Corporate VP, Global Operations at Proofpoint
Impactful Engineer shares the stories and journeys of women and men who are making significant impact in the software industry. The purpose of Impactful Engineer is to inspire young software engineers to see that are many paths they can take to move forward in their careers and grow their impact wherever they work.
Interviewed by Tony Tam
Editing by Hunter Shen
Reading Time: 24 minutes
Artwork by Cate Tam
TT: Where do you currently work and what is your role within the company? Also what is the scope of impact that you have within your organization?
LC: I work for a cybersecurity company called Proofpoint, a leading provider of security solutions to our customers. I’m the Corporate Vice President of Global Operations. Proofpoint Operations includes our NOC (network operations), our network team, the data center, and data center technicians. We have engineers who are responsible for core infrastructure and then we have DevOps engineers who are responsible for product infrastructure—the applications that are running on our core infrastructure. Operations at Proofpoint also include the CapEx (Capital & Expenditures) responsibilities for the company. I’m also responsible for our compliance, both our own as well as the compliance guidelines of our customers. For example, we have a large number of financial institutions that use our products and they have compliance requirements that we need to meet as a vendor. I’m also responsible for our security team, our information security, and the application security for the company. I’ve been here for almost four years. I report to our CEO who is someone that I’ve worked with twice previously over my career. I have a phenomenal team and I work for a phenomenal company.
TT: That a fantastic summary. I looked through your profile and at your college degree. It was the first time I looked at it. Your college degree was actually in English. It’s the same major that my daughter actually hopes to major in.
LC: Good for her!
You can look at someone’s technical skills and know that they are brilliant technically and maybe they’re even a good communicator. But when you start going up that vertical ladder for individual contributors and technology people, to be really good you have to be an influencer.
TT: It was surprising to me how you got here. Could you talk about your journey, and how you got into this part of the industry.
LC: Sure. I originally wanted to be a film critic. My goal was to become the next Pauline Kael. And so I got my degree in English and also studied a lot of film and film literature. But when I graduated from college, as you might have guessed, Pauline Kael’s job wasn’t available. And so I started working in the reinsurance industry. There was a technology aspect that I sort of fell into through selling a computer version of the product to other companies. That kind of morphed into a QA (Quality Assurance) function, which then finally morphed into Tech Pubs (technical publications). And so I became a tech writer and a manager of tech writers, which opened a door to Sybase. Sybase was looking to expand their database technology and they needed someone to start up a new Tech Pubs team. And so I left the insurance industry and went to work at Sybase and my CEO now was my VP then. As I got more responsibility at Sybase for more and more documentation, I got to know him pretty well and when he left Sybase to become the CEO of an early SaaS company, he brought me over to run a small business unit of services for our target market as well as tech pubs and QA.
What I found through that period was how much I liked working with engineers. I like how engineers think. It is very different from my own way of thinking. But I was really kind of looking to expand all the experience that I was getting in the various companies beyond working closely with engineers, so I started working directly with customers by going to another SaaS company where I managed account managers and first and second level support. And at that company was an Operations engineer that I knew who left there and went to Yahoo. And while he was at Yahoo he found that Yahoo Media was looking to expand its service engineering function. They were hiring a lot of service engineers and they needed to hire a handful of managers and so he convinced me that what I didn’t know about technology I could learn well enough to be a good people manager at Yahoo.
After getting into Yahoo, what I found was that my liking for working with engineers was in part due to my strong communication skills. I like the challenge of understanding the context, if not the code, and I’m able to synthesize information and deliver it to different kinds of audiences. And so because I was able to speak and write articulately, I got more responsibility at Yahoo and had some really good mentors at Yahoo who helped me further develop.
And those years at Yahoo brought me all the way back to a former VP who was the CEO at Proofpoint. At Yahoo, there was a period where we had some stability issues for a time. I was having lunch with a longtime friend who worked for the CEO at Proofpoint and he was telling me about their outages and I was telling him about my Yahoo outages. And he said “hey, why don’t you come to Proofpoint and help us improve our infrastructure.” And he pitched the idea to the CEO—and here I am. So I think it was not so much the aptitude for technology as much as the aptitude for working with technologists that got me to this place. The seven years at Yahoo and the four in the Proofpoint have absolutely been the most rewarding of my career.
There are two things that I tell people about meetings. First, I don’t care what your company culture is, shut your laptop, put your phone down and be present.
TT: I have a follow up on that question. We connected on LinkedIn and you say you are a strong supporter of women in tech. Do you feel like you’re an industry insider or because of your background do you feel like you’re an outsider? Are you able to look at the industry from an outsider’s viewpoint?
LC: It’s a really good question Tony. I think I have a foot in both worlds. I’ve been doing this now for more than 15 years if you aggregate the experience with working with tech companies. So I don’t feel like I’m an outsider. I’ve certainly had to develop my technical skills to be conversant as well as to understand a lot of the principles behind them. But I am still an outsider in the sense it’s not the technology; it’s that language and the words that we use—the way we express ourselves, the way that we write—is very very important to me. I’m always going to be an English major regardless of what I’m doing. My philosophy, which is a slight tangent from what you asked me, is if somebody hadn’t given me the job at Yahoo, I never would have found that I have affinity for operations and the kinds of things that we do in operations. And if I hadn’t had that opportunity, all of the things in my life that have happened over the last 15 years wouldn’t have happened. Because of that, I feel a tremendous amount of alignment to women in technology because I think a lot of times women have fewer opportunities. Whether or not there are reasons behind that, I don’t want to say.
But I literally also make opportunities for other people because I really do believe in paying it forward. So, to give you an example, the guy who was the project manager for remodeling my kitchen had a phenomenal customer-facing skill set. He also was able to balance about ten different subcontractors, deal with purchasing, deal with pricing, and deal with me as a customer—and I can be a little demanding. At the time, I was realizing that I needed to up-level the whole purchasing function within Proofpoint, from procurement all the way through to deployment into our data centers. And so I asked this guy who had been in construction his entire adult life, “Hey, do you want to give high tech a try?” He’s been with us now for almost three years. He gets recognized in quarterly meetings. All of the ops people and the engineers love him. He’s doing a phenomenal job and gets to spend more time with his family, and there’s zero physical labor. His whole life changed—and it wouldn’t have, if someone wasn’t willing to take a chance on him.
I brought another woman into the company who was one of my Account Managers and who took over the leadership for that team after I left my second SaaS company. I brought her in to first run the Operations program management office and then our Compliance team. She’s knocking it out of the park and utilizing all of her skills, but in a different function entirely. Everybody just needs a chance to show what they can do and trying to find those opportunities is my responsibility, whether for women specifically or people who want to further their career. That’s what I’m here for.
The difference between feeling like you are controlling your day or your day is controlling you is to consciously decide what you’re NOT going to do today. Try something for me. Make your list and then take 20 percent off the list. Just decide that you are not going to do this, this, this, and this today. .
TT: When I started the Impactful Engineer project, I wanted to interview an equal number of women and men. My original idea was to interview only individual contributors, not leaders in management. I thought I wanted to show the path forward for individual contributors. However, what I found was in our Senior Principal level, there were probably fewer women in IC roles than female VPs. It was incredible. I wonder if what you’re saying about opportunities is also true of our current senior level IC roles. Because senior ICs need peers to nominate and support them to get over an artificial wall, because we try to run pattern recognition to recognize if a person fits in a club.
LC: Right, for sure. I think some of it also has to do with the fact that to be a really good leader and to be a high performing individual contributor, you have to have pretty solid influencing skills. I think that because women at times may have fewer opportunities and potentially fewer mentors who are helping them develop some of those skills, they have the additional pressure of trying to grow their careers without the benefit of some of the coaching that men seem to get more directly.
You know, you can look at someone’s technical skills and know that they are brilliant technically and maybe they’re even a good communicator. But when you start going up that vertical ladder for individual contributors and technology people, to be really good you have to be an influencer. And so I think that it’s key for that skill set to be nurtured very early in both men and women.
But we may need to over-rotate a little bit on behalf of women so that we can catch up. While I think that Sheryl Sandberg sounds like a fantastic person, I think we’ve gone a little overboard on the whole Lean In movement; it’s become more of a catch phrase and now we’re all leaning in all the time. But there is more to it than that, and one of the things she said much earlier—it was quoted in her first New Yorker interview—was that if you offer an opportunity to a man that’s outside of his skill set, many men tend to say “sure, no problem,” even though they don’t know how to do whatever the thing is, whereas women tend more often to say “I don’t know how to do that” and hang back. From talking to people in my network, men and women, it seems to hold true very frequently.
If we were to spend more time with women early on, building awareness in how many of us think by default, and how to think differently, and how to develop our soft skills in addition to technical skills, we can do more. Because it seems for women that we need more than just influence; we also have to carve away at that notion that “I don’t know how to do that, therefore I can’t.”
Everything that you say to your manager is going through a filter. So if you’re one of those people who constantly brings a lot of negatives or challenges, your manager will come to expect that of you and see you as more negative.
TT: Do you have any tips about how you stay productive, how you protect your time while managing a large organization.
LC: I have one really good one that’s particularly relevant. The company that I was at prior to joining Yahoo was a small SaaS company and the CFO was a woman I admired greatly. My teams were all customer facing, and my entire day was interrupt-driven. Our customers were so sensitive to stability at the time that we had to over-communicate whenever the Ops team needed to apply patches or do anything in production that MIGHT be noticeable. And one of my responsibilities was to notify everybody every time we were going to make a change, which was just not a scalable way to run, and as a result, I was just constantly overwhelmed.
The CFO came by my office one day and said “You know, you look frazzled. What’s going on?” By the way, that’s the biggest thing I’m still working on because I still don’t do a good job keeping my face impassive. Anyway, I was telling her how overwhelmed I was feeling. She said “What’s your normal process?” And I said “Well my normal processes is that I get in super early when it’s quiet, I make a list of everything that I need to do, and then I attack the list.” And she said “OK, so, how’s that working for you?” I replied that I was never able to get to everything. And she said, “The difference between feeling like you are controlling your day or your day is controlling you is to consciously decide what you’re NOT going to do today. Try something for me. Make your list and then take 20 percent off the list. Just decide that you are not going to do this, this, this, and this today. I don’t care when you do it in your workflow—just practice consciously choosing not to do certain ‘must do’ things.” And it was the single best piece of coaching on how to not feel overwhelmed by aspects of a demanding job that I’ve ever received, and I’ve relied on it for years. And I find that it works so well, if I occasionally don’t manage to grab a little bit of quiet time and decide what I’m not going to do, I really do feel like I’m flailing a bit and I can’t lead effectively if I seem scatterbrained or distraught. I always try to make sure that I’m controlling all of my inbound, even the stuff that comes to me on the fly, and just say “You know what? I’m not going to do that today.” Eventually, it became largely subconscious, and that’s how I’ve managed to keep my sanity over the years.
A lot of the credit for mentoring has to go to people who cared enough about me to give me feedback in a way that I could absorb it. Because it took me several years to be able to absorb feedback with gratitude as opposed to feeling “Ow, ow, ow, that hurts.
TT: And do you have a process of ranking, even in your head?
LC: There are certainly buckets of ranking. Whoever my boss is at any given time is always number one.Then customers. Then the people who work for me, and there I try to be mindful of the balance between people who are growing in their careers and people who are struggling. I try to stick to some of the great teachings at Yahoo about facing forward and not overly investing in the strugglers and instead investing in people who are growing.
So those are kind of the three buckets that I tend to think in terms of. At my level, they wind up being interchangeable to some degree because I’ve found the higher I report in my career the more it’s easy to see the intertwining of all of those things. It’s not as stratified as people think—there are those three, and then most other stuff that can be punted when the day is overly busy.
TT: You talked about a mentor or several mentors. Could you please describe some things that you carry with you that you still practice from these mentors?
LC: A lot of the credit for mentoring has to go to people in my Yahoo career who cared enough about me to give me feedback in a way that I could absorb it. Because it took me several years to be able to absorb feedback with gratitude as opposed to feeling “Ow, ow, ow, that hurts.” Early on, when I got promoted to Director, I got pulled into a conference room one day by my VP at the time, and she said “You need to remember that you’re on a stage.” She knew I was a Disneyland person, so she said “Think about being a Disneyland cast member. The other cast members look to you. If Snow White is having a bad day, Mickey Mouse is going to freak out a little, as are the children. And so you really do need to remember that you’re on a stage whether it’s walking through the hallway or in a meeting.” As I said earlier, working on keeping my face “open” has probably been the hardest thing for me to do but it is something that I try to stay conscious of and whenever I’m in my office with my door shut, before I open it and walk out into what is basically a large open space, I try to remember to smile, or at the very least not frown.
There’s one other thing which is kind of odd but is very important. Because of my non-technical background, I had a lot of trouble with impostor syndrome for the first several years at Yahoo. I know impostor syndrome is something that often gets assigned to women in general, but I actually talk to a lot of guys about it and men feel it too. I struggled so much that at one point I even tried to resign, but a senior VP intervened and stopped me from leaving, and also gave me a raise to convince me to stay. That was this weird sort of validation for me—I couldn’t be an impostor because they were choosing to pay me more rather than lose me. I also talked to my boss at the time who told me, “You’re the only one in the world who has this job. There’s nobody else in the world who is responsible for this collection of things. You’re unique.” So those two people’s feedback and support helped me to finally put aside this notion that I’m an English major hanging out at tech companies and sooner or later somebody is going figure out that I don’t know what I’m doing. I had never managed a network team before I came to Proofpoint, as well as some other areas in what I’m responsible for now. But I don’t have that impostor syndrome pulling me back into a lack of confidence. Fortunately, I have more of the attitude of “You know what? I’ll figure it out,” or “I’ll trust the people I work with to know, and we’ll do it together.”
So, I think those mentors all really had a tremendous influence on me.
I think that because women at times may have fewer opportunities and potentially fewer mentors who are helping them develop influencing skills, they have the additional pressure of trying to grow their careers without the benefit of some of the coaching that men seem to get more directly.
TT: When I mentor young engineers one of the first things I tell them is, your job as an engineer is to make your manager’s job super easy to promote you. They want to promote you. Some engineers don’t understand that. Your job is to make it super simple for them. And part of that is just do your job well and do more than they asked you to do. The second thing I tell especially women is, in meetings make sure to say something, ask a question, contribute something in the dialogue, never be silent, because that’s time you just lost, and that’s an opportunity lost, especially when your boss or your VP is in the same meeting. Besides those, is there other advice you would give to young engineers?
LC: There’s a very important component to the second suggestion that I have heard quite a bit, and honestly that advice predates both of us. But what I noticed from the really ambitious people is that they can be so interested in contributing and getting their spot in the conversation that sometimes what they’re adding isn’t always valuable. There are times when being silent, if done correctly, also forms a good impression.
There are two things that I tell people about meetings. First, I don’t care what your company culture is, shut your laptop, put your phone down and be present. I’m not the only person who evaluates others in meetings. People who are sitting there typing away are either are too busy, which is a problem for their manager, or they just don’t understand how important it is to be present, make eye contact, follow the people who are talking, and be 100 percent focused. We’re not as good at multitasking as we like to think we are. You miss things when you’re in your phone or laptop. Being present allows a person to contribute much more meaningfully because they are listening to what is said and they’re watching what’s going on in the room. Those things matter.
The second thing is about body language. I just I hired a guy in a remote office and we did an all-hands meeting to introduce him to everybody—video for multiple locations except for the office in which he is based. He was in a curious position; leaning backward, and slumped sideways in his chair. It was hard to separate the body language of—tired? Overly relaxed?—from his talk track about being super glad to be here. They just didn’t align. So, don’t just be present by shutting your laptop, be present by looking interested, sitting up straight, having body language that shows you want to be there. Because sometimes, when you’re competing with a bunch of other people, you have to also rely on non-verbal cues to stay noticed in a meeting.
Also, to complement your suggestions about making it easier for your manager to promote you: one of the things that also helps is to bear in mind is that everything that you say to your manager is going through a filter. So if you’re one of those people who constantly brings a lot of negatives or challenges, your manager will come to expect that of you and see you as more negative. That’s not to say you can’t vent. But tell your manager, “Hey, look, I’m frustrated. I need to vent for a minute before I tell you what I want to do about it.” Help your manager help you by cueing them that you know you’re not at your best, and then moving on to a more positive place. You know, there’s a lot of communication and packaging that goes into all of these interactions that honestly matters.
TT: I’ll add a little bit to that. The advice I gave to this young engineer—and she might feel like I’m overdoing it—was this: Every meeting I go to, I prep ahead of time. Either the same amount of time or more than the meeting itself. So I go in there more prepared than anybody. And if somebody wants me to, I could probably control the agenda if I wanted. Besides what I said, is there any other tips on meetings that you would give to younger people?
LC: Absolutely. If you are going into a meeting and you know that you want to influence the outcome, whatever that is—you may be doing an architecture review and you’ve got a competing idea for the design or you’re going into a post mortem and you really believe that the root cause is wrong, then the place to begin your influence is pre-meeting. Go find another attendee in that meeting and run your idea past them. You don’t really want to surprise people in a meeting. You just don’t wind up getting A) buy-in, or B) the productivity that you want. Because if you throw a big thing out there that nobody’s expecting, the meeting takes three steps backward and then everybody has to get on the same page and then go forward.
And so, go to someone else who’s in the meeting and let them know what it is that you’re concerned about and let them know what it is you’re going to mention. Because again, it goes back to influence. You want to get people to join you in whatever that thought leadership is going to be. And the way that you do that are through multi-channels as opposed to just in that meeting space.
For women, we need more than just influence; we also have to carve away at that notion that “I don’t know how to do that, therefore I can’t.”
TT: So your advice does compliment my advice that you have to spend time before the meeting.
LC: I think we’re numb to meetings largely. And I think that people just kind of go from meeting to meeting to meeting and they don’t think about the value that their presence can add. The people that I’ve seen do well are the people like you who prep for the meetings or people who are present in the meetings or people who use the meeting for its intended purpose rather than to show people how bright they are. And I’ve been able to correlate those behaviors with people that I’ve watched rise. It’s the people who really do show up in all senses that tend to do well over time.
So I think it was not so much the aptitude for technology as much as the aptitude for working with technologists that got me to this place.
TT: What personal philosophy has contributed to you growing your impact over your long career? I have noticed that you are a “people person” and that groups of people tend to be very loyal to you.
LC: The thing I have learned a long long time ago that has worked for me in every job that I’ve had pretty much since I started working at Sybase in 1993—so a really long time—is this: If you treat people well, and by that I mean you have empathy for them, you are genuinely interested in helping them grow, whether it’s growing a skill set or growing their career, and you are as fair as you can be and empathetic overall to the best of your ability, then they will do good work for you, regardless. And I think that putting people first and knowing—not hoping, really knowing—that good work comes from that, allows you to be able to help them balance their personal lives and their jobs. There’s a balance that comes by putting people first and trusting that they will deliver for you. I’ve never not found that to work. Each time you get to have that opportunity to prove that in action just makes it that much more of a core competency going forward. I’m not saying that putting people first means that you become some sort of nonprofit for making people feel good all the time, and I’ve certainly had to let people go many times in my career. But when you trust that from good comes more good, the philosophy itself doesn’t fail.
TT: Do you have any advice on being mentored, either formally or informally? For example, how do you ask for mentorship or even figure out who would be a good mentor for you?
LC: I’m going to talk about informal mentoring first because I think it’s super important. So, we’re all competing for time, right? We don’t have enough time, and each person that we deal with takes a little bit away. I think that there’s an implied notion that you need to have time to either be a mentor or seek mentorship. And one of the things that I tell people that I work with is that we all have slightly different viewpoints and we’re all in different places. Don’t ever miss an opportunity for informal mentorship. And by that I mean, in a meeting if you know going in that it’s going to be a tough meeting for you, go to someone whose opinion you value, not necessarily somebody you like or that you are a pattern match of, but someone to whom you can say, “Look, I want you to pay attention to me in this meeting because it’s going to be a bit of a struggle. Then afterwards would you be willing to give me feedback?” I do that in advance when I know that I want to get that feedback. I don’t want compliments. I don’t want criticisms. I just want to know how I came across. I want that person’s assessment as a benchmark for how effective I was.
TT: Do you have any advice for making the most of formal mentorship situations?
LC: I really admire my boss. I really admire our CFO. I will ask them after e-staff meetings when I had something important on the agenda, “Tell me what I could have done differently to be more effective.” Those organic moments are fantastic opportunities.
I also do some formal mentoring. I’ve got people who I meet with once a month who I tell that in order for me to work with them formally, they need to come prepared with an agenda. They need to have something in mind, not come to me with a random list of questions. Mentoring is not an interview, it is a series of conversations designed to make some progress. I think people think that if you don’t have a formal structure for feedback you can’t get the feedback, but that’s absolutely not true. There are formal and informal ways in which to gather data on how you’re coming across and to improve.
The other thing that I would say that goes along with that is you learn as much if not more from people that you don’t naturally click with. Some of the best feedback for me has come from people that I really disliked working with or for. That lack of synergy or alignment doesn’t change the fact that you need to be effective with a broad spectrum of people, not just people you like working with. Getting a diverse view is very helpful. And I think that a combination of structured and organic mentoring helps you be the best you that you can be.
TT: What should I have asked you that I didn’t?
LC: What would you have done differently?
TT: OK, what would you have done differently?
LC: I would have thrown myself into my job at Yahoo earlier. In my first year, I got feedback that as a non-technical individual, my entry level was as far as I could go in technology. This was motivating in that I had a strong desire to prove this individual wrong. I was also supporting a VP whose respect I wanted to earn and both of these combined into a tremendous sense of focus, a crazy amount of work 7 days a week, and a drive to achieve that I had never felt before. If I had thrown myself into my work with that same amount of drive in my 20s as opposed to my 40s, I have no idea where I’d be today. I wish I had known what I was capable of earlier in career, because I think I would have done things differently. But I will tell you, on balance, I am satisfied with where I have ended up because of the people that I’ve met and worked with and the opportunities that I’ve been able to create for others. So it works out!
TT: Thank you so much Lyn! I hope this was useful for you as well to reflect back on your career.
LC: Absolutely. Anything I can do to help other people is just paying it forward. And you know, it was really interesting to think back on my career in this context. So it was enjoyable. I’m really glad to have done it.
TT: That’s great. Thank you Lyn!
Feedback from our beta readers!
Reader 1 (Senior Software Engineer)
Things are useful:
- To grow in IC track, you need to be an influencer. Knowing that women are likely say “no” to opportunities because of uncertainty, we as women should consciously push us more out of the comfort zone.
- Lyn’s story about how she came from an English major and grew her career is totally intriguing and impressive. It gives me a lot of confidence because she has come (maybe arguable) from an even more difficult route.
- You need to work hard, throw yourself in!
Things that I will practice:
- For meetings: Shut your laptop, put your phone down and be present
- Ask for feedback from PM and my manager for important meetings
Reader 2 (Software Engineer):
For Lyn’s interview, points I find to be useful:
- Do things you don’t know how to do
- Decide what not to do today to avoid feeling overwhelmed
- Don’t try to multitask in a meeting
Things I will actually practice myself (in addition to the above):
- Think about whether you want to influence the outcome of the meeting; if so, prepare, and talk to the other attendee(s) beforehand so you make sure they’re on the same page
- Ask in advance for feedback on how you do in a tough meeting, or ask how you could have been more effective
Reader 3 (Senior QASoftware Engineer):
1-3 things I learned from interviews:
- When you start going up that vertical ladder for individual contributors and technology people, to be really good you have to be an influencer.
- Each meeting should be an opportunity, make you valuable at presence.
- Informal mentorship, ask diverse feedbacks, to make you be the best one you could be
1-3 things I going to follow and change
- Changing the meeting habit, be present, be prepared and be valuable
- Work less hard, make more impact
- Carve away at the notion that “I don’t know how to do it, therefore I can’t”
- keeping my face “open”, at the very least not frown
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