On the Next Frontier: AI

Her tech career was inspired at CMC, now Paige Costello ’12 deploys AI to shape how we work.

Story by Anne Bergman

Photo courtesy of Paige Costello ’12

Every year without fail, Paige Costello ’12 welcomes CMC students into her Bay Area workplace as part of the College’s annual Silicon Valley networking trip, hoping to inspire an “A-ha!” moment in CMCers considering tech or science-focused careers.

Dedicated both to CMC and the promise of these Silicon Valley industry treks, Costello, who is Head of AI and Product Management at Asana, intentionally replicates the enthusiasm shown to her when she was an eager student taking part in the annual Information Technology Advisory Board (ITAB) networking trip led by the late Bart Evans ’70.

For Costello, it’s more than an opportunity to give back; it’s an opportunity—drawing upon her professional experiences at Asana, and previously Intuit and Intercom—to increase context and confidence for CMC students trying to figure out where and how to start their careers.

“I believe exposure is key to discovering the breadth of possibilities in your career and your life,” she said. “The opportunity to widen the aperture ever so slightly for students is really exciting for me … to help them form a more accurate mental model of the vast array of things you can do to contribute to different types of organizations.”

A Literature and International Relations major at CMC, Costello began her tech career in product management at Intuit, which led to roles at Intercom, and then Asana, a work management platform, where she is on the forefront of the company’s application of AI.

Guiding the strategy and development of a company’s products or features, from planning to launch and beyond, appealed to Costello, who sees her career in product management as one ideally suited for a CMC grad. “Being strategic, analytical, and persuasive are all things that a lot of CMCers are uniquely good at,” she said.

Costello, who found CMC through the QuestBridge program from Arizona, was drawn to the College for its focus on leadership. She seized the opportunity to serve as an Athenaeum Fellow her sophomore year, and later rose to the moment when she was elected by her classmates as their Commencement speaker in 2012.

But that’s not all. A glance at her activities at CMC reveals that Costello left no opportunity unpursued, including studying abroad at the University of Granada; working as an analyst with the Roberts Environmental Center, and serving as a Research Assistant for award-winning novelist Jamaica Kincaid, who taught literature courses (“It was really wonderful to spend time with an author who was such a creative woman,” Costello recalled.).

During her first year at CMC, Costello met Alex Berman ’12, and the couple married in 2015, welcoming a son in August 2023. “We’re trying to pretend that we’re not going to put pressure on him to go to CMC,” Costello said with a laugh.

Costello’s senior thesis, “Prose and Polarization: Environmental Literature and the Challenges to Constructive Discourse,” bridged the disciplines of literature and government and won the Society of Policy Scientists Undergraduate Student Paper Prize.

From her perspective as an alumna working in tech, Costello extols the virtues and benefits of bridging disciplines as a component of CMC’s rigorous approach to a liberal arts education.

“It’s all about learning how to think and how to evaluate different perspectives and formulate an analysis, and draw an opinion or conclusion of your own. And that’s what is required in the workplace,” she said.

In her own workplace, as Head of AI at Asana, Costello is harnessing artificial intelligence to create efficiencies and improve teamwork. In her estimation, critical thinking and “creative leadership” have risen in value since the advent of AI.

“I honestly think being a curious person, and a reader … are still increasingly important. … I believe that it’s extra important to be able to think about whether something is true or false,” she said. “I also believe that (AI) increases the need for people to see opportunities and assess the landscape. … It’s going to be as critical as it has ever been to create individuals who have great character to be the decision-makers of the future.”

Artificial intelligence: whether you fear it or embrace it, has swiftly become embedded into our daily work lives. Paige Costello ’12, Head of AI and Head of Product Management at Asana, considers the power and capacity of AI every day, as she and her team deploy the new technologies to solve current challenges in the workplace, and shape how AI will transform how we work.

We asked Costello to share her insights into the practical applications of artificial intelligence, as well as its wider potential impact.

What is it like to be on a new frontier, leading the charge with artificial intelligence?

Last summer, we were looking at the tides changing in terms of what was technically possible and becoming quickly possible …. Realizing that the opportunity was much closer because the technology has leapfrogged so quickly caused us to revise our R&D strategy and figure out how to effectively ship enterprise-grade AI to some of the largest companies in the world.

Most people’s experience of AI is fairly narrow and brief. Often people approach it first like search. We actually found in our research with Anthropic that when people work with AI more like a teammate, they’re more thoughtful about delegating work to it, and giving it strategic context, as well as giving feedback to improve its work output. It’s a mental model shift that yields much better results.

What do you think AI’s impact on the workplace will look like?

First, it’s going to increase our capacity. We’re going to be able to do more with our existing staffing plans. …. I really think people spend a lot of their workday doing things that don’t feel strategic or high value, and it’s going to be really fun to get more wind in your sails and have assistance in completing the parts of work that are not the things that you signed up for, but are required to get the job done …. Because today, it’s a lot easier to imagine how do we do something, and then say, ‘Okay, now let’s automate it,’ versus asking, ‘What are the new and different things that we can do, that we wouldn’t have even prioritized because we didn’t think that they were so close to being possible?’ And so, I think we’re just at the beginning of our knowledge curve on what AI can help with inventing—or re-inventing—the sorts of applications and problems that it can solve for us.”

What do you think this means for how we prepare our students at CMC?

There will be certain aspects of jobs where, for instance, writing some of the basic code … or doing some math, are going to be easier to do. But just because we have calculators doesn’t mean we haven’t taught people the fundamentals of how math works. And so, I think that there’s going to be some abstraction that we will do around basically creating a more well-rounded, intelligent group of people. How do we continue to NOT teach to the test, because the tests will be easy to game, but actually invest in creating individuals who have the skills different organizations will need over time.