The Chief Strategy Officer

From The Practice May/June 2023
Driving and executing strategy through the firm

Over the past decade, a number of major law firms have created new executive roles focused specifically on strategy. Business has, of course, had individuals occupying such roles for longer. In an October 2007 Harvard Business Review cover story, R. Timothy S. Breene, Paul Nunes, and Walter E. Shill took stock of the growing number of chief strategy officers (CSOs) in the corporate world. In light of “changes to the business landscape—complex organizational structures, rapid globalization, new regulations, the struggle to innovate,” they write, companies began adding CSOs to their executive teams as “it [was] ever more difficult for CEOs to be on top of everything, even an area as important as strategy execution.” At around the same time, strategy itself was undergoing an evolution, they argue, becoming less a static document to be executed and more a process of ongoing refinements. (For more on the durability of strategy, see “Leading the Way.”) These dual trends produced a landscape in which “a CEO needs an executive near at hand to share the load and maintain—or regain—control of a process that constantly threatens to become chaotic.”

Chief strategy officers simultaneously face broad mandates, scant resources, a “menagerie of stakeholders” with complicated (and perhaps conflicting) agendas, entrenched views, organizational gaps, unclear metrics, and talent churn.

Who were (and are) these CSOs? Based on a constructed database of more than 200 CSO profiles from a variety of industries and more than 100 media press releases, and supplemented by interviews, Breene, Nunes, and Shill laid out a number of key attributes of a CSO. Corporate CSOs tend not to be “pure strategists” who work in “relative isolation.” That is not to say CSOs do not have significant strategy experience—many have worked for top management consulting firms. However, that is not the dominant background, nor even the primary entry point into the role. At the time of writing, CSOs are, by and large, seasoned executives with diverse and operational experiences throughout an organization from business to finance to line functions. That multifaceted background is perhaps why the ability to work with people from across an entire organization (and beyond) is critical to their overall success. That is, the authors say, “the heart of the [CSO] job.” They point out that while the CEO and core leadership team tend to create the strategic vision, in large companies that vision risks being opaque, “which [could] create resistance or confusion among senior managers and frontline employees and … thwart execution and change.” That is why the ability to “resolve the strategy” and “clarify it for themselves and for every business unit and function, ensuring that all employees understand the details of the strategic plan and how their work connects to corporate goals,” is so central to the CSO role. While there are no doubt challenges involved in adding a new senior executive, the article concludes by reiterating that “despite such challenges, more and more companies are exploring the CSO option.”

Almost 15 years later, in 2019, a PwC study on CSOs found that the role was continuing to grow in prevalence. Companies, the report notes, “apparently recognize the value of having a member of the C-suite who is primarily oriented to the long-term future of the company, and to sustainability and profitability.” Also, “unlike other C-suite officers such as the chief financial officer, the chief marketing officer, or the chief information officer—whose points of view are influenced by the sometimes large functions they represent—the CSO can provide an independent perspective.”

A separate 2020 report from Deloitte also took stock of the role, finding that corporate CSOs tend to be highly experienced (66 percent of their sample had 15-plus years of professional experience; 44 percent had 20-plus years). At the same time, those in the role are “relatively new” to “corporate strategy” (almost three-quarters were in corporate strategy for less than 10 years, and 40 percent for less than five years). As with the Breene, Nunes, and Shill HBR article, many CSOs were former consultants—60 percent—but almost 30 percent were in such roles for only three years or less. The paper lays out six different perspectives critical to CSO success—as adviser, sentinel, banker, engineer, aide de camp, and special project leader. As was the case in 2007, the diversity of these tasks requires a diversity of skills—something that can be very hard to find in one person. “The CSO must master, or at least be conversant in, a wide variety of skills … [including] conducting top quality analysis, learning how to operate across the diverse parts of the company, and asking the questions that lead executives in strategically sound directions.” CSO roles are, in short, hard. CSOs simultaneously face broad mandates, scant resources, a “menagerie of stakeholders” with complicated (and perhaps conflicting) agendas, entrenched views, organizational gaps, unclear metrics, and talent churn. Despite—or perhaps more accurately in spite of—these challenges, the paper concludes: “CSOs can make significant, lasting contributions to a company’s performance.” But they must, according to one cited interviewee, “show their worth to the business units by getting out of the ivory tower and actually working on the big decisions and driving results.”

The growth of law firms and the increasingly competitive market landscape have prompted firms to gear up their executive functions and develop sophisticated internal processes to deal with added complexities. 

Why should lawyers care about the evolution of a role in corporate life? Why is history important? In short, the growth and development of law firms in terms of size and complexity, and the increasingly competitive market landscape, have prompted firms to gear up their executive functions and develop sophisticated internal processes to deal with similar added complexities. Law firms now have thousands of lawyers, many more support staff, offices in dozens of cities around the world (each with different regulatory rules), and shifting client needs and requirements, and they compete in competitive marketplaces made up of an ever-growing number of competitors.

As we have documented elsewhere in The Practice, one of the most notable (though certainly not the only) responses the law firm sector has made to deal with these new challenges has been the proliferation of new executive-function roles. When firms became larger with more clients and more partners, some of whom did not know one another, a firm general counsel became key. When competition became fiercer, chief marketing officers entered the foray. When clients started developing internal legal operations and innovation functions, law firms responded with their own chief innovation officers. And when diversity and inclusion debates took center stage, firms supplemented their diversity committees with chief diversity officers. And, perhaps most recently, when firms began recognizing the need for professionalized and centralized strategic leadership, the chief strategy officer entered the field.

To help shed initial light on the burgeoning CSO role within law firms, in this article, we talk to CSOs from three major firms: Jeff Grossman, chief of strategic initiatives, Proskauer Rose; Stephen O’Neil, chief of business affairs and strategy, DLA Piper; Jason Bovis, chief strategy officer, Pillsbury Winthrop Shaw Pittman. In doing so, we are interested in what experiences led them to their positions. We ask about core responsibilities and probe how they hope to make an impact. It is important to note from the outset that the chief strategy officer title itself is complicated. As the HBR article said in 2007, there was (and is) a diversity of titles that might fit the role and functional responsibilities. The same is likely true in law firms, and more research should be done to identify the exact trends. What is clear is that an increasing number of major firms have people with the CSO title. Asking who they are and what they do seems a good place to start the discussion.

Jeff Grossman, Chief of Strategic Initiatives, Proskauer Rose

As a child, Jeff Grossman’s family called him the “why child.” He was constantly asking questions. What might have been considered an annoying habit in a child would become a boon in his career when he grew up. As chief of strategic initiatives at Proskauer Rose, Grossman likes to guide people by asking, “Why do you do it that way? Could you do it another way?” “Strategy is about getting others to bring their ideas to the table in a disciplined and refined way,” he says. Questions help them do that. From there, they can make a plan together. “To me, strategy is everywhere,” Grossman says. “It starts with a vision and big ‘S’ strategy, knowing who you are and where you are going. That needs to be communicated at the broadest levels across the firm. Then, we can work meticulously to insure that at every lower level, it all ties together.”

Before Grossman joined Proskauer, he had a similar role at Cooley. At both firms, the position was a newly created executive role, something that Grossman admits has both challenges and opportunities associated with it. Fleshing out your own role can be liberating, he says, but when others also don’t fully grasp your position, you have to contend with meeting others’ expectations, prioritizing, situating yourself in the organizational chart, and balancing bigger strategy imperatives with smaller ones—something that the Deloitte CSO study notes is one of the major challenges of the role irrespective of one’s particular industry.

The most important part of building strategy is the discovery process itself. And that’s why I ask a lot of questions, and over time the questions tend to narrow.

Jeff Grossman, Chief of Strategic Initiatives, Proskauer Rose

At Proskauer (and Cooley before), Grossman felt already a bit ahead of the learning curve for someone who is not a lawyer. He came to the legal profession with a deep understanding of the cultural norms and language of the profession through three decades in providing banking specifically for law firms. He had built Wells Fargo’s Legal Specialty Group, together with a founding group, from the ground up before transitioning to the same type of work at Citi. He left when the pandemic hit, and as he was considering starting his own law firm financial consulting practice, several law firms made overtures to come join them in house. “The biggest adjustment was learning how law firms operated under the hood—the mechanics view—especially where they store and harness data,” he says.

Leading strategy, Grossman stresses that he tries to be forward-looking, a benefit to a profession built on precedent. To get lawyers to look into the future, he relies on something many of them learned in law school: a sort of Socratic method. “The most important part of building strategy is the discovery process itself,” he says. “And that’s why I ask a lot of questions, and over time the questions tend to narrow.” For instance, Grossman performs one exercise early in his discovery process—“a type of straw man approach to rule out what they don’t want to be to help them understand what they want to be,” he says. Grossman doesn’t have a defined team; he works with everyone—firm leadership, practice chairs, associates, support staff—to try to understand their priorities. If he finds daily practices that aren’t aligned with the firm’s mission, he doesn’t assume fault. He merely asks, “Can you tell me what’s happening here?” He tries to get people to talk and, he says, “find out where those bottlenecks are, find out why they’re doing it differently.”

To be an effective CSO, Grossman stresses, you have to be “a very keen listener and observer.” He spends a lot of time on listening tours before he starts planning, meeting as many people as possible. This later helps with buy-in. “In order for a strategy to be effective and to be the right one, everyone in the room or in the firm or in the company needs to own it,” he says. “And if they’re not instrumental to that process, both in the ideation and in the development, then how are they going to execute against it?”

Through banking and in the law firm sector, Grossman’s ideas about strategy haven’t fundamentally shifted. “The most effective strategists draw from others to build strategy,” Grossman says. “They may rely on data, experience, and intuition to drive others, but they most definitely rely on others.” Strategy, he says, “is about getting others to bring their ideas to the table, in a disciplined and refined way, building a road map for what success looks like. My role is to help them visualize what success looks like and encourage them to dream big. I serve as a guide helping others find their path or go to greater heights.”

Stephen O’Neil, Chief of Business Affairs and Strategy, DLA Piper

When Stephen O’Neil interviewed for his first accounting internship as a junior in college, the firm’s managing partner asked why he wanted the role. “Because I believe it’s rewarding if someone asks for your advice—and it’s valued,” he replied. Today, that insight continues to guide O’Neil, who joined DLA Piper in July 2021 as the firm’s first ever chief strategy officer. “I remember believing that all these years later,” he reflects. “And it remains core to how I approach things today.”

Before arriving at DLA, O’Neil was the Americas Markets Leader for International Tax and Transaction Services at Ernst & Young, where he had built more than 30 years of experience in global professional services across the Americas, Europe, and Asia. The experience gained in serving some of the world’s most sophisticated clients while overseeing highly branded business units required him to interact with diverse sets of stakeholders. This prepared him well for leading strategy at DLA Piper, which operates in more than 40 countries and where he is focused on building a “seamless set of legal and business solutions for clients that doesn’t stop at the border,” he says.

Contrary to what is often assumed, for O’Neil, there were similarities coming out of the Big Four to the legal sector, particularly around a devotion to client service. Professional services, he says, are ultimately “grounded in value creation—creating value for your organization, clients, and people. That didn’t change at DLA.” That is not to say there were no differences. The legal profession is significantly more fractured than the world of accounting, consulting, M&A, and tax, where the Big Four dominate. The Big Four are also further along in their thinking on strategy, due largely to their immense size and more centralized structures. But challenges in industry or scope are not one to stop O’Neil, who says that a commitment to learning drives him and brings value to his work. “Were there things to learn about the industry and DLA? Yes,” he says. “But I wasn’t done learning accounting when I left EY either. It was a 32-year run, and when I walked out on my last day, I was still learning new things.”

Whereas strategy focuses on ‘the opportunities we have and what we need to do to get there,’ business affairs is about the firm’s foundation.

Stephen O’Neil, Chief of Business Affairs and Strategy, DLA Piper

About a year into his role, O’Neil’s title was updated to reflect his existing portfolio; he is now chief of business affairs and strategy (CBAS). Whereas strategy focuses on “the opportunities we have and what we need to do to get there,” he says, business affairs is about the firm’s foundation. In managing the foundation, O’Neil is “ensuring that the firm’s financial, market, and talent programs are aligned with DLA Piper’s objectives. By tying business affairs and strategy together, we are able to manage risk, assess opportunities, and invest and execute on our priorities,” he says. “Without a strong foundation, it’s hard to really deliver on strategy.”

O’Neil was particularly drawn to DLA Piper because of its culture—and implicitly saw the links to strategic progress. The firm hires people who “thirst for learning and growth,” he says. As CBAS, he wants to double down on that commitment. “We are committed to having an organization where we are the preferred destination for employees and clients. People want to come because we invest in the organization and provide an opportunity for individuals to invest in themselves, grow as professionals, and enjoy it.”

To do all this, and to operationalize DLA’s core strategy, O’Neil works closely with firm leadership, including chair Frank Ryan and vice chairs Loren Brown and John Gilluly. Key to this is being “thoughtful about the impact of what we’re doing.” O’Neil knows well the challenges of implementing change. He says that is why it is critical to be thoughtful and deliberate about “how change is analyzed, recommended, approved, communicated, and rolled out.” He goes on, “We go about it in an inclusive way that builds consensus.” That’s how one builds trust and enacts strategy. “Strategy in our parlance means growth,” he says. “It’s growth in our people, capabilities, brand, and market share—globally.” For O’Neil, doing all that means providing good advice—that’s valued. 

Jason Bovis, Chief Strategy Officer, Pillsbury Winthrop Shaw Pittman

Jason Bovis began his career in one of the more volatile and tumultuous industries: political campaigns. It’s also in this line of work where, he says, he first began to meet and work with lawyers. From there, he moved into corporate strategy positions, first in consulting, then in a corporate strategy and marketing role at a major outsourcing company. In these roles, he says, he began to appreciate “the power of strategy” to navigate complex environments. He thrived in situations where he could “sit on the outside, look in at a business or an opportunity or a project, and say, with a great deal of directness and objectivity, ‘Here are the opportunities and threats you’re facing, and here are some of the ways that you might be able to navigate these issues.’”

All of these roles also put him in direct contact with lawyers and law firms, with whom he found he really enjoyed working. “From the outside in, I was gaining important insights into the operational issues of a law firm, and some of the issues impacting their ability to compete,” he says. “My engagement directly with those law firms was inspiring. From that point on, I decided I wanted to be doing this work from the inside.” Leveraging this knowledge, Bovis eventually joined Akerman, an Am Law 100 firm, where he would go on to become chief marketing and client development officer, with a focus on marketing strategy, client growth, and innovation. He would spearhead innovative programming with colleagues across the industry and within Akerman, such as Law 2023, a yearlong investigation into trends and challenges across the legal profession, and in response, the first Law Firm R&D Council, an innovation incubator in partnership with clients designed to meet those challenges.

After six years as Akerman’s CMO, Bovis joined Pillsbury in 2017 as the firm’s first ever chief strategy officer. Bovis notes that his CSO position is about both top-level advice and frontline operations. In the first case, he works closely with the chair and managing partner, the board, and lawyers from across the firm, advising them on key market issues impacting the firm and its clients. In the second case, he stresses that being a CSO is much more direct and operational: “It’s facilitating the planning, development, and execution of strategies, and getting together the right people to discuss potential solutions to issues as they arise.” He goes on, “The process itself can help create the glue and the trust that is so vital to keeping a firm and its lawyers engaged, moving forward, and ultimately knitted together.”

In a professional services environment, it’s essential that you create systems for partners and other stakeholders to meaningfully contribute to discussions and, in many cases, shape the actual strategy and plans.

Jason Bovis, Chief Strategy Officer, Pillsbury Winthrop Shaw Pittman

In all of this, collaboration is key. If you bring the right people to the room early in the process, then implementation is easier. “In a professional services environment, it’s essential that you create systems for partners and other stakeholders to meaningfully contribute to discussions and, in many cases, shape the actual strategy and plans,” he says. This type of horizontal integration at the ownership level differs from previous corporate experiences he’s had. It’s also part of the reason Bovis was drawn to working in strategy for law firms. As CSO, he doesn’t try to achieve “complete consensus.” Instead, he says, “you look for a level of trust and buy-in that enables the firm to get closer to achieving its broader vision.”

This “overly inclusive approach,” in his words, likewise was crucial to developing his position at Pillsbury. Like many strategy roles, his was a newly created executive function and thus defined in a collaborative manner with firm leadership once he arrived. After all, a culture that “valued a diversity of backgrounds and experiences” is one of the reasons he was drawn to Pillsbury. His success as CSO, he says, is largely due to a “shared philosophy that lawyers and business professionals contribute meaningfully to the success of the firm in different ways.” Having someone who can speak the language but has different training means Bovis can surface new perspectives. In this, he says, he is comfortable challenging others with uncomfortable ideas. Referencing CEO coach Kim Scott, Bovis says, “I do believe that CSOs need to employ radical candor in order to be effective because simply leaning into groupthink often could be the wrong decision.”

Bovis also stresses the need to embrace a flexible mindset. “There’s some misunderstanding about strategy that it’s a static piece of work product that you can point to and hold on to,” he says. “The reality is that it’s a continuous product that is always developing, changing—or should be at least—based on how rapidly the market continues to evolve and client needs continue to change.” He also notes, “To thrive in a law firm environment, you have to be comfortable with ambiguity. You have to be agile enough to move from strategy development at nine o’clock, to execution at one o’clock, to reassessing everything by five o’clock.”

As law firms (and the clients they serve) face volatility and competition like never before, Bovis believes CSOs should become the industry standard. “Law firms have never had more threats to their business model and experienced so much disruption at a global scale,” he says. “Our ability to adapt to these challenges will enable us to be successful long term.” What that means is that firms are going to need “individuals who can help firm leadership and partners continuously evaluate and adapt to that volatility.”

An emerging role

What do we learn from these three vignettes? As with CSOs in the corporate sphere, law firm CSOs come from a variety of backgrounds: marketing, Big Four, consulting, and more. They are deeply collaborative in their methods and embrace flexibility and a learning mindset to accomplish their goals. CSOs do not simply sit in rooms alone producing big ideas—they understand that strategy planning and execution happens in conversations with others. They are on the floor of the law firm day in, day out, making sure that small to large actions align with visions of success. That said, law firm CSOs are still an emerging phenomena. But as we’ve reported previously, the complexity of our current moment may necessitate that law firms that wish to survive and thrive add such positions to their ranks.


Accelerated Leadership Program

Executive Education
March 19, 2024 - March 22, 2024