Cindy Gordon, Chief HR Officer (formerly of Oscar Health and Policygenius), consultant and advisor, talks to Erevena’s Chris Warner about the need for people leaders to develop their own work-life philosophy and then ensure the companies they’re brought into to build and scale are in alignment with it.

How did your early life shape your career in HR?

To answer this question, I need to go back to my childhood because it colors where I am today. I’m a Korean adoptee and grew up in a white household in a small town in Ohio. As you can imagine, there were few people who looked like me, which I was reminded of quite often in the community and at school. At the time, I found one way of surviving adversity was to observe the behaviours of others and figure out where I could fit in. I eventually grew to enjoy studying social and behavioral dynamics. In fact, it became a passion. So, I knew that I wanted to have some type of people centric profession, as evidenced by my seemingly haphazard studies at college – which included psychology, zoology, and nutrition– although I wasn’t able to pinpoint what I wanted to do. In retrospect, it would have been useful to get coaching at the start of and throughout my career trajectory. I have carried that thought with me all of these years working in HR in hopes I can help others navigate their way.

From college to HR – how did that come about?

On a whim, I moved to New York City shortly after college, spurred by the need to be around more like-minded people. I found NYC’s  frenetic nature very energising. I began applying for non-profit jobs, which I thought would be people centric and offer me the chance to give back some value. Then I got my first job offer and it didn’t even cover a portion of my rent at the time! So, I decided to volunteer and go through an agency to get a ‘real’ job. That’s how I joined McKinsey. I ended up staying there for 15 years, working in a variety of roles under the larger people umbrella, with touchpoints in HR like recruiting and professional development. I fell in love with different aspects of the employee journey and what could be done to empower  individuals to feel more fulfilled in their careers. So, while it wasn’t an intentional path into HR, it has certainly been one of the most rewarding accidental paths that I could have taken – and I am still doing it 20-plus years later!

How did your experience at McKinsey inform the rest of your career?

You’re in an environment where a majority of the workforce is on the same professional track. You are surrounded by extremely talented, high-performing over-achievers, who have set exceedingly high expectations for themselves since that is all they have ever known. . I learned that my role, especially in professional development, was to help them navigate their own expectations and egos, as well as clear pathways so they could do their best work. In order to build trust, I followed a three-pillared approach: 1) understanding the consultant’s individual goals, 2) the company’s values-based goals, and 3) role expectations and performance.  I figured the best way to get my colleagues on board for staffing on projects was to give them “the how and the why” so it felt like a collaboration versus a transaction. They didn’t always land on the sexiest projects, but – most of the time – they understood that it was best for their professional development and the company’s mission. That was a fundamental component to informing my philosophy as a people leader. I like to say it’s a case of leading the horses to water versus dumping the water on the horses! I think it is best to avoid the element of surprise – unless we’re talking about food or swag, of course. You’re working with adults who were hired for a reason, and you don’t want them to become consumers of your own company. So I always like to ask myself and other leaders, “How can you arm  them with the information they need to become part of the collective force? How can you create that shared accountability?”

How did you find yourself in a Chief People Officer role in insurance?

Similar to how I stumbled into HR, I did not seek out the insurance industry. When it comes to my work, I am driven by the people and being a part of something with a purpose greater than self. Two of the most remarkable things about McKinsey are its people and  robust alumni network. One of the consultants I managed had moved on to other things, including advising a healthcare startup, Oscar . Less than a year later, he reached out to me to see if I knew of anyone who would be interested in exploring a Head of People role there. It was a brand new role for the company and my background seemed to align quite nicely with the job spec. I was intrigued by the mission, threw my name into the hat, and never looked back. Similarly, the co-founders of Policygenius, the insurtech company I joined after Oscar, were also McKinsey alumni. I had the opportunity to be part of another compelling mission and build out the people function at an even earlier stage than I did Oscar.

What did you need to do to skill up for life in a start-up?

I didn’t realise this at the time, but there were a lot of parallels between my experience at McKinsey and building and running a function from scratch at a start-up. McKinsey’s New York office complex  was highly over-subscribed with candidates, inbound transfers, and client work. As a result, we encountered, with a great sense of urgency, a lot of disruption – new situations and complex scenarios that the firm had never seen before.  How do we tackle this? What policy do we need to design around that? In a sense, we were paving the way for the rest of the firm. Some of those squishy skillsets around agility, adaptability, and dealing with ambiguity were developed early and I was able to practically apply those learnings at Oscar.

Were there any surprises in your move to a smaller company?

When you transition from a large corporate environment that has a lot of resources and infrastructure to an environment that’s a blank canvas, the impact you make looks very different. That was something I had to adjust to. For example, in my first week at Oscar, I quickly built a little bit of structure around scheduling interviews using Google Calendar. It was a simple plugin through our hiring platform at McKinsey but it wasn’t really top of mind yet at Oscar. I was perplexed when colleagues kept coming up to me to give me praise,. To me, it was merely a calendar invite, but then it hit me that impact looks very different when you’re working from ground zero.  I realised I had to shift how I thought about creating impact. I no longer had to wait for this ‘big’ thing and wade through layers of bureaucracy. Instead, I could make small changes – micro-actions – that could make a big difference.

Was there a different perception of talent in the two companies?

Generally speaking, not really – although, to be fair, I’m not sure I would have joined an organization where its perception of talent differed. The same rigor applied to attracting, hiring, and retaining top talent in high-performing environments.

Personally, I was curious if there would be a difference moving away from professional services and into an environment full of operators. In my consulting world days, I recall spending countless hours coaching people through their fear that they would never find the same level of talented colleagues that existed at McKinsey. Then came my turn to feel that way. However, when I joined Oscar, my fears were quickly allayed. I was so blown away by the brilliance of my colleagues. It was an exciting place full of diverse backgrounds, traditional experience, creative problem solvers, and radical thinkers. I appreciated the intellectual curiosity and the mission of Oscar. It was something that really aligned with my personal values. We were building something that was so much greater than self Those aspects  really spoke to me in terms of philosophy.

How did the CEO’s philosophy at Oscar align with your own?

Mario Schlosser, co-founder and CEO, was very open to taking risks, experimenting, and trying revolutionary things. Maybe that goes hand in hand with the curiosity I mentioned earlier, but I really appreciated this. I came from an environment where the infrastructure was already set up for me in many ways, so being able to take my learnings and apply them in this new environment, where everybody wanted to try something new, was really inspiring. If part of my mandate is to run a talent acquisition function, I need to be able to make sure that I’m standing behind the product or the services we’re selling. The mission through and through was something that was a big passion of mine. The blue sky approach to building a people function was also really alluring.

You joined another start-up next – what learnings did you take with you?

I started to learn more about myself and hone my leadership skills while I was at Oscar. By the time I began considering the move to Policygenius, I realised that I liked building up a function from scratch. Sitting at the intersection of building and operationalizing for scale, context switching, and wearing multiple hats is something I thrive on. I didn’t set out to look for another insurtech company, but knowing the founders and having the opportunity to build again was pretty interesting to me. I’d been the 80th hire at Oscar and joined Policygenius as the 20th hire, which signalled to me that the founders appreciated the value of building a people function early on. It was useful to be able to reflect on how I’d built the people function at Oscar and what I might do a little differently the second time round, whether that was to have more impact through savage prioritization or to  build out a high performing people team earlier to get ahead of  the company’s growth.

How did your own philosophy marry with that of the founders at Policygenius?

I was very clear about my philosophy when I interviewed for the role. While it was still early days for the company values to be fully developed and articulated, I was happy to see that the founders, Jen Fitzgerald and Francois de Lame, already drafted their version 1.0. We discussed how they wanted to grow over time and their vision for building a high-performing organization. I also wanted to see how their philosophy manifested in the wild, so I made certain to chat with other employees to get a sense for what behaviours and outcomes were rewarded. This 360 perspective helped both of us decide if there was true alignment in people philosophies.

On joining Policygenius, I immediately facilitated the design and curation of version 2.0 values. We wanted to ensure the company values were aligned to the founders’ philosophy, easily digestible by others, and helped us make the best decisions in challenging times. This exercise enabled me to strategically align the People function’s mission and goals to the company’s. While it doesn’t have to look exactly like this process, it is critical to make sure there is synergy with founders when it comes to these fundamentals.  Without this alignment – this marriage of philosophies, the backbone of company culture – you’re doing a disservice to the company, to the founders, and to yourself.

Do you have any advice on how to spot a philosophy that doesn’t work for you – before you join?

Do your diligence. Talk to your peers and any trusted common connections to the founders. I’ve got a vast network of peers who are lifelines for each other. This became even more necessary during Covid times. And don’t stop there. Talk to a representative sampling of people at the company during the interview process to see how things look in practice.

Thankfully, a long overdue light has been cast on the people function over the past few years, which has helped founders and organizations understand the strategic value we can bring. It is also possible for people leaders to move the needle when it comes to a company that might not yet believe in the attributes of a people function – you just have to be a people leader who wants to do that type of work and has the ear of stakeholders to influence change.

How important is trust between the people leader and the CEO?

A lack of alignment between a Chief People Officer and the executive team can very quickly and easily turn into a lack of trust. And then nothing gets done. The CHRO’s relationship with the CEO is very special. There are few functions required to have a holistic view of the culture, the people, what’s driving business, its goals, and company performance. For all of this, you need synergy between the CPO and the CEO. They don’t have to agree on everything, but confidence in the other to carry out the role is essential. Otherwise the bulk of time will be spent playing defense instead of acting on strategic priorities. Without this synergy, cultural debt can accrue – especially when it is happening at the leadership level. I love leveraging The Trust Equation to understand the drivers behind breakdowns in trust.

A new playbook for leaner times has seen some CEOs (think Elon Musk) rewriting the traditional HR function – how do you see this panning out more broadly for people leaders?

That’s a very timely question with what’s going on in the world right now. But I don’t know if founders are becoming more radical and going to extremes in their approach to people, or whether it’s simply that it’s more publicised. Leaders are perhaps more brazen in sharing their unfiltered thoughts on social media. Yes, there will likely always be people leaders happy to buy into the Elon Musks of this world, but equally, in a polarising environment, there will be many others who don’t. On one hand, this polarisation will surface clarity on what is valued at certain companies, and that might make the hiring process – and the people function’s job as a whole – a little bit easier to manage when it comes to expectation-setting.

I do think that talent pools could look different – perhaps bringing in more unconventional profiles from other functional areas. Or maybe I’m being too idealistic and the new playbook companies will dissolve the concept of a people team altogether, leading to a fragmented HR industry for a little while. It will certainly be interesting to watch.

How does this polarisation impact you personally?

I don’t believe a people leader’s core philosophy has to change over time despite external influences, such as the new playbook you mention, or personal circumstances. My own journey as a people leader has certainly evolved with my experience, my age, level of risk tolerance, life stages, etc. As a result, my approach to leading the people function has shifted and been honed as well. That said, I don’t think my actual philosophy has budged. If anything, it’s become even stronger. I am crystal clear on what I value and what I want to do in my role over time. That philosophy is my mainstay and has helped me make tough decisions. It’s helped me challenge status quo thinking and find the right people who support the work I am hired to do.

To me, philosophical alignment is more about what is valued. And it speaks to someone’s integrity and character. If there is a radical CEO who pays little to no regard on how their decisions impact their people, then it’s not aligned with my philosophy. That’s not the work I want to do.

But it doesn’t make me less willing to adapt to the changing needs of a business. I think we have to adjust and make new considerations given market conditions if any company wants to have longevity. We’re in a time of discovery, learning, and change.

So, when we talk about the polarisation in attitudes to the people function – and people in general – I’d recommend anyone interviewing for a CPO or head of HR role to be equally brazen. Ask the founders/CEO about their philosophy and values in building and running the company. Are they aligned with your own? What do they care about – and equally, don’t care about? There’s no worse feeling than someone stepping into a role after a long, in-depth search only to find you are not aligned.

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Chris Warner, Partner

Specialisms: Sales, Marketing, SaaS, FinTech

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