Amplify Partners Head of Talent Natasha Katoni

Natasha KatoniAmplify Partners Head of Talent

Joining us on this installment of Talk Talent To Me is the Head of Talent at Amplify, Natasha Katoni. Prior to Amplify, Natasha was one of the very first technical recruiters at Segment, where she went on to become Technical Recruiting Manager. In today’s episode, she shares her somewhat unexpected career journey and what she has learned about talent, scalable processes, and interesting problems along the way. We discuss the importance of really listening to candidates without bringing your own biases into the mix, why building strong relationships with external agencies and platforms is an essential part of the recruitment process, and why there is no one pathway in talent. Natasha speaks candidly about some of her personal motivations, successes, and shortcomings as she has progressed through her career. She even turns her own processes back on herself as a candidate and shares her advice for those currently on the job hunt: be thoughtful and process oriented, but don’t forget to trust your gut!

Episode Transcript





[00:00:05] RS: Welcome to Talk Talent To Me, a podcast featuring the most elite talent leaders on the front lines with modern recruitment.


[00:00:12] SPEAKER 1: We actually want to understand the themes of someone’s life. We want to understand how they make decisions. Are they willing to take risks? And what it looks like when they fail.


[00:00:22] RS: No holds barred, completely off the cuff interviews, with directors of recruitment VPS of global talent, CHROs, and everyone in between.


[00:00:29] SPEAKER 2: Once I went through the classes and the trainings and got the certifications through diversity inclusion, I still felt like something was missing.


[00:00:39] SPEAKER 3: Talent acquisition, it’s a fantastic career. You are trusted by the organization. You get to work with the C suite and the security at the front desk and everybody in between and everybody knows you.


[00:00:52] RS: I’m your host, Rob Stevenson, and you’re about to hear the best in the biz Talk Talent To Me.




[00:00:59] RS: Joining me today on this here installment of Talk Talent To Me is Amplify’s Head of Talent, Natasha Katoni. Natasha, welcome to the show. How are you today?


[00:01:09] NK: I’m doing great. How are you, Rob?


[00:01:11] RS: I’m wonderful. Thanks for asking. I’m back in action. I had three weeks off where I was kind of on vacation and nobody knew, because I was a dutiful little podcaster and I scheduled all my episodes to go out and when they were meant to. We didn’t miss a beat, but now I’m back in action and I’m feeling really good.


[00:01:28] NK: You gamed the system.


[00:01:29] RS: I did. I pulled the wool over everyone’s eyes, now they’ll never trust me again. They’ll be like, “When did you have this conversation? Does he work for Hired? Is this podcast even happening?” Yeah, it is. I promise, but that’s how it goes. Thanks for being here. How are things on your end?


[00:01:45] NK: Things are going well. I took my first – well, I guess not post-COVID, but still kind of in the midst of COVID, but my first vacation. I just got back from Hawaii and feel very rested and ready to tackle the work challenges that are coming my way. I’m just excited for fall and all the – hopefully things reopening soon.


[00:02:04] RS: Yes, me as well. I have so many things I want to talk to you about, Natasha, because you have a really interesting background. I think we should definitely got to your current role at Amplify eventually, because you have kind of structured your career in an interesting way. I want to leapfrog along in all those lily pads of your career stops.


Can we first speak about your journey at Segment a little bit? Because you started there really early on. Segment is now this huge company acquired by Twilio, has this great employer brand. I guess, could you may be set some context by sort of just documenting the ass you kicked at Segment over that stage of your career?


[00:02:43] NK: Thank you. I’m flattered. I’m glad that one of the things we worked on actually – well, many people, but McKenzie Brown on my team did a lot on the employer branding side. I’m glad to hear that it still has a great reputation. Let’s see. What was the question again?


[00:03:00] RS: I would love to just know, you kind of came there as – I think you were just a regular old technical recruiter back in the day?


[00:03:05] NK: I was. I came in as the first recruiter at Segment. I focused on the technical side of the house and we did have a business recruiter come in pretty early on as well, but I got there first. I was hired by the VP of people, Adriana Roche and Tido Carriero, the VP of engineering. He eventually became the chief product officer. But I was able to be there from about, oh gosh, between 50 and 60, who knows the exact number, to past 500. Then I moved over to the VC side. I was there for about 10 extra.


[00:03:35] RS: Yeah. That is tremendous growth. I’m so curious, because you were so early, I’m sure you are putting in processes at an early stage. What were some of the things that you put into place that scaled really well as the talent operation grew?


[00:03:49] NK: It’s a great question. I think that – I had been at early-stage startups before. I was looking for something very particular. When I went there, I wanted to find a place where they had – where the executive team was very smart about hiring, they cared about it, they wanted to invest in it, but they didn’t really have a lot of things built. I mean, we can kind of take this in many different directions, but I’ll say that a lot of the tools that we built in the early stages on the technical side were used by both sides of the house.


I think they honestly used those tools until acquisition. They definitely scaled well. I think one of that top ones was something we called the Checklist, which I’m happy to dive into.


[00:04:27] RS: Yeah, tell me everything.


[00:04:28] NK: Yeah. Scaling wise, we created this thing called the Checklist. When I got there, we were closing people, but we are only closing about 40 percent of our pipeline. If you think about that, that’s less than chance. A lot of times, the startup metrics that are – throughout the pipeline that are quoted are kind of aggregated at the early stage, but they’re not actually questioned. We decided – our VP of engineering came to me and he’s like, “We’re closing some people. We’re just wasting a ton of time in hiring.” Our pipelines were very full, but when he was looking at his engineering team, they were in interviews all day and we weren’t able to build as much product as I think we wanted to.


He did us a huge favor and he kind of took the hiring numbers off the table. He’s like, “Let’s forget how many people we hire for one quarter and let’s just focus on honing in on making the best process possible so that we can hit, let’s say –” he loves to kind of stretch goals, so his metric that he convinced me of and I, frankly, was really afraid of was 80 percent close rate, which is really, really high for the early stage. We also decided to track because of his hunch around like how much time was being put into the hiring process by engineering teams. We also tracked how many hours, engineering hours we spent per hire. That was about 80 hours per hire. That’s like two full-time work weeks in a regular world outside of startups, maybe one and a half for startups.


We said, “Okay. Forget the number of hires. Let’s switch those numbers. Let’s get our engineering hours per hire down to 40 and let’s hit 80 percent close rate,” which I thought was honestly impossible. There were few things that we did to be able to really hone in and make those metrics work. For what it’s worth, we did hit those and we were able to maintain them from the rest of my time at Segment, except from about one quarter when we had to figure out what was changing. We realized it was a really good diagnostic measure.


The way that we did it was, we started to look at closes that we lost and also closes that we won. But we started to do not only a lot more pre-selling, but we really honed in on a list of questions that would allow us to uncover the candidates’ motivations early. A lot of times, startups want to move candidates forward because they pass the interview test, but a lot of time can be wasted if the candidate, if you really get to the core of what it is that they’re looking for and it’s not aligned with what you have to offer, it’s a waste of time, because you’re not going to close this people, or you might close them but you won’t retain them. 


Ultimately, the impact in the business isn’t there. We first kind of narrowed down what are the questions that we need to ask, and at what inflection points throughout the process? To be really sure that the candidates’ motivations were in line with what we could offer them. We also started to become really stringent about pre-selling. We would again, hone in on those motivations and instead of bringing in all of our heavy hitters at the onsite or even afterwards, we would start to kind of pay a lot of attention to timing.


One of the mistakes that I think companies constantly make is they talk about moving as quickly as possible. That’s not always helpful. You don’t always want to move as fast as possible. What you really want to do is capitalize on the recency bias and come in with your heavy hitting cells that are tailored to the candidate as close to their decision-making process as possible. That means when they’re at the end of interviewing and they’re ready to be in that decision-making mindset.


We played with questions that would lead us to motivation. That means we also cut candidates. We played with timing of the onsites and timing of different pre-selling. We also started to be really ruthless about what tools we use for sourcing. We were depending on a bunch of agencies and we are taking in a lot of – we are taking in candidates that really – like we knew weren’t going to be a great match, but that kind of fluffed up our pipelines and maybe they were and edge case, maybe they could work out. We started to just be ruthless about saying, “We know what we’re looking for. We understand the patterning of the resumes and who we’re targeting. Let’s just focus on those people.”


We still use tools like Hired and Triplebyte, et cetera, but we started to be really, again, stringent about who we move through those processes. If they were talking to like 20, 25 companies, we would spend a lot of time, but we thought they were great, we would spend a lot of time narrowing down like how can we get us to be one of their top three choices by the onsite. If we couldn’t, then we would let them go, even if they were a good fit.


To kind of summarize a lot of information there, we started focusing on how do we presell? How do we really uncover the motivations of the candidate and decide if they worth the time spent? How do we time the onsite and the cells within the process to be able to be the most effective, and how do we use tools that we’re not oversaturating our pipeline with candidates that are never going to place?


[00:09:04] RS: Yes. It sounds like the point of trying to figure out motivations early, was to figure out who you thought maybe okay, if they get all the way through the process, they might not take the offer.


[00:09:16] NK: Yeah.


[00:09:16] RS: That’s like the most heroic waste of engineering time, is someone who gets all the way to the end and then doesn’t take it. Like that’s a bigger waste of time than just going on a bunch of phone screens like, don’t go anywhere.


[00:09:28] NK: Well, everything can waste time, I think that what’s important is to know if the candidate is worth it or not. If you have a mid-level engineer who is great, but they’re really prioritizing – this is a pattern I’d see all the time. Their parents want to still have a lot of influence over them. Maybe they’re in their earlier 20s. They really want to be at a startup, but their family really wants them to go to a public company and they’re talking of Facebook, Google and a 50-person company, Segment or whatever it might be. They’ll probably not going to take your offer and they’re not so specialized that you absolutely have to move them forward no matter what. 


There are certain candidates, for example, SREs, where even if their motivations are slightly off, it’s so hard to get them into process that it’s still worth it. But taking an active stance on, what’s the tradeoff we’re making here and is it worth it? That’s what’s important.


[00:10:15] RS: Yes. In the case where someone is in process with 20 plus companies, even if you are like top three, if they tell you top three. I can see why you might be like, “You know what, let’s just like bounce this person because it sounds like they don’t even know what they want.” If they’re talking to that many companies –


[00:10:31] NK: And I have.


[00:10:31] RS: Yeah. What do you say to someone? Say you’re interviewing someone and they’re like, “Oh yeah, I had nine phone screens today and I have seven tomorrow, and I’m talking to all these companies.” If you’re a particular kind of talent, you can drum up those kinds of conversations in a hurry. If you’re a technical talent, if you’re an SRE, if you’re a really in-demand person, then you could be having all those screens. What do you say to someone like that, where they just have all of the conversations and potential offers on the table and you’re like, “You know what? We’re not going to risk not landing in your top three out of 22”?


[00:11:01] NK: It’s a little bit of an art form. It’s not a blanket rule. I would say that in this example, it sounds like this person is specialized, which means, I might want to spend a little bit more time with them. It also sounds like this person is in the early stages. What I would do there is I would collect, I would ask them, what are the things that are motivating their search and I ask them, what are the things that are motivating their search? And I ask them to stack rank it. I also take notes on how people’s answers change over time, because cognitive dissonance – my background is in psychology and cognitive dissonance is something that people really like to avoid and so, people want to be who they say they are. I would ask them probably their top three motivating reasons for looking for a change. I would say to them, “Listen, you are talking to 20 plus companies. That’s fantastic. I’m so excited for you.”


I would have them tell me why X company I’m working at is exciting to them, match into their motivations, and then I would kind of take a step back and start to sell them. Again, because they’re a specialized senior candidate, we already established that, it’s going to be maybe worth it. Let’s say they cared a lot about the product development and the market opportunity. I might put them in touch with our head of product to do a presell before we even move them to the process or if they’re really motivated by the types of potential growth that they could have, I would put them in touch with another engineer who has had a really strong career trajectory at said company.


If those conversations, and if I check in again, they’re still talking to 20 companies, then I’ll probably tell them, “Hey, look, it doesn’t sound like we’re going to be able to standout here. We’re going to back out of the process here. If you start to narrow it down, let us know.” But if they’re really going to do 20 onsites, they’re just going to get confused and probably they’re going to pick whatever comes in last. If they’re fantastic and worth it, and they’re still doing that many onsites, I would then try to time it where we come in last, which is very different than a lot of other recruiters who – a lot of recruiters try to get the process within three to five days. You’ll see a lot on Twitter about, we do it faster than anyone else. That doesn’t always work with the candidate’s ability to make a decision.


[00:13:02] RS: Yeah, that makes sense. You don’t want to miss out on someone, but you can understand where they are in the process without sprinting them through your process. You don’t necessarily need to rush to the offer.


[00:13:13] NK: No. I mean, I think that that’s one of the big mistakes that companies make because they think faster is better because it shows interest, but it also makes you look kind of desperate. 


[00:13:21] RS: Yeah. What have you noticed in terms of the way candidates express their motivations or priorities over time? Are they generally consistent? Is there some gamesmanship going on early stages? What does that look like for people over time?


[00:13:36] NK: Some candidates are consistent. If they’re changed, I’ll ask them. I’ll say to them like, “Hey! I wrote down earlier what your top three motivating factors were when you were looking at job changes. You said three things that didn’t involve cash, and now cash is number one. Tell me what’s changed? Is there something going on in your life that changed?” You can’t ask them if they had a baby or something, but you can kind of ask like what’s going on externally or – and I will try to kind of study like what conversations have led them to that change.


I think the problem I see more often than that though is that, people don’t really listen. Like they will assume that they know – like hiring managers or people at the companies that I worked with will assume that they know what the candidate feels and thinks. But if you’re not asking them directly, then you don’t really know.


[00:14:22] RS: Yes.


[00:14:23] NK: And you’re bringing your own bias into that. That’s the problem I see more frequently.


[00:14:28] RS: Yeah. I was really struck by what you said a moment ago, Natasha, about how, at the beginning of this whole process, you just paused on headcount for what was a month or quarter. Which is fascinating to me because, one, it sounds such a great approach because how are you meant to fill all these roles, and then do the second job of figuring out how to optimize how to fill the roles? You’re just kind of doubling the work. But then also, on the other hand, how do you get the organization to agree to you not making any hires in the next quarter. What was that process like?


[00:15:00] NK: Well, we did bank hires. I think it was more a mentality switch, where what we were doing was working to an extent, but there were faults to it. We’re trying to change the system, and sometimes you have to – if you ask any engineer, like sometimes you have to slow down and look at the architecture of your system and then go and code. It’s the same thing here. If you’re just coding, coding, coding or recruiting, recruiting, recruiting, you’re not actually stopping and asking yourself, do we understand the system that we built? Do we understand the problems within that system? Do we have a hypothesis for what’s wrong? If so, what are our solutions?


We had to kind of take a step back and look at it, but I’d say that Tido was an incredible influence for me because he helped me take my past experience as a scientific researcher and bring it into, how do we think about recruiting from the perspective that an engineer would think about building their own system? We did end up making hires, but it was – I think I had it a little bit easier where one of the top executives of the company was the one driving that versus me. 


Now, when I tell companies that – I try to teach them these processes from the ground up, but I do think it would probably be pretty scary for an executive team to have a head of recruiting come to them and say, “We’re not going to make hires for a quarter.” I think when you want to experiment, when you want to build, when you want to fix a system that isn’t working how you want it to, I would try to speak the language of the person that you’re trying to convince. If it’s a technical founder, tell them about how they would build an engineering system.


[00:16:28] RS: Yes. Yeah, that’s great advice. In general for any time you have to work interdepartmentally, like think about the recipient of your messaging, what do they actually care about and put it in those terms. I think you’ll go far if you prioritize that way.


[00:16:41] NK: Yeah, just persuasive communication, it’s the same thing as any time you’re trying to get something from an executive team, but you have to show them the value of it.


[00:16:50] RS: Yep.


[00:16:51] NK: Can I actually characterize that differently? I don’t think the engineering hires – that was an indicator to us that something was broken. It wasn’t really the reason for success. The reason that we are so successful at closing at Segment was because we did a lot of pre-selling, we timed the onsites in our selling in the right way, and we did a lot of motivation uncovering early on. We spent time on the right things.


[00:17:12] RS: Okay. So then, the engineering hours was an indicator of those things being misaligned it sounds like.


[00:17:16] NK: Yeah. The engineering hours was essentially showing us that we are spending a ton of time with people that weren’t closing. That paired with a lower close rate, that was the indicator in itself. 


[00:17:27] RS: Got you.


[00:17:28] NK: I think it’s an important metric because most people don’t even quantify those hours spent.


[00:17:32] RS: Yeah, exactly. Also, just thinking about like, “Okay. How do we get engineering hours to hire down.” That strikes me as just like a vanity metric. That’s sort of like the BandAid on the bullet wound, like you have to incentivize the right problems. Does that make sense?


[00:17:48] NK: Yes. Again, it was an indicator, and then from there, we did get it down to about 40 hours per hire, which we felt was healthier. We didn’t have any standard metrics for this, because not a lot of people quantify it, but then we stopped measuring it after a while, because it was more anecdotal that the engineers felt like their time was going to high-quality candidates that were pre-sold and evaluated well. That’s really what mattered. What we cared about in the end was, what’s our onsite to offer rate? What’s our offer to close rate? Then what’s our top of funnel interested rate? Those are kind of the three golden metrics that I think about.


[00:18:21] RS: Got you. You were able to get the offer close rate way higher. Those three are really great examples. Would you say those were like the main pillars of how you’re able to set Segment up for hypergrowth and to scale?


[00:18:33] NK: Yes.


[00:18:34] RS: Got you. On the other side of that coin. What are the things that can break down? Because there are things that are good enough at an early stage and then, this is almost become like a cliché, “Oh! But will it scale?” Then in terms of processes, what are the things that you think, if you don’t put a time into early as your company grows, will break down and you’ll have to deal with that technical debt over time?


[00:18:58] NK: That’s a great question. I think as the business grows – I mean, from a personal standpoint, I was managing the whole technical side of recruiting and the checklist, as we talked about, was something that I – I become very micromanagy with it, so that definitely didn’t work. I think if I were to go back to my time in Segment, I was very controlling on how the people on my team filled out this checklist, and were they looking for the right things and stylistically, every recruiter that comes in is going to have a different way of doing things and bringing in this different perspective is helpful. But it can also kind of break down what you know works.


What things can break down over time? I’d say that one of the hardest parts of recruiting is that, the business needs to be able to switch hiring funnels on and off. So, in the beginning, our focus was. let’s just build a world-class team. We need more people, we’re going to keep needing more people. It doesn’t matter how much money we’re spending, like just do it. Over time, it turned into – we are getting ready for an exit. We were much more focused on what is our revenue, how does that back into the hiring funnels. Recruiting is kind of always at the end of that.


The process at larger companies we’ll use will be focused on like what are our sales numbers, what are our revenue goals, how many people do we need, and then to sell the product, how many people do we need to build the product? Etcetera. Obviously, this is geared towards a SaaS business because that was Segment was. But I think that what the mistake that we made and what kind of started breaking down was like, we had an internal team that was incredible. Like the technical recruiting team was incredible. We had great sourcers, we had great recruiter but we had a hard time keeping up with the fluctuations of the company.


Like, I think that when recruiting leaders think about their team, what they really need to do in hypergrowth is they need to build strong relationships with external agencies and platforms and tools, where they can find quality people and build those quality relationships to be able to turn the faucet on and off when you need more. You have to have your internal people who are your rocks. If you don’t have a preestablished relationship and you’re not prepared to capitalize on that when the business is asking for more, that’s when it starts to break down.


[00:21:07] RS: Got you. It’s just easier to ramp up an external tool like that than it is an internal team, I suppose, provided there is the relationship, yeah.


[00:21:15] NK: It’s not about easier to ramp up. It’s just like there are going to be quarters where you need more resources based on the needs of the business. Companies will make the mistake of hiring a massive internal recruiting teams, and then they’ll lay them off. Then, they’ll try to rehire them, and it becomes this terrible recruiting brand, where recruiters now that they’re the bottom of the barrel and they don’t want to go there.


In order to do this well, you have to, I would say, keep a smaller team internally, one that can hit what you consistently see. Then, in times where growth is starting to go up and up, have pre-established contracts and relationships with companies like – we us Connery a lot at Segment, but there’s a ton of great consulting folks. Like I work with this woman, Jess Brody, who’s amazing, Alex Macho, like there’s a lot of external folks who are building their own practices right now and who have recruiters and sourcers that you can bring in on an hourly basis, or in a project basis.


Spending time building those relationships with external people to be able to support and add to your internal recruiting team when you need it, but also not bloat your recruiting team so that it’s so big that you have to lay people off, that’s the key. It’s a very hard thing to do.


[00:22:23] RS: Yeah. It’s such a great point to just accept that the growth of a talent team or the size of a talent team will not be one to one correlated with the demand from the rest of the business, right?


[00:22:36] NK: No.


[00:22:37] RS: No matter how well your leadership plans, it’s just probably not a reality. How do you be ready for that? Well, you just explained it. That’s such a great advice, I think.


[00:22:44] NK: Thank you. Yeah, I think that it’s hard because the pattern is, sales team gets into the very last minute of the quarter to hit revenue. Then, we back that into where we’re at with revenue, and then how many people do we need to continue building X product. Then, now let’s trickle that down to recruiting. Sometimes you don’t get to finalize headcount until a month into the quarter. You kind of screwed it if you don’t have levers that you can pull. 


[00:23:08] RS: That is such a great point with sales, because like as the rest of the planning is going on, it’s like, “Oh, well. These the sandbag and salespeople are going to drop down like seven figures each on the last day of the quarter and then that’s going to completely change all of the projections.”


[00:23:22] NK: Well, they also might not, and then recruiting might get looked at the call center and we have too many recruiters and there isn’t enough hiring. I find that the tendency for – it’s very rare for an executive team, like the executive teams will have – they’ll have a VP of people, but they won’t always have a group of people who will really understand what a recruiting funnel is like and what it takes to source a great hire or to get a great hire. You get the bottom of the barrel information, but you’re also expected to perform. It’s just the reality, like [inaudible 00:23:55]. Being able to flex with that is going to make you a much more powerful team. 


[00:23:59] RS: Yeah, it’s hard out there for a talent pro, you know.


[00:24:02] NK: It’s hard out there for a talent pro, for sure.


[00:24:05] RS: Maybe everyone should just leave their internal company and join a VC firm.


[00:24:10] NK: No, we don’t want that. We want great recruiters that are internal. I mean, being in VC is fantastic. I think that I – Amplify, I like it a lot more than I thought I would, but a lot of people who are close to me were saying that I was going to miss being an operator. Amplify is very special because we focus in the area that I’m most interested in and that I think I’m best at.


We do only seed and series A investments. Of course, our portfolio matures and we have companies that have exited, all the way down to our seed investments. But I spend my time with the seed and series A companies. They generally don’t have a sourcing motion, they don’t have a closing motion, they don’t know what their internal brand is or how to message and pitch their company in a differentiated way. If I hadn’t lived through that at Segment, of course, they’re a little bit bigger than the companies I worked with. But if I hadn’t lived through those early-stage problems, I wouldn’t have as much perspective as I do now.


My experience is perfectly suited to the type of investments and the type of work that we do, but other VCs, they work on much bigger investments and they focus more on C and D and later stage, hypergrowth type of things. I think that the profile that will work in VC is different based on the investment type, but I do think that internal experience, where you really can then later empathize with the company and what they’re going through, is really critical.


[00:25:31] RS: Yeah, of course. I was trying to pull off a cheeky seamless segue into your current role. 


[00:25:37] NK: I didn’t even let you.


[00:25:40] RS: You’re like, “No, no, no. This is my show now.”


[00:25:42] NK: Well, I will say – I mean, I think what I’m trying to impart is, that internal experience and living through it, there’s no substitute for it.


[00:25:50] RS: Yeah. That’s definitely right. I am interested though how you said that you’ve thought maybe you would miss being an operator or your other recruiting friends thought you’d miss being an operator and you’ve sort of –


[00:26:00] NK: Everyone said that.


[00:26:01] RS: – to shape this role where you are able to advise people in a way based on your experience as an operator. I’m just kind of curious about your decision-making at that juncture when you were thinking of switching from this internal role, now you’re in VC. How did you kind of weigh the decision and decide if this change to your role is going to be right to you?


[00:26:21] NK: Should I tell the real story?


[00:26:24] RS: I mean, I do love the real story. It’s up to you.


[00:26:27] NK: I’ll tell you the real story. I mean, there’s a funny part of the story, then there’s a real consideration part of the story. I was approached by Lenny Pruce, our general partner. I mean, Segment was very similar type of company to the types of companies that Amplify invest in. They were looking for somebody with the domain expertise and they were looking for somebody with technical recruiting experience, and management experience. It was a good fit. I kind of had a rule that I would always talk to VCs.


I talked to Lenny and I had this dream of being the first recruiter at Segment all the way through to IPO, or exit, whatever. I started referring friends over to Amplify, because I loved the team, I loved the people, but I just wasn’t ready to make the move. I wasn’t looking. It didn’t work out with those friends for one reason or another but, through those conversations, I got a bit jealous and I was kind of like, “Hey! That’s my job.” Tapping into those feelings, I was drinking some rosé in my backyard with one of my friends, and I was just kind of telling her like, “I really regret saying no.” She was like, “You know what? You should text them right now. Text them right now and tell them that you’re ready to go.” 


I did, I reopened the conversation. Texted Mike Dover, another one of our general partners, who promptly was like, “Let’s get on the phone right now.” Which I couldn’t do because I was so many glasses of rosé in. 


[00:27:46] RS: Like okay, now it’s time to pump the breaks. It’s like, the door is open, now let’s think of Monday, yeah.


[00:27:50] NK: I was like, “Let’s talk Monday.” But I’m excited. What I realized was that, I thought there was only one pathway in talent. I thought you become a recruiter and then you become a manager, and then a head of talent internally, and then a VP of people. I really missed, though, the early stage. I love solving the early-stage problems that we had at Segment, but I didn’t really see how to do that without doing the same job again.


Coming back to the Amplify conversation, I realized it was kind of such a unique opportunity to be able to solve those early-stage problems, get more of a breath, a wider scope on the market in a way that I’ve never been able to do before, focusing on one company and living and breathing that one story, while still getting very deep with our founders because they are so early stage. Well, I’m not doing the recruiting for them, I’m doing a lot of the problem solving with them. I think being so close to that is really fulfilling. I hope I answered your questions there.


[00:28:45] RS: Yeah. You totally did. The takeaway is that, if you’re ever in an opportunity, people out there listening in podcast land, if you’re ever in position where you can text the VC, ‘WYD?’, with a glass of rosé in your hand, you should do it because you might get your dream job.


[00:29:01] NK: You might get your dream job. Hopefully they’re the right type of VC that will – I’m pretty sure I told him I was a few glasses of rosé in and he was like, “Yeah. Let’s talk anyway.”


[00:29:10] RS: A disclaimer, yeah.


[00:29:11] NK: But he didn’t care. He was excited. But it ended up being a really good fit.


[00:29:16] RS: Yeah. It’s such an interesting role in VC. You kind of get to be this advisor, you get to be consultative to a whole host of people. How do you think the talent partner can be most useful to individuals who are your first head of talent, your first tech recruiter, what have you, in an early-stage company?


[00:29:34] NK: It’s a great question. I spend a lot of my time with founders who don’t have any background in recruiting or they’ve had background but it’s partnering with a recruiter. Usually, when I kind of start to peel off, is when they do have – when I peel off very intense help is when they hire their first recruiter of first head of talent. That being said, I do spend time coaching and working with our people on the recruiting side internally at companies. I’d say that, I mean it really depends, like it depends on the problems that they’re dealing with. Sometimes they’ll come to me and they’ll say, “Hey! Our sourcing pipelines aren’t working. What the hell do we do?” or “We’re not closing people and we don’t know why, or we don’t know how to create a comms strategy that’s competitive.” 


I think that what’s workable for me in the stage that we work with is, I kind of think recruiting doesn’t sleep. Like things happen on the weekends, things happen over holidays. It’s very different than other types of work, because it’s about people making life decisions. Just being available in unstructured way to hop on the phone, deal with closes, help them problem solve, while also teaching them, giving them many tools you have. It’s pretty generalized answer, but I think that it’s incredibly important and does set us apart.


[00:30:49] RS: Yeah. With regard to not doing the operational things as much, I have spoken to a handful of talent partners who, while it’s not their main offering and while it’s maybe not their most high-leverage activity, they’re also not afraid to roll up their sleeves a little bit and teach companies, “Okay. This is how you do it. This is how you source. Build a pipeline, etcetera.” Do you ever do that? Do you ever kind of get in the trenches and help teams kickoff their sourcing?


[00:31:14] NK: Oh, yeah. I mean, we also have Nate Remy, who’s on my team, he’s fantastic. He is an expert sourcer. I never was a sourcer full-time. I sourced plenty in my past roles, but a lot of my time was spent more on the full cycle. I actually was also never a coordinator. I kind of jumped into recruiting and was given a sink or swim offer and I swam, thank God. But I have so much respect for people who have done full-time sourcing, because I think it’s such an incredible skill and a lot of it is research based. 


While I will help our companies with thinking about sourcing, we also have Nate on my team. He worked with us at Segment and he was on the business side, the go-to-market side. But he moved into the technical side very seamlessly at Amplify. What he does is he builds both a generalized pipeline for our portfolio. We look at roles that are more evergreen across different teams and he’ll try to build networks of a thousand people that we can interact with and hopefully place in our companies, but he also helps with a lot of sourcing diagnosis and setting up those sourcing tools. Both of us kind of tag team there, but I’d say that’s really his area of expertise and I’m so lucky to have him.


[00:32:22] RS: Shout out to Nate.


[00:32:23] NK: Shout out to Nate Remy.


[00:32:24] RS: A possible future guest on this podcast. We’ll see.


[00:32:27] NK: Oh definitely, you should.


[00:32:28] RS: But yeah. I’m glad to hear that like you get that kind of – you had to scratch that edge a little bit. Just as in the interest of kind documenting career development approaches, because like you said, you had expected, “Oh! When you’re a recruiter, then you’re head of talent, then you’re senior manager of, then you’re director, VP, TA, etcetera, etcetera.” But we’re at this moment where talent professionals can be much more creative about their career, where they go and decisions they make for their next job.


I guess I just want to use your own spell against you here. When you are considering Amplify, what were your own personal motivations? Like if someone had used that on you and been like, “Okay. What do you really care about in your next role? What is important for you?” How were you thinking about that at that juncture?


[00:33:13] NK: I wanted to solve – I mean, I think that when you get more senior internally, there are the scaling problems, but a lot of the interesting problem solving pieces are in management. Honestly, I did the thing that I tell all my friends not to do. I usually run a full process for myself. When I went to Segment, I was very clear on what I was looking for. I was looking for a first recruiter role where I could build from the ground up, an executive team that valued recruiting, an opportunity to become the technical recruiting leader. I talked to maybe 50 companies and I really narrowed it down to Segment. I wish I was exaggerating, but I’m not.


When I went to Amplify, I did the opposite of what I tell all of my friends, which is, I really just went with a gut feeling. I figured that there was no downside. If I went to Amplify – I mean, Segment is an incredible company. I was so lucky to work there for four years. I think I just wanted a different type of challenge, and there wasn’t really anywhere to go up there, because we had our head of recruiting. The only thing I could really do was to continue to grow my team, and continue to grow my management skills, which is super valuable. But it wasn’t as interesting to me as, holy shit, we have no idea of what to do because we’ve just started a company.


I honestly went on a whim. I trusted my gut. I obviously said no at first because it wasn’t in the plan and I’m very much somebody who follows the plan, but this was one of the only times in my life that I just said like, “Hell with it. Let’s do it” and, worst case scenario, it’s not the right fit and I go back internal and take a job as a head of talent at one company. I just kind of felt like the risk was pretty low, but I was really motivated, I guess, if I was to look back, by interesting problems, and specifically early stage and interesting problems that I think I’m best at.


[00:34:55] RS: Yeah. I do enjoy that approach, because I think that’s something you afford yourself once you have a few years and a bunch of wins under your belts and whatever your profession is. You know you’re employable. You know you can go out there and get another job versus when you were looking for that role, maybe, I don’t know what your situation was. But when I think of my first real marketing job, I was like really broke. I needed a job badly. I really needed something where I could kind of hone my craft and have something to offer. I luckily found a company that kind of took a bit of a chance on me.


[00:35:28] NK: Well, I had been laid off and I think it’s really easy for recruiters to get laid off. We talked about earlier the mentality that a lot of the executives have around recruiting cost center and looking at it at something that you can – a team that you can lay off and build back up as needed. I had been a part of massive layoffs or big layoffs before because it was just what the company was doing. That’s not necessarily a terrible thing, but I was looking for somewhere where I could distinguish myself and grow. That’s what I really cared about at Segment. I wanted to find some place that I could really plant my feet in and stay more than a year or two years. 


I found that because I was very careful. To your point, I had spent – I can’t even remember how many, but I had spent a good amount of time in recruiting at that point. So I knew that if I wanted to go back internally, I’d be able to find something, especially with how the market was developing and how much VC money was being pumped into the ecosystem. But I do think that my advice to all my close friends and anyone who I care about is, you should be very thoughtful and process oriented when looking for a job and to use the checklist process on yourself as a candidate as well.


[00:36:33] RS: Yeah, definitely. But at the same time. I mean, worst case, you just take it off your LinkedIn, pretend it never happened and go there and do it again. Do the job search again. 


[00:36:42] NK: Yeah, I think that you do have to – I believe in trusting my gut. I think that I’m lucky and that when I make decisions based on a gut feeling, so far they’ve worked out. I know I think it’s a very lucky thing, but what I’m trying to say is that I was very thoughtful earlier on and that helped me a lot and it got me to a point where I could take more chances. But I also grew up in a family where both my parents are immigrants, and they built amazing lives for themselves, so we still had a lot of money and security, and I wasn’t somebody in a position where I was going to mess around with my career and have something to fall back on. I had to be very careful about how I was building myself in my career earlier on. Now, I’m in a position where I can take a little bit more of a chance. 


[00:37:23] RS: Yep. Exactly. I think it’s important to trust your gut, and your gut isn’t just like blowing in the wind, your gut is years of instinct that have been like formed from your experience. I wouldn’t discount that too much. Right now, my gut is telling me that we are at an optimal time to wind down this podcast episode because we are creeping up on optimal podcast length.


Natasha, this has been such a delight getting to know you and hearing about your journey, and where you are now and all of that. At this point, I’ll just say, thank you so much for being a part of the show and for joining the podcast today. I’ve really enjoyed meeting you.


[00:37:56] NK: I enjoyed meeting you as well. I did want to put in a plug that I may be expanding my team at Amplify. We are thinking about potentially bringing on recruiters I can work with, embedded with some of our company. If you’re interested and you’re thinking about a different approach to recruiting that is still working with early stage but in a different format than with just one company, hit me up on LinkedIn. 


[00:38:19] RS: I love that. What are the actual roles? 


[00:38:21] NK: TBD. This is something that we’re still kind of building. We found a couple of folks that we thought are interesting and opportunistic, but one of the things I love about Amplify is we care about bringing on really strong, smart, accomplished people and an opportunistic person kind of led into a discussion about what the team could look like. If you’re a great recruiter, I always want to network with you.


[00:38:43] RS: I love that. If VC sounds like your kind of jam, if you like the cut of Natasha’s jib, reach out folks. For optimal results, ping her between 4:00 and 6:00 PM on a Friday afternoon.


[00:38:53] NK: Exactly.


[00:38:54] RS: Natasha, thanks so much for doing this. I really love chatting with you.


[00:38:57] NK: Of course. 




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