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Head of Revenue Operations: Rowan Bailey of Peakon

Rowan Bailey jumped onto Sales Operations Demystified to share his knowledge and experience in Sales Operations.
Check out all the other episodes of Sales Operations Demystified here.
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Tom Hunt: The Sales Ops Demystified podcast. We’re joined by Rowan Bailey who’s currently head of revenue operations at Peakon?

Rowan Bailey: Hello.

Tom: Hello, Rowan, and worked previously in both sales and sales operations at Perkbox. So we have a salesperson in our midst, or not. Maybe I read that one wrong [crosstak].

Rowan: I was an account manager as role so it was post-sale, but definitely lived and breathed next to the salespeople at that company so yes.

Tom: Did you have a quota?

Rowan: Ish. We had the portfolio value that we had to bring back. So yes it was a bit more free form than that but yes.

Tom: Got It. Okay. So not like out and out sales but kind of almost fair?

Rowan: Yes, exactly. It was a retention and land expand model per se.

Tom: Got It. Okay. Cool. Then you had an interesting transition, right? Because within Perkbox you went from account manager into sales operations.

Rowan: That’s right.

Tom: So could you just talk a bit more about why and how you made that jump?

Rowan: Yes, sure. So Perkbox employee benefits platform, I joined it in 2015 and it was around 30 people at the time, a bit of a rocket ship at that time. It was like really kicking off. By the time I left two years later, as 180 people just to get an idea of the growth and then my transition into Ops happened quite organically. I started mainly out of necessity trying to migrate my processes off of spreadsheets, which the whole company seems to run on at the time. Then as a result of that, the rest of the company just started looking over and being like, “Hey, how come you’ve done all that stuff so quickly? Like, what are you using to do that? And like the tools that are already at your disposal, do you mind coming over and to show me how to do that?”

So what started off as smoothing out processes and data input for the account managers quickly became redesign the whole sales process and integrate salesforce with finance and that sort of thing to squeeze along, collections by direct debit and invoicing so it was organic, makes it sound quite pedestrian. It was still progressing at a rate of knots and the workload was huge, especially as my own team at that time was growing. By the time I moved away from that position to focus solely on Ops, I was looking after a team of nine at that point. Looking after their own portfolios of say like a million ARR each and then dealing with the Ops stuff as well, as you can imagine was a lot to take on. I was quite happy when my boss at the time the CEO said, “Do you want to just focus on this hundred percent of time?” “Yes, I do. Thank you very much.”

Tom: When you joined, you weren’t managing account managers, you were actually an account manager?

Rowan: Exactly, yes.

Tom: You progressed to managing account managers and that’s when you started doing the Ops work and then you switch up, is that right?

Rowan: Yes, it was quite good for in terms of how I then started to approach problems, what started is, how can I make this easier from a purely selfish perspective? What’s right? What scalable? What’s repeatable? What works for the rest of the team? It was quite an easy sell after that to be like, do you how we do it now? And takes half an hour to fill out, a few columns on the spreadsheet, couple of clicks, and you’re done. Yes, that was how that progressed.

Tom: Good. Do you think that there’s something like, why do you think you gravitated? Or what is it within you? I’ve just got a deep question early on in too. Was it within you that gravitated more to the operational side rather than just managing more account managers?

Rowan: It is a good question. I think my just inherent repulsion for being bored. That is something that comes up when I have to do a job more than once, the same thing more than once. I’m just like, “Okay, I know how this works now, done.” Maybe it is a drive to find out how things work, the nitty-gritty and then try and build stuff that automates that for you.

Tom: Cool. Moving on to Peakon today, talk to me about revenue operations.

Rowan: Okay, in what sense?

Tom: We’ve had ever since I started this podcast, which is other one is called Sales Ops Demystified. We’ve had people saying that actually, sales Ops is just one piece in a trimester. Operations department trifecta, yes.

Rowan: Trifecta.


Tom: I like to run that past you because it seems like you’re running a more integrated operations team.

Rowan: Yes, that’s the plan. It was revenue operations in title only to begin with. As Peakon was growing, the focus naturally is on sales, and that machine getting that taking over but the vision was there from the start, which is nice to incorporate, yes, the top of funnel marketing work, and also then post-sale retention, which is the cornerstone of any ARR, SaaS business. That was there from the beginning and right now currently building out the team. We’ve got someone focused just on the sales upside, and we’re hiring currently for CS Ops role to look at that post-sale. Actually, I feel a bit bad like CS have been a bit neglected but they’ve taken the backseat as we’ve been scaling the business over the last few years. Now, not that we have a problem there, I think it’s more preventative. It feels quite nice to take a proactive step for once. You are right, having that integrated team that set across the tech stack specifically, and making sure that data is flowing from department to department as it should without getting too siloed or too caught up in the flavor of the month stuff that comes from managers within those tiers. That’s quite nice. It’s quite a nice position to be in as a Ops professional to say, “No, actually, I can see your need for that but please understand that this has to take priority now.” Having that impartiality is quite nice and I think, is quite well respected actually at Peakon as well.

Tom: Got it. Can you create us a taste for the numbers of people within the operations team? Then I guess we don’t need– and rough number for the marketing sales and customer success team just so we can understand the whole thing.

Rowan: Yes. Sure. Until last Monday, there were two of us in the operations team. That’s myself and Bart. I had Bart last September and he’s coming as a revenue systems engineer, I believe his title is now. He codes in Apex and builds stuff out in Salesforce that’s custom for us. Avoiding actually twice now he’s helped us avoid quite a hefty bill from Salesforce for additional functionality that they provide in a different products but actually, we just needed a simplified version of said product and he’s been able to master up. He joined September, Ada joined last Monday and like I said, we’re hiring another one, hopefully for a start date around October this year. That is servicing the company is just gone, just crossed the 200 mark, I think and I joined when I was about 38-ish.

Tom: Wow.

Rowan: Quite an lean team, I would say. It’s how the challenges but it’s also been quite good because we’ve known everything so intimately and it’s forced us to build for scale. It’s like our number one principle. If it’s a flavor of the month, kind of problem or topic that comes up, we really asked three questions, the three Ys or whatever, to drill down, is this actually necessary? Will it still be relevant in six months, one year’s time? The sales team right now I think we’re about 60-ish, salespeople CS maybe 20. Then there’s a lot of product people here in Copenhagen where I am currently sat.

Tom: Cool. The marketing team just roughly.

Rowan: I will say 25,30. I should know that.

Tom: No, it’s fine.

Rowan: I actually know [crosstalk] basically it’s first one. I know because I was in a room with them drinking cocktails last Friday, so I shouldn’t maybe like 15, 20.

Tom: Cool. That is a lean operations team, I try to get the ratio from every guest. I think that average is between one Ops person per 15 to 20 reps [crosstalk] It seems like you are significantly [crosstalk]

Rowan: I’ll use that as a pitch to get more headcount. [crosstalk] Actually, it’s an interesting point. I don’t think that the Ops team should scale linearly with the company at all. If you’re building an efficient Ops team that’s concentrating on the right problems, focusing in on those real leavers that are going to drive that growth, then actually your headcount should be spaced out by, I don’t know what the mathematical term would be, but as a function of headcount in the business. You make your first hire after 30 people. Your next one after 60 people, you should make your next one after 150 people, for example. That makes sense to me and it shows that the team is efficient and working on the right problems.

There’s another school of thought which would say that there’s only so many hours in a day and so many problems that you could be working on in order to accelerate growth and so maybe adding headcount to the pile is an answer to that. I’m on the fence on that argument.

Tom: Nice. Can we quickly review the current sales tech stack at Peakon?

Rowan: I was quite lucky in the sense that the sea level or the cofounder’s attitude towards buying tech is first of all, very positive. They see the value in adding tech to the stack. I came in, for example, with salesforce already in place, bailout using standard objects. Five stages and the opportunity– it was a dream compared to some of the horror stories you hear of Ops people having to inherit in companies that they joined.

Our co-founder, for example, got salesforce in when there was only two salespeople, I think, which at that stage is quite uncommon. His reasoning for doing so was saying, as we scale, salesforce is going to be at the core of our sales operation. If we want that to be the best in class product, and we can’t afford to scrimp or to save sorry– That’s not the word. Spend extra money like 60, 70, 100 extra dollars a month then we’ve got bigger problems than the CRM that we’re using. Which I quite liked, because it meant that my job was a lot easier. We’ve got salesforce at the core. We use Marketo for our marketing automation, SalesLoft for outreach for the SDR team. We’ve got a tool called Chili Piper, which I’m a fan of and anyone from Peakon knows that I’m evangelist for that product. Meeting booking and also lead assignment through round-robin keys is quite an hefty thing. We use NewVoiceMedia for making calls, we’ve got basically a tool for every occasion. I’m actually trying to consolidate a little bit and and cut some of the chaff out. My problem with some of those tools is the fact that they have overlapping functionality.

As soon as you have that in a sales team, it’s very easy for a sales person to start coming up with their own processes. “I’m going to run my cadences from this lead enrichment tool rather than SalesLoft, for example, where the team cadences lie.” Then you end up with this situation where you’ve got different people doing different things. You try and make a change, some people love it, other people are like, “What the hell is that?” It’s the recipe for chaos, unless you stamp it out quite early.

Tom: You’re saying that if a product had, say three functionalities, and you already had products covering the other two, would that go against it in its by in the buying cycle for that product?

Rowan: That’s a good question. I think the lack of flexibility around which elements of the product we can and can’t use, definitely. I’ve made or not made buying decisions based on that before because I could anticipate the level of chaos it would have bought into the sales team.

Tom: Got it. On that topic, I want to talk more about how you interact with sales reps, whether that was back at Perkbox or here at Peakon. How were you able to get a salesperson to do something that maybe they didn’t want to do because it wasn’t directly associated with their calls but you wanted them to do it?

Rowan: To do with work, right?

Tom: To do with work.

Rowan: Involving sales reps at every stage of that thought process and buying cycle. Actually, not every stage, you can do the shortlist, and I think Ops people should be in charge of the shortlist. Once you’ve got, say, your two, three tools that you’re trying to consider to implement, for example, involving them in that decision-making process and running past a trial phase, letting them impact the user experience specifically, massively helps when it comes to adoption, because once I’m presenting it to the whole team, it’s like, “Well, actually, you’ve already got validation from your peers. They’ve been involved in shaping this process. If you don’t like it, then you have a problem with them as well as me.” It’s less Ops versus sales, and you got that collaboration there from the off.

I’m talking completely idealistically here. I’ve not done that fairly recently, and it’s come back to bite me, so it’s a lesson recently learned. Actually, when I look back at the times when I have done versus the times that I haven’t, adoption and that lack of friction has always been there.

Tom: Got it. I really like that tougher term, it’s less Ops versus sales but actually, it can be more sales versus sales if you get the right people on your team.

Rowan: Yes, and actually picking your champions for that team is quite important. It’s less about picking the people that you would assume to be champions and more making champions of the people that would probably give you the biggest fuss if you just rolled it out without telling them.

Tom: The detractors.

Rowan: Yes, exactly. If you can turn a detractor into at least a neutral, then you’re good to go.

Tom: Then you have obviously, in both of your roles in sales team scale, any tips for onboarding, for efficient and effective onboarding?

Rowan: Honestly, our onboarding process needs work. I think it is a symptom of the fast growth. As soon as you start to try and standardize your onboarding process with processes and tools that are in a constant state of flux, you might make it a lovely presentation and a great onboarding video, but if it’s irrelevant two weeks later, it’s like, “Ouch. Okay I don’t have to keep making this video every two weeks.”

We’re currently in a position now where we’ve stabled out a little bit in terms of our processes, and there are some parts of that onboarding journey that I’m looking to just have as a non-recurring meeting in my calendar and have it as a video or something like that that they can join instead. We’ve just invested in a tool called Showpad, which is quite good at building out these custom courses, and that sort of thing. You can add, say, a training video, then a PDF to read and then a quiz. Basically, a comprehension quiz at the end, see if they’ve understood everything. I’m going to be leaning on that quite heavily to put my onboarding experience into specific paths and specific courses.

Tom: Got it. Then making teams or sales reps specifically, more productive, do you have any wisdom to share?

Rowan: It’s tricky. I think for us, we’re reviewing the spiff, the concept of the spiff, especially at the SDR level where some of the work that they’re doing is quite repetitive and not in and of itself inspiring to them, so you have to add that level of inspiration for them, so we’re building out this thing called Hustle Points at the moment and any outbound activity, outbound meetings, conversations that kind of thing will score differently and provide a leaderboard, weekly incentives, that sort of thing. Hopefully, that shouldn’t be that revolutionary to anyone.

Using Showpad as a means for getting knowledge out of reps heads and basically, I think that the result of that is you end up with reps unconsciously benchmarking themselves against their peers in a way that they don’t do unless they overhear a conversation across the room, for example. Actually, tapping into the competitive instinct of salespeople, in order to drive their own learning and their own productivity is quite a nice way of doing it. That’s what the spiff does, and it’s also having this situation where we’ve got everyone’s best pitch in one place, for example.

Tom: Got it. So you’re actually having salespeople upload content in the Showpad after any materials for other salespeople?

Rowan: Exactly. The nice thing about that is twofold. You’ve got the pitches there for reps to compare themselves against and actually borrow the best bits from each and actually update their own pitch. We’ve only run it through once, but the second iteration is going to be really interesting to see the osmosis of ideas between pitches. Then the second thing is we’ve got a massive repository of everyone’s best pitch for onboarding as it fits back into that really nicely when you’ve got a new start. We’ll actually, go and listen to everyone in the business, including the CRO’s pitch, you will learn very quickly how to talk about Peakon in a very short period of time.

There’s one more thing, actually, I just looked at my notes. Win analysis and loss analysis. There’s something that we had in salesforce from pretty much the start. Can you write a small paragraph about exactly why we want this deal? What would you have done differently? What would you do next time? That kind of thing. The game-changer for us was actually putting that into slack. Every time they win a deal, or close loss and opportunity, you end up with that analysis attached to it. We saw the quality of those go up. I can’t even put a number against it like a hundred-fold, rather than lead gone cold or opportunity going cold, we’ll pick up next year. It’s like “Oh, actually, what did you try? What resounded well with them? What didn’t?” That sort of thing. That’s a good way of also sharing the learnings, not just in the celebratory moments, but when things aren’t going so well as well.

Tom: That’s nice, we can only show won and lost– In fact, we don’t include any of the custom fields. That’s actually we’re going to take away. Very nice. Can we quickly go over forecasting? How involved are you in the sales forecast?

Rowan: Forecasting is something that has been under the microscope at Peakon for last few months. A few months ago, we moved everyone over to using the standard functionality in Salesforce, the forecasting app, having quotas in there, everyone update their best case pipeline and commit deals for the month, and there’s a layer that’s missing, and that’s the judgment call. Sure, you’ve got four deals in best case, but what’s your actual pledge number? What are you actually going to bring in, rather than being opportunity-driven being that top-down rep gut field side of it?

On the plus side, SDs, the CRO, everyone now looks at that forecasting app. We take a screenshot of it every Monday for our revenue meeting, the whole sales team is singing from the same hymn sheet which is nice, and we’ve now got a deal review process in place with reps, so that every Wednesday they have an hour blocked out to go through their apps, make sure they’re in the right stage, the right amount, and they’re making the right call against that, and close day, obviously that’s important. Everything is improving, but we’re still looking at third-party tools to bring that extra element and that extra layer over the top of our forecasting. Think clarity as well when we’re reviewing, there’s a few out there that we’re having a look at the moment.

Tom: Are you or the Ops team responsible for making sure that data is useful and accurate that’s your role in the process?

Rowan: It’s my role to make it incredibly transparent when those things aren’t up to date. Things like how long is this opportunity been in that stage? What’s the health of this opportunity we have like this smiley face system. It’s very, very advanced. That basically shows if it’s been in the current stage for longer than the average close one deal, and whether or not the next steps are in the future and up to date, then it’s very much process driven from the sales directors and other sales managers to say, “Right, what’s the quality of those next steps? Why is that next step in two weeks and not tomorrow?” That’s the coaching piece that comes around it. That feeds into the forecasting.

Tom: Got it. We have a question here from Zack. How do you keep KPIs aligned with unforeseen data capture? I’m not really sure what Zack means by that, Zack if you could clarify. Rowan, I’m not sure if that makes sense to you.

Rowan: Unforeseen data capture sounds scary.

Tom: Okay, Zack can you clarify, we’re going to quickly move on. You probably going to have about five minutes to clarify that question. Cool. Next, let’s talk about KPIs. What do you think is, I’m going to put you on the spot here, throughout your career in operations, the most useful or insightful sales-related KPI.

Rowan: I probably, is quite a high level but I have to go with win rate. It’s all very well and good celebrating a rep smashing their quota and a high fiving in the office. If they have crashed and burned and mountain of opportunities to get to where they are and raise themselves up that way, then actually that’s not good for business, not good for the rest of the team. If they caught on on that’s the way that that person made that much money by cherry-picking Ops to that degree.

For me, win rate is super important, and just to clarify me, I know, I’ve had win rate calculated in different ways at different companies. For me, it’s the value of closed one opportunities versus all closed lost opportunities in a given period. For us, we don’t take the reps close loss value, we have a model that assigns a fair value to an opportunity based off of previously closed one opportunities of set of similar characteristics. Certain size, certain location, that sort of thing, and that’s a model that looks at the last 180 days and keeps refreshing itself as we go along. Therefore, we’ve got a stable baseline for comparison for the win rate, and that’s why I trust it so much.

There’s another angle on that though, which is the interplay between the acceptance rate of an opportunity and the win rate. If the SDR is a booking, a hundred meetings, but only 20 of them are getting accepted into actual live pipeline, then you expect your win rate to be 100%. The balance between those two is something that I’m particularly interested in. I haven’t cracked it yet, but I keep a close eye on it and try and model out what a change in one will do to the other and what’s good and what’s bad.

Tom: Good. So you’re saying that a salesperson could gain their win rate by having low acceptance?

Rowan: Yes, absolutely. If I only accept one opportunity, and they’ve already told me on the phone, that they love it so much and they want to buy it then you’re going to have a win rate of 100%. Yes, it’s a balancing act between those two, and you shouldn’t look at one without the other really.

Tom: Good. Zack’s back.

Rowan: Zack’s back?

Tom: How you leverage your data and do you have a way of knowing what you need to drive the business forward? I can understand Zack a bit but, Rowan, up to you.

Rowan: Okay. I think how I’ll answer that is you’ve got to decide what your non-negotiable are. That’s a phrase borrowed from our CRO. It’s about what do I need to know as an Ops guy in order to make decent decisions and to identify where the problems are in the funnel? For me, and we’ve just talked about one of them the acceptance rate from SQL for us to SAO. That’s huge and I need that in place in order to make the decisions I make.

Anything else, the data capture that comes around that first of all, we have to ask is it going to be relevant in a month’s time, in six months time, in a year’s time? If yes then are you actually going to do anything with this data? It might be great and you might see the value of theoretically capturing this data. If you’re not planning on doing any analysis that involves that data point then don’t bother. It’s just extra admin for the reps and they hate that so try and keep your processes as clean as possible. I think I feel I veered away from this question slightly.

Tom: Yes. [unintelligible 00:28:17] I am sorry Zack it was a great question. Finally, who they’ve taught you the most in that field operations.

Rowan: It’s an interesting one. I’m actually quite new to the sales Ops group in London and already I’ve learned a lot and just by listening to your podcast and a couple of other operations podcast as well. There is that side that I’m nurturing now and I’m still finding my feet in that world. Thank you very much for having me on. It’s great fun so far.

I think really the people that empowered me to kind of follow the Ops route have been very fortunate to have two good managers. The CRO at Perkbox, Gautam Sahgal, he is fantastic and basically pointing me at an interesting problem and then stepping back and being like, “What do you think? How would you solve this? How could Salesforce solve this or is there a tool out there that can help us get around this problem?” That laid the groundwork for me thinking like that about every problem.

That has led to where I am today. Yes, definitely he is a big role model. Then Dan one of our co-founders here as our CMO he is very similar and that’s highly analytical but he’s got a very high bullshit filter as well which is great for me. I’ll get it him and be I’ve got these numbers is what they look like. He’d be, “Okay, what about if this was the case?” He’d be, “Okay, I’ll get back to the drawing board and reanalyze.” Yes, both of these characters have been instrumental in where I am today.

Tom: Got it. Now let me share some things I like from today. I never heard this before about how revenue operations can help you avoid flavor of the month projects within the siloed revenue generating profitable operations. Building for scale, like that being criteria for anything that you’re looking to implement. I’d be interested if you developed the algorithm or the formula for the amount that an Ops team should scale with.

Rowan: Me too.

Tom: [crosstalk] agree. I’m not sure if it should be linear. What I’ve been doing on this podcast has been asking and then assuming linear growth. Less Ops versus sales and trying to influence or get people to buy into the process. Actually, you can do sales versus sales if you get the right people on your side. Then yet having salespeople uploading their own content into any repository, so they can benchmark each other and get competitive, I think is awesome as well.

Rowan, that was really really good. Thank you so much for your time.

Rowan: Thanks, Tom. Yes, that has been great. Those were really comprehensive notes, I didn’t see you writing those, that’s impressive. [chuckles]

Tom: Thanks, man.

Rowan: Take care.

[00:31:23] [END OF AUDIO]


Rowan bailey of Peakon

Rowan bailey of Peakon