permission to anyone, essentially. Especially when you are a co-founder, you are free to express yourself. Which exposes you to, okay, I made the decision and I immediately know if it works or not. So I learn fast. I close the loop fast. And I move to the next.
Federico Ramallo (58:19) very interesting.
Yes.
Right, right, yeah. Very interesting. So I appreciate Dario for being here. ⁓ It’s been very interesting to learn about what you’re doing at Tweelin, and I’m excited to see what you are going to come up next.
Dario De Santis (58:59) Thank you, thank you very much. Thanks for having me. It’s been immense pleasure. All the best for your podcast, Federico. I hope you’re gonna grow your audience to the millions. And thanks everyone who has been listening to this episode.
Federico Ramallo (59:20) Thank you.
Dario De Santis (59:22) Thanks.