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Director, Commercial Operations: Stefanie Tial of The Rainmaker Group

Stefanie Tial 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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Interviewer: Hello, and welcome to another very special episode of the Sales Ops Demystified Podcast. We are joined by Stefanie Tial, of The Rainmaker Group. Now, Stefanie is a two times Salesforce certified, and for the past two years, have been building the self-help function at Rainmaker Group from the ground up, and have previous experience with a VMware product in sales operations as well. I’m looking forward to diving into this right now. Stefanie, welcome to the show.

Stefanie Tial: Thank you. Thank you for having me. I’m excited to be here.

Interviewer: We’ll kick off with the first question. How did you initially get in sales ops because from your LinkedIn profile, you’ve had a variety of different roles before jumping in, and I wanted to understand how you first were exposed to the role.

Stefanie: Straight out of college, I actually began working in sales. I’ve been on the front lines. Did that for three to four years. I’m not the best salesperson. I was always looking for something that was a little more analytical, more process-oriented. The couple of times that I had the opportunity to do that from a sales standpoint, I knew that’s the direction I wanted to go career-wise. A good friend of mine from college, we had actually studied abroad together over in Germany for a bit. I noticed he was working at the startup called AirWatch.

They had sent him to Australia to help build out an office there. They were looking for a sales operations analyst, and I’m like, “I don’t really know what this looks like, but the job description looks pretty interesting to me.” I pinged him, he actually referred me for the role, and that’s how I got started at AirWatch. That was my introduction to sales operations in general. It was a crazy ride. AirWatch was an Atlanta based startup turned unicorn. We ultimately got acquired for one and a half billion dollars by VMware, and that’s where I earned my sales ops stripes. That’s where I got started.

Interviewer: Quick question, why do you think you weren’t good as a salesperson?

Stefanie: For me, I struggled with a couple things. I’m borderline between extrovert and introvert. Reaching out to people, doing the 50 dials a day type scenario is not necessarily my cup of tea. I wasn’t very persistent either. If somebody was like, “Yes, we’re not really interested.” I was just like, “Okay, sounds good, talk to you later.”


Interviewer: Okay.

Stefanie: Definitely missing some of the assertiveness, I think, from a sales standpoint.

Interviewer: Got it. Then fast forward into the Rainmaker Group now.

Stefanie: Sure.

Interviewer: Can you give us a flavor of the size of the operations team supporting the amount of sales reps, so I can get the ratio of operations people to salespeople?

Stefanie: I feel like this is always a good question. Rainmaker, I’ve been there for four and a half years. We’ve been through two acquisitions now. When I first started, they didn’t have any sales operations folks. I was the first one there. The company was founded back in ’98. When I started in 2015, it was one to 20 plus sales folks, and really just trying to figure things out. Shortly after that, we brought in a Salesforce admin, and a sales enablement person as well. I would say, we got it up to about three people supporting the larger sales organization.

In 2017, Rainmaker sold off their multifamily portion of their business, which was a large acquisition. Then we had the hospitality side remaining. We work with hotels and casinos. We lost all of our systems and a couple of those folks, so it was back to one. We converted one of our admins to a sales ops specialist, and then over time, added a Salesforce admin as well. A smaller team, but a lot of rebuilding that needed to be done. At our max, we got back up to three, to about a 10 to 12-person sales org.

Interviewer: Got it. Because you’re also certified in Salesforce, it sounds like quite a technical sales ops team you have running.

Stefanie: Yes, I would say so. We really grew from just being sales ops to, we call it commercial ops. Really starting to think, a similar concept to revenue ops that some people see are your BizOps. Really starting to look at, across the entire company, how can we start to take the information that’s maybe gathered at the very beginning of the process, like an SDR is collecting information? That information is used by many, many people throughout the organization.

Instead of doing something multiple times, let’s do it once, let’s capture the information. Then how can we figure out how to make that information flow, not only to the sales rep, but to the folks who are going to implement or deploy the product after the deal is done? Then even the support team, who’s supporting those customers once they’ve signed on, and they’re up and running.

Interviewer: Got it. Can we now quickly talk about the tech stack you have running at the Rainmaker Group at the moment?

Stefanie: Yes, for sure. Salesforce is our CRM. I think that’s pretty common nowadays. If you’re trying to run with the big boys, Salesforce is the go to product there. We use Sales Cloud and Service Cloud. From a marketing automation standpoint, we’re on HubSpot. We just got acquired a little over a month ago. We’ll be actually flipping over the part out there in the coming months. From an outreach standpoint, we use SalesLoft. We use LinkedIn Sales Navigator, and then have really worked to automate some of the contracting portion of the sales process with Conga Composer and in ISA tools as well.

Interviewer: Got it. Your team is responsible for managing and maintaining and training for all those tools?

Stefanie: We own everything except for HubSpot. We own the integration of HubSpot into Salesforce, but our marketing team handles the setup of HubSpot and the actual outbound emails and campaigns and things like that.

Interviewer: How is that integration between HubSpot, because we currently use Pardot and Salesforce, which obviously have a good integration. Have you ever had any issues with the integration or they work fine for you?

Stefanie: We may have had like a couple of minor issues, but nothing that really jumped out at me. I would say, in general, we’ve had a considerable amount of success in making those two systems work well together, and talk to each other.

Interviewer: Yes, you would expect that HubSpot would invest heavily on the integration with Salesforce because probably a lot of customers they want, use Salesforce.

Stefanie: Sure.

Interviewer: Now, shifting to Salesforce yourself, and the issues around data quality, what are you currently doing to maintain and ensure data is accurate within CRM?

Stefanie: This is the age-old question, right? If anybody had a perfect answer, I would be very impressed. From my standpoint, I think data quality is actually the responsibility of the entire organization. I think sales ops ultimately owns the data quality and maintenance from a system standpoint. We have the ability to put in validation rules, required fields, tighten up permissions on who can add what kind of data. We also use a tool called DemandTools, which I’m sure you’ve heard about many times, I assume, on the podcast.

It’s a great tool as far as being able to do regular data cleansing, deduping, merging records, things like that. We basically have it set up so every Friday, we’ll do a massive clean of the system, make sure contacts owners are aligned with account owners, and standardize some of the data, populate missing fields and things like that. Ultimately, I do think it really boils down to the broader organization needing to have buy-in that your CRM is your go-to. It’s the source of truth for the organization, and the folks who are out there talking to customers need to be putting that information into the system as well.

From sales ops standpoint, I can do a lot of the system stuff and the generic cleanup, but there’s no way for me to know if Bobby just switched companies. I need the salesperson or the customer success rep or whoever knows that information, to be updating that in real time as well.

Interviewer: Got it. Sounds like a two pronged approach. You have the changing the culture, and you have your weekly check.

Stefanie: Absolutely.

Interviewer: [crosstalk]. Got it. Awesome. Now, shifting to the sales team, do you have any tips on say, influencing a salesperson to come and do something that maybe they [inaudible 00:08:57] self-interest?

Stefanie: Yes, I think the thing that salespeople tend to care about, it’s a broad statement, but a lot of times they want to know why they’re being asked to do something, and then the other side is like, “What’s in it for me? How is this going to help make my life easier? Help me hit my quota faster, get paid more.” They really need to understand, A, why they’re doing something, B, how it’s going to actually help them out. One thing that I’ve also found, this is for sales or anybody, right? Is being able to identify a champion. As a great example, we had a customer success person join our team early last year.

One of the benefits of working at Rainmakers, they cater our lunches three days a week. It gives us an opportunity to sit down and have some conversations. This customer success rep, the first week, he sat me down and he’s like, “Okay, if I wanted to do this in Salesforce, how would I do it? If I wanted to do this, or how does this work?” He started asking questions. Then he also started asking for changes to be happening in Salesforce, and was already thinking about ways to improve the process, and get his team onboard, and get them out of Excel spreadsheets, and into the system, and look at this cool dashboard.

If you can find somebody that’s like that, who’s engaged and interested, and is really the champion, a lot of times it’s a lot easier for other folks in the organization, whether it’s sales or customer success, to digest the changes, if it’s coming from within their own team. That’s not always going to be the case. A lot of times the leadership team will come to me and say, “Hey, we need to fix this.” Or I’ll notice something’s broken. I won’t necessarily have a champion, but if I can get a rep to at least have some input or provide feedback, I think that helps, and it goes a long way as well.

Interviewer: The champion. The champion from within the ranks [crosstalk].

Stefanie: Yes, for sure.

Interviewer: Alex just asked the tool that you use for deduping. That was DemandTools, right?

Stefanie: Correct. Yes.

Interviewer: Cool. Awesome. Onboarding salespeople. Do you have any tips or any tools you’re using to get people to reduce [inaudible 00:11:12] time?

Stefanie: Yes, from Rainmaker’s standpoint, we’re a pretty small sales organization, and we don’t onboard a ton of reps. I would say our approach is a little bit different. If I think back at AirWatch, I would say there wasn’t a week that went by that we weren’t onboarding like five or 10 reps every week. I would say there’s definitely a different approach depending on your company size, and growth rate, and the style of the company. From Rainmaker’s standpoint, we’re a pretty small shop, we have the occasional rep join.

We can white-glove the onboarding process, and give them exactly what they need. We curate a condensed document, and like, “Start here, go through these tools.” Then we can have more of a just in-time approach to training. Instead of day one like, “Here’s Salesforce, here’s how you create an opportunity and build a quote and send a proposal.” We can give them the high level, let them work through a couple of weeks. Then once they start talking of prospects and have an actual opportunity to work there, then we can sit them down and go through that.

That’s probably a luxury that most people don’t have. When I was at AirWatch, on the flip side, so we had a team that was dedicated, sales enablement are every rep’s first week at AirWatch was spent in training, they learned company history, product knowledge, sales process, Salesforce. By the end, they had to get certified on the product. So, very formal system. Once they got out of that first week of training, and actually went out to their sales teams, our set up at that point in time was that we had a sales operations analyst that was dedicated to like two or three sales teams.

They basically had an individual sales ops person that they could come to to ask questions if they needed help with getting things converted, or needed to record, or to dig into their territory, any of that type information, our sales ops team worked hand in hand with the sales teams and the new hires to make sure they were onboard, and ramping up, and quickly able to start producing results.

Interviewer: Got it. Can we now move to the sales forecasting process. Are you guys responsible for producing that forecast or do you present that data to someone else, like the head of sales to produce it?

Stefanie: I’d say we take a collaborative approach on the sales forecasts. We have regular sales forecast calls with the sales team. Then we’ve set up Salesforce to be able to generate a system forecast as well. Pretty common. I think one thing that we’ve done that’s maybe a little bit unusual, is that we’ve actually separated sales stage from sales probability. Just because you’re in an early stage, doesn’t mean the deal is going to get done necessarily. Just because you’re negotiating an agreement doesn’t mean there’s a 90% probability of the deal getting done either.

We separated those, and we’ll then, when we pull together our forecast, we’ll base it off of probability which is tied to what we call deal confidence, but is the same as forecast category. We’ll pull a weighted amount based on the probability, and then work with the VP of sales who knows the nitty-gritty details about some of the deals, and he’ll give a verbal call as well. We’ve got the system forecast that’s pulling out based on just the data that’s in Salesforce, the probability that’s been set, and then our VP of sales rounds that out with some additional color as to what he thinks will actually happen.

That gives you the ability. If your forecast is a little bit inflated because you’ve got a couple of big chunky deals that may or may not happen, the VP of sales then has the ability to chime in and just add some additional color there.

Interviewer: For the initial probability, is that set by the rep?

Stefanie: Yes. It’s set by the rep using what we call deal confidence. If they’re committing a deal, it’s at 90% probability, if they’re saying it’s probable, it’s just 75% probability. Just a little bit more flexibility, but independent of where they’re at in the sales process.

Interviewer: You also have that second kind of check [inaudible 00:15:39] good sales because maybe he knows that a specific rep is more [unintelligible 00:15:44].

Stefanie: Yes.

Interviewer: Okay, cool.

Stefanie: Definitely.

Interviewer: Is there anything that you’re doing right now to drive productivity with the reps?

Stefanie: Yes. I think our approach, I touched on this a little bit earlier, but when I started at Rainmaker, a lot of stuff was, and this is like most companies, right? It’s not unique to us, but a lot of times you see folks working out of spreadsheets, passing Excel Docs around, things like that. We really tried to, again, make Salesforce be the system of record, and then capture a piece of information once, and then pass it along in the process.

I would say one of the biggest things that we’ve done this year is really work to automate our contracting process. With the click of a button, after a quote has been approved, we’ve agreed to terms of pricing and things like that internally, our reps can literally just go click a button, and it spits out an agreement. They can send it electronically to be signed. This speeds up the process, it also makes life a lot easier on the customer side, obviously. They don’t have to print out a document, sign it, scan it, and send it back.

We’re just looking to find ways to eliminate a lot of the back and forth emails, keep everybody in one place working, and then where we can automate stuff, we definitely want to streamline that. Another thing that we’ve done recently is work on the handoff process. Once a deal gets done, you’ve got a team who’s got to actually go out and deploy it. We’ve really worked to streamline that information. Again, getting it out of Excel and into Salesforce, but then also minimizing the data that the sales reps have to put in because they’ve already done it once on the opportunity and the quote.

We just want to take that information, and pass it along to the next team, and that’s what we’ve been able to do through using Salesforce and custom objects, automations, email alerts, things like that.

Interviewer: Nice. Then from your career in sales operations, what has been a metric that has been the most insightful to you?

Stefanie: Yes, oh man. There’s so many metrics. [laughs] I think if I had to boil it down to a single metric, I would start to look at activity metrics. Activities can tell you a lot. It’s not a perfect metric, so I think sometimes– I feel like we did this a little bit at AirWatch, we just looked at a strict number. Did you hit 50 calls a day? Yes, no. I do think it is important to look at who are you reaching out to? Are you targeting the right folks to begin with? What’s your mix of outreach? Is it just emails, is it phone calls? Is there a combination? Activity is the one thing that reps can actually control.

If they’re targeting the right folks, and they’re logging the right activities, getting demos booked and scheduled, and they’re not getting the results, then that gives you a little bit of opportunity to dig in and maybe they’re not doing a good job of qualifying, or maybe they jumping to the demo too soon. That’s the one factor that a rep can control. I think if I had to boil it down to one single KPI, which is, again, hard to do, I think I would start by looking at activities for sure.

Interviewer: Got it. Final question. Who, in the world of sales ops, has taught you the most?

Stefanie: This is a good question. I’ve got a couple of answers on this one. If I think about my time at AirWatch, and really learning the ropes, and just figuring things out, I have to think back, when we started, I think I was like 25 when I started there, and I was like the old person at AirWatch. There was a group of like 15 of us, I would say. We were basically straight out of college, just figuring stuff out. I have to think of Lauren and Jenny, that I worked with at AirWatch as a couple of the folks, just banging out Excel reports, and Googling how to do stuff in Salesforce. We were all just scrambling, but trying to figure it out.

John Marshall, our CEO at AirWatch, he really instilled a sense of just constant reporting cadence. If it’s not in Salesforce, it doesn’t exist. Impeccable attention to detail. I think a lot of us AirWatch folks still have some of that John Marshall influence, to say the least. Then one of my favorite resources, and I talk about this all the time, I’m in a couple of different ops like groups, and I feel like a broken record by now, but one of my favorite resources, and I constantly go back to it, is that Matt Bertuzzi’s Lightning Sales Ops book. It’s like less than $5 on Amazon, so I would recommend everybody go buy it.

It’s like a step by step process on how to get leads from SDRs, to AEs, and everything in between. He ties in marketing, SDRs, AEs, and then the leadership and reporting. Not going to lie, I ripped off [chuckles] or I borrowed some of his processes and things, and have implemented them at Rainmaker. It’s been very successful. I love that book. It’s so tactical and hands-on. If you’re looking for like, “How do we pass leads off to the sales team? What kind of reporting do we need to have in place?” That book is hands down my go-to.

Interviewer: That’s by Matt Bertuzzi?

Stefanie: Matt Bertuzzi. Yes.

Interviewer: Got it.

Stefanie: Hopefully, he’ll send me a signed copy if I keep talking about it someday. [laughs]

Interviewer: Yes, he will. Awesome. Here are the things that I liked. Your point about how, if the SDR has some data, it’s not just the sales team that want to use that. Actually, you’re a part of a commercial operations team that spans not just the sales department, which I think is very [crosstalk] right now. The two things, most people I ask about influencing salespeople, most people say they are interested. You have to communicate to them the benefit, which you said was just– Wasn’t [inaudible 00:21:57].

The other thing that most people don’t say is, you have to say why we’re doing it. When you couple those two together, I think that’s quite powerful. Then, really interesting about separating stage and probability. I think it makes sense because these are two different metrics, and they’ve been lumped together, when maybe they’re not actually aligned. I think that’s a really good insight as well.

Stefanie: Yes. On that specific point, I think they’re probably two schools. Most people are used to having it lumped together. I think it probably is more accurate to separate the two. It can be confusing for the sales team as well. Maybe we’re testing out for folks, but that’s definitely an interesting approach. Our Chief Commercial Officer, a few years ago, rolled that out, and it’s been interesting for sure.

Interviewer: If people want to learn more about Stephanie, they can probably Google We will link to it below this video. Stefanie, it’s been very insightful. Thank you so much for giving us your time.

Stefanie: Awesome. Thanks. I’ve enjoyed it.

[00:23:15] [END OF AUDIO]


Stefanie Tial of The Rainmaker Group

Stefanie Tial of The Rainmaker Group