Jan Chong: Finding the Right Fit with Enrich

When your usual playbook stops working and you’re left without direction, where do you turn and who do you turn to?

Accustomed to a career where recruiters constantly called, offers came easily, and tough decisions were backed by a solid network, she suddenly found herself in a new market—one with fewer roles and tougher competition.

It was sink or swim, and Jan knew she needed a different approach. 

One that would keep her resilient, sharp, on course, and – perhaps most importantly –- employed. 

Meet Jan

Jan Chong is an engineering executive who began her career at Twitter. She studied both Computer Science and Management Science and Engineering at Stanford University, and is passionate about engineering management, mentorship and growing people to their full potential. 

Leadership Isolation

Jan’s journey to Enrich didn’t begin with job hunting. While climbing the ranks at Twitter, she noticed a big gap for those in leadership roles, recalling that for software developers, there were many different feedback loops built into how they work between things like code reviews and mentors. However, for managers, none of that existed. This meant that she had no idea who she could turn to when her own challenges became too overwhelming to deal with alone.

“What was hard about that is, like, when you're trying to figure stuff out on your own: A, it’s slower; and B, when you make mistakes as a manager, you make them on your team, so your team ultimately suffers for the fact that you're not, like, particular — you’re learning on the job.”

Her solution? The “Manager Fight Club” – a space she created to connect with others in similar roles and talk openly and honestly about management challenges. Unfortunately, balancing schedules and building consistency proved too much, and the effort petered out. 

Jan realized then that she needed an external peer network and was relieved when “the exact week” she began looking outside of her company she received the invitation to join Enrich, describing it as exactly what she was looking for. 

“Jordana [Stein] landed an invitation on my desk somehow to join Enrich. I was like, this is actually exactly what I’m looking for.”

Building a Powerful Peer Network with Enrich Peer Groups

Jan quickly found her place within Enrich peer groups, surrounded by executives from companies like Reddit, Pinterest, and Airbnb, who could relate to her and her industry pressures. “Enrich is one of the places where I found that the group is very much like my speed,” she explained. “It’s really about the composition of who’s in the group…and then what Enrich does really well is it facilitates it, so you don’t have to think about it.”

She loves the different range of perspectives and the candid environment. Enrich is different from other networking or coaching programs, where the focus is often too generic. In Enrich, Jan gets exactly what she needs: a group of tech leaders who fit and understand her fast-paced and high-pressure world. 

When Jan had to come up with a hiring strategy for her startup, she used the group’s collective knowledge on geographic expansion. “I learned that FAANG companies were heavily focused on certain cities like Toronto, where they needed to hire 500 to 1000 engineers a year. As a startup, we only needed 20-50 hires, so we expanded into less competitive markets like Vancouver and Calgary.”

Her plan paid off. “It’s been like shooting fish in a barrel,” Jan joked, reflecting on how easy it was to hire developers – even away from native companies like Skip the Dishes. "It's not like I'm asking them [the peer groups] for secret sauce or anything like that. But it's a really good way for me to hear the lay of the land."

The group also validates the challenges she faces as a tech leader, helping her handle them confidently. With the groups at her side, Jan felt like she’d finally found her “tribe,” a network uniquely equipped to help her with the high-level stuff she ran into daily.

“I get to meet people who are…in it. This is actually a way to get that [Silicon Valley] network on top of the skills.”

Transitioning Jobs and Negotiating Salaries with the Job Search Council

The hit came out of nowhere when Jan suddenly needed to find a new role. Used to an abundance of offers, she now faced a tougher market where top executives, herself included, were struggling to land jobs. “We were all like entitled little princesses that have been fed beautiful jobs all our lives,” she joked, “and now we were getting rejected.”

Jan joined the Enrich Job Search Council, which gave her companionship, solidarity, practical tips, and a structured approach to her search while helping her navigate the challenges that come with being in between jobs. Instead of a super lonely process, she tackled job hunting with a group.

Being in the council helped Jan reflect on what she truly wanted, turning her previous “YOLOing” and knee-jerk reactions into deeper reflections.

“I remember just like blathering at the Job Search Council, and they were like ‘Oh, here’s what I hear: you want really hard problems and a fast-paced environment.’ And I was like, ‘Oh, that’s exactly right.’”

The council also helped Jan with negotiating her salary, something she previously struggled with. She approached her offers more strategically, consulting council members on what she should ask for and how to negotiate. Having peers to share tips, review offers, and guide her through each step made for a less daunting process, giving her the confidence to advocate for herself and command a better offer.

Gaining Clarity and Confidence through Community

With Enrich peer groups and the Job Search Council, Jan didn’t just land a new role; she walked forward into her future with a clear sense of her goals and the structure and courage to pursue them. “It wasn’t about just learning new things or meeting new people,” she shared, “but about making the skills I already had louder, stronger, and more effective.”

Reflecting on her journey, Jan describes Enrich in three words: community, learning, and tribe. For Jan, Enrich became more than a network – it became her retreat for peer support, building resilience, and understanding her potential. 

If you’re an executive like Jan seeking a community of peers who “get it” and  a network ready to support high-level challenges, learn more about Enrich here. If you’re ready to explore how Enrich could support your unique career journey, you can schedule a call with us today.