The Evolution of Sales Operations: Building Agile, Tech-Savvy Sales Teams

Hello everyone. First of all, welcome to the Coffee Time with Sales Table. And we've been doing this for the last year and a half, bringing in great sales leaders. And today we have David Strauss with us. And just to give you a sense of it, David and I met almost 4 years ago, if I believe so. And ever since then, we've been talking about product-led sales, product-led growth, and a bunch of topics in general. But I've learned so much from David in terms of the sales strategies, methodologies, and tactics because it's a rare combination. People can talk about strategies, people can talk about tactics, but it's very difficult to combine both at the same time. So I really respect David for that. Without further ado, David, welcome to the show and I really appreciate you taking the time.

Thanks, Suresh. It's great to see you.

Yeah, absolutely. So David, I mean, you have a great background in terms of the sales leadership roles and in various companies and various segments of tech. Can you briefly describe, I think, where you come from and what you really love about being in sales?

Yeah. So just a little bit about my background. I think I'm coming up on 32 years in sales. I was an individual contributor for 12 years before I came— became a sales leader. And I, when I did become a sales leader, I really gravitated towards sales operations. Pretty quickly. I think, you know, when I was a salesperson, CRM was pretty much the only sales tech out there at the time. But I was with a company that was an early adopter of Salesforce, I think in 2000. I think Salesforce was founded in '99. You know, my CRM prior to that was a Daytimer, you know, writing things down. And then when I became a sales leader, the company I was with just happened to be moving into Salesforce. And because I had that experience, they made me an administrator. And then when I saw the power of it, fell in love with it, became a certified administrator and wound up kind of being a hybrid of a sales manager and a sales operations manager at the same time because we didn't have a sales operations department at that company. And I've continued with that as I've, you know, gone into other sales leadership roles, always have a strong bent towards using technology to make salespeople's lives easier and to drive more revenue.

That's amazing. Yeah. So, David, you've seen a long career path for yourself in the individual contributor roles and the leadership roles. And now, I mean, what you do consulting with companies and helping them to really accelerate is amazing, right? And if we see the progress of sales tech and the sales in general in the last year and a half, a lot of things changed, especially in the technology, and the demand has reduced. What I mean to say is pre-pandemic, for example, there was a super high demand in general. A lot of companies were willing to say, oh, if there is a new tool, let me go try it out. So in general, the demand was high, the supply was high. So from the more of the sales tools point of view, people kind of adopted whatever they wanted to adopt. And in the last 3 years, what you've seen is everybody is in the consolidation mode. The sales leaders are saying, hey, you know what, I don't want to be dealing with 30 different tools. I want to really see what tools really work for me and if everything is really needed or not. And in a way, it's also really frustrating for sales leaders as well as the vendors others because at the end of the day, everybody is trying to provide the value. And that's really where we are, right? So, and then added to that bit of complexity is where we've seen in the last year, year and a half, again, the entire explosion of AI into the sales stack. And so that's really the core of the topic today, right? To really make sense out of, yes, there is so much of the AI sales technology that out there, what does it really mean for the folks in the sales operations as well as for the founders or the CEOs or the VP of Sales who is trying to adopt these technologies? It's not like a one-size-fits-all. I'm sure probably there is a lot of gray area in between as to say, what are the right tools and what should we adopt? But for the discussion topic, David, can you describe really about What does sales operations really entail, right? Because there is a lot of confusion even in the bigger companies as to say, yes, there are these sales leaders and then maybe there are these sales enablement teams that are out there. Sometimes these sales enablement teams could be one person or it's a huge organization depending on how big the company is. But in general, can you show, can you throw a little or light on what does SalesOps mean and the sales enablement and everything? Yeah.

So I think there could be a lot of definitions, but I'll give you my thoughts.

Yeah, absolutely.

I think before the prevalence of technology in sales, there may not have been such a need for this. But as sales has become more dependent on technology, there's a new skill set that sales leaders never thought they needed or, you know, maybe they don't need. So things like understanding data, data analytics, even just being super tech savvy, sometimes sales leaders don't have that skill. So I think that's where it has come from. And it just, so what sales operations does is just facilitates the sales person's day, makes it easier, helps them save time, and supports them with technology any way they can. Pretty general definition, but yeah.

Gotcha. Yeah. So the way I'm kind of thinking through that is sales enablement, sales ops really accelerates the sales team's ability to hit the quota, close deals. Is that fair to say? Yeah.

And instead of maybe your sales leader is going to show you sales tactics and strategies to close a deal, sales operations is going to show you how technology is going to help you do it.

That's amazing. Yeah. Yeah. So with that of a context, David, I mean, a lot of leaders these days, whether it is about founders or the VP of sales or the CROs at that level, Everybody is kind of thinking about, okay, AI is there. We can't ignore the AI. And what is the best way for me to adopt AI? So based on what you are seeing in the market, can you kind of talk through on your perspective on how should the sales leaders be thinking about this?

Yeah. So when you're ready to start integrating AI, to your business. First of all, define clear objectives. What are you trying to, what's broken and what are you trying to fix? So it could be your conversion rates, forecasting accuracy, and then set goals. So if your goal is, you know, helping with qualified leads, set a goal saying we wanna increase our percentage of leads converted to sales by, let's say, 20% within 6 months. Have a call. And take your time and choose the right tools because there's a ton out there and there's new ones every day. And the, and now the old tools that didn't integrate AI all are doing it. So do your research. I also think it's important that whatever tool you choose, it's easy to take that data and integrate it into your CRM. We wanna make the salesperson's life easier, not, not more complex. And they're always gonna look to the CRM as their, you know, single pane of glass as they say. So make sure it's that data, it's easily integrated into the CRM. Before you begin, you wanna audit your data quality because AI is gonna look to your data to provide insights. And the better that data is, the better the job it could do, you know, garbage in, garbage out philosophy.

Right, right.

You may wanna do a data audit and clean up your data. De-dupe accounts, maybe append some data before you start, you're gonna get a better outcome. You want to provide great training and ongoing support for the team. Your sales team a lot of times is not hired because they're tech savvy. I think sales operations sometimes because they have lived with technology for so long, They just assume everybody knows what they're doing, but that's not the case.

Yeah.

So empathize with the sales team, you know, their goal is always gonna be drive revenue and they're under a lot of pressure to do that effectively. They're, you know, they're not always thinking, okay, how do I make our data better? They're thinking about how to get my next sale. So understand that and also empathize that AI is a new technology and Look, sometimes it makes people uncomfortable. I'll never forget the first time I saw ChatGPT analyze a spreadsheet. I was like, whoa, I just saw a lot of jobs disappear. But, you know, my next thought was, well, if we're not leveraging this, we're gonna be behind because if my competitors are doing this, I have to do it. So obviously the power of these new generative AI tools are, it goes without saying, it's incredible. Then after implementation, you wanna monitor your progress, make the proper adjustments. And then after a certain amount of time, you wanna measure your ROI, make sure that either the sales are increasing or the team has sufficient time savings that these investments are making sense.

Yeah. Yeah. So thanks for that, David. So one aspect that I'm kind of kind of thinking through from sales table side is talking to a lot of leaders in the last 2 years or so. Everybody is thinking about, they may have pipeline challenges. How do I create more pipeline? Or how do I kind of really transfer the pipeline into demos? And what is that conversion process looking like? And once I get to demos, how do I make sure that these demos are resulting in, let's say, closed opportunities at that point of time? And especially when sales leaders are thinking about, you know, am I increasing the pipeline? Am I doing the conversions and then closing the deals? The idea really is to say, are we First of all, do we know what the problem is out there, right? Because the challenges that you may have with the pipeline development may not be the same challenges that you are dealing with, let's say, at the conversion time, right? And the vice versa as well. And then on the top of it, do your sales reps, the team that you have, are they getting the right information from the product, the competitive analysis, and your entire, you talked about the CRM hygiene, for example. I mean, those are so critical. Are they on top of these tasks? Because many of the times sales leaders really think about, is somebody hitting the quota or not? But they don't really think about, are they doing the right things or not? Right? So from that angle, I think, David, I mean, what you made kind of really resonates with me talking to so many of our own SalesTable customers because at the end of the day, If somebody is really looking at the pipeline development, let's just kind of, you know, take that example, right? So for the pipeline development, are we kind of, you know, do we have the right ICP? Do we have, are we kind of, you know, going after the right set of channels? I mean, are we using email? Are we using LinkedIn, phone calls, or is it more of partnerships based? Whatever that is, do you know what those channels are and then how you are able to convert those channels? And then the second question is, okay, once we have these leads that we have, are we qualifying them enough? Because to your earlier point, garbage in, garbage out. If we just have thousands of leads saying that, oh, all leads are great, but we haven't really qualified any of them, then again, unfortunately, in the downstream process, everybody, other reps like AEs or account managers, They get really frustrated because they are not qualified, right? So from that angle, knowing the problem that you are solving and identifying the right AI tools to solve that problem, and then making sure that at the end of a quarter, at the end of probably 6 months, are we getting the right ROI based on these AI tools?

Right.

That's probably where the moment you are describing about the path to AI integration, that's how I'm thinking about from SalesTable perspective when we talk to customers. That's really where they come to us, right? Because they will be like, hey, you know what? I have a great pipeline, but my sales team needs those other skills to really get to the next level. For example, somebody is not able to really do great demos or Think about the aspect of my sales managers needing to spend hours and hours with my reps in kind of, you know, role plays or objection handling and whatnot. And if there is an automated way to get these things done, then sales managers can focus on the right things that they need to do, and reps can actually go in front of the customers much more confident. In terms of what they need to do. Right, Evan?

Yeah. And I think if you think of any sales process, any point within that process, there's a technology tool that can help with that, whether it's identifying leads, qualifying them, help, you know, maintaining consistent communication with them, ensuring that they're moving through your sales process, you know, take your pick. There's gonna be a tool to help.

Yeah, absolutely. So as a next part of that, David, I mean, I know reps are the sales teams in general. They do a lot of things, you know, some of them automated, some of them very repetitive tasks. And from what you've seen in the market, what are the things that you think Can free up reps' time? Yeah.

Well, there's a lot. So I'll just give you some of my favorites. I think where we first saw automation work was in 2 places, email, and then, you know, chatbots have been around for a long time. So email automation, email cadences kind of takes up that follow-up away from a rep. Or helps remind them to send those follow-ups. I know that sounds kind of basic, but I work with a lot of smaller and medium-sized businesses that, you know, the reps don't even have their email inbox integrated with their CRM. So the emails aren't going into the CRM that you don't know if they're in communication or not, or their phone, they don't have click to dial. Those are real basics, but you wanna make sure that. I think with, you know, with the launch of ChatGPT, chatbots have become so much better and that can really take a lot of those initial conversations or initial questions prospects may have away from, you know, this, your human capital. And then as those requests get more complex, the chatbot can drive them to, you know, a sales rep. Those are great. Recently, recently we've seen some other tools like the appointment schedulers, one of my favorite. I mean, there's no more annoying email exchange than, hey, does Wednesday or Thursday work for you? Oh no, that doesn't work. I'm out. Okay, how about Friday? You know, going back and forth just trying to set an appointment.

Right.

You know, my sales emails end with, hey, if it's easier for you, here's a link to my calendar. And, you know, try in any stage of the sales process, make it easy for a prospect to say yes. And having an automated scheduler, just, it's great. And, you know, those are, you see them now, like just integrated within the CRM. They used to be like standalone tools, you know, with like HubSpot, it comes along with it. Then also like data entry and management that kind of goes with having your Email, your email connected to your CRM. So you can create new contacts in the CRM, get rid of that manual entry, things like that, or, you know, data appendage tools that will populate fields like industry, amount of employees, things like that. And then the more data you have, the better the tools will work.

Right, right, right, right. So David, I think based on what you just said, the way I'm really thinking through is There's a lot of scope for automation, especially in terms of, let's say, the CRM, the emails, the scheduling side of it, and which otherwise would have taken a lot of manual time and super erroneous in a way, right? Because again, if I, I know, for example, the favorite for me is the Gmail and the HubSpot integration which I use, and it just feels Once you set it up, it's like so simple, right? I mean, we just go to the HubSpot, you see all the communication and the same thing on your email, whether you know exactly whether somebody responded to you or not. And then what is the deal that you are looking at? And those are super simple things. But I'm sure, I think, you know, there is a method to the madness at another way, right? I mean, to really integrate all these things in a way that it is a cohesive set of tools for the reps as well as for the managers to actually look and really provide the right feedback at the end of the day. Because most of these things, the way I really think of it is, David, we don't want to go to the end of a quarter and realize that something didn't happen, whether it is about the tools or people or process. If there is something we need to fix right away today itself, So that there is that right confidence for the reps, and then the managers know exactly what is happening. And I feel all these tools are really coming together at this point of time, especially the generative AI tools and the automation that we have seen, especially in the CRM side of it.

Yeah. Well, there's a lot in that What I love is that using technology to help me ensure things are moving in the right direction before the end of the month, before the end of the quarter where it's too late. So I love using technology to have key performance indicators that are forward-looking that let me know that things are working smoothly. And that could be the amount of leads coming in. The time it takes for us to make contact with them, making sure that they're going through a proper contact cadence, that they're moving through the sales cycle. Those are things that, you know, if a sales leader has good reporting skills with their CRM, they can build reports and then stare at it for an hour or 2 and come up with some insights. But there are tools that just make it much easier and not only let leadership know, But let the sales rep know, you know, always, you know, because maybe because I was an individual contributor for 12 years, I'm always gonna go back to make sure this makes the salesperson's life easier and things like reminders that, hey, you haven't talked to this prospect in 3 days or the ability to record and analyze my calls. So I don't have to like work. Writing down notes. Those are great. Those are great tools for sales reps.

Absolutely. Absolutely. So we briefly touched upon the pipeline management in general. And today I think the ratios keep changing everywhere, but a lot of sales leaders are saying you need to have 10x pipeline to close whatever you have. Previously it used to be 4x, but now everybody's talking about the 10x of the pipeline to close whatever you want to have. So if that's the kind of massive competitive nature that we are in, how do you really think of using these AI and the advanced automation technologies to really build a pipeline?

Yeah, so it's not only build the pipeline, but also validate that it's a real pipeline. So Here are some of the mistakes I made early on in technology. So we got, you know, auto dialer and we were, this is years ago, but we're tracking calls made and talk time for the first time. And we set a goal of, okay, we want you to have a certain amount of calls that are over 5 minutes. And, you know, reps are doing their best and some were hitting it somewhere. And then we realized some reps were just getting on the call with some, with not even the real number, just sitting there for 5 minutes so they could get their, you know, get their point for, you know, this goal. But obviously it's not helping them close deals. So let's not lose sight of the most important thing is driving revenue. What's that like for people? But use technology, like I said, to validate things like, so you have that, you have that 10x pipeline goal. But how long have they been in the sales cycle? How long has it been since it's moved from one stage to the next? How many months in a row has this been forecasted to close? Those are things that, you know, a savvy sales leader may pick up on, but someone who's more junior, they need help and there's tons of tools that can help you uncover that.

Gotcha.

And let the sales reps know as well that they got it.

Yeah, yeah, yeah, yeah. So from that angle, David, when we really think of the pipeline management and qualification at the end of the day, can you talk through from your side of it? People bring in the reps, bring in a lot of leads. And then it's very common to say sometimes there is no scoring or there is no proper way of defining or having an initial discovery call. And then what happens is, especially downstream, leads to a lot of frustration, right? Because probably we haven't done the lead scoring or we haven't done the discovery call. So the AEs or the other sales reps, they're spending a lot more time in talking to this prospect and they don't have the right set of things to kind of take them to the forward in the deal cycle. And they're just simply wasting time on some of these prospects, right? So from that point of view, again, With automation or without automation, David, can you talk through on what is the best way to actually help the reps to say, hey, you know what, whenever we get in the— bring in the leads, they have to be qualified. What is the easiest framework that you can think of to do that?

Yeah, well, you know, a lot of it depends on your business and how your sales team operates. There's some sales teams that are responsible for their own leads, and then there's others that get all their leads from marketing. Or from BDRs. But lead scoring has gotten better and better over the years, and it can take into consideration things like, you know, the size of the company, the industry, any past contact that we've had with that company, you know, that a sales rep may not have time to figure out and then clue the salesperson in to that before they pick up the phone. So they have that information. could help you identify the right people to call within that company that if, you know, there's kind of countless ways it can work. But, you know, what you want to do is always have the best leads at the top of your list or help the sales reps have those best leads at the top of the list and tell them and tell them why, make it easier for them to understand why these are the best leads.

Right, right, right, right. So that leads into my kind of follow-on, which is How do you really leverage some of these predictive analytics in the sales ops just so we are being on top of the right set of prospects or we are doing the right things and all those kind of things?

Yeah, and I think this is like where I've seen the most improvement recently and it's really powerful. So, and it comes as no surprise that, you know, technology can uncover patterns much quicker than even the smartest humans can. It's kind of an understatement. But so these predictive tools are fantastic. Like we talked about lead scoring, but it can also be identifying upsell opportunities. Let's, for example, maybe I'm a great, I'm a sales rep who's really good at keeping good notes in the CRM. And every time I talk to a customer, I make sure that my contacts are inputted and I put in the opportunities. But maybe I'm not, you know, I don't have a head for data analytics and I'm not realizing, hey, this company orders from me every 4 months. All right. And I have a lot of customers and prospects and I don't go look at that account enough to say, oh wow, look, I see now it's every 4 months.

Yeah.

So that's the kind of thing that AI is gonna alert you to. And also, how about, oh, this company used to order every 4 months, And now they're not ordering anymore. So that's something maybe, you know, for customer retention that can help you. So it also can help a company even like a smaller company that doesn't have a lot of customers uncover additional prospects by taking a look at your customer base and then finding like companies that may be interested in your services. And then not only the company, But the people within that company that are similar to your, the contacts you typically sell to and what's their email address. And, you know, there's tools that go really deep and tell you, okay, here's the kind of person this is, their personality, things that help personalize your messaging. So it can get pretty detailed.

Right, right, right, right, right, right, right. That's amazing. So As a— when we look into the predictive analytics side of it, what do you think is the right time for teams to adopt these ones? Because sometimes, I know if there is a startup and then they have probably $3, $4, $5 mil as an ARR versus another big company, $100 million ARR, I'm sure I think the needs for these 2 companies might be different. But what is the kind of stage that you believe, David, that the company should start thinking about? Do I have the right data? Do I have the right tools to really think about this predictive analytics?

Yeah, you know, I think this is important for any company to at least look at as soon as possible because I think, you know, the ROI is gonna be there. It's gonna be certainly cheaper than, you know, a human resource like a data analyst or something like that and potentially more effective. Talked earlier about product-led growth, you know, that's prevalent with these companies. So a lot of times you can try these out for free or low cost to you know, validate whether it's gonna work or not and then expand the relationship from there. So, you know, like I said before, I think this is so powerful that if you're not using it and your competitors are, you're gonna be at a big disadvantage.

Gotcha. That's amazing. So as part of last question, I have so many things to go through, but in the interest of time, as part of the last question, David, what are some of the strategies that you think that we can adopt as a company, as a leader, to make sure that the teams are in line with what we are doing with AI and really increase the adoption within the sales ops teams? Yeah.

So I think, you know, involve the team early. Let them know this is coming. Don't just drop it on the day before you launch it. You know, get their input. It's really important that you clearly communicate to the sales team What's in it for them? You know, they're always gonna be just focusing on driving revenue. That's how their minds work, which is great. So make sure that they know how it's gonna help them. And then, like I said before, provide comprehensive training and, you know, try to show like quick wins, things that happen quickly. I'll give you a story. We were early adopters to electronic signature. And 2 things happened really quickly. First of all, our FedEx costs went, you know, down like 70% and our time to close from the time we sent the contract out to getting it signed went from days to minutes. Alright. So which stat do you think the salesperson is gonna be more interested in? The FedEx costs or the fact that the deals are closing? If you're the CEO, you care about both. But obviously, you wanna show exactly, you know, clearly show, hey, this is gonna make you a better salesperson. It's gonna make you more money and continually highlight the success stories that you have when, when you're gonna have some that, that are, that see the power of this and are early adopters and really focus on it and others who are gonna be afraid of it. And so when you get these initial wins, make sure you're sharing that with the team. So they see the power of it.

Yeah, no, absolutely. I think it's very powerful that you talked about including team early on in the adoption cycle because that's one of the things where the top-down approach versus the bottom-up, I think, you know, that's probably not a one-size-fits-all. And there has to be a hybrid way as to say, yes, you know, probably even if ideas come from, let's say, a CRO or VP of sales, the idea is to really bring the team into the adoption cycle and say, is this tool the right thing for us? I mean, how do you guys like it? And then really have their input so that, to your point, they need to be heard in terms of their feedback and everything. Otherwise, I mean, we can bring in the tools, but we can't force them to use the tools. And I think that's exactly going back to a lot of sales leaders talk about the CRM hygiene because at the end of the day, yes, you might have the greatest of the CRMs that is out there in the company, but if sales reps are not bringing in and inputting the right things over there, then there is nothing that even a tool can do. That's really where I think, David, I think your insights are super valuable as to say the biggest takeaway really is for the leaders out there, Identify the challenge that you are really trying to solve in the current process that you have. And for that specific one or 2 challenges that you have, again, really look into the available AI tools. Make sure that your team is part of the process when you are trying to identify. And there are so many ways that you can automate things, but really try to see what makes sense for your team, your challenges that you are going through. And sometimes probably just because somebody else is doing, don't try to just kind of, you know, adopt everything because that may not be the right challenge that the other company or whoever is trying to solve. So that's really been my takeaway from this. David, before we close out, any final thoughts really on the AI tools adoption and the sales ops?

You know, it's changing really rapidly and it's getting better every day. And, you know, I'm really excited about it. You know, anything that helps sales teams be more effective, close more deals is always gonna be great. So yeah, if anyone has any questions, feel free to reach out to me.

Yeah, absolutely. Sounds good. So David, what I'll do is I'll post this right after this call onto LinkedIn, YouTube and all the channels and I'm sure I'll also put in your website and contact information for people to reach out, and that would be great. Again, David, I know time is of essence, and thanks a lot for taking time and coming to the show, and really appreciate your time.

My pleasure, Suresh. Take care.