LIVE from HYPERGROWTH: Lessons from a Serial Operator (with RapidMiner's Heidi Rawding)

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This is a podcast episode titled, LIVE from HYPERGROWTH: Lessons from a Serial Operator (with RapidMiner's Heidi Rawding) . The summary for this episode is: You hear a lot about serial entrepreneurs. But in this Operations episode, Sean sits down with a serial operator. Heidi Rawding is the Senior Director of Operations at RapidMiner and has been hired as the first ops person at three different companies. Meaning she's gone through hypergrowth and has built the foundation for an ops organization three different times. Heidi talks about what it's like to start an ops org from the ground-up, how she's built a community of operators, and why she thinks that every ops pro should have a background in hospitality.

Sean Lane: Hey everyone. Welcome back for another episode of Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. Today, we've got a really special episode of the podcast for you because we recorded this episode live from Hypergrowth. If you don't know, Hypergrowth is Drift's conference. We held this at the Wang Theatre in Boston in September. We had one in London over the summer. We've got one coming up in November in San Francisco, but this was our Boston one. And we actually set up a podcast booth in the middle of the conference. The whole Wang Theatre was all decked out for the conference. We had amazing speakers. People like Alex Honnold from Free Solo, Sara Blakely from SPANX, Danny Meyer, the founder of Union Square Hospitality and Shake Shack. The list went on. It was an incredible day. But we had this podcast booth and we got to set up in the middle of the booth and all of the different podcasts across the Drift's Hypergrowth Podcast Network got to record throughout the day. Even DC sat down with some of our special guests as well. You'll hear all that content soon. But for the Operations podcast, I sat down with someone who... You hear a lot about people who are serial entrepreneurs. I sat down with someone who's a serial operator. This person started as the first ops person at three different companies, three different times. She has gone through hypergrowth and three different times she's been the person who has built the foundation upon which the operations team has been built. So I wanted to learn more about what made her motivated to do that, what it looked like to be the first ops person. And we went on off on a whole bunch of other topics as well. So I'd like to introduce you to Heidi Rawding, who's the Senior Director of Operations at RapidMiner. Heidi and I talked about her being a three- time operator. We talked about why operations people should have a background in hospitality. Yes, background in hospitality. And we talked about building a community of operators. After all we were at Hypergrowth, it was a great time to talk about community. So without further ado, here's my conversation with Heidi Rawding live from Hypergrowth. Hi Heidi.

Heidi Rawding: Hi Sean.

Sean Lane: Thanks for coming.

Heidi Rawding: Thank you for having me.

Sean Lane: Welcome to Hypergrowth.

Heidi Rawding: It's been very fun, the hyped up music. Love it.

Sean Lane: Good. Is this your-

Heidi Rawding: Very energetic after-

Sean Lane: Is this your first Hypergrowth?

Heidi Rawding: ...Labor Day.

Sean Lane: Labor Day.

Heidi Rawding: Yeah. One of those holidays. It is my second.

Sean Lane: Cool. So did you come last year, or the first one?

Heidi Rawding: First one.

Sean Lane: You were at the first one? I wasn't even at the first one.

Heidi Rawding: It was really well done actually. So I actually enjoyed it.

Sean Lane: I heard it was like fire code status, there was too many people in the room.

Heidi Rawding: There were a lot... The lines for the bathroom were terrible. We'll just say that.

Sean Lane: Honestly... So we're at the Wang Theatre today for this Hypergrowth.

Heidi Rawding: So much better.

Sean Lane: And I feel like I'm walking out when the... We have the coffee breaks and things, like intermission to a show. It was like everyone going their separate ways.

Heidi Rawding: I want a ballet to come out soon, I'm not going to lie.

Sean Lane: I mean, you never know we have on tap for the second half of the day. So first of all, thank you so much for being here, taking time away from part of the conference to be here with us. Heidi is the Director... Excuse me, Senior Director of Revenue Operations at RapidMiner. She's also a Drift customer, so thank you. So first, before we get into anything else, you've been in ops for quite some time. But here's the thing you majored in biology-

Heidi Rawding: Marine biology, specifically.

Sean Lane: Excuse me, marine biology. And your first gig out of school, or one of your first gigs out of school, was at a zoo.

Heidi Rawding: Yes.

Sean Lane: So first, tell me about the zoo you worked at?

Heidi Rawding: Okay. Huge shout out to the Phoenix Zoo in Arizona, a nonprofit. We saved rhinos from other profits who were going to kill them because they wanted the baby animals to come in. We took the rhinos in, bought their very expensive arthritis medicine, and it was just literally the coolest gig of my life. I have to say that.

Sean Lane: That is so cool. How long were you there?

Heidi Rawding: One year.

Sean Lane: And is it only rhinos?

Heidi Rawding: No, they have otters, zebras, giraffes, you name it.

Sean Lane: Wow. I have to ask now, what was your favorite animal at the zoo?

Heidi Rawding: The otters. Actually that tied with the orangutans. Apparently both O animals, but...

Sean Lane: Wow. All right. That's amazing. Okay. So I have more questions about that, but I'm going to save them.

Heidi Rawding: Okay.

Sean Lane: So tell me, connect dots for me. How do you go from being a marine biology major who worked at a zoo to working in operations?

Heidi Rawding: Yes. So I had zero business acumen coming into the business world. I stumbled across Rapid7 on a Craigslist ad, which is how we found jobs back in the day. But the reason I departed the zoo, backing up just a step, is it was not paying off my student loans. I was waitressing on top of it. It was a really, really great experience, but I had a lot of debt to pay off. So I moved back to Boston, back to my college friends, and came across that Craigslist ad. I went and interviewed there and then two other companies and I just loved the vibe they had. It was super startup mentality. They knew that I had no experience, but they just asked really intelligent questions around work ethic. And they just knew, apparently... This is what the VP of Sales says, that I would be a very good, hard worker. And what I quickly found out is that a startup is a zoo and it really translates really well.

Sean Lane: Wow, you really did connect the dots. Okay, I like that.

Heidi Rawding: It's just from one zoo to another. I came back full circle. It is truly a zoo. And what I loved about it and probably why my waitressing after worked, always helped, is I like making chaos into order. I don't mind being in the weeds. I actually start to get, I think, even better and more excited when I'm in the weeds. And even though I didn't understand any acronym whatsoever that they threw at me, I didn't know what VC funding was because I started before that came into play. I just knew it was exciting to be part of and I love trying to find solutions to problems. And there's plenty of those with a startup.

Sean Lane: And starting so clean... Starting with such a clean slate, starting with no experience, how did you go through that evolution to start to pick up on those things?

Heidi Rawding: I do think that business actually translates fairly well with biology. It's trying to understand what happens over here and then how does that effect something way over here? Whether it be upstream or downstream, everything's connected or should be connected in some way. And I'm just trying to make a flow chart of what's happening, where are the gaps, and how do we make things more effective and more automated.

Sean Lane: So you must really enjoy that connecting piece because you did four years of Rapid7.

Heidi Rawding: Yeah.

Sean Lane: Then you went on to be early, if not the first person on the ops team at Acquia. You did that for nearly four years. And then now you are kind of on your third tour duty at RapidMiner again with nearly four years there already. So I guess my first question is why do you keep doing this over and over again? Not just the joining an ops team or not just joining a startup, but literally being the first person in to start an ops team from scratch.

Heidi Rawding: I'm sick and addicted to it.

Sean Lane: There's definitely something.

Heidi Rawding: I really, really enjoy the chaos. And it is a lot of chaos. I think you can achieve something every day in startup and that is so gratifying in it's own way, but I also love the relationship side. You have to have, to be successful, every relationship across the board, whether it be the developer who works by himself in the corner with the hoodie on, or the CEO who has no idea what you do but knows it's helpful and just wants you to keep plugging away. I had to learn how to adapt to every single type of audience and connect. And the social part of it is really, really fun. So I do enjoy that. And then I really enjoy building teams. I keep in touch with pretty much every single person I've ever hired in my last 12 years. And I hire a lot of green or entry- level people and try to help them grow because I really find their success path is way more interesting than sometimes what I do.

Sean Lane: Tell me more about that, because that's a question we get a lot from people who listen to this show is," How do I grow in my ops career?" And you're finding people who, it sounds like more likely than not, are kind of like yourself and didn't really have an ops background coming into that.

Heidi Rawding: Yes. I personally love anybody that has waitressing, bartending, sort of hospitality experience because again, they're the ones who are okay being in the weeds. And operations, you're always in the weeds. The better you are, the more stuff you get thrown your way. So I am a big fan of those green people that are open to coaching. So they don't come in and say," Well, we did it this way at XYZ company. So we should do it again this way." You don't know what you don't know, and there's so many ways of doing things so having these people that are completely green and just want to learn and grow are my absolute favorite. And they are now running teams themselves pretty much... I would say 75% of my hires. We're all going to work for them someday.

Sean Lane: I'm so glad you said that thing about hospitality though because one, I worked in hospitality as well and it's always something that I thought was helpful to me in operations. I think what you're saying about being in the weeds is definitely a huge part of it. But I think for me at least, another big part of it is the customer service side and the fact that going to different tables or being behind a bar, you have to engage with and interact with totally different types of people and based off of their wants and needs, react to those. And ops is basically the same thing. The way one VP of Sales thinks is not the same way as a different one thinks and if you can take all those different inputs in and put something back out there, then I think that makes you probably pretty good at ops as well.

Heidi Rawding: Absolutely. And I think Danny Meyer this morning actually alluded to it with his emotional traits. I could not have encapsulated that better myself. It was dead on.

Sean Lane: Molly Sloan who produces a whole bunch of our podcasts for us and sitting outside the booth right now, we'll have to get a blog post with her about why being in hospitality is going to make you good at ops.

Heidi Rawding: Yes.

Sean Lane: That's an idea if we can get that crosstalk.

Heidi Rawding: If you have happy employees, happy customers, everything comes full circle.

Sean Lane: All right. Back to you, and you're on your third go around, right?

Heidi Rawding: Yes.

Sean Lane: So I would assume that some things on this third go around were easier than your first two go arounds. So what did you take with you from those first two times building ops teams that you knew coming into RapidMiner,"Okay, these are things I definitely know I have to do."

Heidi Rawding: Defining how many customers you have as a company. I have not worked for a company where I started we could say," We have X number of customers." Whether it be a difference of definitions or systems not aligning between finance and CRM. But I would say that is probably one of the first things I tackle everywhere is," Okay, what is our definition? Let's come to agreement." And then I love getting my hands dirty, another reason I love startups. So we get into the systems, clean it out, and make that a perfectly clean slate if it wasn't already, which in my case was not.

Sean Lane: Systems first.

Heidi Rawding: Yes.

Sean Lane: Systems first.

Heidi Rawding: Systems and customers, I almost put them together.

Sean Lane: You were telling me that one of the companies you... Don't say which one-

Heidi Rawding: I won't.

Sean Lane: ...Literally, they were handing you pieces of paper for what the customer was buying or something crosstalk.

Heidi Rawding: Yes. We didn't have customer success in the CRM, we didn't have renewals, everything was tracked in a spreadsheet by Excel.

Sean Lane: So starting with the systems, any other things that you brought with you from the previous gigs?

Heidi Rawding: I think it's being okay with that I don't know what I don't know and being completely okay with ambiguity. Startups have a lot of ambiguous situations that you have to be okay navigating and trying to find out what's your north star, where do you need to focus your time. And that does differ from company to company, but being okay with that ambiguity, it just gets you ahead of the game because people get scared, they start reeling, and again, it's making that chaos.

Sean Lane: So it's almost like you're not going in and saying," Okay, I've done this two times before, I know exactly what we need to do."

Heidi Rawding: Would never do that.

Sean Lane: It's more like you have this framework that you're working within and you by now have the context to be able to look around and say," Okay, this is what's happening here, this is what's happening here. I recognize this, but the solution might not be exactly the same as it was at Acquia or Rapid7."

Heidi Rawding: And it usually isn't. And I'm okay with that. Yes.

Sean Lane: Right. And if it were, it might be a little boring.

Heidi Rawding: I agree.

Sean Lane: You probably wouldn't get your," In the weeds," thing that you're talking about. One of the other things I want to talk to you about was the fact that you've seen, as your career has evolved, the role of sales operations and revenue operations and biz ops, whatever you want to call it. You've seen that evolve as well to the point where, when you first started, you weren't even sure what to call this. You weren't sure what to tell people your job was.

Heidi Rawding: Yes. So the Craigslist ad said," Sales support."

Sean Lane: Okay, got it.

Heidi Rawding: And that was fine by me, sat in my chair, and was like," Okay, what is this?"" Just do anything and everything sales needs you to do." And I was okay with it. What happened was simple scenarios such as sales reps writing down their call connects on a piece of paper, writing down their name, email, and title and how long their conversation was. If it was over two minutes, we would consider that a connect. And they would hand me that sheet, and all of a sudden I'm like," Why don't we just throw a check box into this person's lead in the system?" And then I run a report on connects versus me typing everything in, them spending time writing it down. We're just wasting everyone's time and energy. So that's when I started figuring out everyone's working hard, but no one's working smart per se. And I started just asking around, searching the internet," What do people do for this? How do they do this?" Trying to find other people in my line of work that I could connect to and see how they did things. So it was really just learning where can I automate, where can I be effective and try to get sales just selling. Not spending time on paper, not spending time filling things out in the system even. If I can make it a one click, that's a success.

Sean Lane: And do you think that through the work that you've done to either make some of those sales people successful or to make some of those processes less painful, that you were able to kind of change the lens through which you saw your role and other people saw your role? From this sales support-

Heidi Rawding: Yes.

Sean Lane: ...To a more... People always say" Oh, I don't really want to be in a support function for the company. I want to be in a strategic role for the company." But it's just fluffy language, but that's what everybody says.

Heidi Rawding: Yes.

Sean Lane: And so have you been able to change your lens through which you see your work, and more importantly, the way other people see your work?

Heidi Rawding: Yes. When I found the definition of sales operations back then, it was really trying to make systems, processes, and people more effective.

Sean Lane: Got it.

Heidi Rawding: And that's exactly what I was doing every day. And so I dug a little more, there weren't a lot of people with that title in smaller companies. It occurred more in larger organizations. So it was hard for me to find others. When I did, we started saying," Oh, you're operations, you're operations," and their title might not have matched, but people were starting to hear this word more and more, whether in marketing or finance...

Sean Lane: And you started to latch on to some of those other people, right?

Heidi Rawding: Yes.

Sean Lane: So that, I know, is something that you're passionate about is building this community of other operations people.

Heidi Rawding: Yes. Absolutely. I have learned so much from the companies I've been at, but I know there's so many other companies that do things differently and I still have so much to learn. So I built a LinkedIn group, I was trying to find the date... I think it was five years ago. I believe it was. And I LinkedIn connected a bunch of people that had similar responsibilities, if not titles, and asked them," Would you like to meet up?" Boston only, tech company only, and I had two people plus my best friend who was a nurse and not even in the field-

Sean Lane: Plus your best friend or including your best friend?

Heidi Rawding: Plus.

Sean Lane: Okay, all right.

Heidi Rawding: So there are two new people, thank God. We showed up at Tavern in the Square and we sat down and just talked about what we did and what worked, what didn't work, what questions they had, what I had. And it was awesome. It was just two new people that I could connect to and brainstorm with and just didn't know other ways of doing things that they had accomplished, which were super successful for them.

Sean Lane: Well, ops is I think a little bit unique just in the sense that usually the team is smaller inside the organization. So that's problem number one. Problem number two is there's often not a lot of other people even within an ops team that are doing the same job as you. Usually people are a little bit more varied and independent. So whereas a sales person can turn to their left and turn to their right and have a whole team of people doing the exact same job and lean on them, ops are a little bit more isolated. And so having a community like that can be really helpful. Even if it's only two people.

Heidi Rawding: I'm just glad anyone showed up. It's funny for being such an isolated team across companies, you're also the bridge to every other team. So you're the grease behind the wheels.

Sean Lane: Totally.

Heidi Rawding: But you're right. Finding those other individuals was difficult. But I think the more I stuck to it... Our group now today is over 500 people, and this is Boston sales, marketing, revenue ops, biz ops, you name it, ops folks.

Sean Lane: And it's not just LinkedIn anymore, there's a Slack channel. I know because I'm in it.

Heidi Rawding: Yes. I would almost say we've outgrown our LinkedIn group and we've grown into more global or... Well, I think right now we're United States, but we will be global revenue ops group. And I can't even count how many people are in there. But you see the activity, we have five different channels. There's someone on it all the time.

Sean Lane: And you still, in addition to those virtual resources, are still doing physical meetups too, right?

Heidi Rawding: Yes.

Sean Lane: And can you give me an example of a topic that you guys have covered recently that might be helpful for people?

Heidi Rawding: Our last topic was change management. Very great panel that we put on, including one of the guys I'd hired at my last company. And before that was clean as you go, so helpful tips and tricks on how to keep your CRM clean.

Sean Lane: Cool. So I have a question that I need your help with. As one of the people who runs some of these events... And I'm not saying this happened at your event, but I've been to ops events before where you show up and all of it is ops people complaining about their jobs.

Heidi Rawding: Or about salespeople.

Sean Lane: Yeah. So here's the bad version of that change management panel, which is not the way it went. A bad version of that is everyone shows up and is like," Yeah, I had this great idea that inaudible person thought was amazing. I wanted to implement it, and then a bunch of people got in my way and I couldn't do it. And so therefore I'm now sad."

Heidi Rawding: Yes.

Sean Lane: Right? And then they tell everybody about it and it's just not helpful.

Heidi Rawding: Correct.

Sean Lane: So how do you, within your communities at your building, prevent that from being the case? How do you stop that finger pointing and woe is me attitude?

Heidi Rawding: I actually think our community is a much better off place. It's almost more internal in the work environments where people don't understand it is that mentality. So I would say the people that invest the time after their hard day of work coming to these events aren't too negative. Thank God. But internally I think it's about adoption and enablement. I always recommend if you're going to roll something out, no matter how small it is, go to your top achieving rep and go to your biggest hater or your saddest rep of them all. Win them both over and see," Okay, I want to do this. Do you like it? If you don't, why?" Work with them. If you get those two people, those are your most extreme.

Sean Lane: That's such a great point.

Heidi Rawding: So that's actually a great way to... And then they're also behind the enablement before you can roll it out to the rest of the team. So getting them to almost be your advocates.

Sean Lane: Top rep, biggest hater. Get them together.

Heidi Rawding: Yeah.

Sean Lane: I like that a lot. I also like what you said about... The people who are taking that extra time to go to an event, to listen to a podcast, to read up on a specific topic or post in...

Heidi Rawding: Go getters.

Sean Lane: Yeah. Those are the people who you want on your team in the first place, and so it's a great place to do that. Amazing. Before we go, I've got a quick lightning round of questions that we ask all of our guests. Okay, ready? Best book you've read in the last six months.

Heidi Rawding: Taking on Water by David Rawding.

Sean Lane: Okay, I have not read that.

Heidi Rawding: That's my brother.

Sean Lane: No way!

Heidi Rawding: Sorry, you set me up.

Sean Lane: That's amazing. Is it fiction?

Heidi Rawding: It is, yeah.

Sean Lane: That's amazing. I can go on Amazon and buy this book?

Heidi Rawding: Yes. He has two books.

Sean Lane: Oh my God. This is a talented family. All right. Taking on-

Heidi Rawding: Taking on Water by David Rawding.

Sean Lane: Look it up. Favorite part about working in ops.

Heidi Rawding: You might go in thinking you know exactly what you're going to do that day, but there's a very good chance that you don't touch any of it because other things happen. You never know what you're going to get.

Sean Lane: I might know what your answer to this is going to be as well. Least favorite part about working in operations.

Heidi Rawding: Yes, I could revert back... But no, my least favorite part is when people think sales ops is CRM system admin. Nothing fires me up more than that.

Sean Lane: How do you fight that?

Heidi Rawding: I say," Clearly you haven't worked with a revenue operations professional. You've worked with a system admin and that's a very important strategic role, but it's just one portion of what sales operations does."

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

Heidi Rawding: Tom Wentworth, CMO, huge Drift advocate.

Sean Lane: Yes. I don't know Tom in real life. I just know him on Twitter.

Heidi Rawding: He was my CMO at Acquia. He's also my CMO at RapidMiner.

Sean Lane: Awesome. And one piece of advice for someone who wants to have your job someday.

Heidi Rawding: You don't know what you don't know. And I think that is so important. And going in... Especially if you inherit a team, just let the time to absorb, ask questions, instead of coming in and mandating. Even if your framework has worked before and let other people fail, meaningful failure experiences. I've failed many times and I've learned something from each one. So just don't do it twice.

Sean Lane: That's awesome.

Heidi Rawding: Those might have been a few.

Sean Lane: No, that all lines up. Awesome. Heidi Rawding, Senior Director of Revenue Operations at RapidMiner. It's a mouthful.

Heidi Rawding: Yeah, it is. I agree.

Sean Lane: Thank you very much for doing this. Really appreciate it.

Heidi Rawding: Appreciate it. High five.

Sean Lane: Thanks so much to Heidi for being our guest on today's episode and thanks to the team at Drift who made the podcast booth at Hypergrowth happen. Thanks to Janna and Mark and Molly and Elizabeth, and the whole team who helped get everything set up and record that episode. Quick plug. We did this at the September Hypergrowth in Boston. We've got one more Hypergrowth event before the end of the year. It's November 18th in San Francisco at the Masonic. This is our second year going back to San Francisco. Last year, it was an enormous success. We're super excited to be going back to San Francisco. Again, that's November 18th. If you listened to the Operations podcasts and you live on the west coast or you're going to be heading to the west coast and you need a ticket, shoot me a message on LinkedIn, Sean Lane, or email me, slane@ drift. com. And I can hook you up with a promo code. I've got a few left that I can give out for the Hypergrowth in November. Also, if you like the show, leave us a six star review on Apple Podcasts. That's going to do it for me. See you next time.


You hear a lot about serial entrepreneurs. But in this Operations episode, Sean sits down with a serial operator. Heidi Rawding is the Senior Director of Operations at RapidMiner and has been hired as the first ops person at three different companies. Meaning she's gone through hypergrowth and has built the foundation for an ops organization three different times. Heidi talks about what it's like to start an ops org from the ground-up, how she's built a community of operators, and why she thinks that every ops pro should have a background in hospitality.