Ep. #26, Solving Complex Problems with Rita Scroggin

Rachel Chalmers: Today I am thrilled to welcome Rita Scroggin to the show. Rita has been an executive search partner since 2010 and has established herself as a trusted partner to leading VCs, private equity founders, and the C-Suite.

Throughout her career, she has successfully conducted hundreds of critical searches, ranging from director to board level, collaborating with clients who are driving rapid innovation and changing the world. Her clientele spans from Fortune 500 companies to early stage startups and mission-driven organizations.

Recognizing the need to create more diversity in the boardroom of her clients, Rita founded Firstboard.io in 2020. Firstboard.io is the only curated collective of diverse female founders, CXOs and operating leaders in technology and health tech across multiple verticals and disciplines.

Rita, thank you so much for coming on the show.

Rita Scroggin: Thank you so much, Rachel, for having me. Super excited to chat with you today.

Rachel: Firstboard has put together an AI council to help boards navigate the huge disruption that's happening because of generative AI. Can you talk about some of the problems that you see boards facing?

Rita: Yeah, I think right now, boards are talking about the impact of AI on their business models, right?

In one of the most recent CEO studies, 40% of CEOs don't think that their business model will survive the decade.

So business reinvention, including integrating AI in their business strategies are top of mind of many existing businesses, along with shoring up cybersecurity in light of threats and data breaches, and responding to geopolitical threats and opportunities.

At the same time, we have a new class of AI-native companies working on use cases for AI or new use cases. The boards of these companies need to stay on top of the global regulatory landscape, data privacy, legal challenges, and investor perspectives among other things.

Rachel: That's a crazy number, isn't it? 40% of CEOs don't think their business model is going to survive 10 years.

Rita: Yeah, that's a crazy number, right? Yeah.

Rachel: And is that attributable to large language models or AI more broadly?

Rita: I think it's a number of things, right? So I do not think that the study had indicated like one leading factor, but I do think that plays into it, right?

I mean, technology is changing, you know, at a very rapid pace faster than we've ever seen, I think, right? And the question is sort of, you know, how is it going to look like five years, 10 years from now?

But I think there's so much disruption going on. And then we have a lot of changes globally, which of course also play into all of this as well.

We have changing demographics, right? We have a new generation now at the age of, you know, working, making buying decisions.

We have a large section of the population, which is starting to retire and anywhere between, so I think we have a lot of, you know, dynamics and changes.

And then of course, political changes too come, is needed to navigate around it. So I think there's a number of factors, but I think AI, generative AI specifically plays a big part in it.

Rachel: We are definitely cursed to live in interesting times. Where do you think the AI council may be able to help boards?

Rita: Well, we're bringing together a group of thought leaders across different domains in different companies who are at the forefront of developing and implementing generative AI.

So right now we're working on developing a framework, including key questions for boards to help them assess and innovate, you know, their current business models.

In general, many boards right now are also assessing do they have the right people on the board with expertise in generative AI? And I think the answer is probably for many boards, that they do not have that expertise.

And so that's where we come in. So we have curated a collective of board-qualified and board-experienced women technology leaders and one of our goals is to connect our members to boards who are seeking to add this specific domain expertise to their boards.

So we try to help companies in many ways, more from a thought leadership perspective, but also helping them identify, you know, where are the gaps and how can we help bridge that?

Rachel: Does that logic work in reverse as well? Can diverse candidates prepare themselves for potentially serving on a board by studying AI, becoming experts around generative AI?

Rita: Well, I think studying AI is probably definitely good and advisable for anyone right now, but I do think it's more than that, right?

I think getting involved in key AI initiatives or joining companies who are AI-native and who are developing new technologies, new ideas, new use cases, I think is really critical. But then I think it's also really important to be visible about it, right?

I think a lot of diverse candidates, particularly women, tend to focus on doing a good job and really, you know, driving impact and results, but they're less focused on paying attention to who they are and who they are as technology leaders and experts.

So I think there's a lot of opportunity to get involved, for sure, right? To be part of companies where they're really doing something at scale with AI and then be visible about it, right?

The other thing I think is also kind of to really be realistic on, you know, where one is in their career. So a senior director at a company somewhere probably has not a very high chance of being selected to a board somewhere. So getting to the C-suite, I think is the prerequisite of being selected to a board.

And I had a conversation with a former CEO who's now on the board of several very high level and well-known technology companies, and we started to talk about, you know, her journey.

And it started really, you know, assessing where she was, you know, in her career at that time. And she concluded she needed a bigger role.

So she subsequently became a CEO who really worked intentionally on building her network, and at the same time establishing herself as a thought leader in a particular segment of technology.

So I think these things kind of coming together are really, really important for anyone who has broader aspirations.

Rachel: You've also, and this really resonates with me, you've been a champion for the voice of the customer on the board. Is that an avenue for non-traditional candidates?

Rita: I think it's absolutely an avenue, right? So within our Firstboard.io collective, we have a number of CIOs, CMOs, these are individuals in, just to name a few chief legal counsel officers.

These are individuals who make buying decisions, right? Oftentimes a startup is selling to that particular audience and having somebody in this case, maybe from a larger company on their board who can help them understand how does a CIO at an enterprise company make buying decisions?

Why would they explore buying new technology? How does it need to be positioned? How does it need to fit in the general stack, I think can be very, very helpful in getting a company with early stage, you know, to lead a stage in scaling.

And I think a lot of companies are missing that opportunity to adding that particular profile early on, you know, to their board. And I think Andreessen Horowitz came out with the board persona, and I would encourage everybody to look at that 'cause I think it's very, very helpful.

And they talk about basically different board personas and at what stage in the company are these personas most helpful? And these personas include that voice of the customer profile.

So I think, yeah, that's an opportunity, you know, for women and other diverse leaders who are in these roles right now, you know, to really be, you know, a board member who can add value, especially as an earlier stage company.

Rachel: Speaking of business models being threatened, how do you think large language models might be harnessed in executive search? Are, are they a threat to your core business?

Rita: Well, I think every industry should consider AI as a potential threat, right? But it's also an opportunity. So it's both.

I do think that AI will play a role in executive search, no question. Particularly I think in the candidate identification, the stage of the process, I think AI can be very helpful there.

And I think right now it's early and companies trying to figure out, okay, what are the other use cases for different stages?

You know, for AI to be part of it, LinkedIn has integrated that into, you know, so if you have LinkedIn recruiter and you pay for it and you can reach out to candidates and it sort of generates an AI outreach message, so at this moment-

Rachel: I've seen a lot of those. They're getting really good. They really do sound like they're coming from a human.

Rita: Yeah. Well, I mean, I don't know. For me, I haven't found them that valuable, right? 'Cause I oftentimes reach out with a very unique proposition or message.

So I have, to me, they seem relatively generic, but it's interesting that you feel receiving those messages, that they're getting fairly good, right?

Rachel: They're identifying things I've written, or topics that I've podcasted on and like singling those out, which is a lot more sophisticated than I've seen in the past.

Rita: That is a really good data point, right? That they make it more personal. And there's, you know, more data AI can gather about, you know, somebody like you who's highly visible.

And so it makes it feel like this is really personal, right? So yeah, and I think this message will get better. I mean, no question, right?

So I think in these initial stages, AI will play a big role. Now in executive search, what I found is oftentimes these searches are not necessarily linear, right?

You have different stakeholders involved, different perspectives, different viewpoints, and different interests. And the biggest challenge, I think in any kind of search is to align all the different stakeholders on who are we looking for, right?

And that oftentimes does not happen in my mind, in a job description, right? I mean, it maybe happens to some degree, but it misses all these nuances.

So I think, you know, humans will still play a big role in putting the pieces together and bringing people, you know, on the same page. So I don't think that humans will go away, but AI will play a big role in executive search in any other industry for that matter.

Rachel: Can you see a future where LLMs perform some of these roles where they serve as a C-suite officer or a senior director?

Rita: I don't know. I think it's too early to tell. I think anything is possible. So I can't really make a statement one way or another. We will probably know more in a few years from now, right?

But one thing I can say, I've been talking to a few C-level members in my Firstboard.io collective, and so one of the members talked about, you know, this is a big company, how they're using AI and what's working for them, what's not working for them.

So some parts are working really well. Think like the meeting notes, you know, was pointed out as were working really well and other things were, the technology isn't quite there yet, right?

So I think we're just building this right now and we don't know yet how far it can go, how much regulatory pressure will come in too, right? So that, I think those are factors we just, we're not aware yet.

I mean, you can, looking at Europe, you can already start seeing a little bit of a trend of, you know, more regulation starting there and eventually that trickle over here, right?

If you think about GDPR, it started in Europe and then privacy regulations, you know, were implemented here in the US pretty much modeling, you know, what GDPR looked like in Europe. So I think there are many different factors which should come into play.

Rachel: Rita, what are some of your favorite sources for learning about AI?

Rita: Well, I mean, I look at it more from how is it changing the business landscape, right? How is it changing society? What are the opportunities? I look at it from a personal perspective, running two companies, really.

You know, my executive search practice and Firstboard.io, I look at it, one, AI tools are out there, which can help me, right? You know, run more efficiently. So I look at it from that standpoint too.

And then, so I read a lot of things. You know, I read, you know, studies maybe done by venture capital firms. I look at what new companies, you know, bring out new solutions.

I always like what the New York Times, oftentimes has very interesting articles about, you know, all kinds of things and including AI. Coming from Europe, I also like to look at what is the European perspective on all of this.

So I read the Frankfurter Allgemeine, I read Die Zeit. Die Zeit very interestingly enough, so when that whole Cambridge Analytics scandal came out here, Die Zeit had already written about this, I think a year or two before.

So I try to get a really broad sort of perspective, but also read the Wall Street Journal and, you know, other publications, Fortune has a number of newsletters, you know, specific to different audience and topics, which I find very helpful.

So I'm trying to kind of really have a comprehensive picture of the landscape of business in general and AI specifically.

Rachel: Very helpful. Thank you. I'm going to make you the ruler of the world for the next five years. You're going to be the boss of everything.

Everything goes exactly the way that you think it should. What is the future going to look like?

Rita: Alright, so I see a future of hope and opportunity.

I think for the first time, we have a chance to disrupt the status quo in a meaningful way. So over the next five years and beyond, I think people will come together creating companies who are solving complex problems, centered around energy, climate, cybersecurity, health tech, and many more. These companies will evolve to include a range of diverse perspectives and new and innovative models of leadership to meet these challenges.

And I think the future of leadership is more collaborative and inclusion and Firstboard.io is already operating under that model of collective leadership. And I think we're already seeing how that's driving impact and change and bringing different people together.

And I think we're going to see more companies operating like that and moving away from this very traditional, more military style hierarchical model where we have, you know, we have a boss and somebody who reports to them and some other person, you know, reporting to that person.

So I think that model will be disrupted to some degree. And I hope it will. And I also think we will have a chance to really bring more people to the table in the next five years if everything goes according to my plan.

Rachel: I mean, that sounds great. Say more about this emerging model of collective leadership versus the command and control hierarchical model. What are you seeing there?

Rita: I mean, I'm seeing that I think where people will collaborate more about outcomes and projects. And so let me take Firstboard.io. So I'm the founder and there are founding members.

And we have different, you know, councils. We have a leadership council, which works closely with me. We have a partner network. And my role is to really bring all these different pieces together.

Now, keep in mind this is all volunteer work, right? You know, we don't have staff, but it shows that if there is a mission, everybody can get behind it.

Now our mission is to increase, you know, the number of women technology does on company boards. People will take time and will use the energy to drive things forward.

So I think if we create companies who have a real mission of creating change, whatever it might be, and creating sort of these kind of parts within these companies and working together, then the role of the leader is more making sure, you know, everybody's sort of working together, driving outcome and really pulling the pieces together.

I talk about it like, it's almost like painting a picture. I paint a little bit as my hobby. And for me, what we're creating right now at Firstboard.io resembles a little bit a piece of art, right?

So we have the paint, we're putting it together, and at the end comes all the pictures. This picture is getting bigger and bigger and bigger. And I think this can also translate to companies.

Now, this is a very, of course, visionary idea of running a company. And at the end of the day, it's all about of course, profits and KPIs and all that kind of stuff.

But I think it can happen. I mean, this is, you know, if the world goes according to my plan and my vision.

Rachel: Yeah, I've definitely seen that work in nonprofit contexts where everyone's primarily motivated by getting the job done. I think as soon as you introduce money into the equation, it complicates things. Power hierarchies are likely to reassert themselves.

Rita: Oh yeah, and it's probably not going to be, but there might be a few companies who try to, who are starting to do a different thing, right?

And then, you know, if they show it can be done and the financial results are there, it might create new models, right? I think right now I think everything is on the table, right?

Business models are on the table. How we work together is on the table. So then I think, you know, if that is so, then we should also question, okay, so how do companies run from an operational perspective?

Rachel: I think that's right. And I think, you know, the best model that's emerging for working with AI is to collaborate with it, to use it to amplify and augment human capabilities.

You know, real work that humans do together is the same. It's amplifying and augmenting each other. It's creating something that's more than the sum of its parts.

That's what a company exists to do, I think that's a really interesting provocation and a really exciting vision of the future, thank you.

Rita: Yeah, it maybe include more alliances between companies, right? And you see that in security.

So a lot of security, companies are coming together right now in trying to, you know, basically work collaboratively on solving, you know, these tremendous threats we're having, you know, on that end.

And 'cause they need to, so I think that will probably translate to other things too, where companies starting to collaborate more, even though they're competitive, but there might be areas where it makes sense to work together.

Rachel: Yeah, it's interesting. I'm starting to see that in early stage investing as well, rather than people trying to take whole rounds for themselves, there's much more desire to bring more investors in and recognize that everybody's bringing something more than monetary value to the table. It's kind of an interesting time.

Rita: Yeah, it's an interesting time. So, and I think, you know, I mean in general, I think we will see more collaboration. In what form, and to what degree that remains to be seen, right? But in AI, it will probably play a role in somehow, somewhere because it might help us realize these new ways of operating.

Rachel: My last question, my favorite question, a Generationship is a huge space ship that's flying to the stars. And because the stars are so far away, it takes several human generations to get there. So it's a biosphere itself. If you have one of these amazing ships?

Rita: If I have one of those ships, right, I would call it The Power of the Collective Express.

Rachel: That's fantastic. Because the generation ship is a collective by definition.

Rita: There you go, right? The power of the collective. 'cause I think if we come together, we can do a lot of things right?

Rachel: We have wicked problems. So I hope you're right.

Rita, it's been wonderful to get together with you and to work on this podcast together. Thank you so much for your time.

Rita: Thank you so much for your time, Rachel, thanks for inviting me and hope we'll talk more soon about how to change the world.

Rachel: Sounds good to me.