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RevOps, think about it as sales ops, serving the sales community, serving the client success community and servicing the marketing community. So sales ops, client success operations, marketing operations, servicing your field organization. That’s how you should look at it. Your field organization consists out of your account executives and their leadership team, your SEO organization, your account management organization, your CSM organization, your field marketing organization, your partner organization.

That’s everything touching revenue and driving revenue basically. Welcome to Revenue Insights. Every week we’ll be joined by revenue leaders from some of the most successful and highest growing companies. Together we explore how they built their revenue teams, the journeys that they’ve been on and the lessons they have learned along the way. Revenue Insights is brought to you by Epstor.

We’re a revenue intelligence platform designed to help revenue teams to build more pipeline, close more deals and retain more customers. Hello there. You are listening to Revenue Insights. Today I’m chatting with Jake Hoffmeck. He’s the VP of Revenue Operations and Enablement at Contentful. He’s also designed and built go-to-market programs at NetSuite, Yext, McAfee amongst others.

Jake, pleasure to meet you. Pleasure to meet you, Lier. Finally connecting. That’s awesome. Yeah. We’ve finally got it together.

Really, really keen to dig into things because you’ve been in operations for, I don’t know if it’s polite to say how long, a little while.

For anyone that hasn’t met you before, Jake, what’s your story?

What’s your background?

Yeah. First of all, thanks for having me.

Yeah, my story and my background. I grew up in Amsterdam, so I’m Dutch and started out my career with McAfee a long, long time ago and moved to the US in the late 90s, sort of during the dot-com hype, primarily because I wanted to develop as a leader and learn more about sales, specifically sales in the tech world.

The Bay Area really was the place to be back then if you want to learn and develop.

I also, quite frankly, and to be blunt, didn’t want to spend the rest of my life implementing somebody else’s vision in rev ops or sales ops, as we called it back then. Decided to pack two suitcases and move and never look back. I had a great ride there. We did it by IPO with McAfee dot-com. That suite obviously was fantastic. Yext was amazing.

Moved to New York for Yext and we did the IPO with them. Great place to live as well, New York. Now back in the Bay Area, San Francisco, working for Contentful, running rev ops and enablement. Amazing. There’s so many ways I think we can take this. Let’s begin with that serious amount of time dedicated to operations, particularly around a time that revenue operations wasn’t a thing, sales operations was pretty new.

What would you say has been the biggest thing that has changed over the past couple of decades in the operations industry?

Yeah, that’s good. Maybe it’s good to sort of backtrack and sort of explain the rise of rev ops and what it is and what it should be and what it often isn’t actually. I’m going to travel back in time and sort of walk through sales ops, client success ops, marketing ops and now it all came to be.

A long, long time ago, before the turn of the century, you had a thing called sales ops and we used to sell perpetual software and you got your software in a box and most of the time that was a CD-ROM or a floppy disk. You got it to a two tier channel, so a distributor and a reseller and they typically speaking installed it.

And so a good sales ops person back then, where we’re selling perpetual software, was able to process a sales order because you actually had physical inventory that had to ship somewhere. You could design a comp plan that attracted sales talents because the number one goal of a comp plan is to attract and retain sales talents and pay them handsomely if they perform.

And so that part of the house, run a forecast goal. And so if you could do all of that, design and implement an awesome comp plan, run a forecast goal, help out with KPIs, do some reporting because we didn’t even have CRM back then and run your order management, you were amazing.

And it wasn’t easy because shipping of physical goods was quite difficult actually back then, making sure you had enough inventory and etc. So then we saw the move to subscription and I got lucky working for McAfee because McAfee moved from perpetual to subscription to host it in the time span of I think two years.

So subscription obviously is the superior model for any tech company because your revenue just becomes more predictable and you tend to retain your customers better. And when we sell a subscription, client success became a thing.

And so then we have to think about things like, ooh, our install-based metrics, we have to think about churn, we have to think about GRR, we have to spin up an account management organization, or our AEs going to take care of all these clients that we have. So we had to start thinking about coverage models. We had to think about client success apps and software.

We had to think about our engagement model, we had to think about our customer journey, all these buzzwords that everybody sort of talks about right now. And so it was really hard to make sure that the person who was really awesome at order management, the person who was really awesome at designing comp plans. I think it works right now, so we’re good.

Yeah, thank you. Don’t let me jump in with the network. I think we are good. I think we are good.

Yeah, I think we are good. And so it was really tough to basically focus on the sales side of the house and the client success side of the house because we’re just completely different skill sets. So client success ops became a thing. For a while we had sales operations and client success operations. And eventually that boiled into a single role because operating in silos isn’t ideal.

And that’s the main purpose of rev ops really. And then a little bit later on during my career when I was at NetSuite, SaaS was a thing and SaaS was a thing with McAfee as well. Because obviously making sure that your customer can download directly is superior delivering updates and is superior versus the old way of shipping software. There are all kinds of benefits to the cloud.

I’m not going to go into that right now and bore your audience with that. But marketing ops really came into the fold when all these SaaS companies went to a huge growth spurt and we all started to hire SDRs, BDRs. And I think we kind of lost the way on why we hired SDRs, BDRs in the first place. It was a training ground for the sales community.

We couldn’t find AEs fast enough. So we all developed college recruiting programs and enablement programs to hire an SDR, BDR.

SDR, BDRs used to be in their role for about nine months and they would either get promoted to an AE or an AM role or cycle out of the company. But with these hiring programs, we would hire hundreds at NetSuite in any given year. With these hiring programs and the influx of all these SDRs, BDRs, we kind of had to figure out how we would get them up to speed.

And the best way to get somebody up to speed in sales, as anybody listening to the podcast, probably knows, is cold calling or dealing with inbound flow. And that’s sort of the marketing ops side of RevOps.

So how are we going to measure the funnel?

How are we going to see if MQLs are converting to SALs, to SQLs, to SQLs?

What are the conversion rates?

What does the journey look like for an SDR?

How can we enable them better?

What kind of collateral do they need?

And so basically RevOps, when people talk about marketing ops and RevOps, RevOps plays a role in the top of the funnel side of the house, but definitely not in campaign management. So you need to have a clear distinction.

So anyways, at some point in time, we all thought it was a bright idea to sort of marry the traditional sales ops component with the traditional client success ops component and that top of the funnel component, that marketing ops component and call it RevOps. And here we are. And it makes sense because you don’t operate in silos.

And larger companies, I see right now still a lot in the marketplace where just larger, more legacy companies, they still operate in these silos. And that’s not ideal. You don’t want to have a separate system in marketing, separate systems in client success, separate systems in sales. Things don’t talk to each other. You’re going to create a data soup. It’s not ideal for your customer because you don’t develop a consistent customer journey.

So they deal with all kinds of different people.

Like, hey, this is Jake calling from sales and then somebody from the client success house is calling or you have a PDR call and all on the same account. So it’s really, really, it’s not a good look. And plus it’s just also not a wise use of your resources. So tons of benefits.

I know that was a long story, but hopefully, hopefully that sort of, I like to tell it because people don’t know where it came from, RevOps. And also find that when people talk about RevOps, they really either do a little bit of sales ops, they do a little bit of client ops or a tiny bit of marketing ops, but not really RevOps, which I find interesting.

No, I love it. I was actually writing down, I was thinking if you fancy the job as a RevOps historian, then I think there’s probably a good place for you there.

Man, that really sounds like grandpa.

I mean, it’s not, it really hasn’t been around that long, but no, I love it. So with that in mind, and I think what really stood out to me from that is kind of where we are today. And so often speaking to people in revenue operations roles, it still feels very much like it’s being fleshed out.

It’s not quite like marketing, which is my background, where it feels very clearly defined the way of doing things. Now you generally get some variations on it. Whereas for revenue operations, I think, aside from the whole idea of breaking down silos and having consistency across the go-to-market function, there’s still a lot of ambiguity around what it’s responsible for. And I think it varies by business. Now that’s my opinion.

I’m interested to know, would you agree with that or do you see it in a different way?

No, I agree wholeheartedly with it. In order to demystify it a little bit, RevOps, think about it as sales ops, serving the sales community, serving the client success community, and servicing the marketing community. So sales ops, client success operations, marketing operations, servicing your field organization. That’s how you should look at it.

Your field organization consists out of your account executives and their leadership team, your SEO organization, your account management organization, your CSM organization, your field marketing organization, your partner organization. Everything touching revenue and driving revenue, basically. So your field organization, underneath there you have marketing ops, client success ops, and traditional sales ops, supporting all these different functions.

So if you want to establish a good RevOps crew, I think you break it down further into four pillars. So we understand now the organization, the different flavors. And below that you have what I call business operations or business support. And that’s typically speaking your classic sales operations. So anything that keeps the wheels turning. Whether that’s a dual desk motion, whether that’s sales support, whether that is business partnerships.

So if you have a tech company, you might have somebody running EMEA, North America, APAC, or maybe you have different verticals depending on your coverage model.

All these sales leaders need to have their RevOps person, their business partner, just to help them out with forecasts, with QBRs, to help out with onboarding of new reps, finding their way through a maze of retake that probably exists in your company because people blew up all kinds of processes, helping out with comp queries, your name. So your classic sort of sales ops, KPIs. And so I call that business support.

Dual desk is also firmly underneath that. So that’s basically servicing the individuals in the sales organization depending on your coverage model. Then you have what I call strategy and insights, which serves the overall company. So that’s the second pillar.

And so think about that as comp plan design, KPI designs, your planning cycle, rolling up your forecast, maybe organizing a global forecast goal, QBR cadence design and bringing them to life, your bookings policies, your rules of engagement. So basically, other companies might call that biz ops or maybe it sits a little bit in sales ops, but basically strategy and insights.

Second pillar, so servicing the company as a whole because you do need that. You need to have a referee that sets out rules and comes up with strategy. Then the third pillar would be systems, basically taking care of your tech stack. And that could be either taking care of the tech stack all the way, the sales tech stack.

So adminning, engineering, or it could be working together with the CIO and just basically providing requirements to them and having them implemented. I don’t really care either way, as long as we have people dedicated to the sales tech stack. So that could be your CRM, your data tools, your sales productivity tools, your LMSs. I can go down there. I don’t want to mention any brand names.

Your forecasting apps, there’s so much tech right now out there. There’s too much actually. Most of it is really not leveraged properly, which is one of the benefits of rev ops, quite frankly. I probably cut a couple of million of costs at least out at Contentful, just a frivolous tech spend.

And quite frankly, saving a lot of work for our team, maintaining all these things and saving a ton of time for our EEs, right?

Because their manual inputs were just absolutely ludicrous. So sales tech. And then number four, enablements. And I think enablement, you could call it rev ops and enablements, but enablement is really where your sales methodology and your sales process come to life. But you still need to bring it to life in your CRM, for example.

And so it helps that enablement sits in rev ops, because you got to make sure that every step is well designed and laid out. Your sales methodology is more… So your sales process is more like how you sell. Your sales methodology is more about what your selling culture is like.

What do you believe in?

What do you want to embrace?

Is it MedPic?

Is it TAS?

Is it Sandler?

Is it selling to curiosity?

Is it winning by design?

Are you going to design something yourself?

Which is really cool. And I highly recommend that actually, because I think homegrown sales methodologies and processes that have been designed together with your best performing reps and your sales leadership team resonate much better in the sales organization and getting an outside vendor in. Hopefully they don’t pick up on that comment, but it is true. The field knows best. They really know best. Think about your RKOs.

Think about communications to your sales organization that also sits squarely in enablement. This is big. So your monthly sales meetings that are hosted by a CRO, email communication. I find communications to go wrong so often and are so poorly designed. And so it really pays off to have somebody in enablement just focusing on comps. And that’s how you structure a rev ops organization that scales.

And that’s what we did in NetSuite very early on in edX and so I’m doing it contentful right now. So field organization, if that made sense, then sales ops, marketing ops, client success ops and then the pillars below that would be business operations, strategy and insights, systems and enablements. Yeah. Hopefully that was clear. Excellent summary. I’m going to steal that. I feel like I can draw it out beautifully now.

And actually I think it really helps to start to capture all together in terms of all of the different responsibilities. Right. You kind of alluded to it while explaining it where, you know, some businesses call it something else and sometimes it kind of lives somewhere else. But in reality, I think you’ve certainly framed it really beautifully. Yeah. I think so because we’re going back and forth.

So what I see right now in the marketplace is, you know, you have somebody who’s really awesome with sales systems. Right. That’s not rev ops, man. Or you have really somebody who’s really awesome in sales process and sales methodology. That’s not rev ops. Or you have somebody who’s really awesome in KPI designs and scorecards and comp plan design and that’s not rev ops either. Right.

Or you have somebody who’s an awesome business partner. Right. These are all super valuable roles, but they’re all just a component of rev ops. Right. And I find the market is a little bit confused about everybody’s using a rev ops title.

I mean, we all know why. Right. But they only do a sliver of what rev ops actually is. Yeah. Yeah. But one that I really wanted to call out that I felt when coming into this conversation was certainly unique to me.

I don’t see it as frequently and would love to get your perspective on it because you’ve included it as one of your pillars in their enablement, which I think very more traditionally tends to sit within the sales function. But you obviously keep responsibility so much that it’s literally in your title.

So what’s your perspective on enablement?

Why do you see it fitting underneath operations?

Yeah. So a couple of things. I have one rule, only one rule in my career. I only work for CRO. I would never. That’s another thing. It’s my own personal opinion. If rev ops reporting to CFO or CLO, you should run for the hills. I have zero interest in doing that. I only work for CROs. End of story. Because I’m part of the sales organization.

I should be part of the sales organization, really, because I’m here to drive growth and it comes with way more stress. But it also comes with so many benefits. I think enablement is a separate pillar in the rev ops world. You have an enablement leader, obviously.

I think it’s really important because remember we talked about, I don’t want to use the word sales process and sales methodology too much because otherwise your audience are going like, yeah, we heard it right now. So think about your field organization. Your field organization consists out of all these roles I previously described. And all these people have different responsibilities in your sales process.

When you engage with an SC or when this makes time to engage with an SC, when does a BDR hand over an opportunity to an AE?

When is the AM going to engage?

What’s the role of the CSF?

So baking and really spending a ton of time on your sales process and really making it clear, hey, these are the steps in the sales process. These are the people that are responsible. So really defining roles. This is the type of tech. We need to support each step of the sales process is really key. And so a great enablement leader will take charge and develop this for you for sure.

And then that enablement leader certainly needs to bring it all to life. Not just with enablement and assets and collateral and playbooks, but also with the people who run systems. Because every stage needs to be clearly visualized.

How are you going to do that?

Which piece of tech do you need to buy?

The roles and definitions play a part in compensation design, for example, or your bookings policy, so your rules or engagement. And so if you have somebody in enablement working in a silo, it’s hard for him or her to really get their vision across. It’s harder for your CRO to get his vision across the entire sales organization.

And you just have less of that in rev ops, where it’s just a clear, consistent flow. Yeah. Yeah.

I asked the question and the way that you described it is exactly what I had certainly in my head, which very frequently when we talk about revenue operations, what we’re talking about is often in your full pillars, the business support role in terms of providing data and providing insight on where we’re winning deals, here’s what we need to look at and here’s what we need to address.

But so often, sometimes the shortcoming then is, okay, now how do I implement that insight?

How do I take that golden nugget of information and actually leverage it within what we’re doing on a day to day basis?

So for me, again, opinion, but that’s where I see enablement coming in because I mean, I’m going to do exactly what you did.

Like process then comes into it, right?

In terms of, you know, for example, it might be, you know, going after this specific persona or this specific company in this country, we’re seeing that our velocity is up 50%.

Okay, how do we do that?

It’s not just a case of well, just tell someone and it happens overnight, right?

It’s going to be built into how the organization is being structured. So it doesn’t surprise me to see enablement starting to come underneath that umbrella.

No, it’s a great lever.

And I mean, if you think about, you know, also KPIs, which you track in these business insights, right?

But I mean, what can you really influence in sales enablement, right?

It’s ramp time, so time to productivity for an AE.

So when are they starting to hit their quota, time to first, time to second deal, right?

Pipeline development, average sales prices, right?

So making sure that you get more out of an existing customer.

I can go on for hours, right?

But you know, like those are pretty, like in cycle times, right?

Sorting your cycle times, right?

Those are probably like the five big ones, right?

So if you have a good enablement leader, right?

They go like, yeah, raising my hands, I own ramp time, so time to productivity, right?

Time to full productivity.

I own making sure that, you know, we increase our ASPs, right?

I own reducing sales cycle times, et cetera, et cetera, right?

And so if you have somebody, you know, reporting on that, that’s great, right?

It’s also a supportive function for your CRO, right?

So then they’re not going at it alone.

And then giving them the insights, right?

It’s small of your, it’s easier when it’s a small company, right?

But I mean, you know, at NetSuite or Nutanix, right?

Larger companies with like thousands of AEs, it’s really hard to figure out who’s ramping, who’s not ramping.

And believe it or not, systems even to this day aren’t that great, right?

If you talk to the average DevOps person and say, can you just click on the button so you can see, you know, how an AEs ramping time to first deal, time to second deal, ASPs, right?

Most of them say, yeah, we can do it.

And they can do it, but it’s a lot of spreadsheet jockeying and just getting that entire flow down is really important, right?

So when you do your functional QBRs, so QBRs with your enablement leader, right?

Like here are the KPIs I’m responsible for.

Here’s how we’re doing, right?

And sort of becomes a, becomes a group exercise, which is great. Yeah.

Yeah, definitely. I want to change it into a slightly different gear. We’ve talked about everything from a high level.

I’m really keen to know, you’ve touched on, yes, NetSuite, McAfee as well, but what were the learnings that you took from that into your role at Contentful now?

So we’ve talked a lot about your experience, but what did you take that was like, okay, I need to do it differently this time to make it work?


So at McAfee, I learned a lot about, again, I was just lucky to see the motion from perpetual to subscription to host it, right?

That’s priceless, right?

Because people don’t know that anymore, right?

And that’s okay because it’s not maybe super relevant, but it’s nice to look in your rearview mirror and understand how things developed a certain way, right?

And it resonates really well with leaders who grew in the tech industry, right?

The rise of SaaS, right?

And working with channel partners a different way, for example.

And so at McAfee, it was very much about learning about different, almost delivery models, right?

Because all SaaS is in the end, it’s like we turn it into this big, right, complex thing.

It’s not, it’s easy. It’s just a delivery model. It’s how you deliver software.

You don’t have to, you know, host it yourself anymore, right?

We do it for you. That’s all it is.

The subscription model before that, that was really the big shift, right?

If you think about it, the SaaS just piggybacks right on the subscription model.

So that was really valuable and then having the IPO at, which was a spin off, right?

It was cool, right?

Just getting IPO ready and talking about subscriptions per subscriber and coming up with all these different SaaS metrics.

Then going to NetSuite, right?

So learning all of that, but not really being conscious about, yeah, I learned all of this, right?

But then at NetSuite, you start getting conscious about it, right?

And then seeing the rise of the top of the funnel, right?

And then scaling a tech company is so, I mean, let’s be honest, right?

Like that was the best thing that ever happened to me, right?

Going from 80 million, whatever it was in ARR to well over a bill, right?

And how we did that and how we reinvented the sales organization and how we spun up verticals and how we changed our strategy year after year.

And it’s never like, people think it’s easy, right?

When I started out at NetSuite, it was, dude, it’s never going to work.

Nobody’s going to put their financials in the cloud, right?

It’s not going to work, right?

And to us basically closing $50 million deals and winning against SAP and Oracle, it was priceless.

But, you know, the other thing I really learned was shifting from an inbound to an outbound organization because every company will, if they need to cross the chasm, which is not a buzzword, you better make sure that your inbound leads are going to dry up. You have to start knocking on doors. Your efficiency and your investments in marketing is going to decline.

And you just got to become a sales growth company, right?

So all of that, and that playbook really was pretty similar at Jaxxed.

At Jaxxed, we had to create our own category as well, which was harder, right?

And so it kind of made me, Contentful was sort of a perfect place for me to be because we have to create our own category. We have to cross the chasm. We have to evolve from a product-led growth to a sales-led growth company.

And I say product-led growth because, I mean, what do you think Mac, if you was, download your free virus cap, right?

I mean, talk about a product-led growth company, right?

There’s nothing new under the sun here.

It has been done before, right?

I think product-led growth is a great lever and it’s a very valuable channel for us at Contentful.

But, you know, customers aren’t going to sign you a $1 million or $2 million deal without talking to an AE, right?

And without doing an ELA and you got to negotiate all that stuff. So I think everything I learned in the past and sort of coupling it together made me, yeah, this role at Contentful is perfect.

I can, you always, whatever you, yeah, you only get richer during your career at Tech.

Like, even if you have bad experiences, it happens, right?

Like Flexport wasn’t my finest moment, right?

It was also, it’s not really a tech company, right?

You’re actually a freight forwarder with some tech on top, right?

What am I doing here, right?

There’s little value of me to add, right?

But I learned a lot there too, right?

And I’ve formed some great relationships there. So if you work in the industry, I guess you’re going to fall in your face once or twice, just deal with it. And if you don’t, you’re probably not pushing yourself hard enough.

That’s just part of it, right?

But every company you work for, good or bad, you learn something.

Just put it in your backpack and eventually you get to stitch it all together, right?

And yeah, that’s at least what I have been doing during my career. Yeah.

Jesus, I sound old. You really make me feel old.

Hey, I just asked the question, so there you go. I’ll give you a question that you absolutely cannot sound old on.

What have been three things from the past 12 months that you’ve done, implemented, whether it’s a small change or a big one, that has had the biggest impact on your go-to-market function?

I like that. I like that. That’s good. Unfortunately, I got some good answers on that because I’ve been pretty busy here. So I’ll take you over three things that were pretty massive here. Number one is, and this is the biggest one, we basically unified our field organization. That was huge for us.

So prior to me joining Contentful, we had AEs reporting into ACRO, right?

We had, which is normal, it’s normal, and SEs, so that’s normal, right?

Now we had a partner sitting in marketing for a bizarre reason.

I don’t know what the reason was, and it’s fine, right?

The part partner was sitting in marketing. The CSM organization was a complete silo organization to get other professional services reporting in a separate leader. Our AMs were reporting into our North America sales leader.

Our BDRs were reporting into marketing, right?

And talk about a mess, right?

And so A, we got to make sure we have a unified field organization.

So all these groups need to come together, right?

Number one, right?

We need to have a unified field model.

But that means people need to move around, right?

And that means you have to deal with a ton of resistance.

And why, right?

Like, why is this happening?

Well, it’s happening because our spend on technology is completely insane.

But most importantly, think about your customer experience, right?

You’re talking to AEE and some BDR and then some CSM somewhere else.

We’re not even aligned, right?

So the segmentation in the CSM organization was different than the AM organization was different to the AEE organization.

So customers didn’t even know where they would end up, right?

I know it sounds really bizarre, but this is how startups operate, right?

As another part of that, as another function of that was people weren’t operating in sales territories properly, right?

A little bit round robin.

I mean, how’s that going to scale, right?

So good luck also building your customer journey, but good luck building efficient prospecting strategies, right?

If it’s not clear, if it’s not clear that, hey, this is Jake.

Jake is the enterprise AEE in, I don’t know, the Benelux, right?

And here’s this AM and here’s the CSM. And we’re with you every step of the way as you get up to speed on Contentful.

And so that was a massive, I make it sound really easy, but it was a massive shift, right?

The alignment of the field organization, making sure everybody was aligned into pods and how are you going to shift accounts around?

And it was massive, right?

So we did that. So I think that was number one.

Number two is I spoke a little bit about crossing the chasm in terms of evolving from a PLG to an SLG company, right?

And PLG is a super important motion for us. It will never go away. It’s very valuable.

But we have to start outbounding at Contentful, right?

Because we have to, I’m not here to build a $200 million or $300 million ARR company.

That’s not interesting, right?

To me at least.

Maybe I want to have a ride like Ed and Ed Sweet, right?

Or you know, Yax or you name it.

Like, I want to go over billing revenue, right?

And so we’re not going to get there.

We’re not going to PLG ourselves to a billion dollar in ARR, right?

But we will get there if we get really clever about outbounding, right?

So making that shift from a reactive inbound organization to a more aggressive outbound organization would be another one. I think those are two really big ones.

I mean, I can talk about. And I think number three probably, I really took ownership of a planning cadence.

If your planning is done by finance, oh God, do you have any CFOs listening to this podcast?

Very little.

Very, very little. If they are, then feel free to skip to the next episode.

No, no, no.

Because they’re quite often very myopic in their thinking, right?

Well, here’s the number and you’re going to hire this many reps and here’s the productivity and we’re going to crush it. Right. And quite frankly, what’s happening in the marketplace right now, it’s not me. Right. Like I’m just all the all the layoffs, all the firings. Talk to your CFO.

I talked about this incredible, disgraceful planning job that has been happening in our industry as a whole for the last couple of years. Right. So as a CRO, you better make sure that you want to get a number from finance that you need to hit. Fine. Totally makes sense. Right. Because they have to make sure that they appease the investors. Right. It ties back to a budgeting number.

But you know, you as a CRO, you better make sure that you get together with your rev ops crew, try to figure out what does that mean for hiring?

What does that mean for capacity?

What does it mean for your marketing plan?

Where’s the pipeline going to come from?

Pipeline by parties. Right. So you’re inbound, you’re outbound, you’re PLG motion, your partner pipeline.

What are they going to deliver?

How do they how do those targets look like?

If you have a gap versus plan, cycle it back up to finance and great.

Like, hey, I got a 15, 20, 30 or one million dollar gap.

Like are you going to develop a new product?

Are we going to open up new offices?

Like how do you want to make up for this?

Right. Really. So really taking ownership of the entire planning cycle and liaising with marketing and finance and product to make sure we can get where we need to go. Right. Because the answer quite often isn’t let’s hire 50 or 100 or 150 more reps. Right. I want to hire 150 more reps, but I want to make sure that my marketing engine can support it. I want to make sure that my product team has a vision.

Right. I want to make sure that my CFO is is aligned to expanding our distribution, meaning opening up new offices. Right. And so those are but these are very classic. These are not contentful problems. Right. These are just classic issues that everybody everybody’s struggling with in the industry. But I think honestly, I know the market has not been working in our favor. Right.

So what you’re seeing right now in the industry relates to piss poor planning. Right.

Really, really bad performance. And so you don’t want to be in that in that shape as a company, obviously. Unfortunately, we’re not here in that in that mode. Right. But it helps if you take take ownership of planning. Right. Because we could have conversations.

Well, I can hire 90 more AEs. Right. If you ever don’t have a product to sell or if you don’t really want to expand the distribution footprint or if you can’t keep up with our marketing motion right now, maybe it’s not the best investment. Right. So we got to figure out other other levels of growth. Right. Maybe making our current AEs but productive or whatever it is. Right.

There are plenty of ways to skin the cats.

But yeah, those were the three things. And I guess I went a little bit off track because I just I just find it I used to be a reseller way back when. And I just I hate it when people don’t people have mortgages, they have kids, they have mouth to feet. Right. Maybe maybe a little bit too too. I don’t want to sound too too emotional.

It freaking sucks if people quit a job, go somewhere else and then get laid off six months because some yokel couldn’t plan the business properly. Right. Yeah. I actually think it’s great because I wrote down earlier because I could sense I could something just told me. I was like, I was going to ask what frustrates you the most. Yeah. And that’s it.

So what’s the what’s the answer then as to the better planning?

Because you know, is that is that a CFO’s job or is that something that you know, I think we can all plan better. Right. And I often find that I’m treading the line between I’m just spending all of my time planning and not enough time actually doing it. I find there’s definitely a fine balance between the two.

And also, what’s the process to make sure that you’ve got a good plan as well?

Because even the best laid plans don’t always literally go to plan. Right. Yeah.

I mean, a couple of things. Right. It is it is a team exercise first and foremost in planning. So make sure you involve marketing, make sure you involve your sales leadership organization, make sure you involve product.

How many how many people are evolving product and planning?

This is not that much. Right.

And, you know, like most revit realms leaders wouldn’t do it. Right. So making sure that everybody’s a stakeholder within this field model to write. So talk to a CEO organization, talk to your partner organization, like involve people. Right. Like a plan shouldn’t be, hey, here’s the plan. Right. The plan should be a back and forth and iterative process. Right. I think that that’s key. I see it go wrong.

I see it go wrong often where people don’t understand the levers. Right.

And sure, headcount is a headcount is a nice we spoke a lot about headcount capacity, capacity versus plan. They have over capacity of under capacity.

What are your feelings about attrition?

Right. We talked about enablement.

Like how long does it take for people to come on board?

You know, the times where, you know, I see finance spreadsheet. But it’s a well, it takes a four months to ramp. Right. Because that’s what it’s in our comp plan or three months versus now it actually takes them nine or 10 months. Right. And it’s going to go out. It might take a little longer. Right. Not talking about contentful specific, just given giving you. Right.

I mean, if you don’t do that, right, you got a huge problem. Right. You got a huge problem. Same with marketing. Right.

How often do I see that marketing doesn’t have pipeline goals?

Right. Per party. Right. So I’m not thinking about just an overall number.

It’s like, okay, more like partner.

What’s your pipeline goal?


You know, what’s our PLG goal?

What’s a PQL goal?

What’s our SQL goal?


What do we miss the CRO?

What are you going to do yourself in that bound prospecting?


How are we going to expand into our existing customers?

And AM, like what you got to get super, super granular in your planning exercise for those who hold people accountable. Right. And I think people often think they were granular, but they have no idea. Right. And I think if you’re planning exercise sits in DevOps together with finance, obviously, right, you get way more granular because they are closer to the business. Right.

And if they do their job properly, right, and they are part of the sales organization and they understand the impact that sales cycle times have, for example, right, or the lack of having a product or the lack of having, you know, an inbound lead or you have inbound lead issues or the lack of having an inbound lead issue in France or in Egypt or in Indonesia because we’re not localized a certain way.

Right. And you can go on for ages. Right. But planning is something you have to really, really do well. And you also have to think, I think, if people don’t hit their number. Right. Quite often, I mean, I mean, sales will take ownership. Right. But maybe you really plan poorly. Right. And poor planning leads to, right, a high attrition. It’s very costly.

But very, very costly.

Like, I think we have to do whatever we can in our industry to make sure that our EEs and anybody in the sales organization can be successful. Yeah. Yeah.

So hopefully, hopefully, it gives you an idea of it can go wrong at a lot of places, but you can guarantee it will go wrong if the people who plan and take full ownership of the planning cycle are far, far, far, far removed from the business. Yeah. I think really clear.

I mean, for one, definitely the granular level of detail. Also what kind of came to mind as you were explaining it was also not necessarily plan B, which is like a completely alternate plan. But to your point, when someone misses a number, right, you know, you can’t be working to a system where it’s, well, if one person misses a number, that’s it, we’re screwed.

You know, what lever can you then pull elsewhere to be like, okay, where can we make up for this elsewhere?

To me, that’s where the granular level of detail comes into it. Because when you’ve got that understanding of if everyone hits these numbers, we are 99% sure that we’re going to hit that overall revenue goal at the end of the quarter.

And then it’s just the question of, you know, having that level of detail then of, okay, if we are short on leads here, or we are short on pipeline there, it’s not a, oh God, mad scramble, what the hell do we do?

It’s fine. We’ve planned for this. We’ve already got this in place. Let’s bring this in. Everything’s fine. Not only does it create a more kind of predictable revenue model, it’s a hell of a lot stressful for people working in it as well. Because it’s like, oh, someone knows what we’re doing. Fantastic.

And that really helps nutrition, right?

No, no, it helps a lot. It helps a lot.

And also just, you know, as a CEO, so maybe there’s some CEOs listening to this podcast, right?

It helps you as well, right?

Because if you want to grow, say you want to grow your company like 100 million in ARR, right?

Or do you want to do 100 million in net ACV, incremental ACV?

Let’s go there, right?

And I come back and I roll everything up and I go like, look, man, I got 100 million in ACV in street quota out there, right?

Let’s say we do about 80% of that, right?

So we can, I can only do 80 million.

And here’s why, right?

And I can really clearly articulate that no sales productivity already is going up.

Like we took a look at all our pipelines, like here are all the parties that are performing, right?

This is the best I can do. Then you as a CEO, okay, got it.

So we got a $20 million gap, right?

It’s not a disaster, right?

But you want to have the conversation, you know, like at least a couple of months before you, we never talked about the timing of planning, right?

But like we can do it in a second if you can remind me of it.

Okay, got a $20 million gap.

Are you going to acquire somebody?

Are we going to build a new product?

You know, are we going to have a pricing and packaging exercise?

Do I need to invest more in my sales organization?

I mean, it’s going to create awesome discussions that you need to have as a CEO, right?

Very, I didn’t, I had it twice in my career actually where we’re like, well, here’s the plan, right?

And we’re like, I had once or twice where I’m like, well, I think you can actually do 150, right?

So if it was 100, like, I know we’re going to crush this.

So most of the time you’re below, right?

You need to have these discussions, right?

Yeah, but and so timing, you need to have these discussions like a couple of months before the end of the year, right?

You need to be baked, right?

So there’s another good, good planning at RevOps. So back to making it relevant to your CRO again is I tried myself on welcome to the new year, day one or day two.

And actually before that, here you quote us, right?

You want to have all that stuff done and dusted.

You don’t want to wait a freaking month and give somebody their number, right?

For example, but all of that planning stuff needs to be flushed out at least 90 days, you know, talking about getting marketing goals and that needs to be done three months before the end of the year for sure.

And you want to do it has to be an iterative process as well, right?

So right now I’m planning for next year already, right?

And I’m doing my three year plan and I do that every every quarter. I take my three year plan. And so if you have a good RevOps, that sounds too cocky. Sorry.

Like, maybe I’m a little cocky. If you have a good RevOps person, right, they’ve done they plan continuously. So it’s not a crunch.

We have to start planning everybody, right?

And then your entire sales team at the last quarter of the year, RevOps team is completely overwhelmed.

Like, I do it continuously. So it’s not that big of a lift.

Yeah, it’s important.

Yeah, I agree. And I love it. And also not the first time I’ve heard it, which is might reassure you.

Because it’s the it allows you to adjust, right?

When things do go wrong or there are extraneous factors, it allows you to pivot. I do wonder how that went for you going into COVID and a pandemic. Did the plan go out the window and it was but or was it just another day in the office like, well, gonna have to replan for this one.

You know, when COVID hit, I think it was in Nutanix, right?

And we moved to a six month cycle, basically, right?

So we planned every six months. So which was, I hated it. But I loved it too.


So if you plan for six months increments, you can adjust quickly.

Whereas if you plan for a year, right?

You’re pretty much stuck.

Of course, everybody’s going to replan, right?

But it needs to, you know, like, pump out new comp plans, right?

And, you know, like rewrite maybe coverage model, ROE, real language finance, real language marketing, right?

And they built their annual plans as well, obviously. And so by having that six month planning cadence, we were more agile, I say we didn’t have to replan because we were planning every six months. I don’t recommend it, by the way, like a six month planning cadence. But during COVID, it totally made sense.

Because who knew where the world was going?

Like, remember, like, sky was falling. And then there was the best thing that ever happened in tech. And then the sky was falling again. I don’t know where we are right now.

Is the sky falling or like, who knows, right?

Reception, right?

I think our industry is doing just fine.


This is honestly, it’s just a little blip. And I think if you look at the macro numbers, it is just a blip.

Like, we have more people working in tech right now than pre-pandemic, right?

Hiring, hiring is, believe it or not, hiring is still hired pre-pandemic, right?

They just went crazy on their hiring and now we’re paying a price. We talked about that already. Yeah.

No, I love it. We’ve got really deep on a lot of stuff, which I’ve really enjoyed. For the final question, I’m just going to pluck us straight out of there and ask a really simple question.

What is one book that you would recommend to other revenue leaders?

I’m making an assumption that you’re a reader and that could be fiction or nonfiction. Watch 22. An excellent fiction book.

Oh, that’s tough.

Oh, this is going to sound embarrassing. Go for it. The first one that comes to mind. Probably Papillon, Perseverance.

Like, if there’s not a route A, then go to route B or route C.

There’s always a solution for anything, right?

But if you think about it, great planning, right?

I go down with great planning, grit, not stopping, dexterity, flexibility, not giving up in times of adversity, not taking things for granted if things are too good. You can go down that list, starting from scratch. That one just popped in, basically top of mind. I like it. I’m a romantic by heart. I also read very little. I frighten myself, actually. That was the embarrassing part.

I don’t really read that many business books. I also think that makes me a better person, actually, to tell you the truth. I really do. Because I do think I’m a little bit more open-minded versus this is the playbook. This is what you need to stuck with. I guess maybe we can wrap up like that. I’ve never operated like that.

Hopefully, I came across like that. What I learned during my career, I put in my backpack, but the industry is evolving. People are newer. People are so much smarter now. I could barely use Excel when I started out in my career, and email. When I see people, just what they do with tech and how they apply it in their work life, awesome. I wasn’t even close.

I guess don’t assume that the playbook you use at your previous company is going to work because it won’t at your next. It’s not relevant anymore. The industry is moving too fast. I think just learn to recognize patterns, but continuously develop and shape your new playbook is key. I do not reading books, business books. I read a lot. I really do, but more novels.

Which I find teach lessons in their own way as well. That’s why I feel the need to mention it really can be a fiction book and not a non-fiction. Any work like that, micro serves is an awesome book or J-Pot. Those are both awesome books if you want to read and learn a little bit about their industry, but in a fun way.

More of the human characteristics in our industry versus boring business book. The Circle from David Eggers is a really cool book. I really recommend it. I can’t recall the writer of micro serves now. That’s bad. I’m going to Google it while you ask me another question. Don’t worry. I’m going to make it even easier because that was my last question. We will include links down to all of those.

So Jake, I’m going to rely on you to send me a link and I’ll make sure to include it on the show notes. So if you can search for it. If anyone is like me, I really could do is a break from non-fiction every now and again. Douglas Copeland was the writer of micro serves and J-Pot.

I highly recommend reading micro serves and then reading J-Pot right after it and then reading the Circle. You’ll love it. It’s also not a business book, but it has a lot to do with our industry and specifically how we work and operate and also how our industry impacts humanity.

Geez, I can’t believe we went all the way there. Let’s pause there. We’ll come back for part two to go into that.

Jake, absolute pleasure to chat today.

I don’t know how active you are online, but is there anywhere where people could connect with you?

Ask any questions or are you going off the grid after this?

I’m just on LinkedIn. After you read the Circle, you understand why I’m just on LinkedIn. You can find me on LinkedIn. I’m active there. I respond. I like to help. You can find me there and you have my email address now, so you can email me. I’m going to follow up after I read the Circle and be like, that’s it.

All right, Jake, thank you so much again. And to everyone that’s listened to this episode, we’ll catch you next week. I really enjoyed talking to you. All the best. Good luck. Cheers. Bye. Thanks for listening to Revenue Insights. If you want to learn more, subscribe to our newsletter and we’ll deliver every episode straight to your inbox. If you have any questions, feel free to connect with us on LinkedIn.

Our links will be in the episode notes. See you next week.

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