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Talking People Ops with Cindy Gordon, VP of People at Policygenius Inc.

We recently had an insightful chat with Cindy Gordon, VP of People at Policygenius Inc. Policygenius is the nation’s leading online insurance marketplace, with a focus on making it easy to find and buy insurance.

Cindy Gordon , VP of People at  Policygenius Inc

Policygenius just expanded earlier this year to offer home insurance and auto insurance. They also offer a way for consumers to compare and buy life, disability, and pet insurance. For consumers looking to shop for health, renters, and travel insurance, they do that too! They have a wealth of content to help consumers navigate their finances, no matter where they are in their financial protection journey.

Prior to Gordon’s role with Policygenius, she was Head of People at Oscar Health Insurance. She also spent 10+ years at McKinsey in roles spanning HR/benefits, recruiting, and professional development.

Below, Gordon shares her top tips on:

  • How to build up the people function at your organization

  • Avoiding common mistakes in the early stages

  • Fostering a diverse and inclusive workplace

  • Easing the transition for employees when scaling


Gordon emphasizes the importance of communication with leaders, managers, and employees in every step of the process.

Interview with Cindy Gordon, VP of People at Policygenius Inc.

Stefan: Can you tell me a bit about yourself?

Cindy: I‘m currently the VP of People at Policygenius, where I started as the 20th employee - now we have around 175 employees! Before Policygenius, I was Head of People at Oscar Health Insurance, a health insuretech company, when we scaled from 80 to 550 employees within a two-year period. Prior to Oscar, I grew up at McKinsey & Company through a variety of roles under the people umbrella.

Over the past three years at Policygenius, my goal has been to help attract, fulfill, and develop our employees. Helping employees, leaders, and teams navigate their way is what truly makes my work meaningful.

As my side hustle, I own a fashion consulting business. The common thread between my work at Policygenius and my small business is that I get the opportunity to guide people in expressing themselves, albeit in very different ways. I also have a 9-year-old yorkie poodle, Bert, who means the world to me - he’s more like my child than my pet!

Getting Started on Building the People Function

“Instead of jumping right into deliverables like performance reviews or developing our hiring strategy, we needed to make sure that we had the right values in place that rang true to our founders’ vision and would resonate with people, both internally and externally.”

Stefan: What were your 3 biggest priorities when getting started with the people function at Policygenius?

Cindy: At the start, there wasn't much built in terms of people infrastructure, but our founders Jen and Francois were ahead of the curve because they valued the people function enough to invest in it early-on, which was amazing! We were very much on the same page in terms of our people and talent philosophy and that was part of why we were able to work together on this so effectively. 



To break down my strategy into three key points, I started with clarifying our values, then worked with executive leadership to map out specifics around role expectations, and simultaneously focused on making our hiring strategy and onboarding practices more consistent.

  1. Putting our values first as the foundation

    Instead of jumping right into deliverables like performance reviews or developing our hiring strategy, we needed to make sure that we had the right values in place that rang true to our founders’ vision and would resonate with people, both internally and externally. We turned the essence of our mission statement into 6 tangible values. We didn’t want them to be superfluous words that you hang on the wall. We wanted to put them to the test in how we conduct interviews, evaluate performance, and make tough decisions.
 We have even woven our values into our skill development competencies. It was important to set those out right at the beginning.

  2. Working with department heads on competencies and rubrics for every function
    We wanted to ensure that whichever position we needed to fill had clear requirements for success in the role and reflected our values to best serve Policygenius’ needs. We were able to do that because of the first step. For example, one of our values is to ‘work the problem,’ which is one of the most highly-valued competencies at our company. We have made certain to clearly lay out what we mean by problem-solving, and our founders lead training modules every quarter to teach folks our approach.

    It is an iterative process working with department heads and managers each time a new role or function is added. All of our competencies have also been made publicly available on Policygenius’ intranet page. For example, if someone from our customer success team is interested in being a software engineer, they reference the rubric online.

  3. Hiring & Onboarding Clarity
    In thinking about Policygenius’ talent model, we wanted to make sure there was a clear and consistent thread from the moment a hiring manager makes a job requisition all the way through to an employee progressing into bigger roles over time. The goal of getting someone through the door can be too short-sighted and does not set up a new hire for success.

    Before a job post goes live on our career site, we work on crafting very clear job specifications that feed into our skill development competencies so new hires know exactly what success can look like in their roles. We also have developed a fairly robust set of onboarding modules at company, functional, and direct team levels to ensure our new hires have all of the information they need to hit the ground running after their first 90 days. Also, building a framework for people managers and setting expectations from the outset with new hires is the start of a long-term, trust-based relationship.


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Avoiding Early Mistakes

“While benchmarking is super helpful, I realized that there may be times that you will need to focus on your company’s individual needs and tailor to that.”

Stefan: Looking back on your past experience, is there anything you can think of that you would have done differently?

Cindy: The ongoing theme in what I would have done differently is definitely related to communication. Specifically:

  1. Keeping leaders in the loop
    I made the mistake of assuming that my co-founders knew where I was in my process for building out performance management. I didn’t intend on launching performance reviews immediately because my plan was to first map out our skill development rubrics so people knew what was expected of them before being evaluated. I fell short by not providing my co-founders with insight and context up front. Previewing and mapping out my strategy with clear steps would have helped to avoid misunderstandings.

  2. Understanding your organization’s own unique needs
    The people function was invested in very early on at Policygenius, and this is fairly uncommon. As a result, it was difficult for me to benchmark my department’s organizational needs against other organizations - even if we were similar in overall size and stage. While benchmarking is super helpful, I realized that there may be times that you will need to focus on your company’s individual needs and tailor to that. Others are not necessarily in the same position as you are, or going through the same stages, so what works for someone else may not work for you. We wanted to continue investing in the people function for scale, which required more people on my team in comparison to other companies at a similar funding stage.

  3. Invest in what you need, but test it out!
    As is the case with many fast-growing companies, we needed to maintain a balance of spending and scaling our processes efficiently. One area I knew I wanted to invest in was performance management software - and I managed to nab a great deal! At face value, the platform appeared to serve our needs, but I made the mistake of not thoroughly testing it out and vetting enough stakeholders. In the end, the platform was buggy and created more churn. Putting more effort in up front via thorough testing and preparation would have mitigated the risk of extra work and stress later on.

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Encouraging a Welcoming, Diverse & Inclusive Workplace

“If the focus is solely on meeting quotas or goals, then we are really missing the point.
”

Stefan: Moving towards diversity and inclusion, what does it mean to you, and how have you worked it in at Policygenius?

Cindy: I think of a safe environment where everyone feels free to be themselves, where differences are celebrated and welcomed. Differences can refer to gender, race, or sexual preference (to name a few examples), but at the same time it can also be differences in perspective, background, and life experiences. 



Sometimes, that is overlooked. For example, if a company is made up of people who all come from very similar educational backgrounds, or the same group of prior employees, then it could potentially lead to a significant blindspot. We need to think about the atmosphere that we are creating, how that may not be very welcoming for those who are different, and what we might be missing out on as a result.



What I love about Policygenius is we have diversity in perspective, background, personality, and even work style. For example, our Chief Design Officer used to be a professional dancer. Many of our software engineers don't come from traditional computer science backgrounds. I can be open about my fashion consulting business rather than feeling like I have to avoid the topic. We also do MBTI mapping across the organization and have a wide variety of personality preference represented.

We aim to build a supportive community where people are encouraged to be who they are and share their ideas which I think speaks to inclusivity. We also run employee engagement surveys and ask if employees feel that they can be their authentic selves at work. My team was so inspired to see how high the rating is on that front. This is not to say we are perfect by any stretch of the imagination. We are constantly looking for new ways to pull for input and encourage those who might be less apt to speak up.

This will forever be a priority for us. Being open to conversations and perspectives is what leads to innovation and creativity, and that fosters a diverse and inclusive workplace. If the focus is solely on meeting quotas or goals, then we are really missing the point.


Easing Employees Through the Process of Scaling

“ I believe that the absolute biggest barrier in successfully scaling a company is lack of communication.”

Stefan: Dialogue is definitely very important. Can you discuss any culture challenges you have faced in any of your experience?

Cindy: With scale, it goes back to open communication and dialogue. I would highlight the following:

  1. Make sure everyone understands their role within the company
    One of my biggest learnings in talking to hundreds of employees is that every single person should understand what their value is to the organization and how their role ties back to the mission of the company. If they don't have that direction from the outset, then it is highly likely that they lack a clear path and do not see where they fit in. That can be detrimental to employee engagement and fulfillment.

  2. Bring your team with you on that journey and avoid surprises
    The only good surprises in the workplace are food and swag. 
In line with this, as a company scales and workplace structure gets more and more complex, there is a greater need to provide ample insight as to why things are changing. The more we talk about change, the more comfortable our employees will be with the process rather than seeing it as something bad. We just need to reframe communications to show how change works in conjunction with a growing, evolving organization. Some people might react to change differently than others. I like to tell our people managers to prepare their employees so there is no element of surprise, which allows the employees to ease through the transition as much as possible. Ideally we’re leading the horses to the water versus dumping the water on the horses.

  3. Make sure your managers are trained to deal with different scenarios
    People managers have a tough job and they need to be equipped and nimble in handling sticky situations. I believe that the absolute biggest barrier in successfully scaling a company is lack of communication. For example, handling employee departures can be quite sensitive. Managers must be skilled in the art of proactive communication by creating a comfortable and open environment so that employees feel safe to speak up and ask questions. The key is not solving for discomfort - it’s going to be uncomfortable regardless. It is more about helping others find comfort in the discomfort.

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Steps to Build The People Function at Your Organization

Stefan: Do you have any advice for anyone building up the people function at their organization right now?

Cindy: I cannot emphasize enough the importance of clear communication and dialogue. I would specifically relate that to ensuring that the organization’s leaders understand your strategy, thinking about how best to support your function, and understanding the individual needs of the organization and its employees. To explain in more depth:

  1. Give context to your plan and be clear with leaders on your direction
    Leaders have very specific goals they want to achieve and know what their needs are. When you’re setting out to align and support them in those needs, keep them onboard and be clear how you are fulfilling their goals. We are the experts in the people space and what comes clearly to us does not come so clearly to others - our vision is on us to communicate.

  2. Think about scale and how best to support the process
    Don’t be afraid or discouraged from asking for resources - this is where benchmarking can come in handy! As an internal function, we have this inclination to do things ‘efficiently’ to save the company money - but we are doing ourselves a disservice and taking away valuable support if we do not ask for what we need. Remember, you can only do your best when you have the right tools in place. Be open to discussing that with leaders. Maybe even get one-off buy-in from a few stakeholders in advance!

  3. Get to know the needs of your employees
    There is no script for how to work with your employees or best support them. It varies company to company, employee to employee, human being to human being. Understand that the needs are very individualized. Meet with employees and really get to know them. Take part in that important dialogue.

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Thank you so much for speaking with us Cindy!

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