Cassandra Roth of Segal Benz: 5 Essential Elements for Creating a Successful Employee Onboarding Experience

An Interview With Rachel Kline

Authority Magazine
Authority Magazine
12 min readJul 24, 2023


Plan ahead. Getting in the weeds is critical to knowing what you need and who is vital to the onboarding process. Anyone who has conducted a manual onboarding process, or one without a clear leader, knows that having a new hire show up without anyone preparing for it happens too often. And that’s not a great experience. It’s the equivalent to being invited to someone’s house for dinner, taking time to pick up flowers or a bottle of wine and when you knock on the door, the host greets you in their sweatpants and says, “Oops, was that today?” Proper planning can help avoid an awkward experience that is shown to lower retention.

Onboarding is a crucial but often overlooked step in the employee lifecycle. A successful onboarding process will make the new hire feel part of the team, provide further clarity around the role and responsibilities, and get them up to speed and performing fast. In this series, we are talking to prominent HR and business leaders about how they seek to create exemplary onboarding experiences. As a part of this series, we had the pleasure of interviewing Cassandra Roth.

Cassandra Roth, Senior Consultant at Segal Benz, the benefit communications division of Segal, finds purpose and passion in engaging with people. The companies she supports benefit from her deep desire to understand people’s needs, use of primary research and behavioral economic techniques to drive results, and enthusiasm to deliver positive, engaging materials for all stakeholders.

Cassandra is an award-winning innovator who uses new technologies, including augmented reality, omnichannel automated workflows and AI, for employee engagement and in developing creative, results-driven health and wellness communications campaigns. She has worked with companies like Amazon, Comcast, Con Edison, CVS Health, Sanofi, Lenovo and NVIDIA.

Cassandra is the Chair and Co-founder of Pride@Segal, an LGBTQIA+ business resource group dedicated to creating inclusive work environments. She holds a Bachelor of Arts degree in English with a concentration in Economics from East Stroudsburg University and a Master of Science degree in Public Relations and Corporate Communications from New York University.

Thank you so much for your time! I know that you are a very busy person. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

It’s an interesting story. I studied English and Economics in college. At the time, the Great Recession was looming over recent college graduates. Finding an internship or a foot in the door was difficult. So, without any viable career opportunities, I took a job working as a barista for a couple of months before accepting a spot in a political science MA program and beginning a graduate assistantship. Almost immediately, I realized that a career in politics wasn’t a path I wanted to pursue. I left that program and assistantship with no plan, but it was the right move.

I ended up taking a job in PR and marketing at a small boutique agency. And I learned a lot that I continue to use helping companies today. I then started freelancing. I was lucky to collaborate with some great companies on interesting projects, but I craved more stability. So I enrolled in grad school once again. This time, I knew what I wanted to study. I earned a Master’s degree from NYU in PR and corporate communications. During year two, I looked for an internship. I had no idea what consulting was, but a professor strongly recommended I look into it as a career path. I applied for an internship with a consulting firm and was shocked when I found out it was a paid internship, something that was unheard of during the Great Recession. But what surprised me most was that I wasn’t just interested in the money; I wanted to learn.

And consulting continues to offer an opportunity to continuously learn, which I love. Solving problems is my favorite part of the job. I enjoy working with a variety of interesting organizations. Knowing that my contributions help improve the work and the lives of their people is so rewarding. I feel privileged to work at an organization that is purpose-driven and makes a meaningful impact on the health and well-being of many.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Ha — I’m still making mistakes! One of my mantras is, “Don’t look down or you’ll go there.” It reminds me that while I can take lessons learned and apply them to new opportunities, I can’t dwell on what has gone wrong. For me to be at my best, my focus always must be on what’s next.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?

During my first consulting job, I connected with a senior colleague. We bonded over being foodies, having similar values and sharing the same sense of humor. Over the years, they have given me such great advice about my career. Their honesty and transparency about pay, promotions, and opportunities has helped me climb the ladder and I’m so grateful to have them as a mentor and friend. They inspire me to do the same for others who seek guidance in growing their careers.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Learn to listen. Opportunity sometimes knocks very softly.” — H. Jackson Brown, Jr.

Listening is such an underrated quality. It’s easy to present information and share your own experiences or expertise, but having the discipline to edit yourself and hear what others are saying is critical in both your personal and professional life. When you listen, there are so many opportunities to give people what they want or need — because they’ll tell you.

Thinking back on your own career, what would you tell your younger self?

Fear less, learn more and be proactive in asking for what you want and need.

Let’s now move to the central part of our interview. What does the onboarding process consist of at your organization?

I absolutely love helping companies with their onboarding process. The best onboarding experiences are the ones that start early, open doors and develop strong bonds with your people before day one and beyond week one. A strong onboarding experience lasts at least a year and creates meaningful connections across your organization. In building these experiences, organizations see higher employee engagement, reduced turnover and increased job satisfaction, among other benefits.

How have your onboarding practices evolved over time and why?

I like to think of onboarding as the welcome party for a new hire. Just as fashion, food and drinks go in and out of style, your onboarding approach needs regular updating to match the moment and the mood. If your organization is competing for highly desirable talent, you truly need to roll out the red carpet with your onboarding approach. When someone joins your organization, they should feel valued, appreciated and — of course — warmly welcomed to your team.

The best thing about onboarding experiences today is that they can be both personal and scalable. Technology allows us to create bespoke experiences for each new person while keeping the time and energy investment as low as possible for all parties involved. Onboarding can be a big brawl between internal stakeholders: HR, people managers, IT, facilities, etc. But it should be a dance — choreographed and rehearsed, then performed time after time.

Could you share a successful onboarding story and what made it successful?

Onboarding is most successful when all stakeholders know their role and feel valued. An example of this is coordinating onboarding during the early pandemic days. While many organizations had experience with in-person orientations on day one, welcoming people virtually was a new challenge. We started strategically reviewing our previous in-person process: Who needed to be involved? What did the new hire need to hit the ground running right away? How could all parties come together and make sure that new hires felt included and weren’t simply alone at home, staring at their screens and waiting to interact with their new colleagues?

We then developed an onboarding experience that would welcome a new hire; set expectations for the first day, first week, and following months. Plus, we made sure all stakeholders knew their role in making onboarding a success. This involved thinking through things like IT and laptop delivery, home office supplies/equipment and furniture shipping. And it also involved connecting the new hire with their manager, establishing how new hires would access benefits information and ways to help them better digest it. We then created onboarding milestones that ensured new hires were able to meet colleagues and make emotional connections. The details make such a difference — for example, providing new hires with a list of who they might work with the most and making sure those people reserve time on the new hire’s calendar to say hello. And it’s about checking in on day one to make sure a new hire has a functioning laptop and knows where to go if they have any tech questions. Without a detailed roadmap of who’s responsible for what and when, important things can slip through the cracks and leave a new hire feeling unwanted.

Keep in mind that creating this structure doesn’t have to be a time-consuming endeavor. It can be a one-time exercise that is repeatable and scalable, so each time your organization hires someone new there is less work for all.

Based on your experience and success, what are your top five tips for a successful onboarding process?

1. Plan ahead. Getting in the weeds is critical to knowing what you need and who is vital to the onboarding process. Anyone who has conducted a manual onboarding process, or one without a clear leader, knows that having a new hire show up without anyone preparing for it happens too often. And that’s not a great experience. It’s the equivalent to being invited to someone’s house for dinner, taking time to pick up flowers or a bottle of wine and when you knock on the door, the host greets you in their sweatpants and says, “Oops, was that today?” Proper planning can help avoid an awkward experience that is shown to lower retention.

2. Put a system in place. This can be as simple as a checklist or as sophisticated as an integrated automation or AI option. What’s most important is having a way to track progress against your plan for each new hire. I recommend that organizations use technology to streamline these efforts and make it easy to repeat. There are many great automated systems that deliver a white glove, personalized experience for all parties, while tracking accountability and ensuring each new hire is treated equally.

3. Measure, measure, measure. Before you launch any new onboarding process, collect available data on what’s happening now. Take a good look at your current onboarding stats: Is there a certain point in the process when turnover is highest? Perhaps it’s on day three, week four or seven months down the line. By identifying when you run into retention issues, you can start testing ways to increase engagement and improve the process around those milestones. It’s also a best practice to measure how your new hire is feeling throughout the experience. Ask them how they feel before the start, take their temperature on how the first week went, check in with them periodically on what’s working and what’s not. Doing this throughout the first year will help not only your new hires, but it will also benefit your organization.

4. Be flexible. If something isn’t working, change it. It’s easy to say, “Well, we built this and that’s the way it is now,” but we always have the ability to improve a process and its outcomes. Take advantage of this opportunity to improve and grow by making regular updates to your onboarding process.

5. Get physical. Employing a digital solution doesn’t mean you should forgo tactile elements. Add some personality to your onboarding process with welcome gifts like company swag — it could be a logo-branded shirt, mug, or something like a Yeti or Stanley cup. Snacks and other tokens of appreciation can get new hires feeling excited and appreciated before they start their new role. The little things make a big impact, showing your people that you care about and value them.

Can you share 3 or 4 of the most common mistakes you have seen businesses make during the onboarding process? What should one keep in mind to avoid that?

The most common mistake I see is diffusion of responsibility. When it’s not clear who’s in charge of the onboarding process, stakeholders tend to become passive bystanders because everyone assumes someone else will handle it. Setting clear expectations by defining roles early in the process can counteract this issue.

Another common mistake I see is indifference to the new hire’s experience. A new job is a life event, which has an impact on well-being. Even those who are really excited to start their new role can be experiencing a lot of stress. There are little things organizations can do to help new hires manage this transition. One super easy and often-forgotten detail to share before a new hire joins is their pay schedule. Letting new hires know when they’ll receive their first paycheck and how much it will be, can help reduce stress and manage expectations.

Additionally, organizations often stop the onboarding process too soon. Giving a new hire their laptop, credentials, and benefits information is not enough to get them acclimated to your culture. It’s important to facilitate meeting colleagues, senior leaders, and people across the organization. These meetings don’t have to be long or in person, but they need to happen to create connection and make sure your new hire has plenty of ways to interact with others and get comfortable asking questions.

How does or how would your approach to onboarding remote hires differ from those who will work onsite?

At this point, any organization that doesn’t have at least a virtual onboarding component is behind. Even if you have an in-person culture or role that requires being onsite, there’s still an expectation that information be accessible anytime, anywhere. In terms of how remote versus onsite onboarding differ, they really should be the same. The components you need to successfully welcome a new hire don’t change. Those components can be broadly grouped as: tools, technology and connections. New hires need the equipment necessary for the job, a way to access information and the support of their manager and colleagues to thrive.

How do you measure the success of your onboarding program?

Measurement is key in demonstrating your successes and tweaking your processes. First, it’s important to have a baseline of what’s happening at your organization now. Even if you don’t have solid, verified data, conducting focus groups with your people and recent new hires can provide rich information about what’s working and what’s not. Then, measure outcomes over time. I recommend developing a multiyear timeline for gathering data. You’ll be able to collect it along the way, and consider this an opportunity for a longitudinal study of how your organization greets new hires. At a minimum, measure year one and strive for year five.

Which tools do you use or recommend for your onboarding?

The best tool is the one that you actually use properly. There are so many onboarding tools on the market, but if you don’t put in the work to set them up and create a process for ongoing updates and maintenance, it doesn’t matter how fancy it is — it won’t work. If your team has the capacity to meet for strategy and planning sessions, decide on a path forward and commit to accountability for each stakeholder, then a tool that integrates with your existing infrastructure is your best bet. These onboarding tools will connect with your human resources information systems (HRIS) or human capital management (HCM) systems. And if you’re a small organization, that doesn’t mean you need to shy away from a tool like this. In fact, it may be easier for your organization to adopt as there are fewer players who want a say in how things work.

We are very blessed to have some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world whom you would love to have a private lunch with, and why? He or she might just see this.

Such a fun question! Jenna Lyons. I just love her, and although I’ve never watched the Real Housewives, I heard she will be joining the New York cast and I plan to tune in.

How can our readers further follow your work?

I frequently share insights on our Segal Benz blog: And I recently presented during a Silicon Valley Employers Forum meeting and for a webinar with The Conference Board. You can also follow me on LinkedIn at

Thank you so much for sharing these important insights. We wish you continued success and good health!



Authority Magazine
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