Learning a New Industry from Scratch with Brightflag's Rebecca Silverstein

Media Thumbnail
  • 0.5
  • 1
  • 1.25
  • 1.5
  • 1.75
  • 2
This is a podcast episode titled, Learning a New Industry from Scratch with Brightflag's Rebecca Silverstein. The summary for this episode is: <p>Operators are constant learners. We seek out new things, we aim to understand the "why" behind what’s happening around us. So what does it look like for an Operator to be dropped into a completely new industry, with new prospective customers?</p><p><br></p><p>That’s what we explore on this episode with our guest, Rebecca Silverstein, the Director of Revenue Operations at Brightlag.</p><p><br></p><p>In our conversation, Rebecca teaches us about the emerging function that is Legal Ops and its similarities to RevOps’ growth trajectory, we talk about what it looks like to learn a new industry from scratch, and why her experiences as both an SDR Manager and an actual SDR were her unfair advantages when she joined Brightflag.</p><p><br></p><p>Like this episode?&nbsp;<a href="https://www.drift.com/operations/review" rel="noopener noreferrer" target="_blank">Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp;review</a>&nbsp;and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.</p>

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hyper growth. My name is Sean Lee. At Drift, we have a series of leadership principles that we use to guide our team. And one of my favorite leadership principles is be a curious learning machine. Based on my time hosting this show, I think that this leadership principle can be pretty consistently applied to operators as well. We seek out new things. We try to understand the why behind what's happening around us, or put very simply, I think we just like learning new stuff. So what does it look like for an operator to be dropped into a completely new industry with a new set of prospective customers? That's what we're going to explore with today's guest, Rebecca Silverstein. Rebecca is the director of revenue operations at Brightflag, the legal operations platform. Yes, you heard me right, legal ops. We're adding another flavor to the ops variety pack. And it's not like Rebecca came from some legal expertise earlier in her career. Prior to Brightflag, she spent four years at Smartling, which sells language translation and localization software. So in our conversation, Rebecca's going to teach me about the emerging function that is legal ops, and its similarities to rev ops own growth trajectory. We're going to talk about what it looks like to learn a new industry from scratch and why her experiences as both an SDR manager and an actual SDR were her unfair advantages when she joined Brightflag to start, let's get a little bit of a foundation about what Brightflag does and what this audience known as legal ops is all about.

Rebecca Silverstein: So Brightflag helps corporate legal departments gain more visibility, be more productive, and engage outside council more strategically. So we target in house legal professionals. This can be a combination of lawyers or legal operations professionals that we target. And we look for companies that have enough legal spend with outside counsel to warrant a tool that will help them optimize those relationships. So that's who we would be targeting. We typically work with larger organizations because larger companies more often than not, have a higher amount of legal spend. Some of our customers include Ericsson, Volvo, Dropbox, and then some technology focused companies like MongoDB, Coursera, Ironclad, and Asana. So we really run the gamut. We work with some companies across the world basically. We have an office in Australia, we have a big presence in Europe, and then in the US.

Sean Lane: Cool. And so you mentioned that a lot of those big brands that you just mentioned will have both an in- house legal team, but then also do a significant amount of outsourcing to outside council as well?

Rebecca Silverstein: Yeah. So there's some sort of relationship between the number of in- house people typically, and the amount of outside council send that they use. The reason that companies use outside council is because these organizations are either specialized in a type of work. And then the in- house team helps to manage and facilitate all of the matters. So they're able to resource to different law firms depending on the type of work and the specialty that they need to get the best outcomes.

Sean Lane: Got it. And so to be honest with you, this is my first time hearing the term legal ops, right? And so is it as simple of a comparison for me to say," Hey, sales ops is there to help a sales organization operate more efficiently, and legal ops is there to do the same thing for a legal team, both the in- house and outside folks?"

Rebecca Silverstein: Yeah. So specifically, it's for it's inside council, so not necessarily even council, but legal operations sits within the legal department in a corporate legal department. And part of what they're looking to do is the exact same thing that sales ops would be looking to do for a sales team or rev ops for go to market team. They're looking to make the team more efficient, to remove manual effort and to find connections and patterns that they can then use to highlight to leadership. So reporting data, highlighting areas of opportunity and potential concern for them to be shifting their strategy. So in the same way that that's what I aim to do in rev ops, the legal ops function is trying to do the same thing. The main difference I would say is that rev op for example, is focused on growth, whereas legal operations is more focused on control and cost saving measures.

Sean Lane: Got it. That makes a lot of sense. And is this a relatively new function or is this something that's existed at these big companies for a long time? Help me understand kind of where this function's at and its maturity.

Rebecca Silverstein: Yeah. So one of Brightflag's goals this year, and in the future is to help to highlight that legal ops professional and the work that they're doing. So the way that we kind of think about it and selfishly, I think about a lot of things as it pertains to rev ops because that's what I'm familiar with. But, years ago, rev ops didn't exist. There was a tactical sales operations team who was helping with some administrative work, then that team became more strategic. Then rev op came together to kind of form a bit more continuity and also a center area that has expertise across all the different go to market teams. In the same way that legal ops is probably five years behind, let's say, the growth of rev ops, legal ops is emerging. There are a lot of people you'll now see are companies that are hiring for legal ops professionals. Typically, just as I got started in sales ops, I was an SDR, and I saw an opportunity to try to do things better, and do things at scale. So I was given an opportunity to create a sales ops role. That's the same thing that's happening in a lot of legal departments. There are people within the department that might not want to be a lawyer anymore and practice law in the company, or even paralegals who see this opportunity and either take on that role unofficially or actually create that function within the organization. And there's definitely gaining respect and understanding of the value of the function, similar to how rev ops is. Now, you won't find a tech company of a certain size without some sort of rev op or go to market operations function.

Sean Lane: So this is a pretty straightforward comparison. Just like a sales operations team would sit inside of sales, legal operations sits within a corporate legal department, and the work seems pretty analogous too. Rebecca said that these legal ops teams are popping up to make those legal departments more efficient, remove manual effort and seek out areas of opportunities and insights. Sounds familiar, right? Since Rebecca had personally experienced the emergence of rev ops in her own career is no surprise that she was able to recognize the emergence of legal ops. For any operator that changes companies, there's a pretty good chance that you'll have to learn a new industry or a new target customer yourself. So how did Rebecca coming from Smartling and selling to IT, figure out this world of corporate legal departments when she joined Brightflag?

Rebecca Silverstein: So there are a lot of things that I think are transferable. It doesn't matter what kind of company you're working for, you understand the fundamentals of people processing systems, and I'm sure we'll get into this at some point, I'd be happy to talk about it. But I took on leadership of the sales development team around the time that I started at Brightflag as well. So I was forced to learn very quickly what we do and who we sell to. So in terms of learning a new industry, I would say, speaking from my experience here, you might come in and think," Okay, I already know how to do X, Y, and Z because I did it at my last company," but there are a lot of things that... There are a lot of variables that really depend on who you're marketing to. So for us, we sell to a very specific group of people at a very specific type of company. So we don't have the same ability that we had, let's say, at SmartLing to reach out to a wide net of people at every company. So we have to be very specific in terms of the messaging that we use, the people that we're reaching out to, and really try to be as consultative as possible, rather than just trying to get someone's attention, which was more prevalent in my past experience where we were selling to a very saturated buyer persona. So learning that new persona and learning what they care about. And again, I mentioned the parallel between rev ops and legal ops, because that really helped me understand what we're trying to do and how we could help. We also kind of would describe what we're looking to do in terms of the big picture with Brightflag is to become the sales force of corporate legal departments. So that also helps me understand. And being able to apply those parallels and think about," Okay, what kind of messaging would I want to hear about... What are the things I care about, especially with the changing economic climate. And of course, COVID." That's right around when I joined and really thinking about how that impacts me also gave me an opportunity to apply that to the types of people that we're reaching out to.

Sean Lane: I really like the north star of, we are the sales force of corporate legal departments. I feel like that helps frame a lot of what you came in and had to do. And so you mentioned kind of look, people, process systems are going to be my foundational elements for learning this, but you also had to actually get to know these people. How did you do that? How did you actually figure out what's important to them? Where do they spend their time online? What messages are going to resonate with them the most?

Rebecca Silverstein: So one of our founders, Alex Kelly, was a corporate lawyer. And that's what kind of led him to create this company alongside Ian Nolan, our CEO. And he held these sessions where it was kind of an AMA type thing, where you could ask him questions. And we also have some other people in the company who had experience. So being able to really pick their brains, as well as speak to people, hear from customers about what their challenges are and how we help them. Reading through case studies that we had, listening to chorus calls that we had to hear from the potential buyer or the customer what they have to say, was a really good way to get up to speed quickly. And the fact that we have all this technology that enables us to do that on our own. We don't necessarily need to call up a customer as your first day as an SDR to ask them a question, you can hear it from them in their own words on recorded calls. So that was a big help. And obviously speaking with people internally who have experienced selling the product and working in the product. And that's shifted since my time being at Brightflag as well. We've changed some of our messaging. We've changed what we understand to be the values that we provide to legal ops professionals. So you kind of have to be flexible with that. And even when you say," Okay, I've learned this persona. There's always something that's shifting and their priorities are shifting, therefore, the way that we're trying to sell to them must also change."

Sean Lane: What I love about Rebecca's approach here is that she just didn't take someone else's point of view for granted as the" right answer." To me, there were three different ways that she started to figure out who her perspective customer base really was. First, she took advantage of internal team members who were her actual target customers in their past lives. At Drift, we sell to sales people and marketers, so guess who we talk to internally to figure out what those people care about? Second, she took advantage of the tools that were available to her, and didn't just rely on only live or first person accounts. She listened to recorded calls to hear for herself what was going on in the field. This concept of listening to those calls is way too rare amongst operators. And third, she started to have the live customer facing conversations herself, through her work leading the SDR team. So with a little more of a grasp on who her target persona was, I was intrigued by Rebecca's observation that legal ops is a slightly less saturated market. How does that fact impact her strategy, or at an even more basic level, does it make it harder to find the right individual people to reach out to in the first place?

Rebecca Silverstein: I think I mentioned this previously, but the concept of legal ops is new, but someone actually owning the function, I think, is newer. So there were people that were kind of acting in this type of role prior. And that is where the complexity is in that, you don't know if what you're asking them in cold's email is going to be something that resonates with them because you don't know that they're the one being asked by their general counsel," Why was the spend over this amount last quarter?" Whatever it may be, you don't know who's really responsible for it. So it has become a little bit more straightforward as we've seen organizations specialize this role a bit more, but even then, so our primary focus and kind of the easiest way for us to figure out if a company, for example, is a good fit, would be looking for companies that have people in legal ops, right? That's the easiest way, because we know the inaudible.

Sean Lane: The center of the target.

Rebecca Silverstein: Yeah. But then there's companies that might not have this. And we look at," Okay, what are the companies with which we've generated opportunities with our conversations with recently, what are the industries that they're in? What are things that we can pull out about them?" Their size, maybe their location, the type of legal work that they might be handling more if they're in a highly regulated industry, for example, and applying that to understand," What is our total addressable market and how do we actually find those companies that we should be focusing on now?" So it's a combination of things that we use to determine that. The best bullseye hit would be legal ops person at a technology company or a Fortune 500 company. But in absence of that, we have to really rely on other types of firmographic data that we might have to try to indicate what are the companies that our SDR should be reaching out to? Who should we be marketing to?

Sean Lane: And to your earlier point about what is absolutely transferable, regardless of the industries you're in, you're building a firmographic score, right? You're trying to figure out which companies are going to be the A's, right? What is that center of the center of the target for Brightflag and who is it that you should be going after? And so whether you are working in a brand new industry or working in one that is much more mature, you still kind of need those key building blocks. We've talked about a lot of the stuff that's hard about going into a new industry, but you also mentioned something before about, look, this is also just a less saturated market to be in. That must be something that's actually to your advantage, no, right? Like it's not like CEOs, CROs, CMOs who get bombarded with prospecting notes all the time. I would have to imagine you guys are probably not amongst a huge volume of people who are trying to reach these very specific legal ops people. Is that a fair assumption?

Rebecca Silverstein: I would say so. So our industry, the types of companies that we're competing against, a lot of them are part of, or have been acquired by large organizations. And they might not have the same approach to generating new business as an agile startup might have with an outbound SDR team, for example. So my hypothesis is that these individuals are probably receiving less outreach than someone in marketing or a CEO, CRO, what have you. I can even take from my own experience of messages that I receive in rev ops, and think about," Okay, what stands out and what does not?" Rev ops I think is now also saturated in terms of outreach.

Sean Lane: Yeah.

Rebecca Silverstein: And I'm sure an SDR somewhere will watch this podcast and we'll use this as a reason to reach out. So if you've made it this far, thank you. But in terms of reaching out to legal, and in my experience in managing the SDR team, what I found is that, they don't really want the gimmicks. They don't want the trying to grab your attention in the subject line, and hoodwinking you into opening the email. It's more professional focused. Here are the things that we can help with. I mentioned before about consultative. So what I find in a lot of the emails I received now are a lot of those gimmicks. Something that's just trying to get you to click on the email and then I open it, and I'm not even focusing on what they're trying to say and what they're trying to sell, because I'm just annoyed that I fell for the trick. So definitely apply that to the types of people that you're reaching out to. In the case of legal professionals, you have to be respectful and professional in how you're doing your outreach. And I think that also leads to better outcomes, is having real substantive conversations with them.

Sean Lane: Real substantive conversations is something I can get behind. Even those of us in saturated, more mature markets can learn something from Rebecca here. Nobody wants gimmicks. Nobody wants to be tricked into opening or replying to your email. She and her team are focused on solving very specific problems for a very specific audience. Now, Rebecca has mentioned a couple of times that when she first arrived at Brightflag, in addition to her ops work, she also led the SDR team. So it should come as no surprise to us that she got to know the customer base so quickly, I'm biased, but I was also an SDR manager at one point, and I've long believed that managing an SDR team is a phenomenal training ground for operators. I was curious if Rebecca found that to be true as well.

Rebecca Silverstein: Absolutely. So, as I had also mentioned, I had worked as an SDR in the past. So I had that foundational knowledge of," Okay, here are the types of activities that need to happen. Here's how we figure out applying the rev ops knowledge. Here's how we figure out the quantity of those activities that you need to be doing in order to hit your target." But actually sitting down and writing some of the content, creating some of those cadences for the team to use, and even doing some of the outreach myself was a very good way to get involved quickly and to really understand the challenges that the team is facing, and that's something that... I haven't been managing the team for about a year and a half, but I still feel very connected to the work that they're doing and that I'm able to offer ideas and advice because I have that experience in doing the role myself and also in managing the function. So I find that is a really strong background for someone in rev ops who's done the actual day to day work and understands," Okay, how do we make this easier for everyone?" But it absolutely was a great way for me to really get involved, again, writing the content, seeing the responses that we're getting, having to help the team objection handle. Those were all things that forced me to really learn very quickly.

Sean Lane: I couldn't agree with you more. What we've said on this show before a bunch of times, that street cred that you now have both with the SDR team, as well as with the broader organization that you actually know what it's like on the front lines, that can't be replaced, especially for ops folks. If people have the perception that you are just the person behind the spreadsheet or the person that's clicking, refresh on the dashboards and doesn't actually know what it's like on the front lines, that perception can be pretty dangerous, right? In terms of how people view the value that your team provides. And so the fact that you already have that right off the bat, I feel like probably set you up to be more effective in your ops role, yeah?

Rebecca Silverstein: I think so. Just because it's easy to say," Here are the numbers, here are the targets," but if you can't sense, check that and say," Is it actually reasonable for somebody to be making 200 calls a day?" Those are basic numbers that if you're not involved at all, you don't even know what's considered realistic. And even though that's something that I would be... And we don't ask for 200 call today, I just want to make that clear. I chose a very high number, but having that understanding of what really... Just a sense check at the start definitely helps.

Sean Lane: You mentioned your you're there crafting messages, you're there working with them on what outreach is going to work. How did you know what was working versus what wasn't?

Rebecca Silverstein: Yeah, so I think, the numbers usually are the thing that we'll explain if things are working, right? If you're looking at the number of inputs and you're looking at the number of outputs and you see that inputs to app, but the results that you're getting are increasing versus the inputs, that's a good way to kind of measure. At the beginning, it was very much a sense check. It was saying," Okay, have we been getting more positive responses than before? Have we been booking more meetings?" One of the first things I did when I joined as well was investigate, what were we expecting the SCRs to do from a... What were they actually being... What was their quota based on and what are they being comped on? And how does that align with the work they're actually doing? So we reset that when I started. We changed the process to be based on meetings booked and opportunities that they created, because those are really things that were within their control. So it took a bit of time for us to really get data on, what can we expect from each SCR and the team as a whole, and what does good look like? And is that going to result in the amount of pipeline that we need, and ultimately, is that going to let us hit our bookings number at the end of the year? So it took a little bit of time to really understand, what are the inputs we need? What are the number of calls, emails, social touches to result in a meeting booked? And how many meetings do we need? So that came at the beginning. And a lot of it, again at the start was, is this directionally accurate? Are we headed in the right direction? If we do more, are we getting more out of it? And then once enough time has passed and we kind of built up the team, we had a pretty good foundation and we continue to look back on that and say," Okay, do we need to change how we're doing things?" Are we still getting the results that we would expect from the level of effort? What would happen if we add another SDR to the team? Would they be able to produce at the same level? So there's a lot of factors there to determine what that should look like.

Sean Lane: And one of the things I love about the stage that you all are at is, your team is still small and nimble enough that you can make those changes pretty quickly when you are having those learnings. How frequently were you all looking at all those different inputs that you just described to say," Hey, we just saw this sequence. The response rate was through the roof, right? here's how we now need to shift the team in order to take advantage of that." What does that cadence look like for folks who are at a similar stage to you?

Rebecca Silverstein: So when I first started doing this, it was pretty much every day we're looking at what's working, what are we amping up? And then as time goes on and you're kind of in a steady state, I would say, I have a weekly touch base with our manager of sales development, where we talk about," What are the things you're seeing? How is the team doing? Where are areas that I can help remove friction?" So I really do think it depends. What it comes down to is your CRO, your VP of sales is probably not going to be asking a lot of questions about what's going on if things are going well. If the team is producing what they need to produce, it's more, it's likely that they're just going to keep doing what they're doing until they're not, but you really hear about it when something's not going well. And that's the forcing function to really reevaluate. So to your point, I think it does make sense to have a more frequent cadence to really understand," Okay, what are those numbers that we're seeing? What do we need to do to book a meeting?" I would say right now we do that about quarterly, but it could be done, I think, more frequently, or we could be looking at different areas of the SCR funnel, for example, at a more regular cadence.

Sean Lane: Rebecca's dual experience as both an SDR leader and an ops leader makes her such an asset in those routine meetings. And if you go back even further in her career, she was an SDR before she was an SDR leader. So for those of you listening trying to create your own path into operations, you're going to want to hear how Rebecca created such an opportunity for herself.

Rebecca Silverstein: Looking for those areas where you can work smarter. I know that the phrase work smarter, not harder, but that really resonated with me when I was in SDR. I didn't really like the monotonous, sorry, SDRs, but the repetitive nature and the quota. So I was looking for ways," Okay, what can I do to be more efficient at what I'm doing and still get the results that I need?" So seeing some opportunities for... In Salesforce, I remember seeing there's all these companies that we hadn't reached out to either ever, or for many months. And I thought," Okay, how much effort would it take for me to write a cadence?" I created this matrix of the different personas and levels that we might want to be reaching out to. And I created one cadence, and then I made copies of that and I personalized it slightly for those different sections of the matrix. And I read a report," Okay, show me all the marketing managers, show me everyone who's a product manager and hasn't been reached out to in six months." And I just loaded them up and sent my emails out. And I was booking a lot of meetings because I was really just managing replies from that. And I think that was an example of where sometimes taking the initiative or identifying things that aren't happening just because it's not anyone's specific job and taking that type of opportunity and then running with it. Because if something's working, you're probably not going to be told to stop doing it, at least not in my experience, but I can't speak for everyone. So that was something that then I could apply to future work. That's still something that works right? It's," Okay, how do we try to personalize at scale? How do we segment the database so that we're working more effectively, maybe we're all reaching out to a specific industry so there are certain things that we could be doing specific to that industry that will get their attention." So I think that's an example of one of the things that I did in that type of role, and same with what you mentioned, which is, scoring accounts or prioritizing accounts. So figuring out, what does a good account look like? What are sub signals that they might be interested in speaking with us? That could be they've been on our website recently, they've engaged with emails that we've sent them, they've downloaded content. And how do we really prioritize that so that the work that we're doing is yielding the best return that we can get?

Sean Lane: I think the other thing too that we take for granted a little bit, I think in ops, but the key part of, I think the first insight of your story is that you were the one who sliced and diced those different contacts based off of those recent activities or lack of recent activities. And so, this is not meant to be a trick question, but how as an SDR, did you know how to do that?

Rebecca Silverstein: That's a good question. I think that that was in partnership with the director of sales at the time, but also I think that's just... I should never have been an SDR, is really the answer to the question. I've always been more focused on solving problems. And when I saw problems that could be solved such as me hitting my quota or me getting more satisfaction out of my job, those were things that I like to do. When there were questions asked about data related things, I would spend a little bit of time trying to build a report. And that's how I learned really how to use Salesforce, is spending some time just trying to answer questions or thinking about," Okay, I want to look at a list of people who haven't been contacted, who are in biotech and have a legal operations professional." So I would kind of challenge myself to do that. I'm not saying that's something that everyone can do, but if you're sitting in your seat as a sales rep, as an SDR, and you're thinking about," Maybe I'm more... I would get more satisfaction out of my job, or I'm more interested in helping to enable people as opposed to doing the work myself." That's just something for me, personally, that I found. So I was really glad I was able to take that opportunity to carve out a job for myself with, of course the help of leadership. I can't just say," I want to do this job, therefore I'm no longer an SDR," but there was a kind of an opening, a gap there, and we had a hypothesis and I had to kind of prove that the work that I was doing like those cadences, I mentioned that would work. And that was more of a reason for them to allow me to move into a different position.

Sean Lane: I think the other lesson I take away from that too, is just, we, as operators, can create an environment to empower other people to find those openings themselves, right?

Rebecca Silverstein: Absolutely.

Sean Lane: Yes, controls are important. Yes, permissions are important. Yes, we want to be prescriptive about where those next best leads or where those next best opportunities are, but that doesn't mean that ops or leaders are going to have all the answers, right? We are still going to need to have those bottoms up ideas that we can generate and bring back from the field to the business in order for them to help bring those learnings to the rest of the team, right? If one person does what you did yeah. And finds one of those opportunities, and then all of a sudden they can enable 20 other people to do the same thing, rising tide lifts all both situation.

Rebecca Silverstein: Absolutely. And I'll say as well, one of the things that I've learned fairly recently is, as you said, we're not expected to have all the answers. We're successful when we highlight areas that are worth investigating further, either as I've mentioned opportunities or potential threats so that those who are actually owning that function can decide what to do with the information. An example I gave where I was an SDR, now I wouldn't say," Here's a cadence that everyone's using, go and use it," right? Just because I have the ability to create a cadence in SalesLoft. Rather it's," Here's something that I've noticed. Here's the data supporting it. I think that we should do something about it." And then having that conversation with the functional lead so that they can use their expertise to determine how to capitalize on that, or how to address it. So I've learned that fairly recently, and it sounds like an obvious thing, but often as I think an operator and a problem solver, you want to get everything done. You just want to see it finished so you could check it off. And you say," I delivered on this." But that's not always the case. A big part of it is making those individual people and teams successful with the scope of information that you have.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months.

Rebecca Silverstein: That's a good question. I've been on a fiction kick. This is going to sound cliche, but everyone's reading this. It's The Seven Husbands of Evelyn Hugo or something. So it's about a socialite, but I have a whole stack of business books to my left that are just staring at me.

Sean Lane: Fiction's fine.

Rebecca Silverstein: Okay. All right. But my library card recently within the last two weeks expired, so I need to renew that so I can get some new books downloaded.

Sean Lane: I love it. All right. Favorite part about working in ops?

Rebecca Silverstein: I think the flexibility, and as I mentioned many times, the problem solving element of it, I love when a new project kind of just pops up, and it's something maybe that personally interests me, and I get really invested in it. So being able to do different things and yeah, the flexibility to really determine what should I be focusing on right now?

Sean Lane: Flip side. Least favorite part about working in ops.

Rebecca Silverstein: Having to tell people no, or that this thing is not possible, or I don't have time to do this. I say it in a nicer way, but you can't take on everything, and that's something that I learned pretty early on because it's just not possible.

Sean Lane: We're enablers. It's tough. It's tough.

Rebecca Silverstein: Yeah.

Sean Lane: Someone who impacted you getting to the job you have today.

Rebecca Silverstein: That's a good one. So I would say my current boss, Kevin. So he is or manager, I should say. He's our chief customer officer, and I have worked with him previously, and we maintained a relationship. He was my mentor for a period of time and I just really value his leadership. And when I had the opportunity to work with him again, it was something that I couldn't pass up. So I would give a shout out to Kevin who hopefully will watch this.

Sean Lane: That's awesome. Shout out, Kevin. All right. Last one, one piece of advice for people who want to have your job someday.

Rebecca Silverstein: I would say, be hungry. Think about things that you could do to make other people's jobs easier, and be really vocal. That's, I think, the number one thing, is you have to be your own advocate. I learned that people aren't just going to hand you a job. You're not just going to be dropped into an opportunity. You need to really advocate for yourself. You need to follow up. You need to push a little bit sometimes within reason in order to get what you're looking to achieve. So I think that that's super important.

Sean Lane: Thanks so much to Rebecca for joining us on this week's episode of operations. If you liked what you heard, make sure you are subscribed to our show, so you get a new episode in your feed every other Friday. And if you learn something from Rebecca today or any of our episodes, make sure you leave us a review. Leave us a six start review on Apple Podcasts or wherever you get your podcasts. It really helps other people to find the show. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.


Operators are constant learners. We seek out new things, we aim to understand the "why" behind what’s happening around us. So what does it look like for an operator to be dropped into a completely new industry, with new prospective customers?

That’s what we explore with our guest, Rebecca Silverstein. Rebecca is the Director of Revenue Operations at Brightflag, a legal operations platform.

In our conversation, Rebecca teaches us about the emerging function that is Legal Ops and its similarities to RevOps’ growth trajectory. We talk about what it looks like to learn a new industry from scratch, and why her experiences as both an SDR Manager and an actual SDR were her unfair advantages when she joined Brightflag.

Key Points:

  • (1:45) What is Brightflag?
  • (3:51) Who are the people Legal Ops serves?
  • (7:34) How Rebecca transferred her IT sales knowledge to the world of corporate legal departments
  • (10:11) How Rebecca studied and came to understand the legal persona
  • (15:51) The pros and cons of selling into a less-saturated market
  • (18:36) Why managing an SDR team is a phenomenal training ground for operators
  • (21:14) How Rebecca figured out what outreach was working, and what wasn’t, for her SDR team
  • (25:08) How Rebecca made her career move into operations
  • (32:13) Operations lightning round

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts, and Rebecca on LinkedIn.