Massimo Rubini Shares His Mission to Help Teachers and Students


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 interview Massimo Rubini and learn a little more about his career and learn some insights about education publishing and some of the unique challenges and opportunities in this space.

How do you see your industry changing in the next 3-5 years, and how do you see yourself creating that change?  

Over the next three to five years the Tech Ed industry will undergo tremendous changes. The pandemic has vaulted our industry ten years into the future.  Tech Ed is the new norm.  I see myself leading this transformation by continue to raise companies’ awareness for a true multi-media approach to delivering and supporting culturally adaptive pedagogy with robust attention to socio-emotional welfare.

How has the global pandemic impacted your business? 

Future needs were catapulted into clear and present mandates. The pandemic aggravated the depth of the learning challenges by adding a technology gap to the struggle of equity.

Can you share your personal approach to managing an effective balance between life and work? 

More than a balance, it’s an effort in successfully integrating work and life. It takes discipline and commitment. It’s important to set boundaries and schedules, and to stick to them, especially at times of the year when we tend to become reactive to market demands. Prioritizing activities that require the heavier lifts in the morning, reserving the latter part of the day for less cerebral tasks, and then unplug.

How do you manage your workflow effectively?

I like to use a reverse pyramid approach to time management. Whereas, the top of the day is dedicated by the more energy-requiring, conceptual tasks, the middle part of the day is usually dedicated to operational functions, and the latter part of the day, when we all tend to run on physical and emotional fumes is functional tasks.  The days I’m successful in sticking to this plan, are normally the days I accomplish a great deal.

What are some of the keys to effective decision-making?  

Information is key to effective decision-making.  Whenever possible, I like to make the process of making decisions as collaborative as possible.  Opinions and POV sharing (imagine a micro think-tank approach) is critical, as it allows for a multifaceted view of the issue, hence a more complete cost/benefit analysis. I then bring decisiveness to the process and deliver on the solution.

What criteria do you use to decide what to do yourself and what to delegate to others and how do you manage the stress of all the things you are not able to complete?  

Competitive advantage.  Let people do what they do best.

By prioritizing, managing time as efficiently as possible, and ultimately finding peace in the knowledge that I have left no stone unturned.

Can you share an example of a recent decision you made and the steps you took to reach your goal?  

I recently decided to read more for pleasure.  I signed up for a Book of the Month Club and scheduled time at night and on weekends for reading.

What qualities and skills do you look for when hiring new talent and how do you motivate your team for outstanding results? 

I look for passion, grit, coachability, courage, flexibility, interpersonal proclivities and authenticity.

My goal is always to inspire, more than to motivate. People who feel valued and appreciated tend to outperform those who are simply motivated by external factors.

How do you help create and sustain the culture of your organization?  

Culture is the alchemy that keeps a company performing at its best. Creating and promoting a culture that embodies the foundational values of the market in which the company operates is fundamental to avoid ambiguity. When facing challenging times, culture is what keeps everyone grounded. 

As a leader, I vest the role of ambassador and promote culture through consistent reinforcement in each and every interaction I have with both internal, and external stakeholders.

How do you handle difficult clients and customers?  

The most fruitful partnerships I’ve had with my customers and/or clients have always been predicated upon mutual respect, and a strong customer-centric attitude. Challenges are a necessary element for growth and expansion, they allow us to stretch beyond our comfort zone of performance and deliver the utmost value. 

My approach has always been to listen, validate and problem solve without compromising the core values of the company, even when (at times) it meant disagreeing with the customer or client.  A reminder of the premises of our partnership usually tend to realign even the most disgruntled partner.

Tell us about a skill you taught yourself.  How did you go about learning and what is your approach to successful training?  

English as a third language. I taught myself to speak English with methodical determination and resilience.

Psychological safety is foundation behind every successful training. A well-structured, meaningful and market-tailored training program is only as successful as the ability we all have as participants to stretch our comfort zone (no judgement) to allow for deep and meaningful learning.

Can you share an example of how you were able to transform a company’s sales?  

I once worked with a company who had a great product, very talented staff, but a disjointed organization. I first worked with the executive leadership to clearly qualify and quantify sales goals and objectives. Then reshaped the culture in order to redirect the internal perception non-sales people had of the process, from a product-dumping practice to a value-based partnership, as a necessary function to company success, then we helped redefine rules of engagement for the sales, and all of the supporting teams.  

This allowed for maximum efficiency, where sales teams were able to generate revenue and market share without being necessarily tied to account management activity.  The process was lengthy, but it eventually returned a 28% sales increase.

What does your typical day look like and how do you make it productive? 

I like to get an early start to my day. I have an espresso with my wife and we share our schedules for the day and then we are both off to work. In the morning, I tried to stick to my plan for the day and not get distracted by “incoming traffic” (greatest challenge ever), then wrap up and reconnect with my family at the dinner table. After dinner, I answer any late emails and then shut down my workday and read or watch a game.

How do you bring ideas to life?

I start with mindful contemplation followed by conceptualization, followed by think taking to vet for feasibility, then the blueprint for application is conceived, and then market tested to ensure viability.

What was the worst job you ever had and what did you learn from it? 

Once between jobs, I worked for a landscaper. I learned the importance of humility and that there is no shame in doing whatever job is necessary to provide for your family.

If you were to start again, what would you do differently? 

I don’t think I would do anything differently.  The journey that made me who I am today has been filled with valuable experiences (some more than others). Every success, and every failure has contributed and shaped my view of life and business. My ability to bring impactful contributions to my work is largely due to this blueprint.

What do you recommend everyone else do and what is one strategy that has helped you grow your business? 

Think before you speak. Listen to understand, not to interrupt.

Relationship and reference selling are, in my opinion, the two most effective ways to grow any business. For these strategies to work, it is critical to approach any sales from a partnership perspective and deliver the highest quality and consistency of services.

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