For this HR “vigilante,” the C-suite was a stop, not the destination

For Cindy Gordon, it turned out that a role in the C-suite wasn’t the destination.

The HR professional with more than two decades of experience working across different companies and industries found that consulting and fractional HR work was a better way for her to tackle interesting people challenges and deliver her expertise to executives in need.

This approach to HR has allowed Gordon to leverage her myriad experiences, deliver on exactly what companies need from her, and protect herself from burnout or over extension, an issue she faced amid her transition away from in-house people work.

Early people skills. Born in Korea and adopted into a white family in Ohio, Gordon said she spent her childhood and adolescence honing her people skills and understanding how humans behave.

“Part of what I did in order to assimilate was to study the behaviors of others so I could figure out how to fit in and be of value,” she said. “It turned into a love of mine…I just became intrigued about human interactions and the study of psychology.”

In college, Gordon knew she wanted to work with people, and after graduating from Miami (of Ohio) University in 1999, she knew she “needed” to be in New York City.

A staffing firm helped place her at McKinsey & Company in 2000, where she got her start in HR. It was a job she thought would be temporary, though she’d end up staying for nearly 15 years, first in benefits and then recruiting before finally moving into professional development, where she worked to support the careers of employees’ she’d helped hire over the years.

“You’ve got a bunch of overachievers who might have been the top in their class wherever they were before, but then you throw them into the mix [at McKinsey], and they’re all the same,” she said, adding, “It was just exciting. I loved the sticky stuff because it felt like something that came naturally to me.”

Starting at startups. Gordon said McKinsey often operated like a startup, so when she was given the opportunity in 2014 to move to health tech startup Oscar, she said she had the right skills and experiences to take the leap and tackle some of that “sticky stuff” for an entire organization as its head of people.

She said she inherited a small team of HR pros and helped oversee the company’s growth from 80 employees to 550 in just under two years. By then, she knew she wanted to build an HR team from scratch.

“I had a lot of learnings from my time at Oscar, because we had to retrofit a lot of the people infrastructure and culture infrastructure,” she said. “This [new opportunity] would be exciting to join very early.”

Gordon was later hired as Policygenius’ first CPO, and 20th employee, in 2016. She helped grow the organization to about 500, building out all the HR staffing and infrastructure along the way.

Reimagining how to serve people. Gordon said that her second stint as a people exec offered her more confidence, better strategic insights, and a “more refined approach” to leadership.

In the role, Gordon said she was able to offer a more “diverse perspective” and worked to leverage her past experience and network of peers to be more decisive and effective.

“That was an exciting experience in many ways,” she said. “Because it wasn’t my first rodeo. I knew what I wanted to prioritize, and I could do it early on without a lot of…retrofitting.”

While exciting, what also became clear to Gordon, especially early in the pandemic, was that she was facing burnout. She had been dealing with both personal and family issues, all while leading the company’s Covid-19 task force.

“All this stuff was piling up.” she said. “The one place I could usually show up was work, and I couldn't even show up for work.”

After resigning in May of 2020, Gordon stayed on at Policygenius for another four months. She left for a hiking retreat and decided to embark on a cross-country move from New York to Los Angeles.

Following a two-month break, she took her first fractional gig as a part-time consultant at Noom. The weight loss app had been searching for a new CPO for more than a year and needed to work on some “back-burnered” people initiatives in the meantime, she said. This role allowed her to keep her skills and experience fresh, while focusing on healing.

“It started out as a risk diagnostic, where I came in and assessed the state of things and where I thought they should prioritize, and then it turned into project work,” she said.

She picked up more work at organizations like Insight Partners, Thirty Madison, and Parachute Health.

“I really liked the flexibility, and all of it was organic through the relationships I had built over the years and my network,” she said.

For Gordon, flexibility meant taking on a project or a fractional role, while also performing in advisory roles in which she was a degree removed from “the trenches.” That way, she could continue to prioritize herself and her healing.

“I was scoping out that work in a way that didn’t have me getting burned out,” she said. “I can change up what I'm focusing on at any given time.”

HR as a change agent. Gordon says it took her three years to address her burnout, and that process helped her understand how HR consulting can be a vehicle to address societal issues, rather than issues solely within a single institution. In her roles she’s able to “coach and upskill any leader and people manager to also serve as healers at companies.”

“What I want to do is turn the archaic industry of HR on its head,” she said. “Create space for it to be a strategic function so people can do their best work and feel able to do that. You can’t do that without healing people, individually, especially leaders at companies, and so they need a lot of help”

Gordon said helping leaders in this way maximizes the outcome, since they’re the multipliers at organizations. She also said that addressing personal issues in the workplace can sometimes be easier and less risky for people than in other settings, such as with a romantic partner.

“I'm like this vigilante for the HR function itself,” she said.

Gordon has also found that she feels more empowered and confident when working with execs as a consultant or advisor. They know what they’re getting when they hire her, so there’s a degree of buy-in to her approach and expertise.

“I have nothing to lose, and being pretty direct and blunt with CEOs and founders about what I think they need and what they don’t need, and how they need to think about things differently,” she said. “It just becomes this very different relationship when they’re responsible for your own livelihood.”

Gordon’s journey from the C-suite to consultancy hasn’t been without its challenges. The business overhead work and invoicing is a challenge. She’s still uncomfortable with the scarcity mindset of always pursuing the next job and the lack of a steady paycheck still makes her uncomfortable. The work can also be lonely. While she’s worked with subcontractors, that doesn’t replace working with a team.

“Consultants don’t replace the in-house operators,” she said. “I think there’s a time and place for both.”