In Conversation with Laura Lai

1. Can you share the journey of how you started in your career and the key milestones that defined your career path?

Coming out of college as a Psychology major, I had no idea where I would land. I only knew I enjoyed research, data, and people. Eventually, I found myself recruited into the Planning and Distribution training program at Gap, Inc. and moved to San Francisco which would begin my career in retail. It was the best learning environment I could wish for and influenced my mindset and values to this day. As the saying goes, “retail is detail” and living through the product to market process has given me great respect for the cross-functional talent required to create strong product offering and a great customer experience.

I joined the start-up team to launch Stitch Fix Mens in 2016. After years of running businesses in established and structured environments, I had to ‘un-learn’ in order to give space to learn a new business model and establish closer partnership with technical teams.

Upon reflecting, there are 2 key milestones that have shaped my career path- 1) shifting to the online business in 2004, to experience the early days of ecommerce and 2) joining an IT project team to implement a Planning and Distribution system. These two experiences unlocked my personal ‘aha’ moment - how do business teams and technical teams best come together to unlock age-old retail challenges?

2. What is a specific project or initiative that you are particularly proud of in your career?

I’m especially proud to be on 2 start-up teams- the launch of the Gap websites in Europe and the launch of the Stitch Fix Men’s businesses. There is nothing like seeing sales come in on Day 1 when there was nothing the day before. You experience a unique excitement and speed that feels different than managing an established business.?

3. What has been the biggest challenge in your career so far? How did you overcome it?

I would say advocating for myself. We spend a lot of time in our minds and with established stories about who we are. But these stories need to be revised in order to showcase the range of experiences we create each day. To overcome this, I reflect at the end of each year- recalling accomplishments I’m proud of, along with any new skills or breakthroughs. It’s a great way to keep your elevator speech fresh and relevant!

4. What do you wish you had known from the start?

I wish I understood the non-linear nature of a career. It isn’t a simple ‘graduation’ from role to role or moving up a career ladder, it is the accumulation of experiences and relationships which result in the “next thing.” Even though a particular role may not feel like it’s rewarding in the moment, your future self will thank you for it in some way.

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

The shift from an individual contributor to managing others. It is a new mindset and how you wield this position has effects far beyond your comprehension. Be humble about the responsibility and take the time to learn new skills - you are now a role model to inspire those around you. I have never forgotten the influence of my managers and how their style has shaped who I am today.

6. What is your advice to women and allies in our community?

Make connections with your co-workers. Find a mentee or a mentor. Have lunch with the person on the project team. There is so much to learn from one another, from functional expertise to personal stories. The work comes and goes, but the relationships are forever.?

7. What does the intersection of retail and technology look like to you?

It means there is tops-down (Management level) and bottoms-up (User community) alignment of how technology is implemented, adopted, and utilized to drive business value. It looks like business teams are given adequate time and resources to thoughtfully determine new processes and ways of working to give technology a fair shot at success. It looks like a leadership vision which values the unique strengths of technology and people.?