In this episode of BTG Insights on Demand, we present part one of a two-part conversation with Dev Mukherjee, a seasoned transformation leader and business and technology executive. Most recently Dev served as the chief transformation officer for Rite Aid where he was responsible for leading the transformation program that supported the organization's emergence from bankruptcy as a leaner, more sustainable operation.
Dev joins Laura Klein, an innovation leader, former Bain & Co management consultant, and head of Business Talent Group (BTG)'s major transformation solution team. Along with our host Sandra Pinnavaia, the global head of on-demand talent strategy and innovation at Heidrick & Struggles, they’ll discuss what’s new and challenging in business transformation today, practical tips for achieving transformation success, and insights on establishing effective transformation leadership.
Listen to the episode, read our lightly edited transcript, or jump right to a specific section of the chat below:
Interview Highlights:
- Enterprise transformation vs. incremental change
- Transformation challenges today
- Best practices for structuring a transformation
- When to consider a full-time chief transformation officer (CTO)
- Characteristics of the ideal CTO
- How executives can support their CTO
- When to consider an interim CTO
- Internal vs. external resourcing
- The importance of industry knowledge
Sandra Pinnavaia (01:13)
Hi Dev. Hi Laura.
Laura Klein (01:15)
Hi. How are you today, Sandra?
Dev Mukherjee (01:16)
Hey, Sandra. This is great. Thanks for having me.
Sandra Pinnavaia (01:19)
So glad to get into this conversation. So let's just get started. Right now, at the top of 2025, the world is just awash in change, right? And as business professionals, we've been exposed to many, many stories about transformation frameworks and best practices in transformation. Today, we'd like to dive in specifically with you two from an executive's perspective. From the perspective of a chief transformation officer who works at the very front lines, to tease out some of the tactical, practical insights and tips for more successful transformations as we go forward.
We're gonna start just briefly with a little setup on what's new and challenging in business transformation today versus in the past. But then I'm hoping we can go a little bit deeper on two things. One, what really makes for a good transformation leader? And two, how do you set up a transformation team, and what are some of the new things about how we set up transformation teams that lead to success?
So a specific angle that we're exploring in this conversation, given our line of business, is where, when, and how companies think about mixing internal and external expertise for transformation success.
So let's get started. Dev. I was just wondering how do you differentiate or define enterprise transformation from sort of the everyday change or incremental change that organizations go through?
Dev Mukherjee (02:48)
That's a great question, Sandra. I'd say that every organization, as you pointed out in the setup, has to be positioned to be able to manage change on a continuous basis.
But enterprise-level transformation really tends to be driven by one of two things. Either there's been an external event—something that has changed: the competitive set, a new product introduction, or market shift that is forcing the company to change—or an internal shift.
We sometimes think about transformation as dealing with a problem. An internal transformation driver could be the launch of a new product that has a huge amount of potential, but you still have to transform what the organization does in order to take advantage of that new product or service.
Sandra Pinnavaia (03:36)
Great. So it's a little bit the size of the motivation or shock and a little bit really differentiating that transformation means really changing how the company does its core business, not just making incremental improvements.
Dev Mukherjee (03:50)
That's exactly right.
Sandra Pinnavaia (03:51)
I'm just curious, do you think that it's more difficult or what is different today about driving major transformation in companies?
Dev Mukherjee (04:01)
There are really three things. The external environment as you pointed out is moving very quickly. We know that AI is having a huge impact in almost every industry across every function. And it's a technology arms race. Those who take advantage of technology get the advantage, and those who don't can quickly get left behind. So sticking with the status quo is really not an option.
So, the external environment—politically, geopolitically, supply chain issues, technology issues—all of those things have ramped up significantly over the last few years. That's one.
Two, we don’t talk a lot about this in business, but the essence of the workforce has changed dramatically since the pandemic. So employee expectations, employee behavior, this whole quiet quitting thing all have really changed the relationship between the organization and employees.
And then the third thing is, the access to talent that you guys have really been a pioneer in has created a whole set of new options for how we can actually bring talent to bear and capability to bear in order to accelerate change in organizations.
Sandra Pinnavaia (05:21)
Super great point. Laura, do you want to add anything or how else would you comment on the potholes that companies encounter in transformation today?
Laura Klein (05:31)
I would agree with Dev that the pace of change has increased tremendously for companies post-pandemic. In terms of potholes—change is hard for people.
It's really hard to do within the structure of a company, because companies are set up to promote people who continue with business as usual. Those that try to do things differently oftentimes don't get promoted, because it's hard to make friends as you're really trying to do things differently.
And you have to do things cross-functionally. Organizations are not set up—the way they are today at least—not set up to do big, cross-functional initiatives well on an internal basis.
Dev Mukherjee (06:16)
I think that's absolutely the case. We've talked for years about organizations operating in silos, and in spite of all of the great communication tools, I would tell you that siloed thinking and that siloed operations have only gotten worse—driven, I think, by the pace of change and just the pressure on organizations to perform.
If we look back over the last few years, organizational growth has not been that great. We're looking at, on average, 5–6% per year. And yet stock prices and expectations have gone up dramatically more. A lot of that has been driven by cost cutting and rationalization of resources. Many organizations are dealing with much fewer resources than the demand and the work might actually have leveraged only a few years ago.
Then the very last thing I would say is that the war for talent is real. Those changemakers that Laura mentioned are not being looked after in the same way that maybe they were several years ago, because we don't know that they're going to stay. The turnover, particularly amongst high potential employees, is really I would say at an all-time high. And the pressure on other firms to poach that talent is much greater than anything that I've seen throughout my career.
Sandra Pinnavaia (07:37)
Really interesting points. Given all of this as background, the need for change has never been less. As companies need to set up transformation—whether it's for growth, or it's for cost takeout, or it's for a carve-out situation or a post-merger integration—what should executives be asking themselves about setting up leadership for that? What are best practices in considering how you construct that role?
Dev Mukherjee (08:08)
You have to start with what do you have, and what do you need? If I can paraphrase the old Einstein quote: doing what you do today with the resources that you have today, and expecting a different outcome is—it doesn't really make sense, right? So a really careful, thoughtful assessment of, “What is it that we're trying to do? What outcome are we trying to achieve?” and then looking internally to say “Do we have the capability to do this?”
Capability could be the technical skills to do it. “Do we actually have the knowledge that we need in order to achieve our goals and successfully complete the transformation? Secondly, do we have the processes, the culture, even the meeting discipline and accountability that is required in order to make this change happen?” I've seen many great initiatives that have thousands of hours of consulting analysis behind them fall by the wayside because the organization was just not equipped to get the work done.
And then third. If you really want to motivate an organization or even an individual, you need some way of measuring what it is that you're trying to achieve and then tracking that. So, “What are the metrics that we're going to use in order to demonstrate success and to guide us along the way?”
Laura Klein (09:36)
One thing I have seen is that if the whole C-suite, especially the CEO and the board, don't have alignment onto what that change looks like from the beginning—unless they are there to back that team, I have seen teams not succeed. What are your thoughts?
Dev Mukherjee (09:53)
I think you're absolutely right, Laura. The board, the CEO, and the senior management team need to be aligned on the fact that they're going to do this and aligned on the elements of the plan we discussed earlier.
Sandra Pinnavaia (10:06)
So Dev, when does it make sense to announce a chief transformation officer versus just having someone in the company lead the transformation? Like when does it become a full-time job?
Dev Mukherjee (10:21)
Great question. As soon as you know that you're going to drive whatever the transformation is, it's important to identify a chief transformation officer—whether it's from inside or from outside.
If it's from inside, you have to be very careful, really, of two things. One is this can't be a side-of-the-desk activity. We know from changes that we try to make as individuals you can't do it part-time. You either have to commit, or it's just not going to happen. And to just have the time to be able to think about the changes that are required, the people that you're going to have to bring along, the buy-in, the action, the capability building—it is really a full-time job.
So as soon as you know that you're even thinking about this transformation, I would identify that chief transformation officer. And I'd make sure that he or she has the time to be able to really embrace this and to get it off to a strong start.
Sandra Pinnavaia (11:20)
When you get involved, are you usually getting involved while the transformation strategy is still being set? Or are you, as a chief transformation officer, really just in charge of the implementation?
Dev Mukherjee (11:33)
It's a great question. The fastest path to results is if I can come on board either during the definition of what it is that we're trying to achieve or at the tail end of that. The reason for that is that the desire to transform is a kind of a top-level, “Hey, you know, wouldn't it be great if we could scale this particular mountain?” The reality of successful transformation is literally hundreds of individual activities that are going on across the organization.
At the peak at Rite Aid, we had 700 people running literally hundreds of initiatives across the organization in order to get the result that we wanted. We know that big transformation activities like implementing an ERP solution get the focus, but very often are quite hard to do, because we assume that we can just drive it top-down, and it's just going to happen.
If you want to do something much broader than that—which is really move the organization in some way, not just put in a new system—you need literally grassroots support and people at the front line embracing the transformation and doing things in order to support it. It really has to be pervasive.
Laura Klein (12:52)
So one thing I have observed is sometimes organizations actually bring in chief transformation officers too soon. They bring them in because they want to make change happen, but they don't know what that change is, and they don't empower the leader. They may report to the CEO, but they don't give them the resources, the authority, or the vision about what is going to happen and how to make that happen.
Dev Mukherjee (13:20)
I've seen those situations and, to be candid, I've come in a couple of times to actually replace a transformation officer who's been in that situation—to help the management team and the board define or refine what the transformation objective should be.
And quite importantly, to help quantify it, right? Because all of this will take time and resources. So yes, it could be too early if they don't have the right support, but I would say that's really only going to manifest if you really don't have the right person who's going to help the organization get over the hurdle that you described.
Sandra Pinnavaia (14:01)
What are those characteristics of the right person to really set up? And now I know this is like a simple question, and yet it's really quite profound. Can you break it down?
Dev Mukherjee (14:11)
Over the last ten years I've given this a lot of thought. I've asked myself, and a number of my clients have asked me, what is it that drives success of this sort of initiative? I really think it comes down to a few things.
One, and probably most importantly, high EQ. This is not change through fiat. A chief transformation officer—even if fully empowered by the board, the CEO, the rest of the management team—cannot act alone. To flip it around, if all of the change is left to the transformation team, we are not actually leveraging the wealth of resources of the rest of the organization. Effective transformation is truly about changing the makeup and the behavior every day of the whole organization, not just the people who are involved in the transformation.
So high EQ is critically important because you have to be able to negotiate with colleagues around the management team table. You have to be able to inspire the entire workforce to take the risk of jumping on this bandwagon with you. And then you have to have the ability to drive the discipline required at all levels in order to drive success.
Sandra Pinnavaia (15:32)
That was such a surprising answer in the sense that I would have thought you would have led with the discipline and, you know, super organizational capability to stay organized across thousands of projects. But you led with the EQ. So interesting!
What else would you add that might surprise us about what makes a transformation officer successful?
Dev Mukherjee (15:53)
You’ve made me pause here and think about your comment. For transformation to work, human beings have to agree, have to support, have to get on board, and have to be passionate about actually doing something differently than they did the day before. And that's why EQ is so critically important.
You also need to have credibility with the rest of the management team. Because frequently you're asking colleagues who have billion dollar budgets to take a risk, to do something different and give up some of their resources. So part of that EQ is to be able to go toe-to-toe—sometimes with quite a hard message—with some of your colleagues, and then to be able to be both humble enough and also engaging enough to go on stage or go on a Zoom call with hundreds of people and inspire them to be part of the transformation. So, that's the EQ bundle.
The second area we touched on earlier. There's a huge amount of data available in any organization, and the ability to filter through that data and work out what's actually important is key to being able to support the transformation. So, individuals who are used to dealing with large-scale businesses, P&Ls, lots of operational data, lots of HR data, and market analysis—being able to assimilate all of that. To have the tools to do that. To be able to bring people in and talk to them about that.
It's fascinating to me, having grown up in the technology industry, how divided the analytics responsibility has become. You have an IT component, there's a data science team, and then you have a bunch of teams in the individual businesses. That really exacerbates the point Laura made earlier about siloing the organization. So you need someone who can really get their head around a lot of data and identify the key points.
Third thing, you have to have someone who knows how to execute. So much in business is let's do it next month, next quarter, next year. Or let's spin up a project and come back next quarter to talk about it. I can't tell you the number of board members and C-suite executives who have called me for help because their internal teams just take that long to get things started.
We really need to get back to basics. What's an agenda? What's an action list? How do we drive pace? And to be able to do that while at the same time leveraging the momentum of the organization. These can't be tools that are used to beat people over the head with. These have to be tools to really excite people and to get them to focus on the things that they need to in order to drive us forward.
Sandra Pinnavaia (18:56)
That third point about knowing how to translate a goal into action with your team—how to execute—is really, really important. What does this mean for your relationship with the CEO? What do CEOs take away about being effective in supporting a transformation initiative and their CTO?
Dev Mukherjee (19:20)
So, as Laura said, the CEO absolutely has to be on board. There is really no point at all to getting into this if the CEO is not completely committed and frankly excited about the opportunity.
Having said that, putting a transformation team in place, putting a CTO in place, gives the CEO the opportunity to let the CTO drive some of the more challenging and difficult conversations to get them framed—and bring the team together and do what great CEOs do really well and say, “Hey, these are the choices. How will we as a team make the choice?”
If I'm a CEO having to do both of those, it's actually quite difficult because whatever friction, whatever breakage I create as I'm trying to push for the change or drive for the change or look for options, I'm going to have to own going forward. If the CTO can break glass, drive things forward, stir things up a little bit, that's a different relationship than the management team has with their boss: the CEO and the board.
Sandra Pinnavaia (20:31)
Dev, we've seen a change emerge over the last five years where companies are more often looking to use an interim chief transformation officer. I think there's two questions involved here, and I'm interested in both your and Laura's observations.
One, when does it make sense to use an interim chief transformation officer versus a permanent one? And secondly, when does it make sense to elevate someone internally into this role versus bringing in an outsider?
Dev Mukherjee (21:06)
So the reason I think it’s great to have even a succession of interim chief transformation officers is really…
Sandra Pinnavaia (21:16)
Oh! A succession—more than one?
Dev Mukherjee (21:18)
I think it was Reid Hoffman who talked about work being a tour of duty—you know, where you have the right person with the right skills at the right time. So dropping in a chief transformation officer for a tour of duty to get a particular type of transformation done, I think makes a lot of sense. Chopping wood and sharpening axes are two different capabilities, right?
So a chief transformation officer coming in to help the organization sharpen their axes, to find the initiatives that need to be done in order to drive the transformation, to get those executed, and to get the transformation done—it’s great for organizations to have closure. I love it when I'm done, and we can actually celebrate that the organization was successful at climbing to the top of this mountain and achieving this thing. That cadence of “we set out to do this thing and we did it,” creates a lot of closure, and actually allows the organization to heal a little bit from the disruption that the transformation may have created—and to then make everything that we've learned how to do in the transformation now officially part of the business as usual.
Sandra Pinnavaia (22:36)
Laura, I'm really interested in your experience on this concept of staged transformation leaders aligning tours of duty with the actual priorities and the type of work that's to be done. It has so many obvious benefits, but clients will push back on this. What are the hesitancies that companies have about that kind of approach?
Laura Klein (22:59)
First of all, they want to grow a future leader within an organization. And a good way to bring in an outside, different set of skills and not to disrupt the existing business yet is to bring in somebody as a chief transformation officer, somebody who can think differently, who's a friend to the CEO, and who can be a future leader and succession to the CEO as well.
So that is an interesting way to bring somebody in to test them and then put them into a line of business—a one-and-done situation. But it doesn't achieve what we have been talking about in terms of implementing a “break the glass” type of transformation, because that leader—if they are successful in climbing through the organization, and that is their goal—it's going to be really hard for them to come in and do something really disruptive and hard when they're first there. Because their goal is to stay.
And Dev, when you and I have talked about it, your goal is your tour of duty, one to three years, and then to leave and to go onto the next opportunity, the next tour of duty, in the next company, and the next situation. So those are really very, very different concepts.
Dev Mukherjee (24:25)
I think you framed it better than I did. When I step in as an interim chief transformation officer, my focus is not on empire building, but building organizational capability.
All of us who have been operators running large organizations, if you're in permanently, and particularly if you want a bigger job, it's very hard because you don't want to take risks. Because you have to make friends, and you have all sorts of other things going on, and you're trying to build up your control, which then puts you at odds with all of the other people who need to be part of the transformation.
Sandra Pinnavaia (25:05)
So even though companies would like this to be a career building and kind of a talent accruing experience, you guys are both pointing out significant issues in terms of the ability of that person to be successful if they're also gunning for a role that has the right positioning for success for them long term.
Dev Mukherjee (25:31)
We live in a world where you have to think about—as a CEO, as a leader within an organization—who do I need right now? What technical skills, what personality, what work ethic is required to drive this forward?
If someone called me up and said, I've had this great job running a division of this company, and the CEO has asked me to be CTO and drive this enterprise change. I would say, if I knew them well, “What skills have made you successful up to now and will those skills and relationships and all the other things help you be successful in this role—and tee you up for whatever it is that you're trying to get to?”
Remember, if we're talking about a billion-dollar division, they're going to go from thousands of people working for them directly to having to influence people who work for other people across the company. So, it could be a great opportunity to grow someone, but they're going to have to embrace that this role is very different from what they've done.
Sandra Pinnavaia (26:41)
Well, based on some of the other things you've said already, in a way it doesn't seem like a surprise that you feel that the most effective major enterprise transformation leaders are essentially interim by design. Is that right?
Dev Mukherjee (26:57)
Yes, I think that's right because of the necessity of the things that the role has to be able to do. In many ways, I think of this as an unleashing of the organization.
For all of the technological change, social change, all of the data that's available, most organizations are command-and-control hierarchies. They're not groups of people who are organically coming together.
That probably is what's required to drive a successful, efficient day-to-day operation. For change to happen though, you have to break the hierarchy. You have to break the existing structure—if only to unleash and free up some of these resources that are required in order to drive the transformation.
Sandra Pinnavaia (27:48)
Such helpful framing. Thank you very much. So what are your thoughts about using an internal person versus bringing someone in from the outside?
Dev Mukherjee (27:57)
Laura, this is probably an area you spend a fair amount of time on.
Laura Klein (28:01)
Sure. How we've seen this be most successful is when internal knowledge is really important—when it is still change, but not “break the glass” change, an internal person works very well. They have all of the networks. They know how to make things happen within the organization and get the resources they need and get the support they need.
When the change is much bigger in nature, then someone from the outside—guided by somebody from the inside—we have seen be more successful because they are not, again, tied up in those relationships.
Dev Mukherjee (28:42)
I think Laura's exactly right. I have seen and supported a couple of situations where a leader was taken from a different part of the organization to drive a transformation. An HR leader driving an IT project, a sales leader driving the introduction of a new product.
I was support to those internal leaders to help guide them on how do they get this transformation to happen? But exactly as Laura said, they were able to bring their knowledge and their relationships to bear. I and the rest of the team were able to help them with the best practices on how to have an effective, high-impact transformation.
Sandra Pinnavaia (29:26)
Interesting. Would you say that you have the same observations across industries? We will often hear CEOs and boards describe their need for a transformation person by starting with the industry. They have to be familiar with the healthcare industry, or they have to have worked in a manufacturing industry. Where does the crossing of, you know, sort of fresh eyes work and where doesn't it?
Dev Mukherjee (29:52)
Maybe ten years ago, I would have said it's great if you can find someone who has industry knowledge. But over the last ten years, I would say you actually purposely want to have someone who does not have industry knowledge.
There are really two reasons. One, if you constrain yourself to the universe of people who have transformation skills and experience—and your specific industry knowledge—that's a much smaller set of people.
Secondly, people I've seen who have done repeated transformations in the same space are essentially implementing the same playbook. And it's not about the playbook! It's about the resources, the assets, the capabilities, the people that this specific organization has. So what you want in a chief transformation officer is someone who's able to unleash the capability of the organization, the knowledge of the organization.
When I started at Rite Aid, I knew what a retail pharmacy was because…
Sandra Pinnavaia (31:00)
Because you were a customer…
Dev Mukherjee (31:02)
But PBMs, flow of drugs, vaccine purchasing, pharmacists operating at the top of their license—all of these things were new. Because I didn't know them, I was unencumbered, and I could focus on what we needed to do. I was forced to leverage the knowledge and the capability and the experience and bring the people along with me who understood all of this stuff really well.
If I had been an industry expert, whether I wanted to or not, on day one I probably would have had a prejudice—you know, which way I want to go—and the people talking to me would know that I had a point of view.
Laura Klein (31:46)
In addition, Dev, one thing I have seen is that the pace of change is so great, and the definition of industries is so blurry at this point in many industries that if a leader comes in from another industry—let's say technology—they know the best practices and where technology companies are going and where they can go and what is the potential. Whereas if, for example, they're in oil and gas their whole life. They are probably not exposed to where industries are going and the blurring of lines between industries.
Dev Mukherjee (32:20)
That's a great point. And to add a kind of parallel to that, if you grow up in an industry, sometimes you don't realize how good you have it in certain areas. At Rite Aid, the strength and the passion and the commitment of the pharmacists that we had was an asset like no other. And as an outsider, I could see how amazing that was and how much we had to leverage that. Whereas if I'd been in the industry, I might have just taken it for granted.
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