Bringing in the wolf: Band-aids and executive gap-fillers

An interview with Ruchi Sanghvi

Ruchi Sanghvi (@rsanghvi) was the VP of Operations at Dropbox. Prior to joining Dropbox, Sanghvi served as the cofounder and CEO of Cove, a collaboration, coordination, and communication product for organizations and communities. Sanghvi holds the distinction of being the first female engineer at Facebook and was instrumental in implementing the first versions of key features such as News Feed. She then led product management and strategy for Facebook Platform and Facebook Connect. She was also responsible for core product areas such as privacy and user engagement. She holds bachelor’s and master’s degrees in electrical computer engineering from Carnegie Mellon University.

There’s a particularly tricky moment in the life of a hypergrowth company, when things have started growing rapidly but the executive infrastructure is not yet in place to handle it. And in those moments, a lot of companies begin applying human Band-Aids of sorts—trusted employees who can fill in on key roles until someone more permanent is hired to build out a given function.

I sat down with Ruchi Sanghvi to discuss this phenomenon and her thoughts on how to make it work. An early employee at Facebook, and later VP of Operations at Dropbox, Ruchi has seen Band-Aids from both sides—she’s worked for them and she’s been one herself. (At Dropbox, people even called her the Wolf, a nod to Pulp Fiction’s famous fixer.) She shared her advice for when to slap on a Band-Aid, when to rip it off, and how to get the most from it in between.

Elad Gil:When you were at Dropbox, you played the role of a “gap filler” or as you call them, “Band-Aids.” These are people whose role is effectively to help a hypergrowth company scale and to step into organizational or functional gaps. Can we start with your experiences with the gap-filler or Band-Aid role?

Ruchi Sanghvi:
My first experience of the Band-Aid phenomenon was at Facebook. Matt Cohler played the role there. And the idea was that for any function that didn’t have a leader or manager, he would step in. Or if there were teams that needed to be built out, he would step in. And I thought it was a really interesting role, because it was obviously impactful in the short- to medium- term to help the company scale. But it wasn’t a sustainable role, either for the individual or for the company.

I had a similar experience at Dropbox myself. When Dropbox acquired Cove (where I was working), it wasn’t exactly clear what role I would step into. The first thing that I did was interview about 50 percent of the Dropbox team. I asked things like “What’s working well? How do you think you could accelerate the company’s efforts? And what are the one or two priorities you think need to be addressed immediately?”

It didn’t matter who you talked to on the Dropbox team, whether it was engineers, product people, sales people, it all boiled down to one thing: We don’t have enough resources to build product, to scale, to sell the product, to market the product, etc.

I had the title of VP of Operations, but the first thing I actually ended up doing was managing the recruiting team. I directly managed the team, set goals, and figured out how we would achieve those goals. And while we had a target to hit, it was just as important to build systems to integrate new hires into the company. These systems helped to increase productivity and strengthen the culture already present.

After recruiting, I focused on marketing. We needed to build out the team and eventually hire a leader. In the same way I ended up managing communications, a third of product, and growth & internationalization.

When a company is in hypergrowth, you want to leverage the momentum and growth. It’s okay to slap on these Band-Aids when a company is in that phase. But the key thing to keep in mind is that you need to be able to hire quickly so those Band-Aids are replaced by people who can actually grow solutions that will scale.

“When a company is in hypergrowth, you want to leverage the momentum and growth. It’s okay to slap on these Band-Aids when a company is in that phase.”

– Ruchi Sanghvi

Elad: What you’re describing is a little bit like what we saw at Twitter. The Band- Aid role was filled between me and Ali Rowghani. The CEO would delegate something to one of us, then we would step in, build out a function, help hire an executive. Then move on to the next function.

You mentioned that prioritization is one key to being successful in that kind of role, and really prioritizing hiring the executives to eventually run teams. What else do you think is key to the success of the gap-filler role? What sort of relationship does that person need to have with the CEO, and with other executives? How should they function in the org, and how should they be empowered?

Ruchi: It’s probably easier to work our way backwards. The person who is playing the gap-filler role is in a unique position where they are tasked with scaling the team and making decisions to help move the team forward. But at the same, you don’t want to push it too far in any one direction because you want to hire the right executive who can come in and bring their people, set the trajectory, and take over. It’s a delicate balance, where you’re not setting big goals and taking the team full steam ahead but you are waiting for the right executive to come on board to do that.

To be successful, you need to have the trust and respect of the CEO and executive team. You can’t manage these teams and run the hiring process yourself. In order to scale, you need the other executives to step in and/or loan you people from their teams. It’s just as important to set expectations about how the team fits in with the company’s overall goals and priorities. And lastly, it’s important for the other executives to recognize the contributions the gap-filler is making.

The second thing—and these are mistakes that I know I made at Dropbox, and other people may have seen other places as well—is that when looking for the permanent replacement/executive, you need to focus on the present and what you need in the next two years. Otherwise you end up chasing unicorns, people who can get their hands dirty, build a team and manage a team of 100 five years from now. Sadly, unicorns just don’t exit.

As a gap-filler you need to be able to convince the CEO and other executives that it’s okay to hire different types of people with different experience levels at different points in time. That’s pretty critical, because as a gap-filler, you end up sourcing candidates, setting up the interview slate, moderating the debriefs, and making a case for the types of candidates that you’re bringing in.

Elad: What do you view as the biggest failure modes in terms of successfully hiring executives to take over these functions?

Ruchi: When companies are in startup mode they don’t prioritize orgs like communications, people operations, marketing, etc. As a result you tend to Band-Aid or gap-fill these functions that aren’t core in the early days. As a gap-filler, if you’re doing a reasonable job at the function, the company doesn’t find it necessary to move fast on hiring the permanent executive or building the right foundations for the teams. They aren’t prioritizing the search and willing to spend longer than usual to find the right person.

“When companies are in startup mode they don’t prioritize orgs like communications, people operations, marketing, etc. As a result you tend to Band-Aid or gap-fill these functions that aren’t core in the early days.”

– Ruchi Sanghvi

The biggest failure mode, is not setting the right expectations. Not just with the CEO but also with people who the executive will end up managing. The gap-filler is able to operate because of trust they’ve built up in the organization, the organizational lines for the new execute will not be the same and aren’t clear. To avoid a mismatch in expectation on both sides it’s important to answer questions like: What is the role definition and extent of their responsibility? What kind of experience do they need? Will they report into the CEO?

Elad: To your point, almost definitionally, the fact that this role wasn’t filled with an exec suggests that for a period of time, it perhaps rightly wasn’t the single most important thing on the company’s road map. You’re trying to get to product/ market fit, you’re trying to get distribution. And then suddenly the company starts working, and the company itself becomes more of the product. Then you have an organization that doesn’t know how to value the role, or how to search for the person who could fill it even if they do value it. So it sounds like being that bridge really is helpful.

How can the CEO be most helpful? What sort of characteristics should they look for in that person? And what are the two or three key things they can do to support them in their work?

Ruchi: The person needs to be deeply respected within the company and have cred, with both early employees and the current executive team. Without that credibility and trust, it’s difficult to collaborate with different teams in different capacities and be culturally accepted and not rejected.

In terms of support, the only places I’ve seen this operate successfully is when the person is part of the executive team and reports into the CEO or COO. It allows them to surface resource constraints, ask for support, highlight successes, etc. They can influence hiring decisions and also expedite hiring decisions.

Elad: So, just for example, reporting to the CEO, having regular 1:1s with them, all that kind of stuff.

Ruchi: Exactly—or reporting into the founder.

I would also add that don’t be afraid to have someone play the role of the Wolf. It’s inevitable, and it is better for the CEO to delegate this than take it on themselves, because it’s not the most leveraged use of their time.

Elad: How do you know when you no longer need this role? Or when should you no longer need the role? Is it a certain critical mass of executives? Is it a certain size of company? When is it too late to have somebody in this kind of capacity?

Ruchi: If someone is playing this role for more than two or two-and-a-half years, it’s already been way too long. If the gap-filler is doing a reasonable job of Band-Aiding then it’s usually difficult to replace them. That’s when it’s suboptimal, because all you’re doing is locally maximizing and not globally maximizing.

Elad: When you say that two- or two-and-a-half years is too long, is that because by that point you should have built out a functional executive team across all the different areas? What’s the driver for that time frame in your mind?

Ruchi: By two- to two-and-a-half years, you should have a functional executive team built out in all areas. You need to build out these functions to support your product development, your business, and hiring and scaling your company.

Elad: So for this Band-Aid person, what are the functions that you’ve found them filling in for most frequently at the different companies you’ve seen?

Ruchi: Recruiting, HR, comms, marketing. Sometimes customer support and occasionally product. The VP of product is really difficult to hire for, since it’s usually filled by the CEO themselves. So it usually takes longer to be able to find the right person for the role.

Elad: And then, as companies start opening up international or other things, do you think executives in their own functions should hire somebody who’s effectively playing this role for that function? Or do you think it’s really only at the top level that it’s needed?

Ruchi: I believe it’s only needed at the top level. When you open up international offices, the main reason is to expand sales. And then over time, to become more cost-effective, you’ll want to build out customer support and other functions. To scale operationally, I believe you need a different set of resources.

Elad: And do you think every company will need this role? Or do you think it really depends on the experience of the executive team?

Ruchi: I think every company that hits—I hate using these words—but every company that hits exponential growth needs this. While it looks like rapidly scaling companies have everything figured out, internally it’s chaos because they are growing so fast. And it’s difficult to plan for chaos which is why I think every company will need this role.

Elad: I think you’re touching on a key point, which a lot of people don’t understand: As companies really start scaling rapidly, from an external perception everybody thinks that things must be going great because it’s growing so fast. But typically, internally it’s chaos. Or slightly organized chaos.

So how should employees, middle managers, individual contributors, director-​level people be viewing their roles at that moment? And how should they be navigating them, given that there’s so much change and so much churn?

Ruchi: When companies rapidly start scaling, I’ve observed the following things:

First, everyone’s workload increases 2–5X. People are scrambling to plug the holes and end up doing a lot of different things.

Second, you start hiring quickly. You think that’s going to solve things but your workload only increases. Because you are doing more not less with more people. You are taking on projects you could not get to.

Third, as you onboard new people to fill out the organization and the org reaches some sort of equilibrium, your role and its scope suddenly becomes narrow. And I think this phase is really difficult for early employees especially, who acceded during the exponential growth phase.

The people who deal with that—the people who deal with the role definition becoming narrower and more focused and are able to faithfully transition through that—are the ones that grow with the company.

Elad: In other words, they succeed while other early employees will be more likely to churn out because they’re not dealing with it well?

Ruchi: Exactly. They’re not scaling the way the company needs them to scale.

Elad: One piece of advice I give employees at these types of companies is don’t sweat it too much. Because every six months, if your company’s doubling, it’s a different company. So if your peer is suddenly your manager, it’s possible in a year you’ll suddenly be their manager’s manager. So as long as you just keep your head down and do good work, things tend to work out. Because it’s growing so fast that if you joined early you tend to be in pretty good shape.

Ruchi: I completely agree with that. Every six months, the company will grow and look completely different. Whatever systems and processes you’re putting in place, you have to be mentally prepared to change them. And all that time you invested in coming up with the perfect process, well, you are going to have to do it again.

Elad: Are there any specific, simple processes or other things that you think are often lacking that people should put in place, from a project elements perspective, an HR/recruiting perspective, etc.? Or is that its own giant hairball to unwind?

Ruchi: I think it’s its own giant discussion. In the beginning, be cautious about putting too much process in place. But when it is needed, don’t be afraid to implement it.

At Facebook, early on, we hired a bunch of “adults” and I was definitely one of those kids that was thinking, “We don’t need to be managed.” I pushed back against all forms of process. And then at Dropbox I ended up being the adult who was brought in to implement process. Now I appreciate both sides of the narrative.

So don’t overdo it when you don’t need it. But when you need it, don’t be afraid to implement it. And then anticipate it’s going to change, and don’t get frustrated.

Elad: If you were to go back in time and give yourself advice while you were still at Facebook—you were a very early employee, very influential in the organization— what piece of advice would you give yourself?

Ruchi: As the company grows and the organization scales, your role within the organization will change. It will become a lot narrower and more focused and this frustrates most early employees. But that doesn’t mean you’re having less impact, you are probably having a larger impact in a more focused area. So, you’re right, if you’re just heads down and do a really good job and you can scale through that, you’ll end up scaling gracefully along with the company.

Don’t look for the perfect person for the job for the next 10 years, the unicorn. The company is changing so quickly that you only know what you need now. So, look for people who are perfect for the next three years.

Elad: Any last thoughts you want to add about the Band-Aid?

Ruchi: As with all Band-Aids, you’ve eventually got to just rip it off. People get comfortable with Band-Aids and if the person is doing the job well it actually deters from hiring a permanent replacement. If you have someone subbing for roles like head of product or VP of communications for more than a year, the only way to force yourself and the team to make trade-offs and decisions to hire a permanent replacement would be to just rip off the Band-Aid. In other words, remove the gap-filler, the Wolf—however you want to refer to them—from the role so you’re forced to build out the organization the right way.

I imagine that you had the same experience at Twitter.

Elad: Yes, Twitter was similar. To your point, I think the key is really building out the executive branch so that you fill out those roles. Because ultimately, without key leaders in place you’re just never going to be able to scale the organization. I always view it as the organizational scaffolding on which you build the rest of the team. And building up scaffolding early is often something that founders miss. Then things start scaling and everything starts breaking.

If they had the experience to think 6, 12 months ahead, or even 18 months ahead, they’d start hiring with the idea that it’s going to take three to six months to find a good executive. That person will then take a couple months to build out their team. Their team will then take a couple months to ramp. So in some sense, you really need a year runway to be able to start building out the organization you need for the future. So it does take a bit of time.

It’s always interesting to see people play these roles. Matt Cohler did it at Facebook, you did it at Dropbox, and I did it at Twitter, and I think we probably have some overlapping experiences.

Ruchi: I think people call the role the Wolf. Have you seen the movie?

Elad: That’s funny. Yeah, from Pulp Fiction. 

Ruchi: People used to call me the Wolf at Dropbox.

Elad: We always called it the fixer or the gap-filler. But the Wolf sounds more badass, so I think we should just adopt it. That should be the name of this interview, “Bringing in the Wolf.”

Ruchi: I had mentioned this, but usually the person comes from within the organization. It’s pretty hard to hire someone for this role. If you actually find someone you trust enough, then you should make them your COO.

Elad: You need somebody who has the organization’s trust and credibility, and has a strong relationship to the CEO and/or founders. And so you need somebody who’s either been there very early or alternatively somebody who’s acquired that the CEO or the founders knew from before. Because otherwise it’s basically impossible to do.

Ruchi: Exactly.


This interview has been edited and condensed for clarity.