An Interview with Cassandra Pratt, SVP of People at Progyny, Inc.

Author :
Stephanie Sutsko

Stephanie: You’ve been at Progyny for almost 8 years. What was it about the company in the early days that enticed you to join?

Cassandra: I came to Progyny for the mission, really. I had been in finance, recruiting and tech prior to coming to Progyny and I knew after my last company that I wanted to be in healthcare. I didn’t know exactly what vertical, but really wanted to be in healthcare and I interviewed with a number of different companies, both large and small, and heard the mission of Progyny and it really resonated. And it’s one of those things where there’s a tangible outcome for doing good and I thought that was really exciting.

SS: Speaking about your own experience, what were the most challenging parts for you and the HR organization as Progyny went from being a high growth startup to post-IPO success?

CP: So when I started I think I was employee #50 – we are now almost 600 – and at IPO time, we were at 167.  With that there were a lot of changes. Early on for most roles there was one person doing  each role, or we had one person doing two or three roles.  There were multiple areas where we had a “single point of failure.”  And as we prepared for the IPO, we really needed to make sure that we had the right functions in place. I remember a conversation specifically around our finance team and an outside advisor telling us they needed to add 22 roles in order to be prepared for an IPO. And we were like “maybe we don’t need 22, maybe we can get away with five and cross-training and you know making sure that we have the knowledge set.” 

And so in preparing for the IPO, we had to make sure that we had the right organizational structure, the right knowledge and people in place to have that IPO move forward successfully. We had to help people understand what the changes would be going from a private company to a public company. So some very specific policies like Whistle Blowers and Code of Conduct, social media. Now that we’re public and we have a public investor base, what will you be able to say? What can’t you say? And I think that was really challenging for many employees because we’ve always been pretty transparent and there’s a change in your ability to be transparent and there’s also a change in timing of communications, especially when you have earnings and those sorts of things. It was really understanding what the differences between a private and public company are. 

Then there is the logistics, getting all of these things in place. It’s evident, even when you sell a company private to private, there is a lot of work that goes in pre-IPO, pre-sale, whatever it might be…long hours for 3-6 months of prepping everything. Having outside consultants, having outside law firms looking at  the key components of your business. It’s very exciting and it leads up to that really great day when you’re ringing the bell, but the amount of work that goes in before that point is  significant. And if you haven’t been through a sale or an IPO before, I think some people just think that there’s a switch you magically turn on once you bring in these consultants and it doesn’t work that way.


SS: One of the things that we see companies struggling with is deciding between finding the person who is right for the business today versus the one who will be right maybe two years or so from now. As someone who has specialized in talent acquisition in the past, how do you balance that conundrum?

CP: It is a balance. I would say you really want to look at a person’s appetite for growth; it’s the willingness to grow, the eagerness to do work, and having someone who has really strong basic skills – so whether that basic skill has to do with certain professional licenses, or educational background or even some early-skills or training that they received, so that they’ve built a good foundation to be able to grow. And then having programs in place and the ability to develop them. 

So what we did early on is we used outside training and development vendors to come in to do skill training, and added individualized leadership and management workshops as we’ve gotten bigger. We actually just hired our first Senior Director of Learning and Development and she’s building out a team now. We’re going to be doing much of that in-house – running mentorship programs and coaching programs, understanding that mentoring and coaching are quite different and  creating programs for both of those. If you don’t have the resources to offer it to all employees, really look at the people that will be able to use the knowledge and scale it across the organization. And so that doesn’t always mean senior leaders, it doesn’t always mean Director level and above – it means people in your organization that you believe have both direct and indirect influence to really make change and to help others grow and look at specific skill sets.

So let’s say we’re moving from a waterfall environment to an agile environment. And so we tapped an outside consultant and we also had some internal champions who are now going to be able to scale that across all of our engineering teams and use that knowledge internally to drive a solution mindset across the organization. There are different ways to scale it and I know I went off on a little bit of a tangent here, but you’re looking for those core eagerness and intelligence skill sets so that you, as an organization, can really grow and develop the people internally. And I think we’ve done a pretty good job at Progyny. We’ve been promoting people year-over-year – about 20% since 2017, I would say – so it’s a pretty significant number. We know if we want to keep being able to do that we have to do more programs to upskill our employees and use their knowledge and outside programs to do that.


SS: It’s been a hectic couple of years. How have you navigated the turmoil of the last three or so years knowing the emotional toll of global events that can have on your people?

CP: It’s interesting… last week we were actually talking about March of 2020 and how we all felt and what we thought COVID would be like in late March of 2020 and July and 2021…you know it was challenging because it was not like anything any of us had ever experienced before. We sort of dipped our foot in and closed the office for a week on March 13, 2020, not realizing that we’d then keep closing it and extending that for another 18 months. 

The mental toll and the change in work have been really interesting. I think that we saw a spike in mental health challenges across the board – both for our employees and also their dependents. How your spouse, your partner is dealing with mental health has a big impact on you. COVID had such a profound impact on children – school aged children and those who had just graduated from college. They really had a quick shift in their life. So by offering good mental health benefits, we had just enacted Spring Health in January of 2020, timing of the benefit could not have been better. Having that ability virtually to get on the phone with someone quickly and not waiting for three months to get on the phone with them – basically a 24-48 hour turnaround during COVID – was important. 

We shifted to weekly stand-ups with all of our management people within the company, regardless of where they were based, just to give updates on thoughts on office closure, how the company was working on certain topics. 

Then we had the murder of George Floyd and that added a whole other mental health and workplace dynamic into it and really understanding how to deal with that as a separate issue, but also now compounded with COVID. I think you had to be a people-first organization in order to address it appropriately because giving people grace and time to manage through these feelings, we gave people extra mental health time to sit and think about what they needed to think about and work through it. Giving people different ERG [employee resource group] resources, which until that time we hadn’t really had ERG, so adding ERG so people could talk about the issues they were dealing with. We added different training and wellness resources for groups to come together and talk about things. We have an onsite clinical psychiatrist, Dr. Georgia Witkin, and she did stress workshops for people. She ran small groups, all-company and one-on-one workshops to really help people work through all the different things that they were going through. 

I think we were one of those companies that said “COVID is mostly over. We want to all come back and be here five days a week just like we were pre-COVID.” And I think that’s also trying to get back to a sense of normalcy, but figuring out what’s right for us. Within a week we pivoted to a hybrid work environment – we still have a hybrid work environment and are in the office three days a week, remote on Mondays and Fridays – and understanding that we’re actually getting a lot of work done. People are able to balance their families and their interests in a different way. And meeting people where they are instead of fitting everyone into an old corporate mold, I do think is really important. It’s been an interesting shift and it helps you stay with the mission and helps us stay people first. We are focused on families and health as a company, as our mission and being true to that with our employees is also really important.


SS: That leads really nicely into my question around the future of work because that remains a fierce debate and figuring out the balance has been a challenge for companies of all shapes and sizes. So when you think you think about the structure you have in place, how are you setting Progyny up for success in 2024?

CP: It’s actually very timely because we came up with our Vision, Mission and Values for Progyny back in early 2017 when our former CEO David Schlanger exited and our current CEO Pete Anevski came on board, and we actually did a refresh in Q3/Q4 of 2023 as we went from a single product company to a multi product company focusing on all different aspects of women's health. 

With that, we tweaked some of our values, although I will say for the most part the core values have stayed the same, so integrity, passion, collaboration, innovation, and growth. We truly believe that those are core to who we are. We adjusted some of the wording to fit with our new vision and mission. 

We talk about them a lot. We actually do employee recognition around our values awards, highlighting people that live these awards on a regular basis within Progyny. We have a critical impact award every Town Hall to highlight a person or team that has really made a big impact on the business. And we have Top Learner, which goes back to your previous question, highlighting people that are trying to grow and learn. It’s really about wanting to recognize our employees so that their contributions to the organization are in the forefront of people’s minds. 

We also just launched what we call our cultural framework. So if you think of the values as what we want our employees to show up with every day, our cultural framework1 is what we want our company to do for our employees. There are six pillars to that, which we’re working with department by department on rolling out, so that throughout the course of every quarter of every year employees are having a curated experience that develops a sense of belonging and understanding at Progyny.   The pillars include elements like: “openness + action = compassion”, transparency, a solution mindset. They’re understanding that this is truly being able to master all the skills you need to continue in your growth, be it at Progyny or somewhere else in your career in the future, and making these commitments to employees to really help them to be able to be the best that they can be here.  Wanting to focus on a people first mentality where we have expectations for employees, but they should also have high expectations from Progyny and the company they work for.


SS: What are the people-related challenges that keep you up at night?

CP: I think a lot of it goes back to what we had talked about in the prior question about “how do you ensure you hire the right people for them to be successful in two years?”, right. Ensuring that we have the right skills as the company continues to scale and grow. The big shift that we made from a single product company focused on fertility to now being fertility, plus women’s health including preconception, pregnancy, postpartum, Progyny Plus, also menopause and midlife care and that is a big mindset shift. We’re not just focused on one core product and hopefully you have the right people in place. 

Sometimes you have to go externally to find them. You guys (Aequitas) helped us with a number of key roles this year (2023) and saw that there are some things we just hadn’t done at Progyny before and needed to find someone that could really bring it to fruition at the company. And I think that’s exciting too, because I have been here for eight years and oftentimes it takes that influx of new ideas, new people to shake things up again. There may be something we thought was working really well, but someone with a fresh set of eyes and experiences can say “you know what, if you just try this, you might get a much different result.” So it could be breaking big processes, it could be breaking and tweaking small processes and that goes to one of our values of innovation: we don’t always want to do things the same way healthcare has done it or the same way Progyny has done it for the last eight years. We want to keep being innovative and coming up with new ideas and we need the entire employee population to be able to do that. That includes long-tenured people down to the person who just started on Monday.


SS: Given that Progyny is a benefits organization, how has Progyny been innovative from an employee benefits perspective? Are there elements that you offer your employees you’re particularly proud of? You talked about Spring Health and I think that’s so amazingly timely and ahead of the curve, but what are some other examples?

CP: So this is clearly my wheelhouse - there are lots of things I’m very proud of. I will start by saying that one of the things where I was really lucky in coming to Progyny and finding leadership that was open to letting me try things and if it didn’t work, you pivot and try something else. So we’ll talk about the ones that worked instead of the ones that didn’t.  

I always think it’s really important to understand what your population needs – and every company is a little different…be it your mission, your culture, or just the demographics of your group and what they’re really looking for. Over the last few years we’ve launched a few things, including Spring Health, which is now integrated into our medical plan, but also available to those people who are not on our medical plan. They may have different care through a partner, spouse, or something else and we want to make sure it’s also available to them. We offer our benefits to our employees, so starting with the Progyny fertility benefit and all the pharmacy benefits – I have two wonderful little boys that were actually born from the Progyny benefit, so I can attest, it’s a great benefit. 

In Q1 of 2024 we are offering menopause and midlife benefits. We’re offering our own preconception, postpartum, and pregnancy benefits. About 18 months ago, we created a sales leave program based around data that allows our sales people who are on commission plans to actually have a structured program to be able to take time off and have their deals in their pipeline worked on and then be able to come back and see the fruits of that. It’s actually pretty exciting – it’s been used by a number of salespeople. It gives them peace of mind that if they need to go out for a month, two months, three months, or even four months – which is pretty unusual in the sales world – to have some kind of structured support and knowledge of what will happen while they’re on leave. 

We have a pregnancy loss leave program – we have had it now for a little over a year. I know California is now mandating it and hopefully other states will follow suit. We implemented a NICU leave this year to aid with employees who have lost some of that bonding time because the child has been in the NICU for a month, two months, three months and so there is a structure there that gives people back a little extra time – partially paid too, so it’s not like FMLA where you’re taking it unpaid. 

We are continuing to grow the number of employee resource groups that we have and our VP of People in DEI has put together a whole program for 2024 to really enhance the viability of the groups and activities that they’re doing and to engage employees from across the organization in different programs – onsite, virtual, etc. We have a lot of Lunch'n Learn sessions. We do “Meet your Employee” coffee chats a few times a year, so that if you are virtual and perhaps you’re really mostly working on the Member Services team, but you want to meet someone in BI or you want to meet someone on the marketing team that we can create those connections for you so that you get to know other areas of the organization and people as humans and not just as a job function or project that you’re working on. 

And then, as I mentioned, we hired a Senior Director of Learning & Development in September 2023 and she is launching a Leadership Journal this month, which will run on a monthly cadence. We’re also doing a whole buildout – we use WorkDay – on a learning and development platform for people to be able to upskill and really understand what’s needed to grow in their career. And there will also be a number of other learning and development programs that are coming throughout the course of 2024, but not quite ready to announce them yet. 


SS: That’s great! Speaking just of the function itself, there has undoubtedly been a sea of change in the way that the HR/People function is viewed, and has been elevated in earlier stage and high growth companies. How do you see the future of HR and the People function evolving?

CP: It’s an interesting question. I came from a slightly different background. I did not grow up in HR, so I came from finance and recruitment and then grew into HR, so my perception of HR is unique to me.  At Progyny, where we are hiring many people out of hospitals, clinics, carriers and more traditional healthcare environments, people often say “oh, I thought HR was compliance. And when you call me and say ‘hey, can I talk to you,’ I think I’m getting in trouble.” Somebody told me that on Monday and I’m like “no, I just want to talk and get to know you and understand what’s going on in your area, so I can learn from you and I can help you develop, help your team develop, etc.” And I think that the latter part is really core to what HR and the People function is and should continue to be, which is a business partner. 

We are here to enable the business to grow and scale. There are a lot of different ways to do that. One is that sometimes people just need an individual to talk through whatever they’re dealing with – good or bad. As a sounding board before you go talk to your manager or before you talk to your direct reports. As someone to help you figure out “where should I be directing my career? What opportunities do you see in the business?” That’s on the employee level and I also think it’s really important for the People function to understand the business well and to understand where the business wants to go so that whether it’s upskilling your current population or understanding what sorts of roles are out there in the marketplace and how will we need to find those people in the future. Generative AI is really interesting and how does that apply both to the People function and the business? Do you have people in the organization who have the proper understanding to really be able to use that appropriately in the future? That is where a lot of areas are going and I think it has some interesting applications in healthcare and also probably some really challenging applications in healthcare to make sure that we’re meeting compliance requirements and it’s used appropriately and you don’t lose the human touch. 

So I think HR has to know really firmly what the business goals are and understand how the business wants to move forward in the long term, not just by the end of 2024. What are those three to six year goals and then how do you help move your biggest asset, which is your people, forward towards that.


SS: Thank you so much!




Progyny’s Cultural Framework

  1. Fostering a Mission driven environment while nurturing Inclusion and Belonging - Monthly employee engagement events, ERG’s, awareness months, Day of Service, other volunteer/charity opportunities
  1. Empathy + Action = Compassion - Sensitivity to challenges large and small and being accommodating to our colleagues
  1. Fostering Openness and Approachability - CEO roundtable – Town halls – fireside chats – open door policy
  1. Driving Transparency - Sharing company performance, company goals, compensation framework, quantifying bonus, decision making, encouraging employee feedback (surveys and Q&A)
  1. Enabling a Solution Mentality - Inclusive leadership, senior leadership offsite, portfolio management team and process (soliciting ideas from senior leaders on vision, mission, goals, strategies, budgeting); Providing tools to enable people to be more solution oriented (L&D, Coaching, Mentorship program); Progyny annual ThinkOff, organizational Agile transformation (SCRUM)
  1. Fostering a Culture of Excellence - Enabling the Pursuit of Mastery; Offering opportunities for growth and continuous learning - Career pathing, Levels of Leadership and Korn Ferry framework; Recognizing and rewarding those who go the extra mile (CIA, Values Awards, Top Learner)

About Aequitas

Founded in 2014, Aequitas Partners is one of the preeminent talent partners for high-growth healthcare companies. We’re called Aequitas [eh.kwi.täs] because integrity is in our DNA and equity is foundational to how we work. With a diverse portfolio of offerings, we work with some of the most exciting companies in the industry, assembling teams tackling the biggest challenges facing healthcare, while supporting Founders, CEOs and Boards in all facets of human capital development.If you’re an executive seeking your new a new opportunity or a leader at a growing organization and looking to continue your momentum, please contact us.

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