In this episode of the groCTO by typo Podcast, host Kovid Batra speaks with Sheeya Gem, Director of Engineering and Product Strategy at ShareFile, about her experiences leading dev teams through mergers and acquisitions.
Sheeya discusses the importance of building collaborative relationships with stakeholders, maintaining effective communication, and fostering a shared purpose among teams. She emphasizes the significance of continuous learning, adaptability, and leveraging tools and processes to keep projects on track. The conversation also touches on managing cultural transitions, supporting teams through change, and ensuring successful integration post-acquisition. Finally, Sheeya shares valuable parting advice for engineering leaders, promoting trust, shared purpose & continuous learning.
Kovid Batra: Hi everyone. This is Kovid, back with another episode of the groCTO by typo podcast. Today with us, we have a special guest who has 20+ years of engineering and leadership experience. She’s not just a tech leader, but also an innovator, a business-minded person, which is a rare combination to find. Welcome to the show, Sheeya.
Sheeya Gem: Hi, Kovid. Thank you for inviting me. It’s a pleasure to join you today.
Kovid Batra: The pleasure is all ours. So Sheeya, guys, uh, let me introduce her a little bit more. Uh, she’s the Director of Engineering and Product Strategy at ShareFile. So ShareFile is a startup that was acquired by Progress from Citrix and, uh, the journey, uh, I was talking to Sheeya, was really interesting and that’s when we thought that we should conduct a podcast and talk about this, uh, merger and acquisition journey that she has gone through and talking about her leadership experiences. So today, uh, the, the main section would be around leading dev teams through mergers and acquisitions, and, uh, Sheeya would be taking us through that. But before we jump onto that section, uh, Sheeya, I think it’s a ritual. This is a surprise for you. Uh, so we get to know our guests a little more, uh, by knowing something which is deep down in their memory lane from their childhood or from their teenage, uh, that defines them today. So give us an introduction of yourself and some of those experiences from your childhood or teenage that define who you are today.
Sheeya Gem: Oh, you got me here. Uh, um, so my name is Sheeya Gem and, um, I am, I, I’m from Bangalore and, uh, grew up in Bangalore. This was when Bangalore was, was, was much smaller. Um, it was, uh, it was considered a retirees paradise back then. And, uh, growing up, my mom was a very strong, um, mentor and, and, and, and a figure in my life. She’d read to me when I was very young. Um, lots of stories, lots of novels, lots of books. So she was an English Lit major. And so, so she’d have all these plays. So I grew up listening to Shakespearean plays. Um, and, uh, one of the books that she’d read and it still sticks with me, and, and actually there’s, I actually have a little frame of this at this time. And it says, “She believed she could, so she did.” And it’s powerful. It’s powerful. Um, I’m sorry. I lost her a few years ago. And, uh, it’s, it’s defined me. It’s a big part of who I am, um, because at every stage in your life, and, and this has been true for me, um, at every stage I have challenged myself, and it’s, it’s my mom. It’s that voice. It says, “You can do what you need to do because you believe in it and you know it’s going to be true.”
Kovid Batra: I’m sorry for your loss, but I think she would be resting in peace and would be happy to see you where you are today and how she has inspired you to be who you are today. Uh.
Sheeya Gem: Thank you. Thank you.
Kovid Batra: All right, Sheeya. Thank you so much for sharing that and it means a lot. Uh, on that note, I think we can move on to the main section. Uh, yeah. Uh, so I think, uh, your journey at, at Progress ShareFile, uh, starts from the acquisition part, right? Uh, so tell us about how, how this acquisition happened and, uh, how things went at that time, some stories that would be, uh, lessons for the engineering leaders and engineering managers sitting out there listening to this.
Sheeya Gem: Yeah. Yeah. Um, so for most leaders who are part of an acquisition, you kind of are part of the conversations as you lead up to the, to the acquisition. And for ShareFile, this journey really started a few years ago. I’m just going to really quickly go through ShareFile’s story. ShareFile is a startup from Raleigh, North Carolina. Um, and it’s, it started up in the early 2000s and was bought by Citrix in 2012 and was part of the Citrix suite of products for, uh, for about 10 years, 10–12 years. And at that time, um, uh, a private equity group called Cloud Software Group acquired Citrix and as part of their portfolio, they have several other products as well. And that’s when ShareFile’s really acquisition journey started and as part of our strategy, ShareFile decided to go back to its roots and the roots of ShareFile was a vertical market strategy. And so for the past 2–3 years, um, and, and this was a fantastic ride because we got to innovate at a scale that we never could. CSG gave us the backing and the financing, the funding and the support and ShareFile had the right amount of talent to make things happen. As leadership, we knew that an acquisition was going to be our, our exit. So we were aware of that and we were very transparent with our, with our entire teams, everybody knew that an acquisition was on the radar. And as such, when Progress started talking to us, um, and ShareFile started sharing our financials, you know, how we do our business and all of those things, we, we knew it was, it was coming. So as such as leaders, you’re part of the journey that makes a successful exit. So the acquisition was a successful exit for us. And then it also starts the next part of your journey where you’re now with a company that has acquired you because they believe in your fundamentals, they believe in your team; and as leadership, it becomes important for us to make sure that that transition is successful and that merger goes as it needs to go.
Kovid Batra: So when you joined, uh, Progress, this was basically a new team coming into an existing company and that experience itself could be a little overwhelming. I haven’t gone through any such, uh, experience in my life, but I can just imagine and trying to relate here. That can be a little overwhelming because the culture completely changes. Um, you are in a setup where people know you, there is defined leadership which you are a part of, you’re part of the overall strategy and then defining, giving directions. But suddenly when you move here, things can change a lot culturally, as well as in terms of the goals and, uh, how things operate. So when this happened with you, was this an overwhelming experience or it came easily? And in either of the cases, how you handled it?
Sheeya Gem: Uh, was it an overwhelming experience? Um, not necessarily. It is an experience. It is different. And, and most humans coping with change and dealing with change is, is hard. And, um, and I think it’s important to recognize that different people are going to handle that change differently. And in many ways, it actually is almost the grieving of the loss of one thing before moving to the next thing, and as leaders, it’s important to make room for that, to give people a chance to, to absorb the change that’s happening, but to continue to be there to support, to provide that clarity, be transparent in what’s happening, where we’re going, and, and just knowing that, you know, some people are probably going to bounce right back. The two days they’re back, they’re okay. And some people are going, it’s going to take longer. It’s, it’s almost like those seven stages of grieving, uh, you know, and to make room for that and to know that, that kind of change from what was, people were comfortable with that, people probably excelled in that, going through the uncertainty of what is to come is a normal human reaction, and I think that’s where leaders shine, to know that this is a normal human reaction. I recognize it. I respect it. And I’m here for you when, when you’re ready to move to the next step.
Kovid Batra: Makes sense. So when you moved here, what exactly was your first initiative or what was that major initiative that you took up after moving in here that made you, uh, put down your feet and get back to work and outshine that, uh, outshine that particular initiative?
Sheeya Gem: Um, are you talking about post-acquisition, the steps that we took? Is that what you’re thinking about? Okay. So, all right. So maybe I could frame it this way. A company exists pre-acquisition. It has a set of goals. There’s a vision. There’s a strategy, right? Everybody is comfortable with it. You’re probably talking about it in your all-hands, in your small group meetings and every leadership meeting that you have in any kind of ‘ask me anything’. The leadership team is talking about what you’re saying. This is our vision. This is our goal. This is the strategy. Once the acquisition happens, you’re now looking at the goal, strategy, and vision of the new company. Now, likely they’re related because there was a reason that the acquiring company went ahead and bought this company. There’s a relationship there, but there’s also likely things that are going to be different. As an example, it’s possible, in our case, this is the situation, Progress has a heavy enterprise footprint. And so some of the strategy and goals are going to be a little different compared to, um, an SMB market where ShareFile continued to, uh, to excel. So, but are there commonalities? Yes. And, and I think this is where, again, leadership comes in where we say, “Hey, this is what we were pursuing. This continues to be our plan and our strategy. This is where ShareFile, Progress’ strategy comes in and in order to manage the transition and have success on both sides, we talk about what needs to happen next. And often what happens is in a mature acquisition, and this is often the case, there is a, there is, there’s plenty of time for companies to say, “Okay, I’m slowly going to bring in the new set of goals that we need to work towards.” Some companies don’t change at all. As an example, when IBM acquired Red Hat, for five years, Red Hat did what they always did. There was no change. Eventually, right, the goal started shifting and changing to align more with IBMs. So different companies have different trajectories. However, what’s common, what needs to happen is communication. Leaders need to be talking to their teams all the time, because without the communication, this is where that uncertainty creeps in. People don’t have the answers, so they start looking for answers and those answers may not be right. So at this time for leadership, it’s important to double down and say, “This is our strategy. This is a strategy for Progress. This is a transition plan to move towards a new strategy. Or it could be that for the next six months, guys, it is business as usual. We’re going to continue with our existing strategy. And over time, we’ll start bringing in aspects of the, of the acquiring company strategy.” So key thing here, support your teams, keep communicating.
Kovid Batra: So at that, during that phase, uh, what was your routine like? Every, uh, board meeting you had, after that, or every leadership meeting you had, you used to gather your team, communicate the things that you had with them, or you waited for a little while, uh, thought through things, how it should be put to your team? Because it’s, it’s a question of, uh, how you communicate it to your teams, because you understand them better, in what state they are, how they’re going to perceive it. So I’m just looking for some actionable here.
Sheeya Gem: Yeah.
Kovid Batra: Like how exactly you did that communication because having that communication definitely seems to be the key here. But how exactly it needs to be done? I want to know that.
Sheeya Gem: Yeah, yeah, you actually almost answered the question here. Uh, so you’re 100% right, right? You don’t necessarily come out and throw little bits of information here and there because that’s not a coherent strategy. Yes, the leadership is continuing to meet and it’s okay to tell your teams that the leadership, leadership teams are continuing to meet and are working through this. But yes, eventually, when we are in a place where we have a handle on how we’re going to do things, that’s when the communication comes up. Like I said, it’s important for teams to know, yes, we’re working with you, we’re thinking through things and then set a clear date, call the meetings, it’s usually like an all-hands kind of situation and then plenty of time for Q&A, gather your teams and present in a format that’s, that’s most comfortable for that culture. And, and sometimes it’s, it’s an ‘ask me anything’ kind of format. Sometimes it’s a chat by the fire kind of, kind of informal thing. And sometimes, and we actually did this year. We did an all-hands, had plenty of time for Q&A, and that evening we took our teams to the closest hangout place that we have. We usually gather there Thursday evenings for beer, and leadership was there and we answered questions. It was an informal setting and sometimes it’s important to, to, you know, go to a location that’s not your usual place of work. So a good restaurant, um, a place where you can maybe just, just chill a little bit, right? And, and, and have those conversations and there you’re able to meet people where they are and then connect with them on that 1-on-1 level and, and maybe answer questions a little bit more deeply.
Kovid Batra: One thing if I have to ask you, which you think you could have done better during that phase, uh, would be?
Sheeya Gem: What could I have done better? Um, it’d be terrible to say we got everything right. Uh, so here’s the thing. No matter how well you manage this, because remember I said that everybody’s going to go through those different stages of change, you will always see people where somebody is, is more agitated, feeling a little bit more anxious than other, right? And, and by, just by the reality of communications, where we say, “Okay, a month from now, we’re going to address this.” There are some people who are going to hit that stage of ‘I need to know now’ two weeks before that. And in that situation, it’s hard, but maybe what people can do is if you’re close enough to that, to be able to just reassure people a little bit more. Um, I think that’s something that, that I certainly could have done a little bit more of, but it’s also one of the situations where you’re kind of like weighing it. How much do I, should I be talking about this where not everything is clear and how much should I just hold? Um, so, so there is that balanced conversation that happens.
Kovid Batra: And in that situation, do you think is it okay to come out and say that I am in a phase where even I am processing the information? More like being vulnerable, I would say. Not exactly vulnerable, but saying that we are in a phase where we are processing things. I don’t want to say anything which, uh, maybe makes you more anxious instead of giving you more certainty at this phase. So making statements like this as a leader, is it okay?
Sheeya Gem: I think it is. I think it’s important to your point. Vulnerability is key where you trust your teams and you’re expecting them to trust you. So showing that vulnerable side, uh, builds empathy and helps people, uh, relate to you more. Um, what I would be careful though is some people could perceive that differently. Oh, leadership doesn’t have all the answers. So yeah, know your audience, know your audience.
Kovid Batra: Makes sense. Yeah, all right. I think, uh, this was really interesting. Anything, uh, Sheeya, uh, that you think had really driven you and made you who you are as an engineering leader in your whole career, not just at ShareFile, but in general I’m asking, what are those few principles or frameworks that have really worked out for you as a good leader?
Sheeya Gem: Yeah, um, I think it’s learning. For me, I, I have this desire to learn and, um, and I believe that no matter a situation, right, you can have a good situation or you could have a bad situation. No matter the situation, though, where you win is learning, learning from the situation, no matter what that situation is. So when you exit that situation, you have learned, you are a better person because you have learned from that situation. So, so that’s, that’s a big takeaway for me and, and something that, that I, maybe your audience will enjoy and that is for humans, you know, there are some things that are going to go really, really well and some things that are going to be downright awful and I think that’s life. But in each of these situations of the mindset is, “Hey, I’m put in a situation that I haven’t dealt with before. What can I take away from this?” You exit that situation as a winner, no matter what the situation was. And I’ve applied that through my life where, um, I’ve, I’ve, I’ve had the, uh, the good luck to work at some fantastic companies and, and be mentored by, by amazing people, um, from Etrade to eBay, uh, Citrix, several companies along the way. And at each of them, uh, when I changed jobs, I went into a job that was just a little different from what I did, and it kind of like opened up things for me. Um, and it helps you learn. So that would be a good takeaway where every time you go into something, try something just a little different. Uh, it changes your perspective. It, it builds empathy. When you do a little bit of marketing, you now have empathy for your marketing department a little bit more. When you do a little bit of work that, that’s not just pure engineering, it helps you see things in a different light and gives you a different perspective.
Kovid Batra: Touching on the marketing bit. I think, uh, the last time when we were talking, you mentioned that you have this urge, you have this curiosity all the time, and I think it’s driven from the same fact, learning, that you work with different teams to understand them more. So do you have any experience, like very specific experience where you had a chat with a sales guy or a marketing team person that led you to build something, like engineer something and build something for the customers?
Sheeya Gem: Yeah, yeah. Uh, that’s a good topic. Um, a part of leadership is besides guiding your teams, it’s about the collaborative relationships you build with other stakeholders. And a lot of people, when we hear the word ‘stakeholder’, we kind of like mentally take a step back. But what if we consider all of those stakeholders, people who are in that journey together with us? Because ultimately, that’s why they’re here. Um, it’s to be successful. And to define success in a way that resonates with each person is the concept of building collaborative relationships. It goes to the heart of shared purpose. Um, so as we were building some new innovative products, um, and, and I, ShareFile is a tech company and which means the product is tech. Who knows more about the product and the tech than the engineers who are building it, right? They are the builders However, all of the other stakeholders that we’re talking about are instrumental to making the product successful. That’s why they’re all here. So for me, it started becoming a case of saying that “Hey, we have uncovered this new way to do something and we believe there is an audience for this. There is a market for this.” Then the first set of people that we start talking to is being able to work with product management to say, “ What do you see? What have you seen in the field? You’re talking to customers all the time.” And it becomes, starts becoming this, this little bit of a cycle where they feed information to you and you’re feeding information back and it’s a loop. It’s, it’s becoming this loop that’s continuing to build and continuing to grow. Um, so there is a, there’s a fantastic book. Um, I think it’s called ‘Good to Great’. Um, and in that the author talks about the flywheel effect and that’s exactly what this is. So as you’re talking to product and you’re building that, that, that coherent thought of, “Okay, I have something here. I may have something really, really big.” The next step is talking to sales because sales tends to be the biggest cheerleader of the product in the market. They’re selling. This is their whole goal. They are your cheerleaders. And so then the next step of building that relationship with sales and saying, “Hey guys, what are you seeing? If I were to build something like this, what do you see, um, in the way it plays out in the market?” And you put that early version of the product in front of sales. Give them a prototype. Ask them to play with it. And most companies don’t tend to do this because sometimes there are walls, sometimes there’s a little bit of a, does sales really want to look at my prototype? They do, because that’s how they know what’s coming next. You’re opening that channel up, right? Similarly with marketing, to be able to say, I have something here. Do you think we could do some marketing spend to move this forward? And just like that you’ve built shared purpose because you’ve defined what success looks like for each group.
Kovid Batra: Right. That’s really interesting. And the, the last word ‘shared purpose’, I think that brings in more, uh, enthusiasm and excitement in individuals to actually contribute towards the same thing as you’re doing. And on that note, I, I think, uh, I would love to know something from you about how you have been bringing this shared purpose, particularly in the engineering team. So just now you mentioned that there could be, uh, walls which would prevent you from bringing out that prototype to the sales team, right? So in that exact situation, uh, what, what way do you think would work for teams, uh, and the leaders who are leading, let’s say, a group of, let’s say, 20 folks? I’m sure you’re leading a bigger team, but I’m just taking an example here that how do you take out that time, take out that bandwidth, uh, with the engineering team to work on the prototype? Because I’m sure the teams are always overloaded, right? They would always have the next feature to roll out. They would always have the next tech debt to solve, right? So how do you make sure that this feeling of shared purpose comes in and then people execute regardless of those barriers or how to overcome those barriers?
Sheeya Gem: Yes. Um, to have something like shared purpose work, you absolutely need the backing of your entire leadership org. And I’ve been very, very lucky to have that. Uh, from the Chief Product Officer to the CEO, to the Chief Technology Officer, we were aligned on this, completely and totally aligned on this. And so what this translate then, translates to then is investments, right? You talked about tech debt and how teams are always loaded, but if your entire leadership team is bought into that vision, then the way you set the investment profile itself is different, where you might say that, you know, half of the org is going to totally and completely focus on innovation. We are going to build this. Right. Then you have that, that organizational support. Now as leadership, as we are building that, when you start talking to your teams about the level of organizational support that you have, and remember, engineers want to build things that are successful with customers. Nobody wants to build something and put it on a shelf in their house. They want it on the market. That is the excitement of engineering. So to then be able to say that, “Hey! We believe in this. Our leadership believes in this. Our stakeholders are excited about this.” It’s the kind of excitement and adrenaline adrenaline pump that happens that nothing else gives that cheer. And that’s what we saw happen with our teams, that getting behind a vision, making that strategy your own, knowing that you are a key contributor to that success of the product and hence the success of the org, that is a vision that sustains and feeds itself. And, and that’s what we were able to build. Um, that’s something that I made the time for every day. You talk to your teams, you connect with your teams, you’re talking to your engineering managers, you’re talking to the principal engineers, and every time there is, there is concern, and there will be many, many concerns along the way, and I’m not going to have all the answers. That’s normal. I should not have all the answers, because if I have all the answers, then the thinking is limited to the max of my thinking, and a group’s thinking is always greater, right? The sum of that group’s thinking is always greater than any one individual’s thinking. So then it starts becoming a case of, this is the problem that we’re trying to solve. How best would we solve it? And when you put it in front of the brightest people in the room, the answers that you get to that problem, the solutions that you get, breaks through every bound that you can see.
Kovid Batra: So do you usually practice this? Like, uh, every week you have a meeting with your team and there are some folks who are actually working on the innovation piece or maybe not every week, maybe in a month? I, I am not sure about the cadets, but in general, what’s the practice like? How, how do you exactly make sure that that is happening and people are on track?
Sheeya Gem: Yeah, we actually meet every week and then any number of informal conversations throughout the day, right? You run into someone in the elevator, you have two minute conversation. You run into someone in the hallway, you have a two minute conversation. But yes, as leadership, we meet, uh, every week. And when I say leadership, and this is where my definition of leadership may be different from maybe some parts, some others. And, and, and to me, leadership is not just a title that’s given to someone. A lot of people think that one year, once you’re a manager, you’re a leader. The truth of it is, you’re going to see leaders in engineers, people who think differently, people who, um, who can drive something to success, people who can stand behind something because they know that area and know what to do next. They’re all leaders. So in my leadership meeting, I actually have a mix of engineering managers. I have principal engineers. I even have some, a couple of junior team leads because they are that good. And that group meets every week. And we talk about the biggest problems that we have and it becomes a group problem solving effort. We draw action items from that and then smaller groups form from there, solve, come back to the meeting next week and they talk about how they are, how they are going about it. So it is very much a team environment and a team success, um, metric the way we go behind things.
Kovid Batra: Makes sense. Um, one last thing that I would want to touch upon is that when you are doing all these communication, when you are making sure you’re learning, your team is having a shared purpose, everyone is driven towards the same goal, one thing that I feel is it is important to see how teams are moving, how teams are doing on different parameters, like how fast they’re moving, how good quality code is being produced there. And you mentioned, like you lead a team of almost a hundred people where there are few engineering managers and then engineers out there. As a Director of Engineering, there is no direct visibility into what exactly is happening on the ground. How do you ensure that piece, uh, in your position right now that everything which you think is important and critical, uh, is, is there, is on the tack on the track?
Sheeya Gem: Yeah, yeah, this is where tools come in. Also, very clear processes. Um, my recommendation is to keep the processes very lightweight because you don’t want people to be caught up in the administration of that process. But things like your hygiene, it’s important. You closed a story, close the story, right? Or let us know if you need help. Uh, so that becomes important. Um, there are lots of project management tools that are available on the market. Um, and again, like I said, lightweight, clear process. Uh, the ability to be able to, um, demonstrate work in progress, things like that. And that’s something else that we have. Um, we have this practice called show, tell and align and, um, we meet every week and this is all of engineering, and just like the title says, you show whatever you’ve got. And if you’re not in a position to show, you can talk about what you’ve got. And the purpose of it is to drive alignment and it’s, it’s, it’s an amazing meeting and we have a fantastic manager who runs that meeting. There’s a lot of energy there and we have no rules about what you can show or where you can show it. You know, some, some, some companies have rules like, oh, it needs to be in production for you to do. No, no, no, I want to see it if it’s on your dev laptop. I want to see it. Your team leads to want to see it. Uh, so we keep it very, very easy. And in that meeting, every senior leader who attends that meeting is encouraged to come in as an engineer and as an engineer only. Uh, they’re supposed to leave their titles at the door. It’s, it’s, it’s, it’s, it’s a challenge. It’s a challenge, but no one can come in and say, “Hey, I didn’t approve that!” Because you’re coming to this meeting as an engineer, which means if, if, and sometimes we’ve had, you know, directors and VPs who have something to share because they’re able to leave the title at the door. Uh, so it’s, it’s been a great practice for us, this ability to, to show our work in progress. Um, “Oh, look, I got this done.” Uh, “Here’s a little notification tab that I was able to build in three days. I’m going to show this to the team.” Or, or “Here’s a new framework that I’m thinking about and I found this. I’m going to show this to the team.” Uh, so this is a regular practice, um, at ShareFile and now at Progress.
Kovid Batra: Perfect. Perfect. Great, Sheeya. I think, uh, this was a really, really interesting talk, uh, learning about communication, learning about learning all the time, having a shared purpose. Show, tell, and align, that was interesting on the last piece. So I think with this, uh, we, we come to the end of this episode. It was really, really nice to have you here and we would love to have you again. Is there any parting advice for our audience that you would like to share? Uh, most of us are like engineering managers, aspiring engineering leaders or engineering leaders. If you would like to share, please go ahead.
Sheeya Gem: Um, we covered a lot of topics today, didn’t we? Um..
Kovid Batra: Yeah.
Sheeya Gem: Uh, what do I have for our, um, for our engineering managers? Trust your teams, but trust and verify. Um, and this is where, you know, some of the things we talked about, things like OKRs, things about lightweight process comes in. Trust, but verify. That’s important. Uh, the second part of it is shared purpose. You want to build that across your, not just your teams, but all of the stakeholders that you’re interacting with. So people are driving in the same direction, uh, and we’re all moving towards the same success and the same set of goals and every opportunity is a learning opportunity.
Kovid Batra: Great! Thank you, Sheeya. Thank you so much once again. Great to have you today.
Sheeya Gem: It was a pleasure. Thank you for inviting me on your show.
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