This week on Founded and Funded, we spotlight our next IA40 winner – SeekOut. Investor Ishani Ummat talks to SeekOut Co-founder and CEO Anoop Gupta and VP of People Jenny Armstrong-Owen about their AI-powered intelligence platform, the importance of not only finding and recruiting new hires but also developing and retaining employees within a company, and maintaining SeekOut’s own culture while seeing significant growth over the last year.
This transcript was automatically generated and edited for clarity.
Soma: Welcome to Founded and Funded. I’m Soma, Managing Director at Madrona Venture Group. And this week we are spotlighting one of our 2021 IA40 winners – SeekOut. Madrona Investor Ishani Ummat talks with CEO and Co-founder Anoop Gupta and their Head of People, Jenny Armstrong-Owen. SeekOut is one of our portfolio companies, and so we were very honored that our panel of more than 50 judges selected them for our inaugural group of IA40 winners. SeekOut provides an AI- powered talent 360 platform to source, hire, develop, and retain talent while focusing on diversity, technical expertise and other hard-to-find skillsets.
We led SeekOut’s Series A round of financing, and have worked with the team closely since before then as they fine tuned their initial product offering. The company has had massive success. And earlier this year they secured $115 million Series C round to scale their go to market and to build out their product roadmap, including powering solutions for internal talent, mobility, employee retention and the like- all topics that are Anoop and Jenny will dive into with Ishani today. With that, let me hand it over to Ishani.
Ishani: Hi, everyone. I’m delighted to be here with a Anoop Gupta, the CEO of SeekOut, and Jenny Armstrong-Owen, SeekOut’s head of people. SeekOut is building an AI powered talent 360 platform for enterprise talent optimization and was selected as a top 40 intelligent application. We define intelligent applications as the next generation of applications that harness the power of machine intelligence to create a continuously improving experience for the end user and solve a business problem better than ever before. I’m so excited to dive in today with Anoop and Jenny, thank you both so much for being here.
Anoop: Hey, Ishani, it’s wonderful to be here. Thank you for making time for us.
Jenny: Agreed. Thank you so much. It’s great to be here.
Ishani: So, I’d love to start out by going way back. Anoop, you were a professor of computer science for over 10 years, co-founded the virtual classroom project that quickly got acquired by Microsoft. In 2015, you left Microsoft to start the precursor to SeekOut. Tell us about what led you to the core talent problem that SeekOut is solving today.
Anoop: So, Ishani, when we left Microsoft, we left because you know, Microsoft was just an absolutely fantastic place to innovate, but what Microsoft legitimately wants you to do is to get on an 18-Wheeler and discover some big island, and we wanted to be on a mountain bike exploring opportunities because it’s such an exciting world out there. Given my background of running Skype and Exchange, actually the first thing we settled on, was Nextio, which was a messaging application. And the whole notion was that today people hide their email address and phone number because once you give it out, people can spam them. And we were not being so successful there, so we built an application called Career Insights. What Career Insights was about is you analyze all resumes in the world, and if you do that, then we can say, “Hey, if you are a UI designer at Microsoft, what are the next possibilities? Where are your peers going? And if they were going to Facebook, we could tell you where are the Facebook UI designers leaving for and doing next. So, it became Career Pathways inside that. And we said, “Oh, this is so useful for recruiters and talent people” that we pivoted there, and since then, our passion, our understanding of what is missing and what could be done better has led to our growth of SeekOut and talent acquisition and what we bring to the table.
Ishani: That’s so great. You sort of found your way to the recruiting market, to the recruiter as an end customer, but beginning with this problem of career pathing and pathways. It’s only something that’s amplified over the course of the last decade, let’s call it and it seems sort of prescient, but now that we look at this moment in time that seems like a very acute foresight.
Jenny I’d love your perspective. This talent environment has evolved so much in the last few years in ways that even Anoop and SeekOut could not have predicted with the pandemic and everything like that. We all see and feel the Great Resignation, the ongoing talent war in the tech world. You’ve been in talent teams for 20 years — what elements of this were predictable and what has taken you by surprise?
Jenny: Well, definitely what is very predictable is that the tech world continues to explode and grow. I read a statistic in the New York Times that the tech unemployment is 1.7%, which is basically negative unemployment. So, that’s not a surprise. What was not predictable was COVID, was the ability for folks to literally work from their homes. And it released the boundaries around what was possible for folks. And I think that’s one of the biggest challenges for organizations. And if you didn’t snap and adapt to that, you were not going to be able to meet your hiring goals.
One of the things that I love about being here at SeekOut, is going and finding people wherever they are. And so for us, we’re not restricted to Bellevue, Washington, or Seattle, Washington, and I think that’s one of the things, especially about our tool, that is so incredibly powerful. If you’re an organization that can embrace remote, that can actually make you so much better than restricting yourself geographically. That’s one of the things that I think has been a huge benefit for us. I think we’re embracing a new paradigm of relationships with employees, and it’s going to be a much more virtual relationship at times than it is a physical one.
Anoop: One of the things when we got into this, is we said, “Hey, digital talent, technology talent, is really important,” and what COVID did was, Satya said “Two years of transformation in two months,” right? So the accelerating rate of digital transformation, something we were focusing on, wasn’t there and that really increased the value of what we’re doing. The second thing that’s happened over the last two years is the emphasis on diversity. A lot of young people are saying, “I don’t want to join a company if I don’t see that they are embracing diversity, inclusion, and belonging in a genuine, authentic way.” We believe a lot of talent exists. It begins with how do you hire, how do you understand what exists in talent pools, and then being able to find them. The problem that leaders have — business leaders, talent leaders — is, they have good intentions, but translating those great intentions into concrete actions and results has been hard, and SeekOut really facilitates that.
Ishani: It’s such a good point on the market, evolving in some ways that you are able to control and some ways you can react really responsibly and control around. In other ways, that they are so out of your control where you sometimes tools can help you with that, tools like SeekOut, and sometimes you have to build that internally. It’s a culture thing. It’s an intangible. But let’s talk a little bit about the tool you’ve actually built. The way I think of SeekOut is it’s a product that’s evolved a lot from a talent acquisition tool to really a more 360 degree talent intelligence platform. But it didn’t start that way. Walk us through this journey from a talent acquisition tool to really an intelligence platform.
Anoop: My Ph.D. thesis was on AI and systems. My co-founder Aravind came from building the Bing search engine. When you look at all of these areas, AI is just a core part of it. So, to use an analogy — when you go to Google and do a flight search — UA 236. It understands that you are doing a flight search that UA is United Airlines, and you’re probably looking for arrival or departure times and therefore this is the relevant information. So, in a similar vein, SeekOut is a people search engine. So, we need to understand a lot about people. So, when I search for Anoop Gupta, our search engine realizes that Anoop is a first name and Gupta is a last name — and that it is a common name in India, right. So, we can get a lot of information that helps us. Similarly, normalizing for universities and companies is really important. SeekOut is very special in that it brings data from many, many different sources and combines it together. So, as we want it to go to technical folks and technical talent, and I’m just using that as an example, and you get GitHub, you see the profile on the GitHub, how does it match to the profile, you know, they might have LinkedIn and they are the same person. You know, it takes AI to figure that out. Then you want to look at all the code and information that you find, and you say, what is their coder score? How good a coder are they? Do they know Python? Do they know C++? So, we started bringing those things inside of it and all of those are inferred things. When we do security clearance, as an example, people don’t mention security clearance often, so what we go and look at is we look at job descriptions for the last many years, and we say did the job description say “This role requires security clearance and top secret or whatever?” And then we say, if there are enough of these positions where that is required at that company, at that location — then we say, you likely have security clearance. So, AI is fundamentally baked into the product, but we also take an approach that while AI is everywhere, it is designed as a complement to the human and not as a substitute to the human recruiter or sourcer that is there. That is an important principle for ourselves. The human is doing what they are best at, and all of the AI and logic are doing what they are good at to facilitate the human being more successful.
Ishani: We talk a lot about intelligent applications having a data strategy. And in order to augment workflows and make them solve a business problem really better than ever before. All of what you described is so well steeped in that philosophy around pulling in data from a host of public sources and then being able to really drive a better product around that and surface insights that matter. Customers love as one of the core features of SeekOut, the search functionality. So I’m sitting on top of all that data, the search just works. Can you talk a little bit about how you handle and process all of this data to just make it work like magic for a consumer?
Anoop: So one is, you’re very right. It’s actually a very hard problem when you have 800 million profiles and data coming from lots of sources, and the data is not static data — people are changing jobs, people are changing things. It’s all dynamic data, so, how one makes it work, how one makes it very performant? You know, my co-founder again — one of the movers and shakers behind the Bing search engine, and because we come from that background, Googles and Bings have to handle very large amounts of data, so how do you construct the index structures? How do you do the entity formation combined together? So that is core to what we do. And then on top of all of that big data, when you say can you clone Jenny and find us similar features? Now that is an impossible task. Because people may do the job with her humor, and her other parts are so hard to replicate, and the nice person that she is, then you have to do all of the matching, right? Or when you parse a PDF resume, how do you extract the skills or when you parse a PDF job description, how do you parse the requirements and what are the must-have requirements? What are the nice-to-have requirements? So, there’s just infinite amounts of problems, and we keep tackling them one at a time.
Ishani: It seems like you also, though, have to be so semantically aware of the context, right? That’s exactly what you’re talking about with the job description. How do you parse out requirements versus any of the other components? And how do you parse out whether someone might have met those requirements? So much is evolving in this field of semantic awareness, semantic search, and natural language processing. What are the kinds of underlying models that you use? Have they really evolved in the last few years as we see some of the transformer models or CNNs start to make a step-change in technology?
Ishani: So, it really goes back to this concept of having a data strategy early. Being able to be nimble in evolving underlying technology and application intelligence. We always talk about garbage in, garbage out. So, being able to really understand where your data’s coming from, semantically parse and structure it to then be able to give to your end user as we call it magic.
Anoop: Yes. Yes. The problem with data is data is not clean. So, you know how you can efficiently clean up that data and use ML models to say these are extreme, exceptions and what to look at become super important.
Ishani: So let’s zoom out a bit. We’ve talked about this briefly, but over the last two and a half years or so, work has changed so much. Hiring has become hard. Engaging with employees has never been more important than it is today. Retention is hard, and SeekOut is doing really well in part because of that macro tailwind. From a company growth perspective, how did you recognize and take advantage of that moment in time?
Anoop: Helping companies get a competitive advantage, recruiting hard-to-find and diverse talent was a model for us from the very beginning. Then all these things happened and we’ve grown 30X in revenue over the last three years, our valuation is 50X where it was from three years ago and we have very high net retention and amazing customers. But we hadn’t thought of everything. We were focused on talent acquisition. That is how do we bring external people? Then with COVID, and the great reshuffle, the great resignation, many companies like Peloton stopped hiring externally and we said, what are the opportunities we can create for the people that are inside? So, our more recent focus on retention is really big. So, here’s the big story that we talk about. It is truly about the future of enterprise. We believe winning companies are realizing that the growth of people and the organization are inextricably linked. So, our mission has broadened, and it’s become to help great companies and their people dream bigger, perform better, and grow together. So that’s the mission and it’s a fundamental mission for every CEO and business leader and not just the HR leader. Then what we are doing is, you know, use technology to ensure that companies and talent are aligned and empowered and growing together. Or in another way what we’re saying is, “Hey, we going to help organizations thrive by helping them hire, retain, and develop great and diverse talent.”
Ishani: You know, SeekOut was really the right place at the right time to take advantage of, and actually really help people through that transition. But you have to be experiencing this internally as well? You talked about 30 X in terms of growth, but you also have triple headcount in the last year. I think you anticipate doing it again this year. How do you maintain, and Jenny, this is a question for you, culture and such a high growth environment?
Jenny: It’s one of my favorite questions I get it a lot in interviews. Culture has become probably the most important thing in a world where people are free agents, and they want to work at a place that aligns with their values and the way that they want to grow and develop with a company. So, I will share this. For me, I was looking at a number of different companies, and I met Anoop, and our first conversation, Anoop, I don’t know if you remember this, it was supposed to go for an hour. We went over 90 minutes, and in that moment, I knew that this was different. This was a different place. The culture here really does emanate from Anoop, Aravind, John and Vikas — the folks that started this company. From my perspective, our job is to make sure we don’t have cultural drift because we don’t have to fix our culture. Our culture is phenomenal. Candidates across the board tell us they’ve never had a candidate experience like this before. Everybody they meet with is super kind and helpful and collaborative. So for us, it’s really keeping our eye on these cultural anchors and making sure that we’re staying true to those.
So, in the hiring process, making sure that every single person who comes here, there’s a diversity interview where we talk about what is important to you in terms of diversity, belonging, equity, and inclusion. To Anoop’s point, people want to go where they feel like they’re going to belong. And then diversity can thrive, and equity can thrive, but you have to have that sense of belonging first. So for us, it’s very much staying focused on that. And everything that we do is around driving programs and opportunities and conversations that reinforce that. We start every Friday All Hands — in fact, I will admit, I suggested to Anoop early on that this was not going to scale as we grow. We’re 150 people today. But we start every all hands with 15 minutes of gratitude. I admit that it is absolutely scalable, and we’re going to continue to do it because it is by far the most favorite meeting of the entire week. That moment that we set aside to say nothing is more important for us in this moment than sharing our gratitude with each other. So I think that’s, for us, I feel super fortunate to be able to be at this intersection at a time where, it is tough, right? Companies are struggling to keep their culture intact in a world in which everything’s shifting so quickly.
Ishani: That’s such a good point that begins in the interview process and it continues in the onboarding process. Then it’s an everyday commitment to reinforcing your culture. I think people do have really good elements of each of those. But it’s rare that you find somebody so committed to all of them.
Jenny: It starts with Anoop.
Anoop: So, you know, so Jenny said it so well it comes from just a deep belief that people are the most foundational element to our success. We truly, believed that for ourselves. I’ll give you an example in a story. So we were looking for, I think the CRO, we had an executive search firm, and they said, ” Anoop you seem to be open to meeting a lot of people. Are you sure you have enough time?” And I said, ” I’m always there when it’s a people question. People are so important.” We have four OKRs now, these are the company goals. Our main goal is our people, culture, execution are our competitive advantage. I truly believe in that. It is not our AI knowledge. It is not we are smarter. It is that as a company, who we bring in, how we think, how we execute, how we collaborate, how we decide to disagree, yet, find commitment, you know, hold each other accountable, be nice.
We want to be the ones to show that nice people can win. Kind people, people with empathy can win. You don’t have to be a jerk to get ahead. So that is just a fundamental belief for us. And that has helped with our retention. That’s helped with our recruitment. That’s helped with the energy and their whole self that people bring to the company every day. And I think that’s a huge part of our success.
Ishani: The recruiting example of the CRO is so interesting because it really does delineate there is a real and important place for tools, but there’s certainly a line where that stops. Where you, Anoop, taking the time, you know, it wouldn’t be a little bit facetious as a talent optimization platform, if you didn’t take the time to bring in your own talent and really make sure that they fit the organization’s culture and the ethos, and they want to be where they are. So certainly, it has, there’s good continuity there with SeekOut’s mission and SeekOut’s product and how you operate.
But also, that there’s a role for the talent optimization platform that you use. And that presumably you use SeekOut, at SeekOut.
Anoop: So, you know, the other side story is. Every exec firm that I talk to, they give me some candidates and sometimes they are diverse, sometimes they’re not diverse. I say, well, let me find you some women candidates, let me find you some, you know, black candidates. They exist — you just don’t know; you need a better tool.
Ishani: It’s very much clear that there are roles, and these tools are augmenting how people do their jobs and in ways that haven’t ever happened before. But that it is an augmentation with learning, with intelligence, and with automation. But there’s still very clear roles for how do you build, for example, a culture like Jenny, right? And how do you maintain that? It also speaks to one of the product focus areas of SeekOut, which is on retention and really retaining your talent and looking internally. Jenny, talk to us a little bit about some of the strategies that you use, whether or not it’s related to SeekOut’s product, to maintain the talent and retain talent.
Jenny: Yeah. And thanks. I think it’s actually one of the reasons why, when I with Anoop, and he cast the vision for what SeekOut was going to be, was what got me so excited. As someone who’s led people teams now for way too many years to admit, I think getting folks in the door, getting them hired, is absolutely critical and important. I think growing, developing, and evolving as teams with folks who are committed and engaged, that is the job, right? That is every day. All day thinking about the people that we already have here. That’s one of the things about the enterprise talent optimization, where we’re going there, it’s going to revolutionize people teams. I mean, it’s like the best way for me after so many years of not having really effective tools on people teams —you know, we’re building a world in which they are going to be so complementary and it’s going to free people teams and leaders up to do what they do best, which is really about developing people.
So, for example, yeah, we’re 150 people. Well, we’re going to be implementing a people success platform. We’re going to be making sure we’re touching base on the things that matter the most to people, which is all about skill development, acquisition, growth. That’s fundamentally why folks will leave, right? Especially in the tech world, because they want to do different things, or they want to be able to stretch and grow. One of the things that’s awesome about startups is you have infinite ability to grow your people in whatever direction they want to, because the opportunity is here. It’s one of the reasons why I stayed at my first tech company for so long — I was able to do and grow and be so many things, and that’s one of the things that we talk to people about in terms of our value prop when we’re interviewing them is, “Hey, we are interested in you for this, but guess what? The world is your oyster at SeekOut and wherever your passion wants to take you, we are going to support that passion.”
Ishani: What you’re saying around giving people, the opportunity to grow is incredibly aligned with SeekOut, with the mission of the company. But also again, the product. It is also very hard to execute on. To say — we have a high-performing software engineer in our machine learning division who wants to go try out product management. Right? What are the tools that you used at SeekOut, and how do you actually execute on that?
Jenny: Well, I think that we are still in our nascent stages. We started last year at 40 people. We’re now at150 people. What I would say is building the capability in leaders to be aware and to be having these conversations and to be free enough to be able to think beyond the roadmap and the things that are getting done today. So, I think you have to hold both things tightly and loosely at the same time, if that makes any sense. And it requires a high level of change management and org development skills. Like we have to build whole-brained leaders who can look at our people with both things in mind. Executing on the deliverables that we have today, but fundamentally making sure you’re having this other conversation and that you’re driving that consistently in a way so that there’s never any dissonance. I think that’s the challenge? Creating too much space between those conversations or even having those conversations at all creates the dissonance. Then that creates the drag and the drifting. So, for me, that’s one of the things that we talk about a lot is who do we have?
Anoop, I would love for you to give your kind of ETO summary, because I think it is so compelling about the tools that we’re going to be able to provide. To your point, Ishani, I don’t have specific tools today. I mean, I can use my SeekOut tool, which is awesome, but we’re also small enough that we kind of can do a lot of this, you know? One-on-one but Anoop, if I would love for you to add onto that.
Anoop: You know, the cost when a great employee leaves is almost two X their salary for the annual salary, because it takes so much for the new person to come in and get up to speed, and meanwhile, the products are delayed and other things that delay whatever function they might have been going. So that’s why it’s so critical. And that’s why people care about it a lot. One of the things I say is that companies are deluged with data. There’s data flowing out of everything, but when it comes to data about their people, companies don’t understand the data is siloed. The data doesn’t exist. They may not have the external data. They may not have what they did before. And there is missing data. You know, your manager doesn’t know, Hey, in a large company like Microsoft or VMware or Salesforce where are the open jobs. What are the matching jobs? What are the skills? What does it look like? So, the data about employees is missing, the data about opportunities is missing, and then how do you take opportunities and data to match them to people? So, we can tell you about career path, if you’re going from a software development to a product manager, we can point you to people who made a different transition. We might be able to point you to people who made that transition, who might be from the same school, might be from the same gender and you don’t have to talk to the hiring manager, you can talk to people below and say, what is the culture of the team? Basically, we bring amazing data from outside. But then we take data from inside the company —this may come from management hierarchies. This may come from Salesforce. This may come from your developer systems and GitHub — and give you the most comprehensive thing. Then we engage with people. We really have two audiences. One of our audiences is the employee. Okay, who in a private secure way are mapping out their career, their growth, their learning journeys, their growth and development journeys. The second is the HR and the business leaders who are saying, we’ve got to deliver. There’s a strategy we want to do. Do we have the right talent? How does my group compare to competitors? How does it grow across the companies and how do we optimize?
So, we are super excited about it in any conversation that we are having, with CHROs, with other leaders, there’s a lot of excitement about what’s possible what SeekOut can do for them.
Ishani: So, SeekOut today is a really amazing example of an intelligent application for 360 talent optimization, not just the external component, but also internally. This speaks so much to both the environment and you’re reacting and being nimble around, how do you create offerings that people need? Without revealing too much, give us a peek into what the future holds for SeekOut.
Anoop: So future wise, Ishani, each of these broad areas that I’m talking about, there is immense depth in that. As we go deeper into it, there is a lot of work that is involved. So, if you look three to five years just executing on even the components that we have talked about and becoming a star We’re thinking you know, I believe this is a new category. HR don’t even realize what is possible in terms of data, the insights they can have, what they can do for their employees. So, there’s always a market and a mind shift that is involved and people are the slowest to change in some sense. So, I think our journey just making it, and if we do it right, and if we are the leaders, this is more than a hundred billion-dollar company, I believe. Okay. So there’s lots of growth and possibility, in this because talent is central to organizations and their success.
Ishani: Anoop and Jenny, we tend to end these podcasts with a lightning round of questions. So, we’ll go quickly through three questions that we ask every company that comes on this podcast. The first for both of you, aside from your own, what startup or company are you most excited about that is an intelligent application?
Anoop: So, for me, I would say, you know, some company like Gong or basically people who give you intelligence about how your salespeople are doing, how can you be better? What those calls are. Do the natural language analysis and all of that. So, it is just a hot topic, so it could be more, but that’s top of mind for me.
So let me just name that.
Jenny: I have an appreciation for Amperity and what they’ve been up to and what they’ve been doing. So that would be mine.
Ishani: Awesome. Both actually are also intelligent app top 40 companies. So, congratulations to Amperity and Gong. Outside of enabling and applying AI and ML to solve real-world challenges, what do you think will be the greatest source of technological innovation and disruption over the next five years?
Anoop: Certainly, you know, machine learning/AI will have a huge impact. But I think it will also be coupled with that it works on lots of data. We are instrumenting everything, on how the washing machine is being used, how your toaster is being used, how you’re driving. So, I think, the data and the machine learning together. But with the caveat of us making sure that it is not biased. Every tool in humanity can be used for good and it can be used for bad. But I think if we use these things intelligently, we can make a lot of good happen.
Jenny: Yeah, I would have to agree. I can’t say it any better than Anoop did. I think that making sure that technology is being inclusive as well. I think that’s a huge area of focus and concern.
Ishani: I couldn’t agree more. Final question. What is the most important lesson? Likely something you wish you did better, perhaps not, that you’ve learned over your startup journey.
Anoop: I will say, throughout my career, I always kind of knew people were important, and culture was important. You know, people would talk about it. But my appreciation and conviction that it is about people and culture as the fundamentals and foundations to success has been a realization. You know, if you asked me this question five years ago, I would not have answered it this way. You kind of take culture for granted, is not granted in the sense that it is already kind of baked for you in a larger organization. I think here, there was the opportunity to say — you get to define it — then it just made so much sense that this is the thing to focus on.
Jenny: That’s awesome, Anoop. I love that. I would say that for me learning that, you can put people at the top of the pyramid, and you can be very successful, is something that makes me incredibly happy that I’m getting the chance to learn and experience.
Ishani: Anoop and Jenny, it’s been so great to talk to you today about SeekOut, but also about people and how important they are in the organization. SeekOut is a great tool that enables you to find, recruit, and hopefully retain the best people that are going to build your organization. Thank you so much for taking the time and it was a great chat.
Anoop: Thank you so much for having us really appreciate the time.
Thank you for listening to this week’s episode of Founded & Funded. Tune in in a couple of weeks for the next episode with UW’s robotics expert Sidd Srinivasa.