Ross Romano: A Leadership Coach Guiding the Education Industry

Ross Romano

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Business leadership has undergone a radical transformation in recent years. The pandemic, the rise of remote work, and the entry of GenZ into the workforce played a significant role in this shift. Today, employees expect and demand freedom in their work lives. As businesses face new challenges, the responsibility of retaining talent and fostering a positive work environment falls on the shoulders of today’s leaders. With the introduction of modern-day leadership coaches, the future of business leadership appears bright. Ross Romano (Founder and CEO of September Strategies) is one of those strategic coaches whose creative solutions are driving a leadership dialogue and changing the face of the education industry.

Leadership Insights Can Take You Far ― and Fast

“The difference between a great product and a great business is a great story.” As Romano explains this, he makes clear that storytelling is a critical leadership function. After having partnered with nearly 100 companies to date, he concludes that a great story stems from authenticity, values, and meeting customer needs. “Sometimes the ‘best’ products don’t win because they fail on those points; they fail to make people care,” he says.

Over the years, Romano analyzed the challenges faced by leaders and observed the differences between those who thrived or struggled. Leaders who foster a collaborative mindset with respective teams and industries, rather than focusing on competition for example, tend to go far ― and go far fast. Additionally, developing empathetic leadership traits is a key to attracting and cultivating talent.

“Leveling Up” Education Leaders

“We help organizations and high-performing leaders in the K-12 education industry communicate their vision and make strategic decisions that lead to long-term success.” Established in 2022 as a consulting and advisory firm, September Strategies thrives with this mission. The company is headquartered in the Washington, DC metro but works globally to help organizations with strategic decision-making that enhances their mission-aligned impact.

Romano takes a holistic approach to working with leaders, but the following areas of support are among the most critical as organizations move toward success:

  • Leadership Consulting: Advisement on developing and implementing a strong vision, assembling a capable team of employees and partners, and building a solid culture.
  • Brand Storytelling: Connecting an organization’s value proposition with relevant influencer and decision-maker audiences to build engagement and compel action.
  • Communications Strategy: Using multimedia, multi-channel communications, and content marketing strategies to build awareness and understanding.
  • Business Development and Sales Enablement: Breaking down organizational silos to form the foundation for effective partnerships and sustained success.

Industry leaders seek Romano’s advice to improve their impact in the ever-changing learning space. He established a reputation as a trusted advisor to founders and C-level executives from education technology (ed-tech), publishing, professional learning, events, and nonprofit organizations across K-12. Additionally, media organizations, B2B technology companies, and membership associations seek his advice.

Relief for Persistent Pain Points

Why are companies struggling? The reasons are numerous, but Romano shared his insights on some of the most common issues he’s observed in recent years. By addressing these, leaders immediately increase their chances of success:


  • Companies are failing to make quality products relevant to customers’ needs.“Companies should always begin with the end in mind ― their desired customer and/or end user’s challenges, needs, and ambitions ― and work backward to design a solution from there,” says Romano.
  • Sales teams of some firms are struggling to close sales after initial interest was sparked.
  • Most organizations require better support for their sales and marketing teams, as well as better alignment of their product, marketing, and sales efforts.
  • Growing businesses face difficulties in expanding their workforce.
  • Businesses that need a mission-driven partner to ensure their work consistently has a major impact.


  • Leaders are having trouble defining or redefining their organization’s long-term strategy.
  • Influencers who need to enhance their thought leadership. “This is true externally, but also internally,” says Romano. “Leaders who become and remain successful can move and motivate stakeholders through their vision.”

Differentiating from the Competition

There are many good business consultants. The job of organizations is to find the adviser who’s the right fit for their approach. Romano described a few of the differentiators September Strategies has implemented:

  • Connecting “Attention to Detail” with “Big Picture”: Romano doesn’t focus on an isolated area absent the context of larger objectives, and he helps leaders achieve the same for their teams. A company’s vision is the very definition of “big picture,” yet it requires relentless attention to detail to bring it to life at scale.
  • Increasing Effectiveness and Audience Understanding: September Strategies emphasizes the importance of doing great work, but also the necessity of publicizing that work consistently. “Consistent storytelling is such a trust-builder,” says Romano.  
  • From Strategy to Execution and Adaptation to Improvement: Romano stays with clients through the execution, as part of their team. He tries new strategies or makes adjustments as needed, and continues to grow together.

Transforming Business from the Ground Up

When it comes to business success, it all starts with a clear and compelling vision. Romano describes his work as “guiding leaders from vision to decision.” As a coach, he helps founders and organization leaders define their mission, vision, values, and value proposition. September Strategies helps leaders put themselves in the mindset of their key audiences, the influencers around those audiences, and the pressing pain points they want to be addressed. Romano adds, “We then speak, in their language, directly to those pain points and how we can solve them. Every action stems from this and every decision traces back to it.”

Romano’s relationships with clients are long-lasting and integrated. He prefers to approach these relationships as a partnership or teamwork, rather than a typical “client” dynamic. He takes a holistic approach to strategic planning, starting with a well-defined vision and values. This provides a foundation for developing cohesive sales and marketing plan, incorporating thought leadership and ongoing engagement to build and maintain an audience.

Keeping Focus on the Team

The team always comes first,” says Ross. He believes that being a true leader requires more than just having the title. It needs to be someone that the team recognizes and willingly follows. “I’ve come up with what I call the 3 ‘Cons’ of Effective Leadership ― Conscientiousness, Consistency, and Constancy ― and they just come up over and over again in the leaders to whom people really respond,” he explains. What makes these important is their effect on the people who make up the organization.

Words of Wisdom

Secrets to success? Romano says it’s about follow-through, not secrets. And he says to start simple with these three tips:

  • Put people first
  • Tell your story
  • Find great partners


Ross Romano_Quote

Also Read: The 10 Influencer Business Consultants of 2023

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