Director of Sales Operations: Ian Stuart of Riskalyze

Ian Stuart 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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Host: Welcome to a very special episode of Sales Ops Demystified. We’re joined by Ian Stuart of Riskalyze. I think it’s going to be an interesting chat because Ian has experienced entrepreneurially, and then five and a half years of experience in sales ops, and is now currently director of sales operations at Riskalyze, so I think there’s going to be some sweet insights here. Ian, welcome to the show.

Ian: Thank you. Good to be here.

Host: Can we kick off by trying to understand how you got into the sales op role? Did you join Riskalyze as sales ops or as a different role and then switched into it afterwards?

Ian: I was employee number 11 at Riskalyze, so I started with a lot of hats. [laughs] I was an account executive when I started, doing your type of work, doing data projects, I helped implement Salesforce [inaudible 00:00:58] both knowing. That was a fun multi-hat role. [laughs] I was a Salesforce admin since the beginning when we had launched with it, did implementation for that. Once we have a sales ops role, I was offered it. I’ve been doing that ever since at Riskalyze.

Host: Cool. Were you the first account executive?

Ian: I wasn’t the first account executive, I was the [inaudible 00:01:22]

Host: Cool. Then, how many year into your journey with the company did you switch out into sales ops?

Ian: Sorry, say that one more time.

Host: At what year in the journey did you join sales ops?

Ian: Year number one and a half, I think. Yes, one and a half or two years, then I joined sales ops.

Host: Cool. You were– [crosstalk]

Ian: Riskalyze and then I have other years of sales ops experience in doing my own stuff.

Host: Were you the first sales operations person at Riskalyze?

Ian: No, we had another sales ops person for, I think four months, who was more like a finance [inaudible 00:01:56] doing on the more finance side, and they reported to the CFO, and then I came after that month, we moved it to sales.

Host: Cool. Now you’re running a sales ops team that supports all of the sales reps within Riskalyze?

Ian: Yes. I’m underneath revenue operations, so we have revenue operations, sales operations under that. I have one analyst under me and a Salesforce admin and [inaudible 00:02:18]

Host: Great. Approximately, how many salespeople are you guys supporting?

Ian: We’re supporting 40 salespeople and 20 SDR’s people.

Host: Nice. That ratio– I’m trying to track ratio, so that’s, you could take 50 in total, four of you between 60, that’s about what I’ve been experiencing. Current sales ops tech stacks, I know you guys are using Salesforce. You actually implemented Salesforce at Riskalyze. What else are you guys currently using?

Ian: Salesforce through CRM. I’m using HubSpot for marketing automation. Maybe you could use Zuora if you print your work for CPQ and our subscription management. Domo for business intelligence, using Zoom for video conferencing, Chili Piper for– We just actually got Chili Piper [inaudible 00:03:07] for our appointment scheduling for the SDR team. Let’s see, what else? Using Gong for our call recording and sales enablement, SpringCM for contract management, DocuSign for eSignatures, SalesLoft for [unintelligible 00:03:22] We’re using Cloudingo for some of our data management in Salesforce, and then we keep the data feed setup on Discovery Data. Not [inaudible 00:03:32]. [chuckles]

Host: Got it. Quite a comprehensive overview there. Quickly, can you– You sound like you’re getting a little bit muffled, you’re cutting in and out, if you could have your mic just closer to your mouth, that’ll be– [crosstalk] Awesome. Okay, cool. You guys, as a sales team, are responsible for all that technology and making sure it’s integrated and working together. Ian, does that fit within your agreement?

Ian: Yes, that’s correct.

Host: Then you’re also responsible for, I guess, assessing new tools and then deciding whether they would or wouldn’t fit within your stack?

Ian: Yes.

Host: That’s cool, fantastic. Can we move now on to data quality? You mentioned I think Cloudingo, which can help remove duplicates, if I’m right?

Ian: Correct.

Host: Cool. What else are you doing to ensure that data is accurate inside Salesforce?

Ian: That’s a good point. This is a two-fold answer. One, the industry we’re in, we work with financial advisors, so they are legally required to register their information with regulatory agencies, so we have public record on them. I have their last four home addresses, which is totally creepy.

Host: [laughs]

Ian: We have way much data points on them. It’s all public record, so we have an API feed that we can set up in that, which we pump into Salesforce. What I do– I want that data to be as untouched as possible, so we have something called data-provided fields in Salesforce on the record and then I’ll have a human-provided field on a record. [laughs] [unintelligible 00:05:01] so if someone wants to– they think the email address is of something versus what someone claimed their email address was, because we have a monthly feed coming in from that data set, that database, we’re going to do that, but we’re not going to touch the information [unintelligible 00:05:14] submitted information, so that’s good.

Now, they can have all their information in [inaudible 00:05:21] but then they would have all the backup of all the [inaudible 00:05:24] information. The second part is I have an analyst on my team, Tiffany, who’s awesome, and you could use incoming leads periodically to make sure that stuff- we’re not getting duplicates created. If we are getting duplicates created, she’s looking to see what type of rules and stuff we can implement.

She’s also– We have the ability for reps to open a case in Salesforce anytime they are questioning the data relationship that’s coming from Discovery Data. That’s not the right contact, they belong over here, wrong email address or CRD number. That’s how we have a unique identifier, so we look at the identifier number. Tiffany is our steward of the data.

Host: Got it. Shout out to Tiffany. We have [unintelligible 00:06:03] salespeople can flag things that are going wrong, you have some manual stuff in there with Tiffany, and then you also have these two different types of fields where you prioritize things, so a human-given versus data you’ve got from another source? Correct.

Ian: Correct. Yes. We have Cloudingo who’s going in nightly and updating and make sure things are in the right relationship.

Host: Fantastic. Now moving on to the relationship that you guys have with the reps, how do you build a relationship and try to get them on side with stuff that you might get them to do that might not be directly correlated with them getting more commission?

Ian: Good questions. A couple of things, there’s two. One, every Thursday, I’ll come down and I’ll chat with the rep. What I’m doing is I’m– [chuckles] Selfishly, I’m trying– I don’t want to say this. [laughs] I’m just trying to steer them on different things that we’re doing, because most of the stuff we’re working on, right–? There’s two types of projects. Sales ops firmly does theirs. The customer-facing stuff that is going to affect sales and customer success. Then there’s the stuff that I’m doing that’s all background. I’m mostly going to see it, the [unintelligible 00:07:07] operation’s team [unintelligible 00:07:07] are going to see it. It’s Salesforce administration work or whatnot.

It’s not that’s customer-facing. When I’m shadowing the reps, I want to make sure that they’re aware of what’s going on, they know it’s coming well in advance of it actually coming.

Second thing we do is we do two things. We have a roundtable discussion with all of our [inaudible 00:07:24] like a customer advisory board of salespeople. It’s [inaudible 00:07:29] different things that were [inaudible 00:07:32] the rest of the team. That team is always changing, so we’ll sit down with those people and we’ll go through what sales ops or DevOps are working on, what’s coming down the pike, different trends that they’re seeing in the industry, trends that they’re seeing in Salesforce will [inaudible 00:07:47] when we talk to the managers.

When we launch those new systems and processes, we have the beta team that get early access to the system of process. We have a slack channel, we’ll do daily stand-ups and talk about what’s working, what’s not working, get feedback on idea with your future career.

Host: Got it. If I do reckon, you have a customer advisory board but it’s not customers, they’re salespeople?

Ian: Yes. [laughs] What I learned early is to work with sales as a customer. Not that the customer is always right, that the customer always knows what they need, but to work with them like a customer. They’re my primary [unintelligible 00:08:22]

Host: Cool. Then, every Thursday, you go and sit with them, same time every week. You get them in a room and understand what’s going on for them and share what you’re working on?

Ian: Not so much get them in a room. We have an open office and we have two floors. I’m up on the top floor and then I’ll go down to the bottom floor and sit with them. We have some FlexNets that are open, and so I’ll go filter quickly in those. [chuckles]

Host: Got it. I figure you sit down there all day?

Ian: Yes, I’ll sit down, I’ll get ongoing calls, I’ll listen with them or give them some feedback about what they’re doing in Salesforce. I’ll just see what’s going on, what’s actually happening on that [unintelligible 00:08:57]

Host: Nice. How are you guys currently onboarding new salespeople?

Ian: A good question. I’m not personally responsible for onboarding, but what we do at Riskalyze, we use something called Lessonly. I don’t know if you’re familiar with that. That’s the other tech stack. [laughs] Lessonly and then Guru for now in [unintelligible 00:09:17] and so we have all of our really important documents and just pieces of knowledge in Guru. Guru let’s you verify and and have like a trust rating on something. It requires a verifier, so someone has to verify every three months or six months or something. [unintelligible 00:09:33] the freshest knowledge as far as the [unintelligible 00:09:36] doing something, talk track [unintelligible 00:09:40] We have most of those documents in there.

Then in Lessonly, we’re walking them through like Industry 101, like how we work the devices, all the data we collect in Salesforce. We do about two ongoing. SDRs are required to get on the phones in the first week, so that’s pretty [unintelligible 00:09:56] ramp for that quarter. They get up to speed, built that one. We normally have people– We’re pretty transactional, so we have people close the deals. It’s not like [inaudible 00:10:06]

Host: You’re still just cutting out like every 10 seconds or so. Maybe if you’re moving your mouth. Cool. Okay, so Lessonly is– Have [unintelligible 00:10:21] takes reps through as they join. Then, the other tool, Guru, you mentioned, keeps asking you to refresh content so that you know it’s up to date. Is that right?

Ian: Yes, that’s right.

Host: Cool. Moving on to productivity, what are currently you doing to increase productivity of all of your reps?

Ian: That’s a– Couldn’t quite– I’m actually going to see if Zach Smith asked the question of how we approach the process of filtering leads from marketing to sales, so that’s a relevant question. Today, we actually just went back to the lead object in Salesforce. What’s been happening is when we have new marketing create leads, they go to a queue in Salesforce.

Now, in that queue, we’ll have Tiffany and other people that are on that and they’ll go through and clean up the leads, depending on the waiting of the lead. That’s something that needs to go on immediately where we’re filtering that out and distributing it to SDR team and the sales team, but if it needs to be reviewed again, maybe it’s something from a conference or an attendee list, we’re going to have Tiffany go through that. Tiffany will go through and analyze it, like [inaudible 00:11:28] duplicates or anything.

We just recently, for productivity, we now have a setup where SDRs are passing opportunities to sales, and so they’re doing a lot of pre-qualification work, and they’re also organically receiving leads now. Before, just for a lot of compliant reasons, we had– SDRs, they weren’t able to create leads or [unintelligible 00:11:47] because we’d require a CRD number, a bunch of different other compliance list, but now, it goes straight to them. Their process is not hindered. They can still create those leads, they can still create contacts. Work those opportunities and create them. We have the case created at Salesforce for us to go back and verify it.

It’s very rare we’ll have to go back and verify something. We have most people will just go market inside of Salesforce [unintelligible 00:12:07] Sorry. Blessed. [laughs] We have all that defined in Salesforce and then, we’ll go back periodically and clean up things that are not new, incoming.

Host: Cool. Quick question on that SDR function. In the leads, are they split between the whole SDR function or do you have, say, inbound SDRs and then pure outbound?

Ian: Yes. They were split up between the whole inbound SDR or the whole SDR function. We just recently, about two quarters ago, went to five inbound SDRs, which is in about good for the volume we have.

Host: Cool. How do you think that segregation of process and skill from what– [unintelligible 00:12:44] too early to say anything?

Ian: I think it’s too early to say anything just because of the volume. We have some of them doing outbound work still. We don’t have a large piece of inbound just yet. Partly, because our target market’s like, their average age is 60, 65, so we’re working with a unique set of prospects. [crosstalk] As it’s working right now, it’s looking good. We have a higher conversion on those segment, so it’s looking good now.

Host: Cool. You have seen increased productivity from having SDRs qualified before going to the [unintelligible 00:13:20]?

Ian: That part, we just launched today, so I can’t tell you that much.

Host: [laughs] A bit early of that. Okay, cool. Then, I didn’t quite feel your– More like your tech side is pretty comprehensive, so I assume a number of those tools were brought in to boost productivity, such as, I think you mentioned Salesforce, right?

Ian: Right.

Host: That [unintelligible 00:13:44] revolution is probably pretty awesome. Okay. Can we quickly talk about sales forecasting? I’ll be interested to know if you guys are responsible for producing the forecast that goes up to the VP of sales or are you, the managers, sales managers create that forecast with the data and process you create.

Ian: Yes. We’re doing both. I will do a forecast based off of those currently closed production against open pipeline with rhetorical close rates. The method will change. Sometimes, we’ll do standard deviation to give us a range of what we’re expecting. The 95% [unintelligible 00:14:22]. We’ll do that. Then, the managers do a poll forecast, which is the combination of the reps’ forecast rolling up to them. We have them call their forecast every week. I believe every Friday morning ten o’clock, they have to update their pipeline. Make sure it’s up to date and good to go. Then, Monday morning, we make the call.

Host: Cool. Are you saying that then, you have two forecasts that you combine or do you compare that and do a forecast?

Ian: We don’t combine them, we compare the different ones. I look at my forecast against the roll up of the reps. Normally, if my forecast is looking better than theirs, I know that deals are missing. [laughs] Missing in the process or if theirs is looking better than mine, I can normally go down and look, and be like, “This person thinks this opportunity is way more valuable than it actually is.” Go ahead and chat with that person, work with it.

Host: Okay. Then your allies– I mean, you go back to the managers, and then they might go and speak to the rest to get more info?

Ian: Yes.

Host: Cool and then, you submit that final forecast to, I assume, VP of sales or finance?

Ian: CEO. Yes, CEO, Finance, and VP of sales.

Host: Fantastic. An official question here a little bit. You’ve been in this role for approximately three and a half years, right? During this time, which KPI or metric has been the most insightful? I know it might be a hard question to ask, but which metric do you think is giving you really interesting insights about sales performance?

Ian: Sales performance. It’s a good question. We track something called debooks. I don’t know if you’ve ever heard that term. [laughs]

Host: No.

Ian: A debook is a deal that was signed and then regressed pretty much out of the booking. We booked it and then it pretty much turned into not a booking, for a variety of reasons, because normally, when you’re booking something, it has different terms and [unintelligible 00:16:12] all that. For a variety of reasons, we’ll see things degrade there.

That’s been the most interesting as far as a rep’s personal debook rate. When they [unintelligible 00:16:22] with what actually turns it to not a real deal, or an implementation failure, or a whole variety of different things. That’s the most interesting per rep.

Other than that, I think the good thing, which is just like a heatmap. It’s a scorecard of every rep, and I have it going back to 2015, which is just every rep, their performance for the entire time they’ve been at Riskalyze; different quotas, different attendance, everything. That’s been the most helpful because I can plug that into Domo and I can do a lot with that.

Host: Nice. [unintelligible 00:16:54], so would that feed into, say, coaching by the manager if you see over the past three quarters a rep who’s had a higher than average debook rate? Would then you send the manager in to go and tweak their approach to closing or–?

Ian: Yes. We’ll work with the manager. We’ll get him to take the [unintelligible 00:17:11] very familiar [unintelligible 00:17:13] rights. It’s the actual call that led to that deal. Pull out some specific areas in which they could’ve increased that debook rate, and work with the manager on that.

Host: Nice. That, I feel– Definitely have not heard about the debook rate before, but that’s an interesting one. Final question. Who in the sales ops world who’s taught you what you know and who would you like to take out for lunch to thank them for the knowledge they’ve imparted?

Ian: Jeremey Donovan from SalesLoft has always been super warm and welcoming. I have hit him up a couple of times on LinkedIn and been like, “Hey, can we jump on a call?” and ask him a couple of questions on stuff I was working on. He’s awesome. He’ll just jump on stuff. He has a blog, but he does a ton of really good book reviews. I don’t know if you’re familiar with MSP, Marketing Sales Pros, but he’s also in there.

Host: Yes.

Ian: He just pours so much knowledge in there. They’re a community, but yes, Jeremey Donovan, I’ll take him out to lunch. Then, Frank [unintelligible 00:18:12] I’d do two people. [chuckles] Frank comes from [inaudible 00:18:14]. I met him at OpsStars a couple of years ago, conference down in San Francisco. He’s an all-round cool dude, as in really knowledgeable about sales comp. Taught me a lot of what I know about sales compensation and then the method that– [crosstalk]

Host: Nice. Shout out to them then. Third one?

Ian: No, I said from one phone call.

Host: Okay. Cool. Got it. Okay, awesome. Now a quick fire round. Here are the things that I liked. Actually going and sitting with the sales team, I think is very powerful, because especially with you being on a different floor, it’s like– I’m not saying there is a vibe like this, but there could be a vibe where they’re like, “Oh, the sales ops team are up there and we’re around here, and [unintelligible 00:18:55]” That, I think, is such a good idea.

Having the contact of the customer advisory board as your customers or salespeople, that’s the first time we’ve heard that. Then, debook rate. It’s the first time I’ve ever heard that metrics over 40 interviews now. That’s should be interesting insight.

Ian, thank you so much for that quick fire around, loads of like, boom-boom-boom answers of the questions, highly valuable. Thank you so much.

Ian: Yes. Thanks for having me. I appreciate it.

[00:19:33] [END OF AUDIO]


Ian Stuart of Riskalyze

Ian Stuart of Riskalyze

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