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Advice / Career Paths / Training & Development

Here’s What It Looks Like When a Company Wants to Help You Learn and Grow

Jason O'Neill, the Director of Learning & Development at Squarespace
Jason O'Neill, Director of Learning & Development at Squarespace

Jason O’Neill knew early on that he wanted to dedicate his life to helping others—a somewhat foreseeable path given that he grew up in a family of educators. His initial dream was to become a doctor, but an undergraduate degree in biology was as close as he came to achieving it.

“I decided to take a gap year to travel the world prior to committing to medical school,” O’Neill says. “After running out of money while exploring Asia, in a moment of serendipity, I fell into a job that turned out to be my life’s calling: learning and development. Everything about the field was fascinating and brought me great fulfillment.”

In the years that followed, O’Neill gained experience in a variety of areas of learning and development (L&D), organizational development, and leadership disciplines across different industries, geographies, and cultures—including time spent living and working in Japan and for companies like Apple and Uber.

His latest role is the Director of Learning and Development at Squarespace, where he and his team are currently working to establish department-level L&D plans. “This is an important step forward in offering greater customization to org needs and demonstrating direct business impact through L&D solutions,” he says.

Here, O’Neill talks about how a Super Bowl ad drew him to Squarespace, what sets the company’s L&D program apart, and how he approaches his own career growth.

What attracted you to work at Squarespace?

I remember little about the 2018 Super Bowl, with the sole exception of a curious ad featuring Keanu Reeves standing on a motorcycle propelling full speed ahead. I recall being moved by the creativity in the ad’s storytelling and at how much it stood out in contrast to the other ads and the Super Bowl itself. In discovering more about Squarespace, I learned that the ad was in many ways a representation of the company’s mission itself: to help creatives tell their stories, to stand out in a crowded world, and to provide access to simple but powerful tools. Culturally this was something I was drawn to, and when presented with the opportunity to join the team, I didn’t think twice.

What are you responsible for as the Director of Learning and Development?

My role is to lead the creation of a shared vision, strategy, and plan toward the development of a learning culture at Squarespace. This entails the development of L&D solutions that increase the skill, autonomy, and level of connection to the company and others felt by each employee. We envision Squarespace becoming a place where people come to not just do their career’s best work, but also as a place where they learn and grow in unimaginable ways.

Why is learning and development so important for companies?

Research shows that great talent will be both drawn to and stay at companies that invest in employee development. This is intuitive and makes sense. Each one of us feels fulfilled and motivated when we are growing and measuring forward progress toward our individual purpose.

What are the hallmarks of a strong L&D program?

Formal programs can be powerful in accelerating the growth of individual employees. The best L&D programs are targeted and purpose-driven, and grounded in clearly defined business and learning objectives. Moving far beyond in-person training led by subject matter experts, programs should seek to leverage the collective talent and expertise within the company. Ideally programs also include an experiential component where employees gain opportunities to apply newly acquired knowledge, whether through real or simulated practical experiences.

What are some of Squarespace’s learning and development offerings?

If you are a new employee joining Squarespace or moving internally to a people management role for the first time, the team does a great job in offering a robust, white-glove experience to support and accelerate your transition into your new role. There is also a broad array of offerings in place for employees to navigate their growth, from self-paced learning resources to open enrollment professional development sessions to employee education reimbursement benefits.

What do you like best about the company culture at Squarespace?

Kindness and care for others is pervasive throughout the company to a degree I have never experienced. Teams gravitate toward collaboration, inclusion, and support for one another, creating a positive environment that makes coming to work every day an absolute joy.

I’ve also been inspired by Squarespace’s obsession toward simplifying and building ideal solutions and products for customers. This ethos translates well into how we operate as an L&D organization, and how we approach the development toward a one-of-a-kind internal growth culture.

What are some ways you’ve taken advantage of learning and development throughout your own career?

In our field we often talk about the holistic “Three E’s” of L&D approach—learning through Experience, Exposure, and Education. In addition to promoting this philosophy through my work, I’ve also been mindful of growing myself in a balanced manner, with each “E” complementing one another. To illustrate, 2009 to 2011 was a period of pronounced growth for me professionally, where I went back to school to pursue an MBA (“Education”), established new mentorships and professional networks (“Exposure”), and actively applied the knowledge I was gaining on the job in a new role (“Experience”).

What is the best career advice you’ve ever received?

“Don’t be the bean dip guy.” A seasoned executive I once worked with shared the analogy of a person who goes to an amazing party filled with great music, close friends, and everyone having an incredible time—and then, among the lavish food display, proceeds to complain about how bad the bean dip is. Failing to see the bigger picture rarely helps you succeed in business. Negative attitudes are rarely rewarded with new opportunity and growth. By contrast, embracing an elevated view of the world with an appreciation for the vast volume of opportunity that we have access to can lead to an exciting and fulfilling career journey.