A Conversation With Massimo Rubini, VP of Schoolwide

Massimo Rubini is Vice President of Sales and Marketing at Schoolwide, Inc., a leading education management company based in Huntington Station, New York, with a mission to effect positive and lasting change in literacy teaching and learning, and improve students’ reading, writing, and learning by increasing the tools teachers can use to teach effectively.

Massimo Rubini attended Mercy College, where he obtained a Bachelor’s Degree in International Business and Finance and received a Masters in Education from the University of Bridgeport.

After seven years of teaching, including five years as an adjunct professor at Westchester Community College, Massimo Rubini joined Pearson, a global learning company focusing on Virtual Learning, English Language Learning, Higher Education, Workforce Skills, and Assessment & Qualifications.

At Pearson, Rubini rose to become Acquisitions Editor where he was responsible for conceiving, commissioning and contracting new titles, as well as revising existing titles based on market analysis and assessed publishing needs. Rubini was responsible for successful management of a $12M publishing revenue stream and helped the company maximize revenues and profitability through strategic P&L management.

In 2014, Rubini left Pearson to join Houghton Mifflin Harcourt as Director of Sales for the Northeast.  In 2019, Rubini was promoted to Vice President of Sales & Regional Manager where he was responsible for designing and implementing the Sales team’s strategic plans for HMH’s product verticals (Core, Supplemental, Intervention, Services) including market penetration, market expansion, and retention of current clients.  Rubini led the success of a 20-person Sales team through the creation of a $80M pipeline, and $42M Sales Revenue.

Massimo Rubini joined Schoolwide, Inc. in 2021, and is looking forward to helping the company exceed revenue targets and achieve consistent market growth and operational excellence. With expertise in quota development, pipeline management, gap strategy development, forecasting, sales resource planning, and budgeting to meet company financial targets, Rubini is very excited to pursue this new professional opportunity and help Schoolwide further its mission.

We recently had the opportunity to speak with Massimo Rubini and learn a little more about his personal and professional journey.

How did you get started? 

After acquiring my Master’s in education, I taught primary grades for two years, then made the decision to bring my teaching to the world of adult ESL education. The reason to become a teacher was to support a positive change in education, and, at that point, I couldn’t think of a better place than the world of English as a Second Language to make the most impact. 

Along the way, the college for which I taught offered me the chance to add business credit courses to my teaching portfolio.  After all, I had a Bachelors Degree in International Business and Finance, so why not taking advantage of this very promising opportunity.  

After seven years of successfully instructing thousands of students, I finally gave in to Pearson recruiting efforts and joined, first their Educational Consultant team and, two years later, the Editorial Acquisition Team. 

Consulting on educational resources was my window into the true reality of primary and secondary education.  My early years in the classroom had not prepared me for the challenges that plagued inner city education, and how drastically different, it was from suburban, and rural education.  So, this was yet another opportunity to stretch my contribution to the betterment of young learners’ education.  

As the new Acquisition Editor my challenges were to assess market needs and wants, anticipate educational trends, monitor funding streams and new potential allocations, and funnel it all under a pedagogical offering that would boost the company profits, while addressing educational gaps.  

This position allowed me to delve deeper into the needs and struggles of classroom teachers and administrators, and provide solutions that would help address equity, and achievement gaps.  

Long before the concept of °Culturally Responsive° instructional materials hit the top three billboard of educational reforms, I was keenly aware of the importance of recognizing one’s individual cultural values and their critical importance of incorporating those values into educational materials, and practices.  

I was able to conceive and produce over four new series, and contributed to the revision of many more.  After a long and fruitful seven years with Pearson, Houghton Mifflin Harcourt became my new professional home.  In the six years that followed I would successfully manage sales for their curricula, supplemental, intervention, and assessment lines, first as a Field Sales Manager, then a Director of Sales, and eventually as Vice President for the Northeast Region.  Finally, in late 2020, I left my post at HMH and focused on consultative and advisory work, particularly for companies looking to expand their presence into the K-12 US Educational Market.

What inspired you to get involved with management consulting? 

My inspiration for getting involved in educational sales and consulting came early in my career as a teacher, when I realized the pervasive lack of resources available to students in the primary grades. I realized, at that point, that I could be a greater multiplying force by bringing valuable resources to these students.

How did you get your first client / customer? 

Growing up in a busy, Italian, urban setting, playing street soccer was a daily activity for any kid in my neighborhood. We played in an abandoned lot that had a tiered retaining lot and often balls would get lost, usually ending our game, unless of course we could scrounge up the money to run to the local corner store to buy a new ball. One day I climbed to the top of the terrace and retrieved about a dozen soccer balls. I sold all of them to local kids for half the price of a new ball and with the proceeds I opened up my very first business, a used soccer ball stand.

What is one marketing strategy (other than referrals) that you’re using that works really well to generate new business?  

Relationship selling.  Educational sales, in many ways is a market where great attention is placed upon key districts (aka light-house districts). To penetrate such districts and establish a solid footprint via an efficacy study/implementation pilot, or a managed focus group allows the company to create a user-base to be leveraged in its expansion strategies.

What is the toughest decision you’ve had to make in the last few months? 

The most difficult decision I’ve recently had to make is to select which up and coming company to partner with and drive their expansion. This is a new and growing field and there are many promising entities and start-ups that are poised to provide exactly what the market needs at this moment.

What is the biggest challenge you are facing right now? 

To design and deliver an instructional ecosystem that is both culturally responsive and pedagogically viable. Unfinished and/or interrupted education are plaguing young students now more than ever. Technology infrastructure, access, and a sustainable implementation strategy will determine the rate of recovery for our current generation of students.

What do you think it is that makes you successful?   

Empathy with a knack for problem solving and a strong desire to bring the best out of people.

What has been your most satisfying moment in business?

I think the most satisfying moment in business is to watch my strategies and coaching transform underachieving contributors into most valuable players.

What is the one book that you recommend everyone should read and why? 


Make Your Bed: Little Things That Can Change Your Life… And Maybe the World by Admiral William H. McRaven.  It is an easy read, and it speaks to the importance of resiliency, and grit in life and business.  These are the qualities that are truly foundational to success and a well-balanced life.

Published June 16th, 2021