Stitch Fix Exec: Don’t Fear the Machines and Other Career Advice

She manages the finances of one of the hottest young public companies, identifies with a lioness, considers earning an MBA while raising two kids as a single mother a “time to reflect,” and is breaking all our stereotypes about accountants.

Jessica Ross, formerly a managing director at Kaiser Permanente, joined the online personalized styling service Stitch Fix as vice president and controller just three months before its initial public offering on November 17, 2017. “While I did not have prior IPO experience, the depth and breadth of my career experiences leading up to that moment built the competencies and confidence required to jump in and lead during that exciting time,” Ross said in an on-stage interview with Loren Mahon, Oracle vice president of global finance, at the Cal Poly Women in Business Symposium in San Luis Obispo.

There were plenty of gems in Mahon’s wide-ranging interview with Ross, which focused on success skills for millennials. In the interest of fair reporting, Ross’s story of admiring a hunting lioness with her cubs while on safari in Africa was in response to a Mahon question. That said, Ross could well be the spirit animal for millennials seeking a career in finance at a time when, she predicts, “30 percent of finance roles as they exist today will not be there due to automation in the near future.”

The finance career is at an inflection point, Ross maintains. Her role as a leader, then, is to “create a roadmap of how the Stitch Fix finance team can shift from transactional to transformational.” She’s helping build the company’s “finance operating system,” applying the company’s values to the process of using algorithms and data science to redefine its financial processes. Read on for Ross’s career advice.

Grow Your EQ

Stitch Fix has a hiring standard: It seeks people who are bright, kind and goal-oriented. Bright, Ross said, layers in the emotional quotient aspect of being book-smart. “If you don’t have that EQ piece, navigating business can be really challenging,” she said, noting that Stitch Fix “definitely has a kinder culture” than is commonly seen in the finance world.

For example, Ross said she applied a range of soft skills during her mission of cost transformation at Kaiser, which required her to mesh with seven regions led by seven different presidents. “Being able to navigate the people aspect of it was critical,” she said.

Pause for an MBA

In 2010, following a recent divorce, Ross underwent a “perfect storm of events”: discovering her daughter was facing learning challenges at school, helping her son transition to high school, and being diagnosed with diabetes — all while working 100-hour weeks trying to make partner at Deloitte. She left public accounting and joined Kaiser, where she says she “got every single bit of work-life balance that I needed at that time. I got married and had my first child when I was in college. Up until that point, everything had been about being a mother and being a professional. It was time for me to focus on myself and the things that mattered to me most.”

It was at that juncture that her boss suggested that she go for an MBA. That process, while still working at Kaiser, “brought clarity to so many things for me,” Ross said. She realized she had a passion for retail, which was at a technology-induced inflection point just like finance.

Have an Exit Plan and a Personal Strategy

Ross displayed enviable pragmatism and vision while facing the vicissitudes of business.

“Throughout my career, I’ve always thought about two things when approaching transitions—even in 1998, when I was first starting out,” she said. “How am I going to grow from this experience? What are the competencies that this is going to set me up for? Second, what are the opportunities that this is going to set me up for? What’s the exit plan?”

Similarly, Ross put her analytical skills to work on herself. When a mentor told Ross that she needed a “personal strategic plan” but refused to share his as an example, she put together a PowerPoint deck with her own vision. Then she created a gap analysis to determine action items in terms of experience, education, and exposure.

Create a ‘Lens of Possibility’

Crafting organizational strategy and being comfortable with the uncomfortable keep her going, Ross enthused. At Stitch Fix, not only is there the challenge of transforming retail and finance, but there’s also the opportunity of working for the only female-led company to go public in 2017. Stitch Fix also joins a select group: only about three percent of American public companies have a woman CEO.

Some 86 percent of Stitch Fix’s employees, 50 percent of its management team and board of directors (including founder and CEO Katrina Lake), and 35 percent of its data scientists and engineers are women, Ross said.

“I would challenge you, as you think about defining your future, to think about the lens of possibility you are creating for others,” Ross said. “If you do that, I guarantee you will have very rich and meaningful lives.”

Don’t Fear the Machines

For recent college graduates worried about how technological disruption will affect their career prospects, Ross noted similarities to 1998, when the dot-com boom and bust were just around the corner.

Just as job seekers around the turn of the century managed to succeed in industries shaken up by the internet and the emerging World Wide Web, today’s college grads shouldn’t be too apprehensive about what automation will do to the finance discipline. “It’s the very manual, transactional types of activities that aren’t using the human element to its best ability that will and should go away.”  Addressing the fear that machines will soon take over the world, Ross assured the audience, “They’re not, and they can’t.”

Mahon agreed, noting that as the workplace changes to where more machines and people work side by side, all jobs will still require sound human judgment, as well as a sense of values and ethics. In board meetings today, Mahon said, much of the number crunching and analysis has already been done by machines. “We walk in there with nothing but our iPads and our brains,” she said. “Keep your brains sharp. You’ll be fine.”

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