Tom Andrews jumped onto Sales Operations Demystified to share his knowledge and experience in Sales Operations.
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Interviewer: to a very special episode of Sales Ops Demystified. We’re joined by Tom Andrews and this is the first time we’ve ever had two individuals from the same company. Of course, we had Kirsty in I think our third ever Sales Ops Demystified interview. Now we’re bringing Tommy to the fold here. He just joined the Signal but does have sales ops experience from the likes of Stack Overflow and Hewlett Packard. So I’m looking forward to diving into those experiences. Tom, welcome to the show.
Tom Andrews: Thank you very much for having me.
Interviewer: First question as always, how did you manage to get into sales ops? Tell us a bit about your journey.
Tom: Of course. It wasn’t completely intentional. I don’t think it ever is. My undergrad degree was in Computer Science and then my post-grad was in Marketing and Management. I started HP on their grad scheme as a technology consultant and very quickly the opportunity came up to help their sales managers out with some Excel. They just got really stuck into the whole commercial side of it instead of the client side. Then as soon as the permanent role came up to move into sales operations full-time, I went for it. Then pretty much spent the next year doing nothing but forecasting, pipeline all that kind of thing across a couple of different business units within Hewlett Packard Enterprise.
Interviewer: Do you think that’s a good way of I love the phrase help the sales managers with Excel, do you think a lot of people will get into sales ops by doing that?
Tom: For sure, I think a lot of people start their career as an analyst of some sort. You’ve probably got an ability for data but you’re probably also quite communicative and able to take that data and apply context and paint a real picture for people because I think that’s sometimes where it falls down. Then very quickly I think you start to see how you can use that data to start affecting the sales process and rebuilding the way things are and making more efficient, increasing your velocity. It just naturally builds on that underlying skill set as a bit of an analyst.
Interviewer: You touched upon something there that we see in a lot of these interviews which is [unintelligible 00:02:33] you really need that data analytical side but then you also really need the soft skills side. Working with salespeople at HP, how do you find the soft skills side of that? Were you able to engage with the sales team? I assume they’re probably like pretty talented experienced sales people at HP. How did you as a grad build the relationships with them?
Tom: Yes, for me, very quickly found it relatively easy to get on with them all. They were very talented as you said. All of them knew exactly what they were doing which really helped. They also had great insight into what they didn’t necessarily know. It was very easy to figure out like what they needed help with and as soon as I got some quick wins from that, the relationships grew and from there it was relatively easy to– Sorry I just saw the chat and it was pretty easy to build that commercial relationship as well.
I think it really is the role where you do have to build quite a lot of faith and trust in your own skill set because what you are doing is something that is generally quite alien but once you’re able to make that progress, you very rapidly become a business partner or trusted adviser to the people in your sales team that you support. Which actually, as a young grad, was one of the most inspiring things about the role. I was able to do something that was really strategic. I was able to make quite a big impact but I was doing it really early on in my career.
Interviewer: Just being able to go in there and because you had a Computer Science background, you were able to immediately show you a value, I assume you had pretty awesome Excel skills. So you would have had all these sales guys coming to you being like, help me with this, help me with this and you were immediately able to help them. I’m sure that started to help build a relationship. Like they could go to you and you can help them and because some other grad in these companies, sometimes you’re pretty useless because you don’t have many skills. But yes, I can feel exactly– Your video, I think is currently off, Tom, so if you could turn that on.
Tom: Yes, sure. There we go.
Interviewer: Okay, awesome. That’s how you got into sales ops and can we just like from there- we covered just the first or two at HP. Can you just take us through the other X amount of years after joining Signal recently?
Tom: Yes, sure. After about two years at Hewlett Packard or maybe a bit longer than that actually, I moved on to Stack Overflow. A relatively big name in the world, one of the largest developer, well, the largest developer forum there is. I’m pretty sure they’re in the top 50 most visited websites on the internet and it was crazy because doing my undergrad in Computer Science [unintelligible 00:05:39] Stack Overflow an awful lot to figure out how to do programming. They had a role as a Sales Operations Analyst and I wanted to move into a much more startup/midsize enterprise instead of the beast that is Hewlett Packard Enterprise, see the other end of the size meter.
Moved over there, spent about six months building out a few different things. It was very focused on specific projects. I was building out an integration between Salesforce and DocuSign deploying an enterprise model looking at some stuff to do with compensation planning. Then the opportunity came up to work with Reconcile that I recently left. I’d known my boss at Reconcile for all the years leading up to that.
We had a brilliant relationship and he just said to me one day, “We need someone to come in who’s very digitally savvy. Help us figure out what we’re offering in the digital space, how we are using marketing automation, how we’re using sales technology and just be able to bring all of that together but also who could drive some strategic change within the company”. That was a huge opportunity then.
So I went in and worked with a couple of different people to build the first iteration of the digital products. I was doing a lot of go-to market stuff a foray into sales enablement. I was doing quite a lot of back-end changes in the system and just slowly evolved into a fully fledged not just sales operations also well total sales operations. Sales strategy, planning, sales enablement, all sorts of different things. Then increasingly got involved with customers as a bit of a consultant because Reconcile sells a lot of content marketing these days.
To get the ROI from that, you really have to put it to work through marketing automation which if you know a lot about sales tech, you know a lot about marketing automation generally. Then very recently, the opportunity came up to work for Kirsty and I’ve known her a while through her meetup group.
Interviewer: Oh, really?
Tom: Yes, and it was it’s the kind of role you don’t see a ton, in my opinion. It’s sales operations but it’s very focused on the system side which is my strong point. I can learn the rest of it from Kirsty . She can specialize in the processes and the overall compensation design and everything like that. I’ve got a massive tech stack to optimize and build which is what I find the most fun about the whole sales operations role.
Interviewer: Moving nicely into our second question is the current Sales Ops tech stack at Signal, it may have changed in the past four or five months since we spoke with Kirsty .
Tom: Yes, it’s definitely grown. It’s quite big. We’ve got a lot of different technologies within it and actually one of the challenges is going to be optimizing the integration between all of them and really getting the data flowing. Our SDRs and our EDR, Sales Development and Enterprise Development representatives, they will live in outreach. We do all our calls through NASA box. We’ve got Gong for analysis and that makes the trifecta of the inputs as it were. Our marketing team [unintelligible 00:08:57]. They all feed into Salesforce which is the brains of the organization.
Then we’ve got Hoopla and Insight Squared that’s it on top of it. Then, of course, LinkedIn sales navigator that sits alongside outreach and Salesforce. I’m probably forgetting a couple of other elements of it but you can see there’s a lot of different things happening. It’s brilliant in a way because it’s the best of pre-tech search. It’s got some of the best providers, the biggest names in each of those different categories but the real art there is them bringing it all together.
You need your data running all the way from the very beginning through to the very end when it’s with customers and it’s accessing customer support and informing your marketing and outreach efforts all over again. It’s that continuous cycle of data flow through the systems that is going to be part of a lot of wondering over the next few months. Then beyond that, Signal is currently still on Salesforce classic and in October, it’s [unintelligible 00:09:59] classics-4 is being switched off, so we’re also on the process of moving over to Lightning. I’ve done it two times. I’ll move two companies to Lightning. It’s really fun for me, but a lot of change for the sales team to get grips with.
Interviewer: I can tell why the pace at which you ratted off the names of all the tools that you know these and are passionate about these. You’ve knocked about eight names in 15 seconds. Are you then responsible for– Are you the [unintelligible 00:10:32] admin if the sales force were now yours?
Tom: Yes. I’m the product owner for all those different technologies as well as the admin on all of them. Basically taking ownership of that whole tech stack, which is very exciting. A great opportunity to bring it all together, but I would say that one of my USPs is the market knowledge of the sales technology and the marketing technology. Whatever the problem may be, I’d probably know the technology that could help to fix it. I try to always keep on top of all different tech startups. There’s so many these days that it’s all penetrating different areas in order to constantly be able to build that best-of-breed tech stack.
Integrating them all might be a bit of a pain, but ultimately, it is best just to use the best-in-class products and then build an environment around them that helps them to work together.
Interviewer: Will you actually be coding custom integrations yourself?
Tom: Yes, to an extent. There’ll be a certain amount of Apex and API integrations. We’re also looking into a couple of different technologies that could help with that. Salesforce acquire MuleSoft, I can’t remember when. Which is brilliant for API integrations. We’re investing that as a use case. A lot of them are relatively native integrations. We’ve been good at picking a tech stack that is built around Salesforce, but there will be a certain amount of custom integrations, especially when we get into the automation part.
There’s already some very complicated flows going on some process builders and there will need to be a lot of Apex triggers as well for where we’re putting other stuff in. The automation profile is very impressive, if I do say so myself.
Interviewer: The structure of the Sales Ops team now at Signal, so Kirsty, I assume, can now lift herself away from the detail of the tech more and be more strategic. Is it just the two of you at the moment?
Tom: No. We’ve actually got a couple of other people. Kirsty is the vision. She does all of the big process stuff, a lot of the interface for sales management, things like setting out the mission as well. I deliver and own all the systems underneath that, then we’ve got a sales researcher who does a lot do with data cleansing, let’s call it, data cleanup, who’s an intern. Then I’ve got a gentleman working for me who works on with the systems as well who does a lot of the day-to-day administration while I do a lot of the structure and architectural stuff, let’s call it.
We are also currently hiring for a Sales Operations Executive to work directly for Kirsty who’s going to be very focused on the BI layer and things like commissions. A lot more along the side of an analyst role.
Interviewer: Once you’ve hired this person and we’ll put a link below to the job description if you [inaudible 00:13:36], there’ll be five in the team?
Tom: Yes. Then we’ve also got Kirsty’s equivalent in the US based in New York, which is really important because that’s a very high growth market for us. Our head of sales ops over in the US does tons of really remedial fixy reactive stuff as well as a lot of taking what we do in the UK and expanding that process overseas, as well as being an on-the-ground point of contact because the rest of us are all based out of the UK. For example, the end of my day isn’t the end of their day, so if something goes horribly wrong, there needs to be on-the-ground. That will be a full complement to the six of us.
Interviewer: Got it. Just quickly supporting how many salespeople?
Tom: We’ve got approximately 70 to 80 salespeople, I would say. I know I’ve got 89 users of Salesforce, but nine of them are in customer support, some are marketing or integration users. Probably 70 to 80 in sales.
Interviewer: Let’s move on to data quality. If you are the product owner for Salesforce, how are you currently managing data quality?
Tom: Luckily, we have a sales researcher. [laughs] No, I’m kidding. We’ve got a ton of different dashboards, we’re building out a couple of different form fields that look at blanks. For example, if you define your golden criteria for an account as these 10 data points, how many of them are filled out on average and then setting a rough percentage of that.
That’s the overall, how many fields are filled out. Obviously, it doesn’t take into account the accuracy. There’s certain amounts of validation to try and improve the accuracy. Then we’ve also got a series of boards that look at data governance and hygiene. Are our sales moving through the correct stages in the right ways? If they’re not, are we understanding why and can we figure that out and improve the process, or enable the salesperson to better understand what the stages for them to be moving them.
We’ve got some dashboards that are called red flags. It’s things that are just wrong and need to be fixed, which would be fields not filled in or opportunities that haven’t moved for over 100 days, things like that. Then we’ve got yellow flags. These are talking points. As a sales manager, I expect you to go and speak to your reps one on one about this and figure out like, if it is okay, and then that’s fine. All of it is around building the confidence. We call this all project confidence. Building the confidence in our ability to forecast and have a really solid view of our pipeline because I think one of the failing points sometimes between sales operations and sales management is exactly that issue around data quality.
If you’re not properly monitoring it, if you’re not constantly rebuilding confidence and helping all of the sales team to understand where the database fits into your value chain, that it is a valuable resource and how it actually impacts future sales, then you’re not really incentivizing them to do what you ultimately want them to do. I’m a big fan of the metaphor about carrot and stick but would prefer to stick with the reward methodology where possible.
Interviewer: For sure. On that kind of getting buy-in from sale team for new things you’re implementing, like maybe if you shift the lightning or maybe if you’re trying a new data quality initiative, what is your top strategy for getting people to actually want to do the thing that you want to do?
Tom: A lot of is building business cases, which Kirsty is amazing at. I am also quite evangelistic about a lot of the products that I want. A lot of it is taking people on that journey of understanding, like what is the scenario of the problem, which actually in many cases, is what the sales managers will often bring to me. They’ll say like, “This is the challenge we have. It would be great to know how to fix it.” Obviously, I will always try to come up with solution that doesn’t involve buying another piece of technology to go into the tech stack. If ultimately–
Interviewer: You really liked [unintelligible 00:17:52] don’t you, Tom?
Tom: I really do. The more the merrier. I want thoroughly integrated, of course. Then there’s also that whole thing of like, if people do understand the problem and the pain points, and you’re able to remedy all of them, you’re able to work through the USPS of the provider that you’re looking at and really get to grips with how exactly they’re going to meet those pain points. You can plan in a very visible way for the integration of that, whether it be new tool or new automation or just whatever you’re doing, I think it again goes back to that whole thing about building credibility and faith.
Just like a product development team would, I’ve got a visible roadmap of what I’m doing and lightning or what I’m doing with system integration and modernization. Everyone can know where we’re going and when they’re going to get the fix to whatever that problem could be. Then if it’s bigger things or more exploratory things, then that’s something that will naturally be a bit further out. It takes some more research, but then it would be a change management process to bring in so that be a lot of– With lightning, for example, we’ve got a lightning champions program.
For people who want to be early adopters, who want to get to grips with lightning maybe before the general sales team, they’re involved in that, they can become my internal evangelists. They can help with getting the whole sales teams buy-in and so, if you use that peer-to-peer that word of mouth, that tips and tricks approach where if your top salespeople are using a function and everyone knows there a top seller and they say, “Actually, it’s because I use this bit. It’s really useful.” Again, that whole methodology around the carrot that you’re showing people the reward they get for using the thing you want them to. That’s my whole go to market with my changes.
Interviewer: Got it. We did have a question here. How do you approach the process filtering in from marketing to sales. A very good question for Tom.
Tom: A very good question. It’s not the world’s easiest thing to do. It does require essentially an elevation of what we’ve historically called sales operations to revenue operations which is that wonderful new buzzword. I do look after paddle as well as Salesforce and increasingly, we are sort of seeing the integration between our demand generation tools with our sort of system of record for sales.
All of it is about building a cohesive, visible and very easy to understand process where you can see the marketing needs coming in through the campaigns which you can build in any piece of marketing automation software and then filtering that through your lead assignment roles and then handing them off to reps but doing all of that with as much transparency about what’s happened as possible.
In Salesforce, there’s a really cool widget called engagement history where you can actually see every single activity marketing has done and how it’s been engaged with by the prospect for the salesperson, then they can paint a picture of okay, this person received this email, went to this webinar, got this follow-up. I know roughly why they’re being handed to me as a lead. There’s also things you can do around regrading and lead scoring where you can show the quality of the company and how it meets sort of the criteria of your organisation’s goals account and also then scoring looks at their engagement.
A lot of modern methods of lead generation will be able to show you cumulatively why someone is warming up as a lead and then trigger them being passed over and then through enablement and coaching and training, you can help your reps to understand this score means they’ve done X, Y, Z. This grade means they meet this part of our criteria, overrule the reason they are my leader is this. Often the hardest part though isn’t actually building the system integration, it’s agreeing that lead flow process, it’s understanding how things are being fed in from marketing and how they’re moving across. It’s understanding your lead assignment rules.
Do you have one STR who gets all the leads and then pass them off to the rest of the team? Do you do it based on territory management? Do you do it based on industry or vertical and then from there building out that very real-time enablement to help people understand why they’re being handed over, that’s often something that’s missed.
I hear complaints all the time like, “I’ve got a lead and I don’t understand it” and that’s where it’s all up to the sales enablement process to bring together what marketing has learnt through their whole journey of warming up that prospect to the other side of it where sales is ultimately then trying to engage them in a profitable conversation and it really as if with all things, it all comes down to really understanding the context.
I’ve just seen a follow up from Zack, what are the best practices of implementing these methodologies? Generally, I’d say best practices are building all of your rules in your marketing automation in order to be able to do scoring and grading and starting from the governance, so starting from having a meeting with your SDR manager and your demand generation manager or whatever you call them and agreeing that lead flow process.
Once you’ve got that, best practices in the system are relatively easy if you’ve got two tools that naturally integrate and pretty much all of the big marketing automation tools will integrate very well with all of the big CRMs because they all know they’re two sides of a coin.
Interviewer: Okay, I hope that answered your question. Moving on-boarding of salespeople, do you have a structured process in place at the moment?
Tom: We do, that I know of. As far as I know of but it’s something that we’re working on quite heavily to standardize especially between the UK and the US and then to also build KPI’s around for ourselves, especially around Ramp. We’ve also realized quite recently through some of my initial work in auditing the way our systems work, that the processes and the systems don’t naturally reinforce what we teach in on-boarding and that’s quite a destructive behavior of the system because the system needs to work exactly the way someone’s been trained for it to work so it’s constantly reinforcing.
For our on-boarding process, there’s a company layer of on-boarding which familiarizes see people with the product, the technology or the different departments blah, blah, blah, what you’d expect at a new company. There’s a lot of sales coaching, going through the go-to-market, going through the sales proposition but at the moment, it’s not as formalized as I would probably like.
At HP, when I was there, it was an extremely formalized process with an entire Academy that was called “Sell School” and whether you were an internal move going from a non-sales department into a sales role or you were coming in as a salesperson, you would go through the sales school process. That was a very comprehensive role plays that would go through a huge amount of iterations of different customer environments where you’d be told, okay, this is the product line, you’ll need to sell in this, go do the research on that.
Then the role-plays would be the check to see if you’d really learned about the products, it’s USPs where it needs to go and the system was quite good at reinforcing that. When you were putting in your qualification criteria, when you were moving through the opportunity stages, it was constantly checking back to the same thing. You had to discover in that role-play process that you went through before. Then the sales process that you went through it always be scored the way the on-boarding was by the system. It was really, really good. That’s the kind of thing I’d like to move us towards by degrees.
Interviewer: To take on that corporate process and bring it to signal. Can we talk about the productivity of sales team? Is there anything you guys are doing at the moment to make the reps more productive?
Tom: Yes. I think this is where actually it does heavily leverage having a very competent systems focused sales operations professional because generally, what makes people unproductive is admin and it’s the systems. There’s that stat that everyone throws around that sells people actually spend only 30% of their time selling. A lot of that is because they’re working in systems that aren’t operationalized and optimized for the way they should be working.
An example would be booking a discovery core. There’s often loads of different hoops to jump through but is there a single screen that loads when you’ve hit the button like a discovery core that walks you through everything you need to know in one go and then instantly puts it in the right places. A huge amount of what we’re doing to improve productivity at the moment is shifting from having random validation rules firing off when you try and move the stage to having everything be almost like a wizard. If you remember the old-school setup wizards in Microsoft Office days.
When you’re moving stage or you’re handing over from an SDR lead to being one of our sales accepted leads, all of these things are immortalized in these little wizards that show you exactly the fields you need to walk through with a lot of guidance put in so you’re really understanding why. While that sounds like it’s making them appear more at once, sctually, all it’s doing is taking disparate spread-out fields, disparate spread out data putting it all in one place.
It’s also quick tricks. You can integrate sales navigator into most CRMs really, really effectively. If you then set up your data rules correctly, what will happen is when you go on a contact record in your CRM, you’ll actually also see those sales navigator details right there. It sounds so minor but just the amount of time that salespeople spend switching from their system of record to sales navigator to their email back, that can waste seconds and therefore minutes throughout the day. Then across a team of 80 something like we’ve got across the 260 odd working days in the year, suddenly, you can save weeks of work across your sales team just by reducing the amount of “tabbing” that they’re doing.
I think a lot of people focus on these really, really macro goals to improve productivity but I think actually you should just be focusing on shaving off every single second you can by just streamlining as many of your processes, automating everything humanly possible but making sure you’re doing it in a non-disruptive manner. Obviously, the problem with some automation is it confuses everyone. You do have to be very mindful of the way this system works currently and then what you’re moving towards.
Interviewer: Awesome. Then KPIs currently tracking.
Tom: We look at the standard KPIs, let’s call them. Like [unintelligible 00:29:06], cycle time, everything like that. At the moment we’re doing a project to establish with the baselines of those so we can look at when we migrate to lightning how that has improved. Fingers crossed, it is improved. We’re also doing more and more investigations to sales velocity as like a macro term because it’s one that I’ve really stuck with.
For me, all the KPIs need to roll up into something very realistic. I think often, you end up with all these random numbers that are quite small in effect but if you don’t know they all roll up into ultimately, like your predictable revenue, that becomes an issue. We’re doing quite a lot at the moment to– Formalize is the wrong word but to tighten up how we’re doing forecasting. To do with our commit best-case statuses. Everything around that working out the amount things and commit to ultimately, you do end up closing and trying to fine-tune that on a rep by rep level.
Understanding do they just not understand what committee is? Do they understand it and use it incorrectly? Are they over-optimistic on their deals? Then how can we improve that, use that as a KPI? We’ve got the KPIs on performance but then we’ve also got it on accuracy because we’re really starting to try and become much much more predictable and much more consistent in what we’re doing.
Interviewer: Got it and the final question. Who has taught you what you know yourself? Who’s been your biggest inspiration.
Tom: There’s actually two people. When I was at HP, I worked for a gentleman called Bricking Kamara, He now works for Amazon and he was pretty much the first person I’d ever worked for in a sales, strategy and planning role which is what HP calls sales ops. He had a huge like what I would refer to as enterprise grade viewer Sales Operations.
He really understood the massive concepts that are still alien to most companies like being able to calculate your total addressable market, your service addressable market, your share of wallet but do all of that in really obvious ways and relate it all back to your market share and then bring all that all the way down to your win rate and everything like that. Like a really macro view of it.
Then I also worked for a gentleman called Rob Dandoff at Stack Overflow, who’s now with a company called [unintelligible 00:31:33]. He was just so passionate, enthusiastic, energetic all the time about everything to do with sales operations and had this deep analytical view that I think you really develop in SAS. Because SAS is built all around these 100 odd KPIs and different terms and really helped me to move from hardware to software.
It’s a huge transition going from a Leviathan like HP to a company like Stack Overflow which has seen tremendous growth but tracks a myriad of metrics that you can only really look at in SAS when you’ve got subscription models and you’ve got all of these things like annualized revenue, annual recurring revenue, monthly recurring revenue, uplift ramp, all these different things in your clients you don’t necessarily need to think about when you’re doing one-off sales. It’d be those two.
Interviewer: Awesome. Well, let me share a couple things I’ve got six different points here. I think the biggest highlight was the thing that we haven’t heard before is when trying to improve productivity, don’t necessary focus on this big massive [unintelligible 00:32:46] but try and shave off tiny parts through automation or through streamlining. The point right start is how you got into sales operations by helping sales managers with Excel. That makes sense. We didn’t really touch on this but the continuous cycle of data flows throughout from marketing to sales to customer success and then back into re-inform marketing I think was super interesting.
Carrot, not the stink when trying to incentivize salespeople and then yes, they hit the big thing actually. How you guys are building a best-in-class ecosystem of tech tools we you try to picking up more from each category and now the challenge is making sure they all talk to each other nicely. That’s six things. I’m not sure if I’ve had six things before but, Tom, that was absolutely fantastic.
Tom: Thank you very much.
Interviewer: You guys at Signal seem to be really building a [unintelligible 00:33:42] celebrations function.
Tom: We are definitely doing our best.
Interviewer: Shout out to every else in the sales ops team at Signal including Kirsty who was a previous guest. Tom, thank you so much for coming on.
Tom: Thank you very much.
[00:34:01] [END OF AUDIO]