The Revenue Architect

The Evolution of Sales Operations with Kyle Himmelwright and Luigi Prestinenzi

October 7, 2021

The Revenue Architect

Join host of the show Jeff Ignacio, as he dives deep into incredible businesses and their Go-To-Market capabilities.We’ll explore how founders, executives, middle management, and RevOps leaders & practitioners achieve their success. The podcast is not only an inspirational guide for those looking to start or scale a business, but also serves as a practical companion to building a world-class revenue function.

It's survival of the fittest and only those who adapt will come out on top! Find out what top sales teams are doing to not only survive natural selection but thrive and scale growth in the evolving world of Sales Operations 💥 👊

In this episode of The Revenue Architect, Jeff talks with Kyle Himmelwright - Director of Revenue Operations at Yelp, and Sales IQ Global's very own Luigi Prestinenzi, where you will learn:

  1. ​How Sales Ops is evolving beyond tactical executors to strategic partners
  2. ​Turning your tech stack investment into a profit center
  3. ​Closing the widening gap between high performing sales orgs and the non-innovators

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Thanks to Sales IQ Global for powering The Revenue Architect Podcast!

Kyle Himmelwright
Director Revenue Operations, Yelp

[00:00:00] Jeff: Welcome to the revenue architects. I'm your host, Jeff Ignacio in this podcast, we're going to bring incredible business athletes together. We'll explore how to build a go to market capability for businesses. No matter the size or shape we'll remix content from a bunch of different. Bring in guests, deep dive into incredible topics. So with that in mind, I want to thank you for joining us. And now onto this episode of the revenue architects,

Thank you to ringDNA for allowing us to have a great conversation with, uh, the master himself, Kyle I'm at AWS Amazon web services, uh, as a sales ops lead, I've been in the. Kind of revenue operations or go to market operations sphere for about seven or eight years now. Uh, prior to that, I was supporting, uh, the sales teams over at Google, uh, as their FP and a partner.

So having an ability to kind of work on both sides of the fence, the last couple of years, I've focused on smaller companies grow and grow. I'm really building up process, building up stack, building up their teams. Um, and then now I'm working in obviously a much larger organization. I'm also the host of the revenue architect, which is kind of the name of the webinars series.

So for those of you who are like building companies or building your revenue agents for the first time, uh, we bring on a lot of great guests like Kyle and so forth to really talk about from a practitioner's perspective on, you know, what are the things that you should be potentially considering as you're building out your company.

[00:01:32] Kyle: I'm Kyle Himmelwright um, I am the director of revenue operations at Yelp. Uh, Jeff good to see you as always Luigi. Thanks for having me on, uh, thank you to ringDNA as well. Um, so I've been in, uh, revenue sales and revenue operations, essentially, almost my entire career. Um, out of college, I did two year and a half in sales and then really, um, Drawn to understanding the why behind selling, um, kind of understanding that the mechanics of why deals happen the way they did.

And, and so I had an opportunity to move into, um, sales operations for a startup in Chicago called the Novo group. And that really started, um, you know, what is my, my career path and love affair with sales, operations, revenue, operations. I've worked at Fiat in the industrial sales consulting and, um, planning organization.

I worked, uh, I've worked at a scaling, um, SAS enterprise company prior to Yelp. Um, and currently, yeah, I'm overseeing revenue operations for our, for our go-to-market organizations at Yelp. So, um, it's been a, it's been a fun and, and ever evolving ride. And I'm looking forward to a really, really great conversation here with you with two who knew who know far more than I.

[00:02:39] Luigi: Awesome Kyle. We're really excited to, to get some insight from you today. Um, and just a bit about me guys. I I'm, I'm a sales professional has spent my entire career, um, selling across both B2C and B2B channels from a variety of different industries. Um, and I've now moved into more of that enablement side of the world, where I enable sellers to be the best they can be and work with incredible people like Jeff, um, in helping, you know, sales, operations, revenue, operations, and sales enablement really take their stack and their process to another level. So I'm really excited about today's conversation. Um, as we go through today's chat, um, please use the chat or the Q and a function to put in some questions. Cause what we'll try to do, we'll try to make this as interactive as possible. And then as we progress through the session, we'll then take some of your questions.

And, and, you know, bring it to life and come back with some, some insightful thoughts and comments. So I want to get started talking a bit about, um, the role of sales ops, right? We've seen, it's been a bit of an evolution and I want to focus on how we can move it more from a tactical to more of a strategy piece.

So let's firstly, discuss what is sales ops? You've got rev ops, you've got sales, enablement, sales ops. How do you define sales operations? 

[00:03:54] Kyle: Um, so for me, I look at revenue operations is and sales operations as being really the, the, the support organization that ties together, your go to market, your go to market teams, right?

So marketing sales, customer success, um, and really sales operations, and, and more recently, uh, revenue operations has kind of expanded to being that the glue that makes it all work together. Right. Um, and I think more recently, um, you know, we've definitely seen an evolution. With the, with this explosion of technology that exists.

Um, there's definitely been a slant, I think, towards the technical enablement component. But when I think about, um, what the, the core responsibilities are, you know, I think about, um, operations, right? So keeping the business running, uh, making sure territories are, are aligned correctly, making sure we have a good understanding of our, of our addressable market.

You know, how are we, how are we staffed from a selling organization perspective? What are the quotas look like? What are, what are the expectation. And how do we keep the trains running on a day-to-day basis? Right? There's that core operational piece of, of sales and revenue operations. I think secondarily, you know, you talked about technology, so it's managing, assessing, evaluating, and optimizing the tech stack.

And really ensuring that it is built in a way that's helping to drive the business. Um, and, and sometimes making some hard decisions on that. The third piece, I look at it as, as sort of a data insights component. I know Jeff sorta refers to it as the, um, as like, you know, performance, but basically figuring out we have this massive amount of data.

What do you do with it? How do you make, how do you make heads and tails of it, and really, how do you present it in a way that your, your top level leadership can commit. Um, actual decisions based on it. Right. And so, so really injecting, um, where are the businesses going and try and keep on, on the right path.

Um, and, and finally, you mentioned the enablement piece, which I think is, um, figuring out how to really empower all of that go-to-market market organization to understand, to, to evolve and to, to really go to market in the most efficient way possible. 

[00:05:50] Jeff: So, yeah, to piggyback off of Kyle said, you know, the way I think about sales operations is you're the COO to whoever's in charge of bringing in net new customers or customers to cross sell up, sell, uh, to expand their values along with your portfolio.

Um, and there's really a couple of key components of that. It's really, for me, in my thinking around a very simple mnemonic, uh, peas in a pod, uh, process enable. Advisory and systems and each one of those four letters obviously have a ton of things that you can break underneath them. And then you try to offer it under a couple of principles.

And I use the, another simple mnemonic called fast and it's focus, alignment, simplicity, and teamwork. And so sales operations has a couple of core, big pillars as part of its, uh, as its permit, obviously, you know, planning, forecasting, You're starting to get to looking at compensation. And obviously, you know, if you're digging into, you know, what those big pieces are going to be, uh, depending on the size of your or small companies, there might be a team of one.

It might be maybe just the team of two, and then you get to your multinational, much larger corporations and folks much have much more narrow roles. Maybe you're focused on justice. Those maybe you're just focused on. Uh, win-loss reviews, perhaps you're just focused on head count and planning. So depending on how your organization is structured, um, you might define sales ops somewhat differently, but the goals of that organization is really serve as that COO to the head of.

[00:07:19] Luigi: So in saying that right. Cause there's a lot of things that you guys have just covered. So there's a lot of components that make up that sales ops role. Um, how do we, you know, from a, a business perspective and if you're in that sales ops function, how do you move away from that tactical component of looking at forecast?

Tech stack adoption. Um, you know, some of the reports, how do you actually move it into a, into a strategic conversation that allows businesses to sort of take your findings and start to set the strategy for the organization moving forward? 

[00:07:56] Kyle: Yeah. Um, One of the things that had helped helped me in my career and I think is really, really important.

And I've, uh, Jeff and I have talked about this, so I'm probably teeing them up pretty well, but, um, you know, it's not something you'll get moving, transitioning from being tactical to strategic is not something that's generally candid to you. Right? Uh, there's a, there's a huge component there, everybody. So revenue operations or sales operations, it should just have a seat at the table.

I think a big part of it. You have to kind of come in and prove yourself and prove your worth. And I think, um, you can do that through number one, not trying to boil the ocean. Right. So establishing a really, really cadenced um, and, um, I guess deliberate, uh, schedule of, of delivering good insights, you know, adding value and being able to document and getting things done.

You know, I think, I think building. Trust from the, from the top line is really important because ultimately you're are to a certain extent you are a support organization, right? You're not. Um, traditionally a revenue driving organization. And so, you know, being able to provide that analysis is, is really, really important from my perspective in, in really garnering a seat at the table.

Um, and, and the other piece that often gets overlooked is, you know, that the technology, um, and sort of the operations pieces are, are fairly straightforward, the data and the insights and the analysis that you can provide is an area in which. Revenue operations plays a really, really critical role in, you know, I've heard people refer to it as seeing around corners or, you know, seeing where the company, where the business is and based on where we're looking to go, how do we get there?

Right. What tweaks do we have to make to our sales motion? What types of things can we, what changes can we, can we make to continue to accelerate, um, and get there. So I think that's a critical component in, in having that shift. 

[00:09:42] Jeff: So I like to talk about having like rungs on a ladder. Um, and the rungs on a ladder are really focused on at the bottom tier your, your, this firefighter and, and then the second rung you're you're this adviser.

And then on the third rung at the highest, and let's just call it sales ops, Nirvana. You're, you're really truly a partner. And there's a couple of key differences. The firefighter is, you know, constantly tackling tickets. They're constantly building, you're not managing. The business is managing you. And some folks like to say, you know, you're not an order maker, you're in order to take her in and that's fine.

The teams under capacity, the priorities are upside down. Ruthless prioritization is super helpful here. So in order to graduate away from firefighting, you focus on ruthless prioritization. Uh, building a business case on why additional capacity is needed and really setting expectations with your key partners in order to buy yourself back some, some critical time or to focus on the tasks that really matter.

The second rung is what I call the advisor. The adviser is, um, you know, you're moving away from the mundane tackling a blocking blocking, um, because you've proven you're a worry free service. And at that point, you're now focused on studying the business with more depth and you're focusing on the business rather than in the business.

Um, and then the highest level is the partner. The partner is where, you know, the business is actually coming to you and you've already. Sort of forecasted the types of problems or the questions they're going to ask, and you have a somewhat, hopefully a deep understanding of the problems that they're trying to solve.

And then you may not have the answers right away, but you will, uh, have anticipated it and put the pieces in motion in order to help unlock solutions for the business. And that's what Kyle refers to as seeing around corners. Um, but it's that anticipating piece and the fact that the business actually coming to you, whether that's a stark difference between those three.

Okay, so just 


[00:11:35] Luigi: that point, right? So you, you're essentially talking about being quite proactive in your approach and actually trying to see problems before they arise so that you can put in a plan in place that will mitigate that from happening. How do you go about influencing senior management that there needs to be a certain change brought into place based on the findings that you've had, that all the, all the research that you've you've done.

[00:12:00] Jeff: So I would say a scalpel. So. When you're in a building phase, you're, you're obviously building the infrastructure of the groundwork, but once you get to a place where you're starting to, you know, go beyond just the learning you're, you're, you're actually running and operating the business. It's extremely helpful to have an operating cadence.

And as operating cadences are going to differ for every business, but across the years, they've been somewhat similar for myself. Uh, there's been some sort of a weekly or a monthly review, uh, and those reviews you're going over, uh, pipeline. They're going over a movement, you're going over areas of risk and making sure that data hygiene is hopefully strong.

Before you go into those meetings. You're not wasting 10 minutes of basically validating the veracity of the data. The second thing is there's going to be win loss reviews. You want to know why you're. Why you're losing and what you can do about it. There's going to be, um, big deal reviews of some sort, you know, where, you know, you have these outliers that throw off your pipeline for whatever reason, but you're going to want all eyes and ears on those reviews.

You're going to want to talk about your hiring standards. Uh, who's up for promo all the things that helps the business. Hum. And once you get those operating reviews in place, it helps the people who are in those meetings who need to not only be informed, but also have. Uh, you know, they're responsible or they're approving certain decisions.

Um, they're actually coming in with the information, brought to them with hopefully some recommendations coming from ups, because again, you're, you're that partner, you're that advisor. And now your head of sales or your CRO whoever's in charge can naturally operate the business because they've got incredible, uh, incredible, um, uh, ability to comprehend what's happening to the business and what might happen.

Yeah, I 

[00:13:46] Kyle: think, uh, all awesome points, I think, to piggyback a little bit off that and what can really help in a lot of, in addition to the cadences is, is having, you know, defined frameworks for how you're delivering, how you're packaging the information up and creating a, uh, consistency and, and sort of an expectation of like, here's, here's what I'm looking at.

Here's how I digest it. Here's what I need to know. And I think that's a real key, as, you know, as you move up the rungs. Hi, how are you packaging presenting and sort of deciphering the information for stakeholders you're working with so that they, as Jeff said, really feel informed coming into the meeting.

So then it can be almost ruthlessly efficient in like, here's what we need to do. I've got, everybody knows what they need to do. You make the decisions you move on to the next thing. And I think you can be really, really efficient in that way. 

[00:14:31] Luigi: It's a really interesting topic. Right? So when a sort of. If we, if you have a look at the evolution of cell of the sales teams, right?

Um, more tech has been brought in and you know, the functions that are required to run a sales team, a growing, but 

[00:14:47] Jeff: yet 

[00:14:48] Luigi: sales teams focused on actually selling is 

[00:14:51] Kyle: decreasing. 

[00:14:55] Luigi: If you're a leader on this session or your you're thinking about, you know, I need myself as spending more time selling. Um, what's a couple of techniques or tactics that you guys can talk about that will help 

[00:15:07] Jeff: a enabled a tech stack to 

[00:15:10] Luigi: allow our sellers to spend more time selling, or what's another strategy that can be 

[00:15:15] Kyle: put in place 

[00:15:18] Luigi: to mitigate that.

[00:15:20] Kyle: Yeah. I mean, I think, I think you have to start it like the tip of that iceberg is, is understanding and understanding your tech stack and really having a good feel for, you know, is, is it healthy? Are you, are you bloated? Are you sort of, you know, are you over-indexing any in any one way? Um, one of the things I do is I keep sort of an ongoing audit of all the systems and, and you've essentially, it's a stack rank of, um, how, what, what is the priority to the busy.

And I have, you know, a whole, whole, uh, kind of readout of what am I paying, what are we paying for the tool? Um, how much, how much enablement time does it take to get people rolled up on it? What's the adoption, you know, there's a, there's a whole matrix that I think it's eight or nine kind of key characteristics that I basically stack rank all of our, all of our, um, our tech on.

And that allows me to figure out like, are we, are we over-indexed or, um, you know, are there holes? And then for me really. As an operator, I try to keep it as simple as possible. Right. And, and, and try and build, build a case for why people need to be in the tools. Um, but I think, and, and how, how it's going to make the sales, the sales reps lives easier.

Um, but as far as the first step is just kind of understanding what your, what your tech stack is and, and what you're up against. Um, I think the second piece too, for me anyways, is having a really healthy partnership with sales, right? Not. Forced forced tools on them. Um, really understanding what w you know, what, what are the needs of, of the frontline operators and how can we facilitate them?

What, you know, what are the keys to understanding how they're doing their job really helps to create, uh, you know, the most efficient sort of ecosystem and tech stack that you can, I think from a, from the backend. 

[00:17:01] Jeff: So I love the idea of a scorecard approach. Right? Cause it helps balance, like what are the core, uh, weights of what's important to all levels of the business, to the team, to the individuals.

Um, but you know, just to take a step back a little bit, you know, what is the key outcome that we're trying to drive? What what's the problem that you're trying to solve for in that. Quite frankly, allowing your sales team to optimize the activities that are related to generating sales for the business and bringing in customers.

And so if you had a way to do a little bit of time accounting for your sales team, you might very well find that they're burdened with maybe 50% of their time doing administrative tasks, because this bogeyman that we always talk about, you know, getting our sellers to sell. Um, but it is, it is a good one.

It's, it's a, it's a great, uh, it's a great compelling, uh, To tell because it helps drive a business case. And so I always think it's really important to know your sales process. And what I mean by your sales process is, you know, what are the touch points that your prospects and your customers are going through in order to understand where they are, how they can move along the buyer's journey and what we are as sellers and sales operators are doing to help them shepherd them along.

The second thing is using a framework of, you know, really working backwards in sitting in the shoes of your reps. What are you doing from a day to day and different environments are different for different sellers. If it's a, you know, a low Trent low ASB transaction, you probably have an inside sales team and a calling bullpen, or they're working from home.

Or if you have an enterprise selling motion, you're probably have field sales, probably not so much today. There's not a lot of and or travel. Um, Those folks are doing territory plans are doing account plans. They need to know the personas of their sellers. They're obviously working with large teams, uh, within the opposite of their customer.

And so if you work backwards, you start to understand what are the tools that are necessary or needed and what information do they need. Uh, and then secondly, Once you design, you know, what tools are needed, come up with an adoption and enablement strategy and then come up with a tracking and reinforcement framework, right?

So when you work backwards, knowing what your sellers need and that need that you need to know your, your, uh, your process. Second is, you know, having some empathy, putting yourself in their shoes. And a lot of that is really just use case or user interviews, uh, and then adoption or adoption enables strip, and the strategy.

And the last one again, is tracking and tracking. Yeah, she'll 

[00:19:32] Luigi: bring pretty good advice. I mean, cause if we think about right, like technology is playing such an important part of the process now, right? And I think five, 10 years ago, many companies were making that migration and knowing that CRM was, it was a fundamental.

Piece of technology that will help drive the sales process. Now there are sales engagement platform, sales intelligence platforms. There's a whole bunch of pieces of technology that sit on top of the CRM. Um, or like from an adoption perspective, because we know that user adoption can sometimes not be as high as one would want.

And therefore the ROI. For Keck isn't there. Right. And we know that sales leaders are being asked to drive more revenue, drop down their acquisition costs and increase that sale cycle time. Right. Um, what can you know, the, the role that sales ops can play in enabling that adoption and ensuring that they're getting a greater level of ROI from the technology 

[00:20:34] Kyle: like I got on one first, Jeff.

[00:20:37] Jeff: Um, I'll, I'll try to tackle it a little bit. Um, I have to be questioned. That's a good one, right? Cause um, if you look at sales tech spend, I think if you listen to a breadwinner or any of the old, like, you know, Salesforce alum, when Salesforce was, was created, a lot of folks thought, uh, what's the maximum, you know, wallets spend per head that folks would spend on sales technology.

Okay. In total. Right. Um, and if you, if you don't adjust for inflation, I think the number was something small, like a hundred dollars per month for user. Well, everyone knows now that if you bring in Salesforce, you're spending easily more than a hundred dollars per month per user, depending on if you're on the enterprise plan.

Now you start to do all these bolt-ons right. You bring on these other categories of software vendors. Um, you're nearing, uh, for outbound sellers close to 600, $700 of spend. Um, and then for inside seller or SDRs. You know, maybe half of that, that's still a material, a burden that you're putting on your operating expenditure expenditures just per head.

And so to capitalize investment from that, um, you really need to say, okay, well, what's the return on investment and how is that expressed? It should be expressed in the form of a seller feeling very natural and confident in their ability to execute their role flawlessly and that they, you know, that's really thinking about prospects.

Staying organized. You know, getting in front, uh, developing meetings and talking to the relevant people, knowing what to say when they're in front of those prospects, and that's not talking about technology whatsoever, you don't even need technology to be able to do that. But in today's environment, it is a bit of an arms race because.

Um, there are, there are companies that are adopting these technologies well, and they are gaining an edge in their particular space. Um, so I would think, um, you know, not under investing in sales operations, uh, is a, is a good, is a very strong, uh, Um, that'd be very strong advocate for that. Um, let's just shamelessly, uh, secondly, uh, spending a lot of time for sales enablement or revenue enabled, whatever you want to call it, not just enabling the front or frontline sales reps, but also, you know, spending time training your managers so that your managers are trained the trainer and.

You have your multi-threaded on, you know, who in the organization can provide benefit and training. Um, and then hopefully from there you develop some strong enablement programs. And to me, those two things are going to be hugely important in order to show the value of what's in it for the seller. And then for the act for the sellers to actually perform their jobs.

When all this investment that we're throwing at them because it quite frankly is a little bit overwhelming. So just 

[00:23:15] Luigi: before we go, you call on that. I just want to, um, ask you a question, Jeff, on that and just dive a bit deeper. Um, what should come first if you're thinking about technology or if you've already got that technology in place and you've got, you want to bring more in, you've just spoke about that enablement piece, right?

And the fact that there's a whole bunch of skills that sellers need to have in order to. You know, the customers get to that point of decision in the buying process. When should that enable them to coach? Should it be pretech should it be, you know, let's stop putting more tech in place until we get our, our skills, right?

Like from your perspective, when should it be happening? 

[00:23:52] Jeff: Oh, pretech a hundred percent. Um, you can sell without technology. Um, customers can find you what. You can, you can definitely bring in, uh, build a book of business, uh, without any sort of fancy technology. But, you know, I will say if your competitors are out executing you, um, on these little, on these with adopting these tools, I mean, there are some companies who don't even have.

Uh, like a Salesforce, right? I mean, they're still using a homegrown CRMs. Um, and those companies, um, are struggling because now they have to find ways to connect to all these new fangled capabilities that are building right on top of the Salesforce app exchange. Um, and so. When you're defining, you know, how to do, uh, how to, how to perform, uh, your sales process or your marketing processes without all this, you know, new technology that, that comes first.

Um, and then technology should be an enabler. It shouldn't be a multiplier, um, or at least something that cuts down on the time, uh, in order to execute those same level of activities, you 

[00:24:54] Luigi: know? Awesome. 

[00:24:55] Kyle: Yeah. Uh, just the one, one thing to on top of what Jeff said, and it really struck me as, like, I think a lot about technology as very similar to similarly to how, when you're presenting, how you think about PowerPoint and PowerPoint when you use correct.

Is it it's making, it's making you reinforce your, tell your story, reinforce whatever message you're trying to deliver in a, in a more effective way. You shouldn't be up there reading and have a thousand words and all these different pictures. It's, it's a support mechanism for you're doing similarly sales techniques.

And, or, you know, go to market technology should be a force multiplier. It should be, uh, a reinforcement and a lubricant for the go-to-market process and really to be most effective, you have to have that defined. You have to know what your, what your go to market strategy is. What does that motion look like?

Because, you know, if your product heavy or inbound heavy, like there's so many different variables that can really dictate how you build out your tech stack and really what's going to bring the most ROI to your sellers. So I think having a good understanding of your business and understanding. The technology you use is going to be a, uh, an a, an efficiency.

It's not, it's not the crutch, it's not the thing that it's not the engine that's driving the machine. And 

[00:26:06] Luigi: how do you quantify that ROI? So how do you go about actually going, right? I need to confirm, you know, whether this, this tech stack is delivering us more efficiency gains 

[00:26:19] Jeff: it's. 

[00:26:20] Luigi: You're delivering me a return on investment.

What's the formula that you use called to sort of define that? 

[00:26:27] Kyle: I mean, that's, that's the million dollar question I think, with some of the stuff. You know, it's, you can do it from strictly from a time savings perspective, you know, our, how light, you know, anecdotally, or you can really track where, um, you know, where a sellers are spending their time.

Um, you know, are they spending more time on the phone? Are they spending less time on the. You know how much less, you know, and sometimes that's a little bit hard to quantify and a little bit subjective, but I think Jeff made a really interesting point earlier about not forgetting about the TA the ROI and the time savings on the backend, 

[00:26:57] Jeff: right?


[00:26:58] Kyle: how much time is it saving your team? Um, and one of the things that I do with my team is I keep a really, really diligent running. Essentially task lists that optimizes all of my team's time. So I know how much time we're spending in meetings, how much time we're spending, putting out fire drills, how much time we're spending running reports, doing all these different analyses on a week to week basis.

And I have sort of a bucket of recurring keen tasks and then, and sort of ad hoc project based work. And I think from there I can see, am I over index? Am I spending. A ton of time running forecasting or, or, you know, w they're using that as an example, if I, if I'm putting a tool in that, and that has come down markedly, then it's, it's a pretty easy, um, you know, story to tell in terms of time savings in terms of ROI that, that we're seeing as an organization.


[00:27:44] Jeff: And that's a couple of ways you can do it. Um, you, you can develop, uh, uh, more of a subjective informal that turns into like converting anecdotes into a quantitative study. So really canvassing your sales reps and understanding, um, how are you spending your time, right. And, and breaking down the different categories of activities.

And if you're balanced towards, you know, spending time finding contacts, finding their numbers, Trying to figure out where your playbooks are, you know, what message to deliver, trying to create proposals by hand, like the simple things like that. You start to take a look at it. Okay. Well, if we add technology, it would be a force multiplier we could shrink down at the time it takes to find the information.

To perform those actions and actually find a way to multiply potentially the number of great looking proposals with great information and part of it. So if you start to do a survey around, you know, how are you spending your time? And you're finding yourself like around 50, 60% of the admin type work. Um, and then you're able to crush that down to something more meaningful to the organization.

Um, like I'll give you an example. I think there is a. Th, I can't remember who published that recently, but sellers, if you were spending more than 25% of their week in, in non-selling media, Right. Um, and that's, that's burdensome on top of the actual selling time that they're doing their time blocks with in front of customers.

And then at the time that they're using to do, um, you know, pre briefs, debriefs, recaps, summaries, um, getting their forecast ready for their managers, you're starting to overload the sales reps in a number of different ways. So finding ways to balance and saving time along those categories thinks hugely important.

And that I think that's one easy way. You can start measuring the impact. 

[00:29:34] Kyle: Okay. There's two, two other quick points. Um, the first piece is I think this is an area of specifically, and particularly when looking at investment, um, piloting is really important. And I, and I know sometimes, you know, when you look at, uh, piloting a of software, you just want to see all the bells and whistles that and see how it works.

But if you go into. And you have yourself, a good control group and then your tests, and then you run it with a few reps. You have it well, stalled out. Here's how we're going to measure. If there is an improvement, that's a, that's a, this is a premium opportunity to really, you know, number one to get buy in from your reps.

But also to understand at scale, like before signing a three-year contract with, uh, with, uh, with, uh, a software, you know, having, uh, some concrete data points there. And the second thing, um, I would say is Jeff kind of alluded to this, but I think it's really important. Not over-index on data and not over-index on sort of feel right.

And I think that's a really good revenue operator has a good balance of sort of the art and the science. Right? You are able to anecdotally work with your frontline operators, understand with sales people, where are your pain points at? Like, let me get a feel for what's going on and then try and marry that up through data to understand, okay, how do we drive?

How do we drive change? How do we measure that? Um, but I think sometimes there is this tendency to say, oh, We're going to get all this, all this data and we're, and it's going to tell us what to do. I think there is, there is a middle ground and that's really the sweet spot for making smart improve decisions.

[00:31:01] Luigi: Oh, so we've touched a bit upon, you know, moving tactical to strategic. We've now looked at the tech stack and how we can kind of ensure that we're getting an ROI and we're looking at it. Um, I want to talk a bit about, you know, closing, closing the gap between high-performing sales, orgs and non non innovators.

Right. Um, and we spoke about earlier that sales are spending less time selling more sales teams are spending less time selling. Um, how do we continue to innovate? How does sales operations influence a business to continue to innovate and ensure that yes, we're using tech, but we're also enabling our sales team.

To really cut through and become that high-performing sales function,

[00:31:48] Kyle: I think, uh, you know, to, to start. And I think, I think, uh, Jeff was talking about this a little bit just before, but having a good fuel for four where, you know, I think there's this, uh, perception of when you're really humming as a business, everything's going well. Generally speaking, there's always room for improvement.

And so understanding, you know, as you're going, you're looking at your selling organization, you know, holistically, how much time are we spending in, you know, non-revenue driving activities. Um, you know, and, and where are we seeing? Where are bottlenecks in the process? You know, are, do we have deals that are being stopped in certain areas or anything that you know, or certain speed bumps and really understand that.

That it's it's, uh, it's, there's a continual improvement process to do and understanding like where, where are the, where are the margins that can be gained? Um, and, and really, I think that's something, honestly, as, as revenue operations, you should be building that into your culture. And part of the, I think like the, the essence of revenue operations is it's, it's sort of a constant evolution.

It's a constant, um, problem solving machine. I think that's part of the responsibility of rev ops is understanding. What, what, where, what areas can you innovate into and what, what are the things that are coming down the pipe and how does that fit into the vision that that's sort of been laid out for the organization, by the way?

[00:33:04] Jeff: So I, I thinking about this, um, and I'm looking away cause I'm just typing up some responses, like how I would respond to this. Um, but developing a flywheel, um, in a flywheel is very different from a linear motion, right? It's basically a virtuous cycle. And so the way I'd like to think about it is how do we make sure that we have the appropriate strategy?

There's a couple of ways we can do that. Um, as sales operators, um, is really helping to understand. You know what segments we should be going after and what businesses we're not in. Secondly, um, I use a framework called the segmentations and the three CS. So that's segmentation coverage, um, capability, capacity, and capability.

So those are the three things that I like to think about coverages. You know, how are we going to go after this segment? We can go after an outbound, inbound, through partners and direct, et cetera. Uh, CA capacity is, you know, how much, how much resources, how many resources should we be throwing at? It should be head count.

Should we be augmenting the channel? Um, and, and the capabilities, like, how do we, how do we make sure that the folks who, you know, where the name brand on the front, um, represent, um, our process to the best of its ability and, and bringing value from the customer. Then second is, uh, you know, developing. The rhythm of the business, really the operating rhythm.

And so I talked about some of these key meetings earlier, a monthly business review when loss reviews, big deal reviews, really going over recruiting and pipeline, really understanding the pulse of the business. And then lastly are these like feedback loops. Um, and so these feedback loops allow you to do a couple of things.

Bring the learnings from across the business. To, uh, your, your, your, your strategic leaders down to your tactical, uh, middle management to your frontline, to your frontline executor's. And that allows you to hopefully rapidly respond to changing and shifting trends that are happening with. Um, 20, 19 and 2020 or 20, or like momentous year.

So obviously everyone went from a T and field based selling and field based marketing all the way to everyone was an inside seller, uh, zoom, which platform we're on right now exploded as a platform. And so, you know, a lot of folks had to develop brand new habits. Um, you know, we were digitally transformative last year and now we're digitally native.

How do we be strategic? I like to think about it as, how do we make sure that we are going after the right strategy? How do we operate the business and create the pulse, uh, or measure that pulse and then create those feedback loops and then apply learnings. And to me, that's how we become hopefully leaders, um, as folks in sales ops or whatever title you might have and what are some of the things that.

[00:35:44] Luigi: We can really do, because if you think about that, the change that we've sort of seen in the last 18 months, you know, that outside sales role has essentially become an inside sales role. Do you guys foresee that the change back to outside is going to happen or will it continue to sort of, if companies have seen that they've been able to execute their sales process with an inside sales model that they'll just adopt that inside sales model.

[00:36:13] Kyle:

[00:36:13] Jeff: personally think it's yeah, I think it depends. Yeah.

[00:36:22] Luigi: I think just, well, drifts pools. 

[00:36:24] Kyle: I think we, I think, uh, so I have a similar answer I'm thinking is, is I think it depends. And I think it depends on the nature of. Of your business. I think it depends on the selling motion that you deploy. Um, you know, I, I think there's a lot of variables and it feels like such a kind of middle of the road answer, but I think there's, you know, there's not a one size fits all.

I mean, using Yelp as an example, we were exceptionally office-based. Um, you know, very, we're a very, very big, um, you know, in-person culture and you think about, you know, the traditional, you have your sales manager, you've got your 10 reps sitting around you, they're on the phones, they're doing what they're doing.

You have almost line of sight, um, you know, sort of reinforcement that people are doing the right things. You can get a pulse of the, the general mood of the team. Um, you know, and so that's from the selling perspective and, you know, going remotely, we had to, we had to completely rewrite. How to read all those signals, how do we make sure people are on task?

How do we make sure that they're feeling included? And I think, I think it's going to be a similar, a similar sort of strategy with sellers is like, you know, are we able to grasp a good pulse on the, on the business? Um, and on the seller without being in person, you know, and, and kind of what, what does that mean?

What do those mechanisms look like? I mean, if you, and then you look also at like, you know, Really really big ticket sales. You know, there is always going to be a component of really being comfortable with, you know, who you're buying from. And I don't know if that's ever going to go away because there's always going to be that human elements of it.

But I think ultimately it really depends on, on a couple of factors that, you know, the least of which is, is what, you know, what type of sale is it? What's the emotional. 

[00:38:00] Jeff: Yeah, I think my internet crapped out a little bit, so I don't know if I like was speaking and that it cut out. Um, well, I'll, I'll just make the point.

Um, you ask a question, like, do you feel that there's going to be a thawing of the ice, you know, post pandemic? Uh, there will be, and I think it depends on what you're buying. One, right. There's some things that are better accomplished in person. So for example, um, you know, these enterprise level deals, um, you really can't meet all the folks, um, on a zoom sometimes, and those conversations are better accomplished, actually flying on site meeting folks, second, some of the demand generation activities.

Um, and we're not talking about selling here. We're, I'm talking about at the very top of the funnel, uh, better accomplish in person. Um, there are many industries that build their pipeline off trade shows, um, and you know, those are, have largely gone away or at least transitioned to a virtual format, um, over the last 18 months.

And so what I would see is, you know, what did we learn is more important? Uh, Um, companies have opened up their hiring policies to hire, uh, across the country and across the world. Uh, those are, those are one way type decisions. You're not going to reverse those. So just because, uh, the pandemic has, is over, uh, you're now living with a workforce status distributed.

Um, second is the buyers, the buyers the buyers have now, uh, become accustomed to meeting, uh, in person, uh, for better or worse. Uh, I can tell you that if I'm on a meeting yeah. I'm looking away. Sometimes I might not be paying attention or I am paying attention. It's hard to sell to this. There's some new dynamics that have to be considered.

So I'd imagine that, um, you know, I think virtual selling is here to stay. It's always been here by the way, for like inside selling, um, It's good. You're going to see more. Um, I think a sizable chunk of field sailing activity done on the inside, um, which I think is great. A lot of people get to work from home, but that presents its challenges as well.

So some new things for, um, sales leaders, enablers, and ops to sail through. Um, I expect that. It's a higher percentage of outbound to be done, uh, in sorry, outside to be done inside. And I expect more buyers to feel a lot more comfortable, um, buying, uh, face-to-face via zoom or whatever software you're using, but I think that's one emerging trend.

And I do think I'm hiring the best and the brightest from across the world and across the country, I think is a competitive advantage for a lot of companies to consider. 

[00:40:32] Luigi: Yeah. So I just want to ask you before we get to some critical, a lot of questions, um, that have come up from the audience. But I just want to ask this, if you know, I was reading a, a McKinsey report about the omni-channel experience that buyers are looking for.

So it's becoming a bit of a minimum expectation from their perspective. Um, and it's been accelerated over this past 12 to 18 months. Many companies weren't will lead down that path and, and some were quite reactive. In their approach because they had to be, they had to bring in certain pieces of technology to allow them to become a remote workforce based business.

Um, if you know that the buyer has essentially changed the way they're interacting with you as a business, and you haven't fully understood what that looks like, what would be or strategy to go, right. I need to get an understanding of what their needs are. And then influence the organization to make some changes to the way our sales process has essentially been executed on to ensure that we're meeting the, you know, the, the, the prospect's needs.

[00:41:41] Kyle: I mean, I think one firm, for me that is often overlooked is, is not being able to not being afraid to leverage your current customer base. Right. And, and I think, um, Mo in a lot of, a lot of places, places are looking more and more to be partners with. You know, one thing that. I think a lot about, you know, when I'm looking at some of the software I use is how are other companies leveraging this technology?

You know, as you know, if you're in my compensation software, like what are other companies doing? That's similar to me that's really cool that I'm not doing, or I'm not thinking about. And I think using that as, especially your happy customers, um, you know, asking them and sort of using them as a, as kind of a captive audience and, and, uh, and a willing data set to understand, you know, how have, how have their buying trends change, right?

Like how have, how are, how are they going about things differently? Um, you know, It gives you an opportunity to there's a little less, you know, sort of, um, guests and guests and see, um, so you might have a, you know, an opportunity there. And I think it's again, often overlooked to, to collect some data that really allows you to, to, to have an understanding of in what like customers may be doing.

[00:42:48] Luigi: Jeff, love your input on this. 

[00:42:51] Jeff: Um, yeah. Do you mind, uh, recapping that a little bit? Just trying to think through, uh, how to thoughtfully respond. Um, that's incremental to whatever I've already said. 

[00:43:03] Luigi: I think it's just about, you know, going how, like, how do we just continue to evolve our sales process? I think it's going to be an ongoing battle.

It's it can't be static anymore. We've just kind of continue to innovate. And I think for me, when I look at sales, operations and revenue operations, that's where the strategy comes into it. It's about enabling sales leaders to actually really start to think, you know, this is how our buyers interacting with us.

These are the things that we need to do in order to help them through that journey because the buying process is a journey. We know that we know that touches to engage. Our customers is getting more and more the requirement, um, to keep engaging with them and keep educating them is 

[00:43:42] Jeff: it's becoming a wider gap.

Like when you look at it, 

[00:43:45] Luigi: um, we know that, so I suppose my question was around, how do we, and this is, this goes back to that first point of becoming a strategic partner. How do we ensure that we're helping ourselves leaders? The ones that are driving the go to market strategy in influencing the way in which I develop a go to market strategy.

[00:44:06] Jeff: So, um, a couple of things, um, one having a process is extremely important to, uh, keeping up with your buyers. If we look at. Some emerging trends that have happened over the last. Um, and then that I'm not being precise here, maybe like 10 plus 10 to 15 years. Um, the information, uh, asymmetry, um, was largely in the hands of the seller, right.

Benefiting the seller. Um, but a lot of the information is now shifted and is more easily attainable by the buyer. Um, and thanks a lot. Thanks to community web, um, abilities for us to publish prices. Although enterprise pricing for software companies, the, you see a button called contact sales. So you actually don't really know the price until you call someone.

But, um, you know, the trend is buyers are researching and evaluating well before they talk to a seller. Um, you know, I can tell you that I'm looking at reviews, uh, you know, G2 Capterra software advice, you know, your. Yeah. Or you're back channeling you're, you're talking to your, your peers and your friends who may have had some sort of interaction, uh, with the vendor you're you're you're considering because you're one you're you realize you're going through some sort of pain.

You're identifying that you need a solution and you're starting to evaluate and research options, and that's kind of typically the mental buying process. And a lot of how they're able to get through that process. They can do it by themselves. They don't need you to hold. They don't need you as a selling organization.

So like hold their hands anymore. Right. Um, they have options. And so where we as sales ops partners can be, I think thoughtful is understanding what is happening to the. You can do that in a couple of ways, you can do that by looking at the data stream or two, you can just go talk to buyers, go talk to sellers and understand why you won, why you lost, what worked well, what didn't.

And that's also going to be hugely beneficial to feeding back to the selling organization also to the top of top of the funnel. Like how did, how, how, how do you generate pipeline in the first place, uh, and doubling down, and then having a process for experimenting for these new outlets to bring in new pipeline.

Um, and be thoughtful and, um, and figuring out, you know, okay. Let's experiment. Um, let's set, you know, a stretch target for ourselves, develop pipeline from these avenues. Um, one such trend that's emerging today is that enterprise software is being purchased with the click of a button and that wasn't available a long time ago, um, or not that long ago.

Um, and, and now, secondly, you know, these folks are coming in, um, you know, the, bring your own phone. Bring your own it movement is largely been, it's all wrapped up. Right? A lot of us are using our personal devices for work, but a lot of folks are now bringing in, bring your own software. And so you have these softwares that are being purchased and use at the department level or an individual.

Uh, it's not, it's not sponsored by the general organization. So these are trends that are, uh, that have been around for awhile. Um, and we have to keep up with that. Um, so as you think about it, I can tell you. You know, when I was first got on the sales ops eight years ago, I wasn't thinking about someone hitting a forum, going through a free trial, converting to a paid user.

And then, and then trying to get them to sign up for an annual or multi-year contract, and guess what goes go across departments and divisions within the company. You know, that wasn't on my radar at that time, but now it is. So, you know, obviously you want to have those, you want to pay attention to what's happening with buyers and how they came to you in the first place or why they chose someone else.

Um, and you'll probably learn a lot along the way as you're going through that. 

[00:47:31] Luigi: Yeah. Awesome. And I just want to be mindful. We've got a lot of questions. So I want to use this last part to answer some of these questions and I really lost one of the 

[00:47:38] Jeff: questions. 

[00:47:39] Luigi: Um, I actually want to focus on the, the building, you know, what can rev ops, what role can rev ops play on coaching reps for skill?

I love this. So merely training automation for process. So. Sure if we can address this. Cause I think this is a common one, right? Um, that we're seeing now, it's that we're bringing in sales teams or salespeople we're hiring fast inductions, quick, getting him on, getting them in the seat very quick. Um, and as you know, the forgetting curve is a real problem that a lot of, a lot of people suffer when, when getting smashed with, with information.

So what role can rev ops play in that, in that, in that, you know, part of the 

[00:48:19] Kyle: process.

[00:48:23] Jeff: Kind of looking at you. 

[00:48:27] Kyle: I think this is a, I mean the most, the best case for why. Not the onboarding is important, Luigi, as you said, but ongoing enablement is equally as important. And I think, like, I think as things have gotten to be more complicated as more and more complex, like the, the rise of enablement, it's just, it's just becoming.

You know, more and more and more. And so I think having a really good and quite frankly, you know, making things simple, you know, how do you, how do you, you know, maybe make the lowest barrier to entry, make it really easy, really digestible. I think that's really important. And having, you know, when you're, as you said, when you onboard, it's like drinking from a fire hose, you're, you're underwater bear very quickly.

And so how can you create something that, you know, once you onboard and then it's also repeatable and, you know, it's something that you can react to. Two weeks down the road and, and or two months down the road and to Jeff, the point that Jess made over Oregon, really having an established cadence of how to do that, right?

Like forcing sellers, Hey, once a quarter, you're going to, you're going to take a, a brief little, you know, training to just refresh on your skills. And, and it doesn't seem like a lot, but just putting that requirement in there and, you know, a trick that I've done in my career is, is tying those trading miles.

To a bit of their comp, right? Like, Hey, you've got to, you've got to create a hunt. You've got to complete a hundred percent of your training modules over the course of over the course of the quarter, it's going to be 5% of your compensation. You got to make it enough that they care, but just tying in and really setting expectations is part of the culture.

That's how the company is going to be successful by, by really by doing that. And I think that's really important to ensuring that, you know, uh, people gain and retain and, and, and are able to be effective. 

[00:50:14] Jeff: Um, I'll add a couple of things here. Um, first is, uh, you know, if you think of people becoming, uh, very productive, um, employees, it's a light it's, there's a life cycle to it.

Um, how do I identify, recruit, bring them in? How do we get them comfortable, familiar with the business that can be somewhat overwhelming on the first few days? Um, Shouldering, uh, lessening the burden of that overwhelming feeling of starting at a new place. Um, getting them to know, uh, their customers or prospects who they're selling into, what are your products, um, and finding ways to deliver that level of knowledge up to a sufficient level of.

Within a acceptable amount of time in order to go out and, and, um, and hit, hit the ground running in their territories. Um, and if we use the, we use the phrase, hit the ground running, but quite frankly, folks are like waking out of bed and they're trying to run a mile or stumbling. Um, and so you want to try to like be reasonable and thoughtful about how you develop your people.

Uh, cause people at the end of the day are the, probably the most important. Piece of a business. It's not the technology. Uh, besides the customers, the people internally are really important. Um, the second thing is, you know, when you're designing solutions, um, you know, design at scale, you know, try not to solve it for just one person.

Find a way to make sure that it applies broadly to the entire team. Uh, and then if you're not investing in enablement today and you're, you're kind of just doing it through, you know, manager to rep that apprenticeship model, um, I would usually consider maybe bringing in a true like sales enablement function.

Um, and that way you can at least start to standardize, um, at least a minimum viable process, uh, across the business. And then everyone can adopt and adapt to their own style afterwards. 

[00:51:59] Luigi: Yeah, that's 

[00:52:00] Kyle: awesome advice. And one thing just to, to, to, uh, back up there, um, I think there's going to be an expansion in the, uh, Jeff, Jeff mentioned this earlier and I really want to double down on it.

It's enabling the manager, the team manager to, to really be a first line of defense. Cause I think a lot of times it's oh, I don't know how to, I don't know how to fix this. So to go to rev ops, right? Like it's just pick up the lifeline and if we can get to a place where the expectation, you know, oftentimes the expectation of the Selma sales manager is just, you're a good seller.

Now you're going to drive. You're going to really espouse that knowledge onto a team and we're going to drive, uh, you know, Drive to a number, part of the manager's responsibility needs to be making your team effective as well. And so how do we, how do we, I think training of managers, it's often overlooked.

It's always just, okay. We're going to enable the reps, that's it. But having a more specific training to them, to that middle management piece, I think will be immensely helpful as well. 

[00:52:57] Luigi: Okay. Awesome. And just before we wrap up, is there another question that we could, we've got a, quite a few Jeff that we should probably try to hit.

Um, before we finish up, but, um, I think one that most sales ops people and, and we've covered this a little bit, but Jay, um, has mentioned, you know, how, how, how to elevate that conversation and get a seat at the table strategically, um, and be seen as a thought leader versus a contributor. 

[00:53:23] Jeff: Shout out to Jay.

Uh, I was just, I was just as manager.

So I think it's about, uh, okay. So the question is how do you get yourself into conversations at the upper echelons of the business as a thought leader versus an IC? Um, and I think it comes from. Bringing the immense value to that level, um, of what the folks care about. Right. Um, and the attention that executives are paying attention to are one, um, they're a little bit more macro than what's happening at say the sales manager.

Uh, level or at the, at the sales rep level, right? The sales rep level is looking at an opportunity. They're looking at their call blocks managers were looking at their territories and getting their people up and running, uh, and solving problems on their behalf. Um, at the executive level, they're worried about a lot of different things.

So competitive. Um, they're worried about what's happening. Um, are we delivering on certain, in certain markets, certain segments? So bringing value in terms of asking like some core critical questions. So your observations at your level super important, cause that doesn't always surface up to the top or to, you know, however, how you want to get it to so make sure that you connect the dots to what matters to the business.

So you ask the core question called, so what, um, and then obviously you do need to do the homework. You have to get to a point where. Uh, you're a performer, um, an exceptional performer and a you've earned the seat to have your voice kind of, uh, you know, your opinions brought up and that, that type of, um, high-performance observation connecting the dots to what, to what matters to, uh, the team and then going above and beyond.

Meaning if you recognize something that's missing. Don't wait around to sell someone, tells you, Hey, you know, Fred to go fix it. Um, why don't you just raise your hand and say, this is an issue in the business that needs to be addressed and I'm going to go do it. So those three things to me are hugely important.

Um, and, and that's how I typically, um, climb that at least in my careers by proving value in that way. 

[00:55:23] Kyle: Yeah. What's one on all that I would say. Yeah, biasing towards action is, is almost always a good thing. Um, and, and, you know, as long as you know, one of the things that I maintain with my team is as long as you have a good rationale in a, in a, in a pretty good logic behind why you made a decision, like either we're going to learn something from it, you know, you make just as many good decisions as bad.

You know what I think th th the really important part is what have you learned from those decisions? And so biasing towards action is really important. And I think kind of to Jeff's point. Um, just coming with solutions, like, eh, you know, sort of an extension of that, like thinking, thinking one step beyond it's like, what is, if I were forced to make a decision here, what's the next thing I would do.

Right. And how do I explore that and bring that to the table. So now you're thinking ahead, and if you're coming to the executives and saying, Hey, we've got this problem, here are your two to three potential solutions. We have. Here's how here's, what the outcomes might look like. Here's what, here's, what we think could happen.

That's really going to be a value add as well, because now you're helping know, see around those corners. And you're just thinking about the business more than you're just thinking. Delivering a report for instance. 

[00:56:28] Luigi: Well, James, this has been awesome. I think the conversation thread has been fantastic, a lot of valuable insights, um, for people across the organization, not just in operations, sales ops, but also, you know, enablement and leadership.

So I want to thank you guys for bringing some thoughts, um, to the table. We'll everybody that's attended today. And for people that didn't get the chance to attend, we're going to send an email with the recording so people can engage with. And also we'll take some of these questions that I might ask you, Jeff, and call to help just bring some, some answers to some of the questions that we didn't cover.

Um, again, thank you for ring DNA for bringing this event, um, where everybody also tune into Jeff hosts and incredible podcasts called the revenue architect podcast. It's very much practitioner driven. Um, the insight that it'll allow you to take and implement to help you scale, um, you know, the revenue line is incredible.

I've learned. Incredible amount, having, you know, listening to it at each and every week. So, um, sign up to the, to the podcast. If you get the chance, I've also put the links for everyone's LinkedIn handle. So send us, it sends us a shout out, give us a share and yeah, really appreciate you attending today and want to thank everybody for, um, you know, talking about the evolution of sales ops.

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