Solving the lack of diverse tech talent in Big Tech with Andrea Guendelman, CEO of Speak_

“Diversity and inclusion is going to become much more important because it’s going to be tied to money.”
– Andrea Guendelman

There’s a leak in Big Tech’s talent pool pipeline. In fact, as much as 89% of underrepresented talent is rejected at the top of the hiring funnel. And for companies that are looking to hire unicorn software engineers and innovators, that poses a big problem. This week on the On Work and Revolution Podcast, Debbie talks with Andrea Guendelman, CEO of Speak_, about how we can solve the problem of lack of diversity in big tech and why it matters so much.

Debbie & Andrea dig into:

✓ Ways to address the lack of diversity in the tech industry today
✓ How Speak_ helps underrepresented talent prepare for interviews at top tech companies
✓ The importance of diversity and inclusion as companies face more regulation and scrutiny from investors

About our guest Andrea Guendelman

Andrea Guendelman is a writer, speaker, and entrepreneur who specializes in Expansive Leadership—helping individuals and organizations unlock potential through openness.

She is a leading force in creating platforms for minority professionals and the tech industry. Through her own experiences as a Harvard-trained corporate lawyer and an entrepreneur, she co-created Bevisiblelatinx, Wallbreakers, and most recently, Speak_ a solution to connect talented computer science majors from universities across the country with companies hungry for talent and looking to build inclusive teams.

Through her deep and varied background, Andrea has come to embody an inspiring and unique kind of alchemy, fluidly transitioning between the worlds of business and spiritual growth. Her strength derives from the intersection of these forces and allows her to bring a unique energy and mindfulness forged with keen business acumen to her work, the speaking stage, and to those around her.

Andrea has curated major conferences and festivals on social entrepreneurship, technology, and diversity, drawing hundreds or thousands of individuals, and speakers, and performers ranging from Al Gore to Devendra Banhart.

Earlier in her career, Andrea worked as a finance lawyer at the international law firm of Debevoise and Plimpton and at the Export-Import Bank of the United States. Andrea earned law degrees from Harvard Law School and the University of Chile. She is in the Executive MBA program at MIT’s Sloan School of Management. Andrea has received significant media exposure and is considered a thought leader in the topics of Latinx career building and creating diverse workforces.

Helpful Links:

Follow Andrea Guendelman on LinkedIn

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Open for Full Episode Transcript

Debbie Goodman  00:05

Welcome to On Work and Revolution, where we talk about what’s shaking up in the world of work and Edtech right now. I am your host, Debbie Goodman and today we have Andrea Guendelman as our guest. So you know how I love introducing my guests. It’s my favorite thing, aside from the actual conversation itself. But Andrea is a writer, speaker, cultural strategist, former corporate lawyer turned serial entrepreneur, and founder and CEO of Speak, which is a talent incubator, which helps underrepresented talent to prepare for passing interviews at top tech companies. We’re going to talk a lot more about that in a bit. Andrea has a fascinating background, she earned law degrees from Harvard Law School and the University of Chile, and worked as a finance lawyer at one of the biggest international law firms in the US. She has curated major conferences and festivals on social entrepreneurship, technology and diversity with some very prominent speakers. And over the last, I’d say close to a decade, she has established two entrepreneurial ventures. Both are platforms that accelerate diversity in the tech industry. And today, we’re going to be speaking to Andrea about Speak, as well as the state of talent diversity in the tech industry right now. Particularly as companies start to tighten their hiring belts. So welcome Andrea. 


Andrea Guendelman  01:40

Thank you. Thank you so much. Thank you for having me. 


Debbie Goodman  01:44

So your career journey is a fascinating and interesting one. It’s actually, there’s quite a lot about it online. But I’d love for you to just share the trajectory of your career with our listeners, to where you are now. 


Andrea Guendelman  02:01

My career has been incredibly, I mean, I just went to Chile and I went to an exhibit of you know, the time of me growing up in Italy under the last years of the dictatorship. And it was like a very, like I was new way, for example. And it was like a very, like, important creative woman in Chile at the time. But there was a lot there was very little creativity was we had been, you know, raised in a dictatorship. It was super not creative. There was no creative things to do and so there was a little like mini elite of very progressive that were older than me. And it was like super small. And so I think that marked me because I wanted to be an actress. But I didn’t go to drama school because I just went to the hardest thing and to be noticed by my father, which was law school. So I went to law school and that kind of for my career. I hated law school. I probably got very good grades, I hated being a lawyer, I hated it. But then I wanted to leave Chile. So I like got into hardware law. I’m like, Okay, that’s the easiest, let me go there. But I want to go to education school, I wanted to maybe get an MBA, but I was like, that’s too much, I have to take all these tests. Like, no, it’s just I want to live. And so I think all those things, I was a lawyer, but more because of convenience, like I wanted to be seen by my father first, then I wanted to practice in the US because I wanted to stay you know, and then I took the bar and I stayed and but it wasn’t a passion. And so then looking for my passion. When I got to New Mexico, I was embedded in the Latino community, which really like affected me because I felt like an identity in the US as a Latina. Whereas before I felt like an international something. And then when I moved to Boulder, this whole entrepreneurial scene affected me in that innovation and tech innovation. And I, when I put Boulder which was all tech innovation and events and innovation, and New Mexico was all Latinos. And I didn’t see that they were together, that kind of like affected me. And that was a problem I wanted to solve, why the stores were not together, you know, the same thing that’s in Chile, why those two worlds have like, very like, and that led the social revolution in Chile away those two worlds, you know, the elite and the rest of the people are not together what you and how you advanced them that like those things were like, important to me. And that’s how I started my my work. 


Debbie Goodman  04:25

As you’ve been talking, I realized how many similarities with our two trajectories. I grew up in apartheid South Africa, very, very heavily censored environment, some creativity but only sanctioned by the government at the time. I went to law school actually. Yeah, I used to be a professional choreographer and dancer, which was my creative outlet. And when I finished my law degree decided that I really didn’t want to be a lawyer, and so went into business. So there we go. We’re twin twin. Before we talk about business, you mentioned some thing that I thought was like really stand out and interesting, like you said, when you reached New Mexico, you found your self identifying as a Latina. Whereas previously, you just thought of yourself as a global executive. Tell me more about that.


Andrea Guendelman  05:16

Not as a global executive. I have been born in the US, by the way. So I was my father got, he was getting his PhD when I was born. So I had a US passport, but I didn’t not feel, I felt like Okay, so there were the Latinos from Mexico, from Peru coming to like New York, or, you know, Washington. So there was this whole international community, a World Bank, Inter American Development Bank, in New York, and in Washington, and I felt part of that community, because there was like, the international community, but then when I moved to New Mexico, I felt part of the national community. Like, I was a Latina in the US, I, the New Mexicans in particular. I’m Jewish, by the way, my family’s Jewish, in like a minority in Chile. But in New Mexico, on top of everything that Latino from like, you know, the Spanish came there, but then the New Mexicans all think that they’re crypto Jews, they really think and not and I think is pretty much probably true. So they consider themselves Jews, although they’re very Catholic. They’re like original New Mexicans, they identify themselves as crypto Jews. So like being Jewish is also even related to that culture. So in New Mexico, I felt like I belonged 100 percent.


Debbie Goodman  06:29

Okay, so it was a sense of real belonging as opposed to anything else, which is so interesting. Okay. And so then the trajectory, from all the things that you’ve done prior, into startup world into entrepreneurial world, I know that you had a venture prior to Speak, but similar, what’s been the common problem that you identified that you’ve been trying to solve for the last many years? 


Andrea Guendelman  06:57

Well, I think I said it a little bit before. Marrying worlds, you know, and the ones that have information, the ones that don’t have information that, for example, in New Mexico, they realized that Latinos in the US and particularly they were getting super educated, the University of New Mexico is great. Many going to college like, it was obvious, but they weren’t gonna ever go to like the Stanford’s, the Ivy League’s because they, their families don’t know about it, they want to stay local. And if you think about the cost, the University of New Mexico, for example, is free. And all these things are free. So it’s a cost. It’s like a knowledge of information, whatever. So then, how do you create so then how you connect this talent to the knowledge companies anything? That was a question that a lot of technology companies ask themselves, and they became really good at it in the sense that the talent recruiting nationally, and I think COVID helped a lot to like, really democratize the access to the candidates, instead of just focusing on one university. Companies were going to everywhere, and so like local and local and became very open minded about it. And so I think that was one of the things that, you know, that was part of my first network called Visible. And then with Wallbreakers, I started basically, trying to make sure that the candidates had all the information. So what happened and we were looking, we’re seeing a lot within underrepresented talent is that a they were they apply to jobs, and sometimes they even get an online assessment. So they were never able to, and they had gone to schools that you know, people were looking for them, but they had less practice and training in the interview thing, because their universities emphasize more the academic stuff, whereas people that were going to our elite universities, they knew it well that you know, passing these interviews were important. So they had horses on it. Like this was just like very organized, you know, like almost the Ivy SAT, right? Like, among affluent people, they know how to take it, they get good grades, you know, scores and less affluent people don’t do worse. Not because they are less smart, they don’t prepare for the SAT. It is expensive.


Debbie Goodman  08:59

All right. Okay, so as I’m understanding it, essentially, you’ve been looking at all and looking at and identifying all of the friction points along the way of a person, Latina, Latinx professional who either gets access to some education but not necessarily the top education. When it comes to the Ivy Leagues or the universities that are the colleges that are known for tech talent that you’ve mentioned. And because the families are not equipped, they don’t necessarily have the all the information and then even if they are going to wherever university in order to get education, when it comes to applying for jobs in tech companies, top tech or even startup tech, they’re just at a disadvantage because of the process of applying for a job, the process of putting a resume together, the process of interviewing in order to get that first foot in the door, is that what you’ve been sort of looking at? All of those friction points and figuring out how to address those and make things smoother.


Andrea Guendelman  10:09

Yes. And I love how you describe it, the friction points. And we call it in our world and when we talk to customers, it’s the pipeline, right. Like the conversion of the pipeline from like, when you finally recruit them, for when they pass your first interview, for when they pass your second interview, whether he’d be interested in the process, the way you know, what experiences they have with your interview process. So that whole pipeline accurately is close. Where is it leaking?


Debbie Goodman  10:34

I saw somewhere previously, you mentioned that 89% of underrepresented talent is rejected at the top of the hiring panel, at the top of the hiring funnel, so to speak. Say more about that. I mean, that is an outrageously huge number 89%.


Andrea Guendelman  10:53

Yes, so these were like figures from a while ago, so I can’t tell you the exact figures. But basically, it was if you calculate it, basically, the number of graduates from the schools in all the graduates from Latino, black, you know, like from the computer science degrees, so you calculate how many graduated, versus how many were employed at tech companies. And so you calculate the percentages and you got, you know, to this crazy abysmally low percentage. So that obviously, the reverse engineering, is that they don’t pass some part of the interview process, if they’re graduating with an going in general, like compared to the other numbers, right? So and then there’s a lot of research that shows that as well from other researchers that show that the interview process very insider driven for this demographic, they’re not used to it. And then you know, and I’ve seen them say, the process in the interview, especially for women, Latino women is like, wow, I mean, some women, when we’ve interviewed a focus group, and they’re like, I would never change jobs, because I don’t want to interview again, like I wouldn’t want like, I hate it so much, I will not even look for a job, even if I’m not happy. Because I never want to interview.


Debbie Goodman  12:08

I’ve never thought about that. But I guess if the you know, if the likelihood of getting through the funnel is so low, and then even if you’ve managed to get through and get a job, it’s such an arduous process and left, you know, almost to luck whether you managed to get through. So if we have to dig deeper into the why qualified…


Andrea Guendelman  12:30

Not to say that software engineers are not going to find jobs and be employed. I mean, yes, they’re in demand, anywhere. So like, I’m just talking about top tech companies, not about the stress at all, by the way, just just to clarify.


Debbie Goodman  12:43

A sort of macro snapshot of what certainly I can vouch for when it comes to even the startup ecosystem. Many of our clients, so Jack Hammer is an executive search firm, we work in a couple of interesting verticals, including Edtech in the US and many Edtech companies from startup level already have been crying out for diverse tech talent. And they want to know where the pipeline is, and why particularly women. Where are the women in tech? Why are they not being promoted? Why they’re not even getting in the door. And this is in all parts of the ecosystem, both the top, you know, the big companies and the smaller companies. And what I’m hearing is that it’s less about the fact that the skills or the capabilities don’t exist, and a lot about the obstacles to getting in the door, where the the friction point or the hurdle in the leaky pipe is at the interview stage. And so I want to ask, what about that? Like, let’s dig a little deeper. I mean, interview readiness is not a new thing. What specific? What specifically is holding companies back from hiring the talent? And what about the talent is preventing them from securing the job through the interview? 


Andrea Guendelman  14:02

That’s the problem we’re trying to solve with Speak. So it’s like, on the one hand, educating the employers about the interview process. And like they answer, like, they’re getting very clear on what the interview process, what skills they’re testing for, because a lot of times there’s internal misalignment in companies a lot on process. So that already creates like how you’re going to communicate something outside if you don’t know inside what you want. So creating, we’re creating our software like basically a solution that is gearing to like answer those questions for employers, so from the internal team, so it becomes an interview guide that they can share with every candidate, everyone goes through a process and put them very specifically in what parts of the process educate them, right? Give them the resources, because it should be a very transparent process that you should be able to know what you have to prepare like, you know, for everyone, not just for the ones that have insider information. All right. So that’s what happens that insider information is something that is a skill, I get it like getting the salary information, but that means that you’re in the inside. So you like leaving a lot of people in the outside, and not as a moral issue. The morals are I need the best workers in the world, why wouldn’t I interview like everyone and get access to the best. Like why just, you know, limit myself to the ones with insider information. I need everybody that is smart. So how do I get that? I only know how to judge the ones that know the system. So that’s a little bit more.


Debbie Goodman  15:32

Speak creates interview readiness programs, which are sponsored by the companies that want to hire, is that correct?


Andrea Guendelman  15:44

Doesn’t necessarily limit to entry level, it can also be for mid level for anyone that hasn’t seen it or has or wants to, like, see, or wants to, you know, get more informed. Yeah.


Debbie Goodman  15:55

And so both companies will pay for candidates to be put through these interview readiness programs. And then individuals themselves can participate in programs from Speak, is that correct?


Andrea Guendelman  16:07

Yeah. Yes, we are more gearing towards these company interview programs, like company sponsor programs. All of them will be company sponsored. And they start everybody can go through different company sponsored programs, if they want to, there will be one path for people that are like invited by the companies, but everyone else can, you know, I guess apply to a company and get like channeled. Anyone that applies to a company, basically.


Debbie Goodman  16:35

So that begs my next question, company sponsored, we know that budgets are being slashed all over the show with hiring, everybody’s tightening their belt, in particular big tech. I was just reading today that Amazon have decided to reduce or completely suspend their charitable donations. So where does DEI spend come into play right now? Have you started to notice any changes with regard to the DEI agenda when it comes to hiring and budgets for hiring?


Andrea Guendelman  17:11

Not yet, and I think we will not see that. I don’t think that we will see changes.  I think that you whether you have seen it’s like everybody like calming down from hiring. I don’t think that diversity and inclusion is going away anytime soon. I think, in fact, it’s going to just become much more important. As we see companies, investors getting really picky about investments, and having more regulation around environmental things, you know, diversity, you name it, right, you will need to play with those regulations. And companies will have to disclose everything about you know, their diversity numbers, and it’s going to become much more important, because it’s going to be tied to money.


Debbie Goodman  17:55

Well, that’s very good news. And an interesting segway into the capital raising prospects for Speak. Because I mean, I read the numbers every year on the amount of funding from a capital raising point of view, that gets that women are able to generate versus their male counterparts. And it’s minute, I think it was under 3% of all startup funding went to women in 2021 to 2022. What was the capital raising process like for you?


Andrea Guendelman  18:27

I’ve been capital raising for a long time since my first event, like my first event in Chile, my first anything. I raised a million dollars for that. But that was an event. But that was different, like there was, and then raising VC money was super difficult the first time, in fact, I only got my first company, I only got angel money, I never got to VC money. It just got to angel and I got a lot of angel investment and big ones, but always angel. And angels are more. The way that an angel manages an investment is not the same as a VC. VC is so much better, because it gives you a lot of like, creative freedom, and they are not you know, on top of you when the angels are like, they think that they know better. So they want to really influence the company. And so that can create a lot of friction because they become the co founders that you really didn’t, you know being there. That happens with angels that they’re like more, not all of them, some of them, some of them, not all of them. And so, the tricky part, and so a year ago, I finally raise money from VC. So I’ve always been funded, by the way, everything I’ve done has been funded. But only this last year in for Speak in my precede round, I got actual VC funding, you know, from two VCs. They were amazing and so that was like a breakthrough for me. It was important.


Debbie Goodman  19:50

Did you need to go through that first phase of just even getting the angel funding in order to get to the level of confidence or knowing how to go about the VC round, or what do you know, now that you wish you’d known at the very beginning around capital raising?


Andrea Guendelman  20:07

Debbie, investors are very, very focused on the bottom line. They don’t know you, you know, they need to see a bottom line and that’s going to be a good business. I think the reason I raised money for my first startup, I lost a lot of angel money, but I mean, but then he was like, sort of that business model, you know, the beginning, like it was an advertising business model, but then you realize that that business model is so difficult, like, then you get realistic about your business models. In other words, you become a better business person. For me, like, that could be small, but like, the assumptions that you need to make to get there, you know, like, they’re not proven in anything. So the more you know, the other assumptions are proven with revenue, and with selling, and I was never trying to sell, I was trying to create a big audience. So it’s a very different thing, you know, to try to sell as you’re trying to sell is just trying to see what the market wants. Right?


Debbie Goodman  21:00

Well, I think the fact that you’ve been funded from the beginning, and have managed to keep escalating or accelerating, that is actually extraordinary. I mean, I only know bootstrapping, and self funding, and the thought of having to go to market to raise capital is, as long as I’ve been in business, that’s something that’s completely new would be completely new for me.


Andrea Guendelman  21:23

It’s a different skill. Actually, being self funded is amazing. It’s kind of the goal, it’s like the dream. I’ve been like, every time I go to market, I want to build a team, you know.


Debbie Goodman  21:35

We can have a side conversation on self funded versus VC funded. It has definitely got its pros, but Oh, my goodness, when it comes to cash flow, definitely wish to have a have some kind of additional funnel. I’ve got one last question. Like, almost every conversation I’m having at the moment has an element of AI, and how AI is going to impact whatever business we’re talking about right now. I know ChatGPT is the big conversation starter for almost everything. But my question is more around AI in the interview process, and how you see it impacting diversity.


Andrea Guendelman  22:17

We’ve seen the impact of algorithms for a while, I mean, we have the scandals at Google and Amazon at the time, everyone’s very aware that in diversity, those algorithms are not good there. They can be Oh, unless you have a lot of data comes from, you know, like, doing, like the good data, you know, that you can improve and make those networks and those algorithms more equitable, you know, can nurture, you know, grow, you know, from other samples of the world? I don’t know, there’s that issue. And I think there’s, at the time that or two years ago, there was a lot of discussion on AI, but it was like, humanly assisted AI for diversity never like just AI but it has to be like AI with human participation or human supervision.


Debbie Goodman  23:02

And if the human supervision or oversight or discretion is not equally well trained on diversity, you’ve got, it’s like two strikes and you’re out. The automated AI technology, that screening on resumes, and keywords, and all of the rest is the one screening out tool and then humans who are not exposed and trained on interviewing appropriately, are also going to be screening people out at the other end of the funnel.


Andrea Guendelman  23:35

That’s a concern. Yeah, so that’s why I think that data you input in the system is so important, where it’s coming from. Like, because when you’re comparing, you know, the top, you know, candidates, you know. That’s kind of like when you’re going for, and then like no one else can perform an interview so that, I don’t know, like, you know, what I mean? Like, what were you comparing, who are you comparing, compared to what? Like, what is the curve? Basically, you know.


Debbie Goodman  24:04

Look, I think that on the one hand technology, automation, AI, machine learning has simplified things, has helped things to scale. On the other, I think it has just made the complex process of hiring diverse talent. There’s ongoing complexity to this. And I really hope that speed continues to amplify and grow beyond just top tech to all verticals and all ecosystems because we really are needing to ensure the funnel at both ends, no leaks. I love that analogy. And Andrea, what do you see for 2023? How are things shaking up?


Andrea Guendelman  24:40

I think it’s going to be a great year, we’re going to see re-absorption of the talent really fast. These numbers that we see sound shocking, but in the greater scheme of things are nothing, especially for support engineers being like, they’re going to be reabsorbed very, very fast. So I have no concerns about that. They look shocking, but it was just gluttony of the system, gluttony, you know, and it has to be reassigned. We align the opinions sentiments of money. Of course those things can not sustain. Oh, you know, so yeah, let’s like more, but there’s gonna be plenty of jobs and plenty of opportunities.


Debbie Goodman  25:15

Well, I love that. I love hearing that. It’s something that I agree with 100% that it’s a matter of redeployment. And these kinds of skills are in huge demand. You know, up until recently, there was like two or three jobs for every single software engineer. So definitely not seeing an overly saturated market by anywhere close. And let’s just hope that the future continues to be even more diverse and equitable in all aspects of hiring. So, thank you. I love the work that you do. And I hope you have an amazing 2023 with Speak and all of your other ventures. Thank you.


Andrea Guendelman  25:51

Thank you so much.


Debbie Goodman  25:55

Thanks for hanging around all the way to the end. It would mean the world if you would rate and review On Work and Revolution on your favorite listening app. It helps people know that the show is worth listening to. And so I really appreciate that. Thank you so much.


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