The Art of Scaling: How to Pivot, Execute, and Thrive Under Pressure

Discussion with Anthony Rotoli

Anthony Rotoli, a seasoned SaaS executive and three-time CEO with over 30 years of experience, is renowned for scaling businesses, driving growth, and leading transformations in high-stakes environments. In this article, Rotoli shares insights from his journey as the founder of Seven Pier, his partnerships with private equity firms, and the lessons he has learned about leadership, strategy, and creating sustainable value.

The Genesis of Seven Pier

Anthony Rotoli founded Seven Pier in 2011 to formalize his work in helping small and mid-sized companies grow, restructure, and transform. Recognizing a gap in the market for experienced operators who could drive meaningful change quickly, he set out to create a platform to address these needs, explaining that Seven Pier “started as a way to formalize what I was already doing - helping businesses navigate challenges and achieve measurable results”. He noted that many early-stage companies struggled to balance operational execution with strategic priorities, a gap he sought to bridge through this initiative.

Over the past 14 years, Seven Pier has been a cornerstone of Rotoli’s career, enabling him to take on CEO roles, advisory engagements, and board positions. Through the company, he has worked across industries and led transactions requiring operational expertise and strategic foresight, experiences that, as Rotoli described, “allowed me to align investor priorities with operational realities, ensuring both short-term wins and sustainable long-term growth”.

Partnering with Private Equity

Rotoli’s collaborations with private equity funds have been transformative, exposing him to diverse industries, operating models, and challenges. These partnerships, he explained, have sharpened his strategic and operational skills while enhancing his understanding of value creation under tight timelines, a hallmark of PE environments where “precision and accountability leave no room for complacency”.

Working with PE-backed companies has also deepened Rotoli’s expertise in areas such as go-to-market strategies, operational efficiency, and M&A activity. He emphasized that these partnerships “taught me how to align operational decisions with investor priorities, ensuring that every move contributes to the broader strategic vision”.

In addition to the operational rigor required, Rotoli has found collaboration with talented investors and executives incredibly rewarding. He highlighted the importance of creativity and rigor in these partnerships, noting, “the opportunity to work with talented investors and executives who approach problems with creativity and rigor has been incredibly rewarding”.

Opportunities Through Seven Pier

Seven Pier has opened the door to several leadership opportunities for Rotoli, including CEO positions, advisory roles, and investment opportunities. One example is his involvement with the Triangle Tweener Fund, a rolling venture fund that supports startups in the Raleigh-Durham-Chapel Hill area. Rotoli considers the fund an avenue to give back to the region that has been instrumental to his career. “The Tweener Fund allows me to give back to the region that has played a significant role in my career”, he explained, adding that it also enables him to “support the next generation of leaders and companies that are shaping the future”.

Seven Pier has also provided Rotoli with the flexibility to pursue projects he is passionate about while maintaining a focus on creating tangible value for the businesses he supports.

Balancing Responsibilities

Managing multiple roles and responsibilities requires strategic prioritization and effective delegation. Rotoli has developed a disciplined approach to ensure his engagements remain impactful without compromising his commitments. He shared that his success comes from focusing on areas where he can bring the most value while trusting his teams to handle operational details. “I focus on areas where I can bring the most value, and I rely on strong teams to execute on the details”, Rotoli said. “Building capable, driven teams and trusting them to deliver has been key to maintaining balance and achieving success”.

Colleagues describe Rotoli as a leader who excels at empowering his teams while remaining highly engaged in critical decisions, a trait that has contributed to his ability to manage complex responsibilities effectively.

Leveraging Expertise for Impact

Rotoli’s extensive experience in areas such as go-to-market strategies, operational efficiency, and turnarounds has allowed him to create measurable and sustainable outcomes for the organizations he works with. He has developed a playbook focused on seven core business areas: Product, Technology, Finance, People, Sales, Marketing, and Customer Success. His “holistic approach”, as he explained, “allows me to assess all aspects of a business and tailor solutions to fit each company’s unique needs”. Rotoli described his ultimate goal as positioning businesses for long-term success.  

Advice for Executives Interested in Private Equity Partnerships

Rotoli encourages executives to understand the mindset of private equity investors, emphasizing the importance of growth, efficiency, and speed. He believes that PE firms value leaders who can execute effectively and provide solutions with minimal guidance. “PE firms value solution-oriented leaders who can execute without a lot of hand-holding”, he said, highlighting the need to align one’s initiatives with the firm’s goals to build trust and deliver results.

He also emphasized that confidence and expertise are essential for success. “When you know your strengths and can articulate your impact clearly, it creates a foundation for a strong partnership”, Rotoli added.

Positioning for Similar Opportunities

Rotoli believes that professionals can position themselves for opportunities in private equity environments by building expertise in specific areas, delivering measurable results, and expanding their networks. “Many of these opportunities come through relationships and word of mouth”, he said, encouraging executives to consider starting small, as advisory or interim roles can often lead to larger engagements.

He also stressed the importance of self-belief and taking calculated risks. “Confidence, paired with a willingness to step outside your comfort zone, is often what makes the difference”, Rotoli said.

Qualities for Success

Adaptability, decisiveness, and clear communication are traits Rotoli considers essential for executives to thrive in private equity environments. He highlighted the importance of being able to assess situations quickly, rally teams around a shared plan, and execute effectively. “The ability to assess situations quickly, rally a team around a plan, and execute effectively is critical”, he said.

Metrics and proactive management are also key. Rotoli underscored the importance of knowing KPIs and using them to make informed decisions, explaining that “knowing your KPIs and using them to make data-driven decisions is essential. It ensures you stay ahead of challenges and builds trust with stakeholders”.

Finally, he emphasized the importance of resilience in high-pressure environments, saying that “being comfortable with the uncomfortable is key. It’s what allows leaders to thrive in dynamic and demanding roles”.

Key Takeaways

• Identifying market gaps and formalizing solutions can create a strong foundation for leadership opportunities.
• Private equity (PE) partnerships demand precision, rapid execution, and alignment with investor priorities.
• Building a strong network and leveraging past experiences leads to meaningful advisory roles and investment opportunities.
• Thriving in high-pressure environments requires adaptability, financial expertise, and a proactive, results-driven mindset.