Top 5 Lessons From 50 Episodes Of Operations

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This is a podcast episode titled, Top 5 Lessons From 50 Episodes Of Operations. The summary for this episode is: <p><span style="color: rgb(0, 0, 0); background-color: transparent;">50 episodes of Operations! We have officially hit the half-century mark for our show, and that would not have been possible without the brilliant Operators who have been so generous with their time and their lessons on this show.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0); background-color: transparent;">After 50 episodes, we thought it was only fitting to look back at the top 5 lessons we’ve taken away from our guests. So whether you’ve been with us from the beginning or you’re just checking out Operations for the first time, these lessons are enduring and impactful.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0); background-color: transparent;">Our 5 lessons come from the following guests:</span></p><ol><li>Brett Queener, Partner at Bonfire Ventures (<a href="" rel="noopener noreferrer" target="_blank">Episode 3</a>)</li><li>Sylvia Kainz, Director of Global Productivity Partnerships at Airbnb (<a href="" rel="noopener noreferrer" target="_blank">Episode 9</a>)</li><li>Melanie Fellay, CEO and Co-founder at Spekit (<a href="" rel="noopener noreferrer" target="_blank">Episode 26</a>)</li><li>Rachel Haley, CEO and Co-Founder at Clarus Designs (<a href="" rel="noopener noreferrer" target="_blank">Episode 39</a>)</li><li>Karen Borchert, COO at ROKA (<a href="" rel="noopener noreferrer" target="_blank">Episode 19</a>)</li></ol><p><br></p><p><span style="color: rgb(3, 28, 51);">Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp;review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts</span></p>

Sean: Hey everyone, welcome to the 50th episode of Operations, the show where we look under the hood of companies in hypergrowth. 50 episodes! I can not believe that we have hit the half- century mark for the show, and honestly, I'm even more floored by the brilliant operators who have been so generous with their time and their lessons for the show. I've always said that my role on this show is something of a tour guide. My job is to ask the probing questions and point out the things that I find interesting along the way. And so after 50 episodes, I thought it was only fitting to look back at the top five lessons I've taken away from our guests. So whether you've been with us from the beginning, thank you, or you're just checking out Operations for the first time, we've put together those five lessons from some of our favorite guests. Ready? Let's jump in. Lesson number one comes to us from one of our earliest guests, way back in episode three, Brett Queener. Brett spent a decade at Salesforce from 2003 to 2013 as an Operations Executive, and he also later ran some of their specific product lines, like and the Marketing cloud. Today, Brett is a venture partner at Bonfire Ventures. And in our conversation, we hit on nearly every key metric there is in building a successful go- to- market machine, but there was one number from my conversation that still lives on inside of drift to this day. Internally, we call it the Benioff number. What's the Benioff number? Here's Brett.

Brett Queener: And a general rule of thumb that I use, and we used at Salesforce and Mark was amazing with this, it's how many reps do you have? And we'd be like," Well, I've got this many ramped or not ramped," And he's like," Yeah, I don't really care. How many reps do you have?"" I have this many reps." He goes," Okay." Let's say we had 40 reps. He'd go," Okay, you have 40 reps. Okay," he go," 40 reps inaudible, okay, we're going to book six billion this quarter." " What do you mean?" He goes, " It's 50K a man." " What do you mean 50K a man?" " It's 50K a man." " Yeah, but STRs and marketing and the ramping." And then he's like, " Yeah, I don't really care. It's 50K a man." So generally within a segment-

Sean: And that was his way of setting the goal? Or that was his way of forecasting," This is what we're actually going to do?"

Brett Queener: Well, this was his way of telling us, keep hiring more.

Sean: Got it.

Brett Queener: He's basically saying, at a minimum we need to do 50K a man. If we do more great, we do less, less. And it was a way of... It wasn't perfect, but from a math perspective, when you got to a segment, if you were doing more than 50K keep hiring and optimizing. If you're doing less than 50K stop hiring and fix something. Which was interesting, because one of the big challenges that the companies that you sell to, the companies I work with, is the following: they get to some level of excitement, things are going pretty well, blah, blah, blah. And then they tell the board they've got to figure it out. And they raise their B round or their C round, and go hire crosstalk.

Sean: Yeah, hire a bunch more reps.

Brett Queener: Hire a bunch of reps, including for segments we're not in. Then we hire 15 reps and we realize that we don't really how to create pipe for them and then they don't make their number and then everybody's sad. And then everybody gets on Glass Door and it says," Company, we're not winning anymore. They've cut back on the snacks. The kombucha is not as good as it was." And the company flames out, it flames out at six months because we have sad reps. So everyone's worried about that. But you don't get to," Oh, I'm only going to hire the reps when I have enough pipeline sitting here ready for them."

Sean: That gets back to the balance we talked about the very beginning, of that growth versus the capacity.

Brett Queener: Yeah. And so this 50K rule of thumb was, if you're doing more than 50K per man and a segment, keep hiring. And if you're doing less in a segment, go figure out what's going on.

Sean: And do you think that... so many different numbers, so many different metrics anybody could look at, but do you think that is the way to just oversimplify this whole thing?" Hey, what's our productivity per rep? Okay, keep going," or," Okay, we got to stop and figure something out."

Brett Queener: Yeah. I mean, if you think about, it's just the math that summarizes all of the complex answers I've been giving you. I've tried to keep them simple, but he just an interesting one and he was always right.

Sean: As a general rule, the simplest lessons from guests on the show have been the ones that have been the most enduring. For me, the Benioff number, or the expected productivity per rep, is something that I'm now just always consciously aware of. As Brett said, if things are going well and you're hitting the Benioff number, keep hiring. If they aren't, and you're below it, stop and figure out where something is wrong. By the way, if you want to go back and hear Brett's full interview, that's episode three. And apologies for the not so great audio quality, give me a break, we were only in our third episode. We were figuring stuff out. Okay. Onto lesson number two. One of the episodes that I still to this day hear about the most from our listeners is episode number nine with Sylvia Kainz. At the time we recorded, Sylvia was the VP of Global Revenue Operations at Eventbrite. And our conversation centered around how to build a rev ops team from scratch, which Sylvia had done at Eventbrite. But the thing that Sylvia was most passionate about in our conversation was not tactics or process, it was the people.

Sylvia Kainz: It's actually the people who go into revenue operations, in my opinion, are the people who have this ability about being pretty technical, but then also being able to be super customer focused. And that's not an easy skill set to get. I mean, we talk a lot about this, but it's a really tough skill set. And if I could lay another skill set on top of that, really it's all about being very analytical and also being very open to this new world. So it's a really interesting species of people who get drawn into this field. And I think it's becoming more and more interesting for people who've been probably more focused on their skillset early on in their career. And suddenly they start seeing, oh, there's a lot of opportunities in rev op where I can still be very broad. So let me give you an example. At Eventbrite, I had a Gainsight Administrator, so on the customer success side, who had been a customer success, then moved into customer success operations, set up the system, the dashboards, et cetera. And then as I built my team, her biggest interest was to say," Look, I want to be more than just the system administrator for Gainsight. I actually really want to understand Salesforce." And so by moving her into my, what I call tools team, so all my technical resources around systems, I actually gave that person the capability to say," Oh, I'd like to move into an area where, yes, I'm still the Gainsight administrator, but I also can learn about the marketing admin side or I can become more of a developer in Salesforce." So suddenly that person's career opportunity chances really widened and that was super exciting for her. Now, not everybody might be as technical as she was. I've seen other people who said," No, I'm really interested more in the analytical side, can I actually join your analytics team? Or can we talk about that?" So rev ops has this ability to be really broad and have different categories of teams that allows, really ops resources that we're sitting in... Now, the different departments before and had a two- year life cycle. But who wants to be doing the same thing more than two years? No, you want to grow, you want to do something else. And so rev ops suddenly allowed a lot of my ops managers analysts to say," Oh, I see a career path in revenue operations." And that's been really fulfilling for me.

Sean: Sylvia genuinely cared about the growth of operations folks and she made sure that they weren't pigeonholed in one specific area. The lesson, though, is in the traits that she looked for in a rev ops team member; technical, analytical, customer focused, and the most important of all to her, intellectually curious. Today, Sylvia is the Director of Global Productivity Partnerships at Airbnb. If you want to hear more from her about team building, how to organize your rev ops team, or how to fight for more head count in ops, go back and check out episode nine. Okay, we're onto lesson number three. Lesson three comes to us from episode 26 with Melanie Fellay, the co- founder and CEO of Spekit. Now in that episode, Melanie and I talked about the intersection of sales operations and sales enablement. We went deep on things like measuring the ROI of different enablement tools. We talked about the reality of tool exhaustion, but the thing that I really took away from our conversation was this distinction that she made between two terms, change management and change enablement. I hadn't heard the term change enablement used before, and as someone who constantly needs to stay on top of the changes in my own tools at Drift, I learned that this term was something that Melanie and her team were trying to codify and promote.

Melanie Fellay: It's a term we're trying to coin a little bit, because I think that's the challenge that every organization out there has, which is, how do you keep your teams aligned? How do you keep the plane flying while you're building it or whatever that expression is. But the one thing every single organization and sales team and operations team has out there is that change is constant. Whether it's in your own product and services, whether it's in your processes, whether it's in your tools, there is so much change and day- to- day decision- making that people need to keep track of. And so how can we make that just a little bit easier for employees and for their managers and for the enablement teams, that are having to keep track of all this change, as well as enable their users on it. Yeah, it's interesting what you just mentioned about people not even knowing what kind of features are available in their tools. I was asking my team member the other day about this feature and outreach, she's like," Oh, I don't know," and it turns out we just hadn't been using that feature for a couple of weeks. And when it comes to the software not getting utilized, there's a lot of tools out there that measure that. But if looking at some of the customers that were prospects that we've been talking to recently, and one of them has over 4, 000 employees and they have a 70% login rate ever in Salesforce. And that goes to show that just introducing tools, if you don't have the right change management strategy around that, if you don't properly train your users on how to use them, then it's really hard. And one of the things I always talk with an organization, I'm like," Listen, I can't solve for the fact that people aren't logging into Salesforce." That, at the end of the day... There's a really interesting Australian study that breaks down the factors that impact technology adoption. I'll send it to you afterwards. But it really comes down to a couple of different factors, the first one is perceived usefulness. What are the benefits to that user? Why, as an employee, do I want to use that tool? What is it going to do for me? And to me, you can't do that in a tool, that is what your in- person trainings should be focused on. That is what your time with your employees needs to be focused on is, here's why we've invested in this tool here's how it's going to benefit you and make you better at your job. And here's what you can benefit from using it. You're going to get more sales, whatever it is. And then there's managerial support, how do you make it easy for them to use the tools? And that's where more of a solution like Spekit comes in, which is, as I'm navigating the tool, any question that I have is easily answered. And then lastly, it's peer influence. And that's why more and more organizations, especially in larger teams, we see have power user boards or champion boards, where they identify some key influencers in their sales teams or operations teams, either because they're top performers or because they've been at the company for a long time. Or because people just listened to them. They're that person that has a lot of friends in the organization. But if you get those people bought into the tools, and they can be your force multipliers, meaning when you're trying to get adoption of new sales process, they can speak on your behalf rather than your IT team pushing that change or sales ops pushing that change. You can really create a little bit more momentum around the adoption of those tools.

Sean: Yeah, I love those three categories; perceived usefulness, manager support and peer influence. And all three of them, I think, combined together, would make for a great rollout of a new tool or a great ongoing enablement of an existing tool. But to me, that third one you just talked about, peer influence, time and time and time again is the one that I see that makes or breaks anything that we use. Anything that we use, if we don't have that third one, forget about it. It's not going to make it.

Melanie Fellay: 100%. That's what I spent a lot of my time on, when I was managing Salesforce and the majority of our tech stack at my last company, I was just spending so much time figuring out who were the people that I had to win over. And figuring out, literally sitting down with them, watching them work and asking them," Why aren't you using this? How can I make this easier? What's something that pains you?" And just identifying those low hanging fruit and quick wins, that I could potentially roll out in Salesforce, sometimes it's as simple as a button that allowed them to pull a report. Sometimes it sounds silly, but if you get buy- in from those folks on your team, then when you roll it out, and like," Okay, great. I just built this thing you asked me, go let everyone know." It's not just IT forcing adoption, it's not your sales ops, it's not your sales enablement, you've now got this champions board of people that can do that. And you can do it officially, you can do it unofficially, I think it really depends on your culture and your organization. But just like there's sales president's club that really rewards top sales performers, I think there's something to say about having power teams, power influencers out there, that really promote operational excellence in their organization. Because at the end of the day, that makes a huge difference on your bottom line as well.

Sean: The next time you're thinking about change management within your company, invert that thinking and focus on change enablement. Enablement is literally the act of making something possible for someone else. The primary focus shouldn't be on the person or the team managing the change, it should be all about who is being enabled. If you want to hear more about how the worlds of sales operations and sales enablement came together in my conversation with Melanie, go back and listen to the rest of episode 26. Okay, we're onto lesson number four. Lesson four is from the most listened to episode of Operations ever. That episode belongs to Rachel Haley from episode 39. In that episode, Rachel and I talked about the art and science of sales planning it one of the fastest growing companies out there, Snowflake. During her time at the company, Snowflake grew from 30 reps to 450, and the operations team alone grew from three people to 40. Now, there's plenty of nuggets to go back and hear in that episode. But my favorite part of the conversation was hearing about the partnership that Rachel had with sales leaders, when it came to planning for the outrageous pace of growth and the outrageous number of hires that were necessary at Snowflake. And as I mentioned, it was a little bit of art, a little bit of science, and a planning process that never stopped.

Rachel Haley: I think Snowflake is a very unique company and very lucky, in the sense that the product is so differentiated and fantastic that, for the most part, when we've set revenue goals or hiring targets... We also had a fantastic recruiting team as well, we were able to hit those. However, your point still holds, Sean, there's an art and a science to this. And that's the interesting thing about working with sales leaders and what I've always really appreciated, because I'll approach the headcount, planning and capacity, or growth modeling with a very quantitative perspective. And I'll have an Excel model or a SQL model or something that's very data- driven and mathematical. And then they'll look at it and they have all of this, basically, street knowledge is what I call it, and years of actual crosstalk in selling. And it's a very interesting and fun conversation to combine the two. You can present anyone with a model and we would do that, and especially some of the east coast sales leaders who I became really close with, I would show them these data perspective and they're like," Okay, this is great. However, this is not actually a viable company to sell to. I understand that the scoring and the data would say that it is however, I can't actually put a rep on this account because he or she will not be able to eat. They will not be able to make their quota. If this is one of their primary targets, they're going to spend two years just trying to get a first meeting. So that's not realistic." Really, the conversation was more along the lines of like," Okay, Mr. and Mrs. sales leaders, these are the assumptions that we've put together and we've been able to aggregate, how do you think about this? Does this make sense? Does this align? And is this directionally correct with what you know and understand about your territory?" And then it was more of a delicate dance. And you are right, and things probably weren't always going 100% according to plan. So we would obviously try to add in additional buffers, in terms of hedging for our revenue goals, we would try to over hire. We would try to hire ahead so that we didn't miss from a revenue perspective. And then, obviously, if that was something that we weren't able to achieve, trying to figure out which accounts we have that existing customers, which ones of those that we could try to actually glean for more of an upsell. So we always had contingency plans, but I think the higher level type of conversation was more of a delicate balance between the art and the science. We weren't just blindly taking the data, it was definitely a very strong input to how we would scale. But the sales leaders needed to agree with it and it needed to fit into what they knew and understood about selling for over 20 years in their respective territories.

Sean: Yeah. I really like the art and science dynamic. One of the things I think of, with our team at Drift, when I think about that art and science is, our sales leaders are always talking amongst themselves and with their frontline managers about the concept of building a bench. And always having folks that are either from previous companies or from their network or folks that they're proactively going out to, to actively build that bench of who's going to be next for the team. And whether that is for growing from 30 to 450 reps or replacing a rep who isn't performing. And so that balance, to me, they're building that bench. And then at the same time, all those timelines that you were talking about become critically important when you're trying to build your bench. How long does it take to recruit somebody? How long does it take to ramp that person? When are they actually going to be productive? And so that, to me, is just another version of that balancing act. How far out were you having these conversations with them? If you're saying," Okay, we need to be at 100 reps by the end of the year." How far out are you having those conversations to make sure you're at 100 productive reps at that point in time?

Rachel Haley: Great question. We were always planning, at Snowflake. I mean, as soon as we had the edict from the board of, this is Snowflake's longterm plan from a revenue perspective, this is our path to an IPO or a revenue goal that it was, which was 10X where we were at the time in 2017. We were always in planning mode. So not only were we looking a year out, it was short term and longterm planning. So we had two years out what we were thinking about, and then one year out, and we were constantly refining that every quarter. I would say, definitely start the conversations as early as you can. I think a year is probably the shortest timeframe I would start. It's not always feasible, but it takes a long time to find really qualified account executives. And especially in 2017, it was a very different economic environment then and it was an employees market. I mean, there were so many startups that were growing at a fast pace and it was hard to find good talent. And so you could never start the conversation early enough. And to your point of building a bench and always having a network of people to which you could draw from, I thought was very helpful. We did that at Snowflake as well. But back to your original question, I think at least a year. And then from the time I started, we were always in planning mode. Every quarter crosstalk, that was just the status quo.

Sean: If you want to take something away from Snowflake's planning process to bring back to your company, I'd say take these two ideas. One, they were always planning. And two, you can never start those planning conversations early enough. Recruiting conversations, planning conversations, the further you get ahead, the better. To hear more about Rachel's experience at Snowflake, including why her CEO said he had wished he had invested in operations even earlier at the company, go back and check out episode 39. Okay, we've arrived at our fifth and final lesson from the first 50 episodes of Operations. And I'm going to be honest, this was the easiest clip to pick out because to this day, the answer in this clip caught me off guard more than any answer I've ever had from a guest. If you've heard the show before, you know that I always end the show with the same series of questions or prompts. One of those prompts is, tell me someone who impacted you getting the job you have today. Now here's what Flywheel COO Karen Borchert said to that in episode 19. Someone who impacted you getting the job you have today.

Karen Borchert: This is a strange answer, but I will say it anyway. The person that impacted me the most in getting the job I have today is Lin Manuel Miranda. That is because when I was in the job I had before this, I was in a job that I wasn't challenging myself very much and I wasn't doing things that I was really, really proud of and energized by and excited about. And I heard for the first time, the full original Broadway cast recording of Hamilton. And I stopped dead in my tracks on a 10 mile run to marvel at that work and that creative accomplishment of his. And I quit my job because I decided that I wasn't doing something that I would marvel at someday and that I was truly proud of. And so I quit my job, I flew to Chicago, I saw Hamilton. I realized that I decided that it was the right choice to make. And then I set about finding a job that I could do something that I would marvel at someday and be really proud of.

Sean: In addition to being just an incredible story, Karen's lesson here is just plain inspiring and it stuck with me. Do work that you can marvel at and that you'll be proud to look back at someday. May all of us be as lucky to get the opportunity to do that type of work. Karen is now the COO of a performance eyewear company called Roka, and if you want to hear more from her and learn about the goal setting framework we talked about in her episode, go back and check out episode 19. That's it, those are my top five lessons from the first 50 episodes of Operations. If you're new to our show, I'd highly recommend going back and listening to all of the other guests who I couldn't fit into this episode. Because I can honestly say I learned something enduring from each and every guest we've had on the show. I also want to thank all of you for listening and joining us on this journey through the first 50 episodes of the show. We couldn't do it without all the feedback we get from everyone who listens to this show. So keep it coming. Special thank you on this show to our five guests, Brett, Sylvia, Melanie, Rachel, and Karen, for giving their time and their wisdom to the show. Now for a second time. If you liked what you heard and you want to stick with us for our next 50 episodes, make sure you're subscribed. You'll get a new episode into your feed every other Friday. You can also find clips of the show on YouTube now, go and check those out, and be sure to leave us a six star review wherever you listen to the podcast. Six star reviews only. All right, that's going to do it for me. Thanks so much for listening, we'll see you next time.


50 episodes of Operations! We have officially hit the half-century mark for our show, and that would not have been possible without the brilliant Operators who have been so generous with their time and their lessons on this show.

After 50 episodes, we thought it was only fitting to look back at the top 5 lessons we’ve taken away from our guests. So whether you’ve been with us from the beginning or you’re just checking out Operations for the first time, these lessons are enduring and impactful.

Our 5 lessons come from the following guests:

  1. Brett Queener, Partner at Bonfire Ventures (Episode 3)
  2. Sylvia Kainz, Director of Global Productivity Partnerships at Airbnb (Episode 9)
  3. Melanie Fellay, CEO and Co-founder at Spekit (Episode 26)
  4. Rachel Haley, CEO and Co-Founder at Clarus Designs (Episode 39)
  5. Karen Borchert, COO at ROKA (Episode 19)

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 @DriftPodcasts