Anaplan's Frank Calderoni Preaches the Gospel of Character as the Key to True Success

By Scott S. Smith Friday, September 10, 2021

Anaplan, Inc., a cloud-based software-as-a-service platform for strategic planning and business management, went public in October 2018 and has returned over 130% to date, driven by a customer base that is now over 1,700.

Frank Calderoni.

While Anaplan’s versatile platform has Wall Street’s attention, it’s CEO Frank Calderoni's message in his new book “Upstanding: How Company Character Catalyzes Loyalty, Agility, and Hypergrowth” that has the attention of entrepreneurs.

Calderoni explains that an organization’s character drives its culture and that winning organizations have “upstanding character,” which helps build loyalty with customers, employees, partners, and investors.

Much like people have character, organizations with upstanding character have deep convictions tied to principles such as being authentic, accountable, inclusive, and having a growth mindset. In “Upstanding,” he goes on to say that character-led organizations operate with a larger purpose, are values-led, and “answer the call during challenging times.” The result is a stronger bond with stakeholders, a highly engaged workforce, and a company reputation that attracts top talent.

Personal Experience Reinforced the Importance of Character

Calderoni comes from humble beginnings. His father and grandfather were Italian immigrants who came through Ellis Island and set examples for him on the importance of hard work. In college, he worked as an intern for IBM for two summers. At the time, IBM was No. 7 on the Fortune 500 with annual revenues of more than $21 billion. After graduating, he accepted a full-time position because of how IBM treated its employees and customers and its reputation in the community.

He was also there in the late 1980s when the company lost its way and things took a turn for the worse. The impact was severe — budgets were slashed, and 170,000 were either laid off or forced into retirement. He witnessed the toll these actions took on the reputation of a company he admired.

In 2004, he joined Cisco Systems, a leader in networking technology and stalwart of corporate character, and became their CFO in 2008. While at Cisco, Calderoni learned that organizations could take a position on social issues. It was a formative experience when the company unsuccessfully took a stand against California’s Proposition 8, which banned same-sex marriages (overturned by a federal court two years later). “If we use our core values as our North Star — just as Cisco did — the right thing to do will become crystal clear every time,” he later said.

After 10 years at Cisco, Calderoni became CFO at Red Hat, a leading provider of open source software. "I learned about the power that comes from cultivating an openness to feedback that is not curated or reviewed in advance," he said. "This allowed employees to ask any question and to answer in a way that is authentic and unscripted, generating heated debates like nothing I had ever seen."

A Character Turnaround Is Needed

When he arrived to take the helm at Anaplan in 2017, it had been without a CEO for over a year. Employees were passionate about its products and great at customer service, but there were competing centers of control and almost all senior leaders were men. Calderoni quickly began instituting changes to create a more character-led culture and improved the diversity of its leadership along the way.

Calderoni earned the commitment of Anaplan’s employees by involving them in defining the company’s new culture from the start, and over 60% stepped up to help. The result was a new company built on the principles of being authentic, open, inclusive, collaborative, creative, and tenacious.

The company also instituted several practices to reinforce its new culture, beginning with redesigning the hiring process to ensure culture fit. Once on board, all new employees took training to help them understand their blind spots and completed a personality assessment to understand their preferences and how to work with their styles most effectively.

And all along the way, they reinforced character through ongoing communications, monthly unscripted Q&As, a CEO Slack channel, and cultural recognition programs aptly named AnaplanLOVE (i.e., Living Our Values Everyday).

In four short years, the changes have made a difference. As a subscription-based platform, customer satisfaction is paramount. Having a strong culture creates an engaged workforce, which leads to a superior customer experience that increases the adoption of Anaplan’s platform. As a result, it’s no surprise that in the first quarter of fiscal 2022, 64% of new bookings came from current customers.

Pandemic Gives Rise to New Corporate Consciousness

Last year, the pandemic, its resulting economic recession, and the rise in awareness of social issues put corporate character in the spotlight. As Calderoni says, “People are holding companies accountable for societal, environmental, and governance practices with little to no patience for inaction.”

"In the era we're leaving behind, part of being professional meant not discussing personal opinions not related to the business," he wrote. "Those times are now gone. Today, we must embrace our shared stake in issues that have the potential to marginalize or imperil the lives of our colleagues and communities. Taking stands always risks making one group of stakeholders happy while alienating others. But today, not taking any position is just as fraught."

Calderoni says in his book that he was pleasantly surprised during the roadshow for Anaplan’s initial public offering that top Wall Street analysts wanted to know about the company’s environmental, social, and corporate governance (ESG) practices. This was a clear sign to him that investors care about a company’s character.

Envisioning the Future of Business

In his final chapter, Calderoni encourages leaders to imagine what workplaces will look like in a few years, even a generation from now. "I see organizations that are profoundly more equitable and inclusive than they are today. I see many that are boundary-less — with teams that function just as well with people physically in the office as with people who are distributed and working remotely, anywhere, anytime. I see those that use technology to unleash the creativity, power, and passion within each employee, enabling them to stay connected in ways that are liberating, not confining. If there is a time when we need to make sure everyone has a seat at the table, is included in the conversation, and feels a deep sense of belonging to their team and their company, that time is now."

Calderoni closes with the following advice: “If you build the qualities that demonstrate upstanding company character, your organization will win today and sustain its advantages well in the future.”

Upstanding companies endure.

About the Author


Headshot for author Scott S. Smith

Scott S. Smith has had over 2,000 articles and interviews published in nearly 200 media, including Los Angeles Magazine, American Airlines’ American Way, and Investor’s Business Daily. His interview subjects have included Bill Gates, Richard Branson, Meg Whitman, Reed Hastings, Howard Schultz, Larry Ellison, Kathy Ireland, and Quincy Jones.

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