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“Run, grow, transform”, With Douglas Brown and Kate Cassino

Deploy a “run, grow, transform” strategy and mindset — Spend time thinking about how to optimize your current business (run), seek ways to expand your work with existing clients (grow) and extend into new markets or market segments (transform). All three are critical to continued success. As a part of my series about “Lessons From Inspirational Women […]

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Deploy a “run, grow, transform” strategy and mindset — Spend time thinking about how to optimize your current business (run), seek ways to expand your work with existing clients (grow) and extend into new markets or market segments (transform). All three are critical to continued success.


As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, 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. Her experience has ranged from restructuring multi-national business units, including acquisitions and divestitures, to launching new products and strategic planning. Prior to joining Hobsons, Kate held leadership roles at Prentice Hall and McGraw-Hill, and served as CEO of Dodge Data & Analytics.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I was very fortunate to receive a good education that prepared me for college and inspired me to pursue a double major in English and education. I wanted to get my teaching certification because I really wanted to give back in some way and contribute to the education field as a whole. After teaching in the New York City public school system to earn my accreditation I realized I could better serve the field outside the classroom. I moved into education publishing to help connect educators with the high-quality resources and support they need to be effective. That time at McGraw Hill launched me on a career in driving service-oriented solutions, and ultimately to Hobsons and back into the education field to help more students plan for and succeed in higher education and careers.

Can you share the most interesting story that happened to you since you began at your company?

As a mother, I know well the doubts high school juniors and seniors feel as they consider what comes next after graduation. This has been amplified during the pandemic as students and families across the nation face challenges balancing work, school and home life.

I’m reminded of a trip I took several years ago to one of our partners, Chicago Public Schools, the third largest school district in the U.S. Many students bear significant socio-economic hardships and 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 school counselors to support students. Our products which help students identify their strengths, search for best fit colleges or their post-secondary career path can be a lifeline.

With the pandemic, I have missed traveling to learn firsthand about our partner schools pain points and the support their students need. I’m looking forward to a time when I can do that again.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Earlier in my career, I was brought into a for-profit company to support a CEO who was also relatively new to the business. He had sold me on the company being in much better financial shape than it was and I wasn’t aware that I needed to help lead a whole turnaround. And of course, that was a little daunting. Ultimately, talking and thinking through the company’s important mission for helping students succeed and realizing the passion of our employees is what really kept me going and focused my work to envision and accelerate the path to improvement. What I learned was, 1) There are always going to be unknowns and surprises, no matter how much you think you know going into a situation, so you need to be ready to respond and shift to meet any challenge; 2) Knowing the importance of getting it right for the people you serve — the customers — will energize and inform your work; and, 3) You can turn anything around by setting a vision and then tapping the expertise and dedication of those around you to help you achieve it.

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? Can you share a story about that?

My husband Dan has been my perpetual cheerleader and voice of reason, helping me overcome any hesitation or doubt in myself. He has helped me push through difficult challenges — both professionally and personally — and reminds me to celebrate the achievements and victories along the way.

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.

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

“When opportunity presents itself, don’t be afraid to try something new.” I often reference this when I mentor women. From my first job right out of college, I have met challenges head on. Very early in my career, a department manager asked for a volunteer to learn about the “new” Internet. I raised my hand. I became the subject-matter expert in our department, taught myself HTML coding and started to create McGraw Hill’s first website. This not only gave me skills which differentiated me from my colleagues, I became essential to the organization. This new knowledge helped me ascend in my career path. So, raise your hand, when the opportunity presents itself, you never know where it may take you.

We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

Even before the pandemic, our partner schools and colleges were grappling with ever-increasing demands to help students succeed along their academic journey. This could mean identifying the right college or the right postsecondary career path. But it could also mean support with mental health issues, food insecurity or access to technology.

At Hobsons we understand these challenges and provide both K-12 and higher education institutions the technologies, services and community support to holistically prepare students.

As early as middle school, students are able to explore academic and career opportunities that align with their strengths and interests. We also provide students with resources to help cultivate social-emotional competencies that are foundational for success in school and in life. We help connect high school students to colleges and universities that fit their interests and needs. As students continue their journey into postsecondary education, we ensure they are able to connect with their support network across campus.

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

Anyone who works in education knows that it is not just a job, it’s a mission. At Hobsons, we all strive to enhance and enrich the educational journey of students. We are student champions and embrace our mission to empower and support them throughout every stage of their academic journey — no matter what their goals might be. To do so, we need to help them begin that process early. It starts in middle school, when students are introduced to this planning process that helps them think about who they are and who they want to become, and the steps that can get them to their goals.

In high school, students are faced with important decisions about their next steps in life. Do they want to enter the workforce or the 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.

Hobsons stands out in supporting all these steps and decisions along the way, supporting more than 15 million students across a lifetime of education decisions, comprehensively and holistically.

Are you working on any exciting new projects now? How do you think that will help people?

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

In K-12, we are extending schools’ ability to drive career exploration and help students track their progress toward postsecondary goals. Students will have the ability to experience work-based learning. This means students can search, take action and track local opportunities such as internships, externships, job shadows, career fairs and guest speakers. Students will also be able to easily access education and salary information for careers, clusters and pathways. With new reporting capabilities, we are deepening parent and guardian engagement by offering more visibility into the progress of their student’s postsecondary plan.

Because we serve millions of K-12 students, we are able to understand their needs, including in the college search process. In a national survey of Naviance students, we found that less than 10% of students have an easy time finding colleges’ and universities’ financial aid information. Yet, for the majority of high school seniors, the cost of education is the “most important” factor in their college search. Based on this understanding, we designed a capability to help get an institution’s financial aid information in front of students much earlier in the college-search process. It is this type of insight that we have continued to leverage as we design ways to connect students to colleges and universities that are best-fit for them.

To help colleges and universities address the needs of their students, we’ve focused on capabilities to keep students engaged, especially in remote learning situations. We’ve seen that students who responded to any nudge in Starfish had significantly better outcomes than students who didn’t, including passing 13% more of their courses and increasing their GPA by half a letter grade. With the shift to remote learning this past spring, Starfish sent over half a million LMS inactivity nudges to students to help keep them engaged and on track. We want to ensure students stay engaged so some enhancement areas include texting, inactivity notifications and remote scheduling.

We care about the students we serve and the teachers, counselors and advisors who support them. This means we need to continuously strive for improvements to be a partner in student success.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

There is a continued gender gap in the industry, even as there are ongoing efforts to increase diversity and improve opportunities. At the end of the day, having greater representation throughout the ranks makes for better team dynamics, bringing important perspectives and experiences in the development of technologies that will be in demand and make our lives better. The core issue of getting diverse engagement in the technology industry is really attracting women in particular to the courses and college majors that feed into the profession. It all goes back to education, early exposure to the options out there, and access to the courses and the training and experiences that will lead students to these rewarding careers.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

It may be hard for young women to see themselves in positions of leadership in tech because women are still in the minority and not in leadership roles to the degree they should be. That makes it more difficult for them to identify a mentor or role model that they can aspire to be like, or, or who can help them navigate a career path. To address this, we need more women to push and persist in the field and then raise their hand to be mentors and to champion their colleagues and encourage and advise young women to do the same.

What would you advise to another tech leader who initially went through years of successive growth but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

There is no glide path in business, even for those that have had a long period of growth and success. You always have to be on a path to innovate further and better serve your audiences. It always comes back to understanding where your market is going and addressing the new challenges. You need to disrupt yourself right before someone else does. Especially in this period of rapid change and disruption, you need to continuously poke holes in your model, and innovate and iterate to meet whatever demands are emerging.

Do you have any advice about how companies can create very high performing sales teams?

You need to have a disciplined and repeatable process that includes strong fundamentals, good sales hygiene, pipeline development, client feedback loops and responsiveness to the needs of the field. Beyond the sales process, your team must have passion for the product you’re selling and know how it fits and addresses the needs in your market. In addition, they need to be able to forge strong relationships with multiple people at a client school or business to ensure the deep connections that lead to long-term partnerships.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

In education, stakeholders want to know they are choosing a good partner, one who understands their work is centered on helping students achieve success. Education stakeholders want to know that we are not just selling a product. They are interested in a partner who offers thought leadership and community. We have found our thought leadership and community building to be effective ways to find and connect with new schools, districts, colleges and universities.

Through our large education community, Hobsons has had the privilege to be involved with many innovative practices and to glean lessons learned. We use this valuable experience to offer thought leadership through resources such as our College, Career, and Life Readiness Framework. More recently, we developed resources around student-centric recruitment and holistic student success for the higher education community.

Earlier this year when everyone had to shift to virtual learning, Hobsons immediately made a variety of resources available, including curriculum around college-, career- and life-readiness skills. We also hosted online events and discussions to help educators adjust to supporting students remotely.

At the end of the day, the schools and universities we serve want to know that we have their back.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

First, you have to know your client well and see yourself not as their vendor, but as their strategic partner. In that role you are helping your client succeed, working hand-in-hand to problem solve and work toward their goals. You should see their success as driving your success. Second, you need to go all-in on supporting those clients and providing an enhanced service approach. Service goes beyond simply ensuring the tools are working and getting customers to renew. We have a Customer Experience team to provide ongoing support and help them get the full benefit of what we provide. Lastly, and related to customer service but taking a step further, you should have regular client check ups to make sure the relationship is evolving and responding as their needs require. By continuing to understand their pain points and new issues that might arise, you strengthen client trust and satisfaction and anticipate future product development opportunities.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

Here are the top five ways to build a successful tech company:

  1. Build a winning leadership team — You need a mix of industry experts and functional leaders that also reflects the diversity of your field, including gender, ethnicity and across the age spectrum to ensure you are looking at issue from multiple perspectives.
  2. Foster a culture of innovation — Make sure to encourage employees to “think outside the box” and solve for problems in different ways. You always need to be disrupting yourselves or you will be disrupted otherwise.
  3. Drive constructive accountability — Everyone needs to do their part if you want to win, so you need to set an expectation that everyone is accountable. But be clear about your accountability measures and incentivize employees in the right ways.
  4. Deploy a “run, grow, transform” strategy and mindset — Spend time thinking about how to optimize your current business (run), seek ways to expand your work with existing clients (grow) and extend into new markets or market segments (transform). All three are critical to continued success.
  5. Strengthen the core — A business needs to have a strong foundation of people, processes and objectives in order to be successful. The fundamentals are not glamorous, but you can’t build for the future on a weak foundation.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I truly believe that making a first-class education available to all is the most effective way to scale up success and to solve big world problems. We work at this every day in helping students understand their options and the path to achieving their academic and career goals. But right now, I’d also like to help inspire a movement to help students learn to think critically and to debate issues and solutions constructively. If we can help the next generation develop skills of sound public discourse and to find ways to respect various viewpoints and compromise for the greater good, we will all have a better future.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Melinda Gates. After a successful career at Microsoft, Melinda has used her power and influence to help women and families across the globe through the Bill & Melinda Gates Foundation’s many programs — women’s economic empowerment, vaccines, family planning, global libraries and gender equality, to name a few. Here in the United States, she has concentrated efforts on education — which is of course near and dear to me. The Foundation supports K-12 students, teachers and principals with instructional materials, assessment tools and helps principals empower leadership in all areas of the schools. And most importantly they are helping low-income communities and students of color to gain knowledge to succeed after graduation. Our work at Hobsons aligns with her work. I think we’d have a lot to talk about.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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