Upskilling and training on a global scale with Cara Brennan Allamano

Are you engaging your employees with continuous learning?

Cara's headshot alongside New World of Work logo

Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. In each episode, we’ll hear from some of the world’s best and brightest people and culture experts on the cutting-edge topics HR professionals are most interested in today, explored through a global lens.

Episode description

In today’s job market, it’s more important than ever to learn unique skills that help set you apart from the competition. Companies need to create a culture of continuous learning and upskilling for their teams, not only to keep a competitive edge, but also to keep their employees satisfied and engaged in their roles. In this episode, Rhys sits down with Cara Brennan Allamano, Senior Vice President of People at Udemy. As an online platform designed to help adults learn new things on their own schedule, Udemy reminds people of the value of continuous learning beyond traditional educational settings. Cara holds a master’s degree in liberal arts from Stanford University, and in the past, she’s held roles in people operations at companies like Adobe and Pinterest. As we continue the transition into this new world of work, Cara offers her insights about how companies can foster a culture of continuous learning and training while working in a remote, globally distributed, or hybrid setting.

Episode transcript

Rhys: Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. 

I’m Rhys Black, Head of Remote at Oyster, a global people operations platform making it easier than ever to build a brilliant team on an international scale.

On New World of Work, we’ll hear from some of the world’s best and brightest people and culture experts on cutting-edge topics that people ops professionals need to hear today, all through a global lens. 

Join us as we navigate this new world of work together and learn more about each other along the way. 

In today’s job market, it’s more important than ever to learn unique skills that help set you apart from the competition.

It’s essential for companies to create a culture of continuous learning and upskilling for their teams, not only to keep a competitive edge, but also to keep their employees satisfied and engaged in their roles.

Luckily, there’s never been a better time in history for self-educating, developing new skills and feeding curiosity. 

As we continue the transition into this new world of work, how can companies foster a culture of continuous learning and training while working in a remote, globally distributed, or hybrid setting?

To help us answer this question today, I’m sitting down with Cara Brennan Allamano, Senior Vice President of People at Udemy. 

As an online platform designed to help adults learn new things on their own schedule, Udemy reminds people of the value of continuous learning beyond traditional educational settings.

Cara holds a master’s degree in liberal arts from Stanford University, and in the past, she’s held roles in people operations at companies like Adobe and Pinterest. 

To kick off our conversation, she shared an overview of her current role at Udemy, some of her prior roles, and why she’s passionate about working in people operations.

Cara: I'm Cara Brennan Alamanno. My current role is heading up the people places and learning function at Udemy and Udemy is was the world's largest private edtech company, and we became a public company at the end of October. And now we want to build the largest edtech company period, and it's a really exciting, very mission driven company. We have 35 million learners that come to our platform every month. So to be able to support a company and build the people function, which includes H.R., recruiting, workplace and and learning, which is thinking about both learning internally as well as externally and how people learn on our platform, is a pretty exciting role for me. And it cut solve about 20 years of working in H.R.. The first half was in a more corporate environment and large enterprises, both in advertising and media and marketing. And then a little more than a decade ago, I moved into the rough and tumble world of startups with the social media company called Context Optional that eventually, through three acquisitions became Adobe Social. And then after that went onto Pinterest, founded the H.R. function. There help that very early company. I think I was number thirty two or thirty three employee at Pinterest grow and provide a solid foundation. Moved on to Planet Labs, which was a space tech companies. So we built satellites that image the Earth every 24 hours and again, very mission driven company focused on on helping we, as humans monitor what's happening on the Earth every day. And that was very exciting, working with a lot of brilliant people and then moved on to Udemy after that. So I've had the privilege to work in a number of different environments have have seen such an evolution in the people function. When I started 20+ years ago, it was much more of an administrative function with the aspirations of being strategic. 

Rhys: Not only does Cara lead a team at Udemy, but she's also founded a network of leaders to drive growth, thought leadership and innovation in the field of people ops.

Cara: And while it's super exciting for me right now, I have a group that I founded about eight years ago called People Tech Partners, and it's a cohort of about two hundred and fifty advisors and the advisors are cpo heads of people at some of the most innovative companies in the world. The folks that that are partnered with me, they're in the network have have had deep experiences in places like Facebook and Google, but currently sit in organizations at the forefront of all of this change. So, you know, the head of people at Zoom and Slack and the current head of people at places like Pinterest and then a ton of really cool, high growth startups that you may not have heard of, but are the, you know, the instacart's, the the of the future. And within that group, we spend a lot of time thinking about how we, as people leaders can have impact. We share a lot of insights about the future of work and how we've navigated the past two years, which have been crazy. And then we also work with early stage founders in companies that are helping to define the future of work. Companies like Oyster and others who are coming in with a new perspective and in are changing how people think about work, and it's super rewarding. And it's a real partnership between those of us who are practitioners who need good tools to do our jobs and those that are looking at the future and helping to create it by building the tools that employees will be engaging with. So I feel like I've been blessed with a really varied career and and I've met some really amazing people along the way, and I just have a real sense of personal mission around the role of the people leader and the critical importance of having an agent within an organization who's thinking every day about employee experience because the world is filled with people who go to work every day. And it's time for us as a society, as humans to think about. How do we optimize that work experience because that is where people spend their most, most of their time?

I get really excited when I when I am now seeing headlines around the future work because this is something that I've committed my life to. And for the longest time, it was super, not sexy. And we sit around and laugh with our friends and colleagues about how well now what we're doing is very interesting and in mission critical. And I love to see people who care deeply about change again for the employees and the employee experience. I love that now we're focusing on things that can really have impact and we're giving agency to people who've spent their careers helping each other and helping employees.

Rhys: As a continuous learner and a passionate champion for education, Cara’s belief in every human’s innate capacity for greatness is infectious. 

It’s not hard to see why she’s had such a successful career in people operations thus far. Cara’s positive attitude and dedication to maintaining a growth mindset have no doubt taken her far in all of her endeavors.

Cara: I have a very strong belief that every human, including myself, has potential to do whatever they want. That's what excites me about being in human resources because I do see it. I see my job as creating possibilities for people to change their lives, to do their best work. The reason I do I've thought I get excited about learning, and I think that's manifested in the fact that I can't seem to stay away from the university. I've basically been in college forever. I'm still taking some sort of courses, you know, at Stanford, and there's a new program at University of Chicago that I'm excited about ethics and leadership. I think it's really important because curiosity and learning is a muscle. It's in and I go back to Carol Dweck and growth mindset, and that's a book that we give every new hire on my people team at Udemy. It's something that really resonates with me is that learning is a behavior and a skill, and the ability to learn the ability to master new concepts is not something that you're born with, right? It's not IQ. It's not that you're born with the capacity to know how to do math and you get to the end of the road on that and then you have, you know, that's it. Nothing's baked. I actually believe in the infinite possibility for each person. So in order to do that, for myself, it's about continuing to be curious and continuing to exercise that muscle. And it's not just to learn new things. It's actually opened up a ton of things in my life in terms of finding really interesting people because they have a different perspective than I do and really wanting to sit down and listen and talk about a nerd out about things related to my work, related to my family, related to other parts of my life. And I actually find the most interesting people in the world who are people that are doing, who ask a lot of questions, who explore, who are curious. And I also think it's really interesting to me. I'm somebody who wasn't, as I mentioned, born and raised in high tech. I grew up in Kentucky and a small town in Kentucky. I was surrounded by people who, you know, didn't go to Ivy League schools and didn't have a fast track to, you know, a six figure job upon graduation. And so when I came into technology, what was really interesting to me is I saw people with a growth mindset, really. Exploring and thinking and building because they were just driven by innate curiosity and they just loved new ideas, and they and they were living in a world where a new idea could turn into a billion dollar business or could change the world in a short period of time, which is super exciting. And of course, as I mentioned before, I recognize there's privilege here and that there's a significant downside if you don't, if you're not being really thoughtful when you're building these businesses and and being really thoughtful when you're when you're building technologies.

It gets me excited to learn and grow. I think some of that's manifested in traditional educational environments and degrees. I think some of that's manifested in wanting to be part of companies that are building and trying new things and really pushing the envelope when it comes to how they can change the world. And I think some of that is really just being around interesting people that I can learn from. And all of it is reinforcing this, this concept for me that there's infinite potential for every human and and a big part of my job is to clear the way for people to be able to do their best work in their days.

Rhys: Like a true people ops leader, Cara’s main focus in her day-to-day role is helping others succeed.

When it comes to her personal philosophy, she believes great things are accomplished when people work together and make space for a number of diverse perspectives.

Cara: I think summing it up in that it's about creating possibilities for every employee that works for the companies that I'm a part of. It's really hard. I want to be clear about that and I have the luxury of working with people that are a lot better than me and most of the areas of human resources and recruiting and operations and workplace I. The part I love about my job is taking people that are really committed to creating amazing employee experiences and at the end of the day, my focus is how do I deliver on the promise for every teammate, that's what we call folks that works work at Udemy. How do we deliver on the promise that I'm going to help them do their best work while they're here working at Udemy and in order to do that, we have a small army soon to be one hundred and fifty people on the people team at a global scale that are spending their days. You know, a recruiter’s thinking about how do I find the very best match to this job so that this person can come in and use their skills and abilities and feel good about their work every day and really align with the team that we have? And also thinking about how do I bring in a diverse set of perspectives? How do we make sure that things like diversity and inclusion are so central to how we do business that we understand that it's so that being diverse and having different viewpoints is really going to make all of us better. So I think, you know, those are table stakes for us on the front end. And then when people are with us, how are we creating feedback cycles and processes so that people are learning about what they're really good at and building on that and then addressing any areas that might be obstacles for them? And how are we enabling managers to do their best work and then making sure, you know, down to the down to the work environment? God bless. Right. Like during COVID, that was such a key challenge. And I think we're just starting as people, leaders and business leaders to really understand the impact of the last two years, both on people's personal lives, but also on future work and what it will look like to be an employee going forward. So a lot of what I think about and a lot of the people on my team think about every day is, Hey, you know, Rhys accepted this job. We have a commitment to tourists because he's going to bring his best to us every day. How do we bring our best collectively as an organizational community?

We look at learning as a key behavior. So we hire people that are learners. We hire people that have proven that they can learn and grow in roles that they've been a part of. We hire people that have different backgrounds so that they can bring learning to others within our organization. And then we do everything we can to help those folks feel that they belong and that they are heard. And then ultimately, we want to give them the right tools so that they can do their job well. And some days we do it while and some days we don't, and we fall down because those back up. I think it's a very emotional job that we have on the people side of business because you are so connected to other humans, which makes it really hard, especially during crisis times that we face the past two years. But I also feel like the folks that are on my team have a level of commitment to really try their best. And we've had the I've seen amazing things happen and when we all work together.

Rhys: Cara’s inclination to view all skills and personal qualities as ultimately learnable and malleable, serves as a testament to her ability to help her teammates grow.

Despite the temptation to give in to our less admirable qualities, Cara’s perspective reminds us that through a little hard work and effort, we can learn to develop new characteristics that will help us in our daily lives.

Cara: I think first, very selfishly, that being a good listener is a skill that I have been challenged to build over my entire lifetime. And it's still a skill for myself that I want to be. I want to be better at. So I think understanding that for me, it's a very personal thing to be a better listener. And I think because of that, I think I value good listeners and a different kind of way than maybe folks said it comes more easily to. I do see it as a skill. I see it as a learned skill. I think the second interesting thing, we have an amazing course on the platform by one of our instructors called conscious listening. And if anybody wants to learn about being a really amazing listener on the benefits of being a good listener and listening is a skill, I think take that course, it really opened my eyes.

I've been in rooms where we've been in decision making environments, you know, at the executive level, at the board level, I've I've really thought about how to help teams be really high functioning. And I've just seen over and over and over again that those teams that have fostered listening and have focused on listening as a behavior and a skill have outperformed consistently people and teams who haven't. So even if I wanted to be able to convince myself that maybe listening isn't as important as people say it is because it's hard for me to really be a deep listener, and I'm focused on that as a skill for me to learn. My practical experience tells me something very different.

Rhys: Given the flexible and accessible nature of Udemy’s learning platform, Cara and her team have firsthand knowledge of just how beneficial on-demand learning can be. 

And with 35 million people using the platform each month, clearly others have come to the same conclusion. 

Cara shared some tips for other companies hoping to increase learning opportunities for their teams, stay competitive, and create a culture of continuous education from the ground up.

Cara: I think you really have to think about access for employees and convenience. The days of taking three days at an off site to go learn something and often doing that in person, like that's over, that's done. If you want to be able to be competitive, if you want to be able to meet, you know, attract and retain the right employees, it's meeting them where they are and hiring people that are curious. And if you do that, you hire people with the growth mindset. These are people that are hungry and they want to learn and they want to grow so. So the next thing you can do is just give them access to a full menu of options to learn and expand and upskill and and in a mix. So what we do is we say you can go learn on the platform. Of course, you have full access any time we give incentives for people to learn on the platform. We have raffles and all those fun things. We try and make it really engaging and fun. I think the other piece that's important is that you do provide some structure and you say we have manager training where we've curated a collection of courses and we've created our own courses on the platform, which is super easy. So we've done that and that's the guided practice, but it's still asynchronous and it's still on the time at the convenience of the employee. And then in order to really reinforce social learning, we have learning labs. So you go and you learn, you learn the skill on the Udemy platform, you take the course on the platform and then you come together as a group and talk about what you've learned to reinforce the learning. And that's where we're finding success. People really appreciate it. And again, it's reinforcing the concept that everybody can upskill. Everybody can grow at Udemy.

I think about competition a lot because we talk about the great resignation, I think. As Josh Parsons said, it's a lot more like the Great Migration, right? It's not the people are just leaving and tapping out. That's a very small subset of people in this scenario. People are just optimizing. They're going to the organizations that are going to help them be the most successful. And what are those organizations when you're talking about an entire world, you know, an entire cohort of knowledge learners. Their currency is our skills. So, yes, you can and should be competitive from a compensation standpoint. But when people can work anywhere and work for anyone, which is really the new reality that we're entering into, it's they are they will migrate to the companies that recognize what they care about and what folks care about are being able to continue to build skills because that's continuing to build their ability to compete individually and continue to for them as individuals to continue to be able to to grow and develop and succeed. And the only way to serve those folks and to continue to retain them is to be a partner in that learning. Right. You're not going to fight it. You're going to you want to come in and say, Come on over, we're going to be the people that help you get to that next level pastis and have fun while you're doing it. So, you know, that's the message we want to send to the world from a Udemy perspective, and I'm seeing more and more of that conversation just in the market period. And I'm seeing people optimize for skills and optimize for learning and understanding. Oh, if I go to that huge behemoth company that pays really well, now I'm going to be solved in this job for the next five years. I'm not going to be learning. So ultimately, I'm not going to make the same amount of money. I'm not going to be as valuable to my employee or so retention and my ability to be successful in my role may not get there. People are understanding much more now that if I go to a company where I can learn. For the next two or three years, then that's actually going to be the biggest return on my investment of time versus going somewhere else where I'm not going to be growing and learning and. And so being really open and clear that we get it, we get that you're your currency is learning and your currency is knowledge as a knowledge worker and we're going to be your key partner in that. That's how I find we find our best people.

Rhys: Finally, I asked Cara what she believes is coming next for this new world of work. Unsurprisingly, she believes skills are becoming a new kind of currency when it comes to the job market.

For companies and individuals that are hoping to stay competitive within the landscape, continuous learning will be an essential piece of the puzzle moving forward.

Cara: I think we spent a lot of time and people leaders like pre-COVID saying, Oh, in the next five or 10 years, we're going to move to like a borderless employee, you know, a borderless employee community. And it's not going to be about where people are or it's going to be like who they are and what they can do for your organization. And boom, here we are.

Here we are now, two years later, in a world where now we have access to a pool of seven billion for talent. And I look at tools like Udemy, I look at what we can do. We have had story after story, after story of people that have gone on our platform and learned how to code Python in two to three months. And done it in an inexpensive way. Learning from people that are practitioners and instructors. The world's best teachers, I think. And we have stories of people changing their lives and, you know, 10x saying 50, axing their salary coming from a small town and in Syria, learning from places that you'd never think that you would hire an amazing software engineer. And that's where we are now. You know, that's the new world. People are self educating. They're enabling themselves and their families to see a new level of mobility and access. And then organizations like mine are benefiting from that. So I get really excited.

Rhys: In the age of information, learning something new every day is not only a possibility, it’s a necessity. My conversation with Cara reminded me of how important it is to stay nimble, curious and adaptable to change in this new world of work. 

Here are a few of my key takeaways from our discussion:

  • Adopting a growth mindset will take you far, no matter the role you find yourself in. It’s important to remember that if you want to learn a new skill or develop a desirable quality like better listening skills, it is 100% possible with hard work and dedication. 
  • Education is no longer something that’s reserved for the wealthy or well-connected. In today’s job market, learning new skills has become a currency that can help individuals and companies become outstanding in their field. 
  • Providing employees with opportunities for continuous learning is becoming a non-negotiable for leadership teams. If companies hope to retain their employees in the future, they will need to become a partner in their learning by consistently championing education.

Rhys: Thank you for listening to New World of Work, the podcast exploring the new frontier of the modern workforce through an international lens. We hope this episode served to expand your horizons and open your mind to a new perspective.

Be sure to subscribe, rate and review the podcast so we can reach more listeners.

I’m your host, Rhys Black. See you next time.

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About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, hire, pay, manage, develop and take care of a thriving global workforce. It lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world with reliable, compliant payroll, and great local benefits and perks.

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