“Take The Time To Get To Know Everyone You Work With On A Personal Level” 5 Leadership Lessons With Kate Cassino

“Take the time to get to know everyone you work with on a personal level. Plan monthly team dinners, have social outings to celebrate a sales win or product launch. Doing this goes a long way in establishing trusting relationship — and is just more fun!”
I had the pleasure of interviewing Kate Cassino, CEO of Hobsons, Inc, a leading educational technology company that develops solutions for educators, administrators, students and families. Kate joined Hobsons in 2016 as Chief Operating Officer and was named CEO in 2017. She has held leadership roles at Prentice Hall and McGraw-Hill, and before joining Hobsons served as CEO of Dodge Data & Analytics, where she led its growth and digital transformation focusing on sales execution, product delivery, and operational improvements.

Thank you so much for doing this with us! What is your “backstory”?

I am a proud, native New Yorker from a fairly large Italian and Irish family, the second oldest of five children. My parents, my three sisters, and younger brother moved to the New Jersey suburbs when I was 10. I made my way back to New York City seven years later, attending Barnard College of Columbia University as an English and Education major. I earned my New York City teaching certification in the process. As part of that requirement, I taught American literature to middle schoolers at Martin Luther King School. I believe my time teaching in NYC public schools provided me with a great perspective on how I could use my own education and experience to help students.

I was recruited out of Barnard by Prentice Hall, an educational publisher, as an editorial assistant working on engineering textbooks. From there I moved to McGraw Hill, where I spent the next 18 years in various leadership roles. I helped launch McGraw-Hill.com, worked on the print to digital strategies for brands such as BusinessWeek, Platts and JD Power & Associates and was named CEO of McGraw Hill Construction in 2014. In 2015, I led the sale of that business to a private equity firm. I joined Hobsons in December of 2016 and was appointed CEO last April. I couldn’t be happier to be part of such a tremendous organization.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

Over the last year and a half, I have had the terrific opportunity to visit many of our customers. In doing these trips, I better appreciate how vastly different every student’s educational journey is. Through my interactions with educators, ranging from leaders of large school districts to individual counselors, I have a deeper understanding of the challenges students face.

This was clear when I visited one of our customers, Chicago Public Schools, the third largest school district in the U.S. Many students bear significant socio-economic hardships. Some come from non-English speaking homes. Others are from families where no one has ever attended college. For these students, the idea of going to college and graduating with a degree often does not seem within reach. In many cases, there are not enough guidance counselors to support students. Our Naviance product — which helps students identify their strengths, search for best fit colleges and provides the workflow tools to apply — can be a lifeline to help them get into college and change their future. It was truly amazing to see first-hand the power of our products in making such a transformative difference in the lives of these students.

What do you think makes your company stand out? Can you share a story?

What makes our company stand out is twofold: the commitment and devotion of our people and the innovation and creativity of our products.

Working in this field is not just a job — our employees devote their professional lives to enhancing and enriching the educational journey of students. We are student champions. It’s our mission to support them throughout every stage of their student journey — no matter what their goals might be. We provide tools that help students realize their potential to achieve lifelong success.

In middle school, students begin to make decisions about who they are and who they want to become.

In high school, students are faced with important decisions about their next steps in life. Do they want to enter the workforce or military? Is college the right option for them? If it is, which college should they attend? Naviance by Hobsons helps students identify their strengths and interests and link their passions to a pathway for success.

If a student decides to choose the path of a higher education institution, they are faced with many options. How do they find their best-fit school when there are over 4,000 in the U.S. to choose from? We have a solution for that. Intersect by Hobsons helps students discover, explore, and connect with institutions that are both a good match for students based on what they are looking for; location, size, academic goals as well as a good fit for the institution. We call this match and fit, ensuring students and institutions find and connect with each other to improve student outcomes.

Once enrolled in college, students need help navigating through the many challenges they may face so that they will graduate on time. How can they find help when they need it? How will the right help find them? We can help with that, too. Starfish by Hobsons empowers faculty, advisers and students within high-education institutions to be informed, connected, and proactive with each other to ensure students stay on track to graduate.

Across our product portfolio, Hobsons is proud to support 15 million students across a lifetime of education decisions.

Are you working on any new or exciting projects now?

Yes — we are working on many new and exciting projects!

At the corporate level, Hobsons is gearing up to host the Hobsons Summer Institute (HSI), a conference that is the first of its kind. HSI 2018 is the premier event that brings together over 1000 middle school, high school and higher education leaders from across the country. With over 80 best practice sessions offered, HSI will create a community of practice in support of student success, across their educational journey.

This summer we are launching Naviance Insights, our latest analytics tool that allows our school and district clients to build their college readiness strategies based on proven results. Insights also simplifies state and district reporting and unlocks insights to improve college outcomes.

Our new Starfish mobile student experience will be live in July. The mobile experience will allow today’s students to find and make appointments with counselors, advisors, and other resources to get the help they need.

In our Intersect product, we will be delivering the most advanced college search on the market. We are rebuilding our beloved Supermatch college search to include more data and options than ever to help every student find the right college for them based on their many interests.

What advice would you give to other CEOs or founders to help their employees to thrive?

I would advise any CEO or senior manager to hire the best leadership team you can — as the saying goes, you’re only as good as your weakest link. Empower them to do their jobs, remove obstacles, give them latitude to make the right decisions. I like to think of myself as the maestro of an orchestra leading a pit of talented musicians. CEO’s should give guidance, make suggestions, and with input from their leadership team set goals and hold the entire organization accountable. I believe if you let people shine in their own way and everyone does their job well, you will make beautiful music in the process.

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

The person I am most grateful towards is my husband Dan. He believes in me even when I doubt myself. He is my perpetual cheerleader and voice of reason.

Another person who has shaped my life immeasurably is my father Anthony Cassino. He was also born in Brooklyn and had very little money growing up. With grit and the strongest work ethic of anyone I’ve ever known, he worked his way up the ladder at Wall Street broker-dealers and eventually ran his own money management firm. As a father of four daughters, my dad taught us to be tenacious, independent, ambitious and strong. He wanted all of us to have careers and urged us to aim high and try to have it all as mothers and as executives. I’m proud to say we haven’t let him down.

How have you used your success to bring goodness to the world?

I am a big believer in using professional success to have a positive impact beyond the company’s results. Every day, the employees of Hobsons demonstrate our firm-wide commitment to improving the communities we serve. One of the things I introduced was including a service project each quarter as part of our employee Town Halls. We have built computers to donate to schools, assembled food back-packs for students in need, and filled totes with books and blankets to give to children in homeless shelters. In the last year, Hobsons has donated over $150,000 to various charities including PLAN Project Peru, AASA Scholarships, Hurricane Harvey relief efforts, and Broward County relief efforts after Hurricane Irma. We always tie our volunteering to our mission to support students no matter what challenges they are facing.

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why.

1. Be sure to celebrate every success along the way. The next challenge will be awaiting you when you are finished.

2. There is no such thing as work/life balance. You have to give what is needed to each situation, according to the circumstances at the time. Technology has fostered a 24/7 environment where we are all expected to be “on.” By the same token, technology also allows us the flexibility to work when and where we want, so you take the good with the bad.

3. Surround yourself with people who will give you honest and direct feedback. The people who work for you should have opinions and add to the discussion.

4. Take the time to get to know everyone you work with on a personal level. Plan monthly team dinners, have social outings to celebrate a sales win or product launch. Doing this goes a long way in establishing trusting relationship — and is just more fun!

5. Schedule time off every quarter, even if for only a long weekend. Being a CEO is a stressful job. Like I said earlier you’re “on” all the time. You will be a more effective leader if you take time to step away and recharge.

Can you please give us your favorite “Life Lesson Quote”?

To those who are given much, much is expected.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this :-)

I would love to meet Oprah! She is a successful business person — the first black female billionaire in world history — and has overcome so many societal barriers and personal obstacles to be a force for change and goodness in the world. Her focus on education — through efforts like the Oprah Winfrey Leadership Academy for Girls — is of course near and dear to me. Her philanthropic efforts are legendary, and she fights for causes she believes in, no matter what. I think I could learn so much from her.

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