e2
Summary
In this episode of the Stronger Sales Teams podcast, Ben speaks with Taft Love, a Sales Operations Leader and Founder of Iceberg RevOps. Ben and Taft discuss the evolving world of B2B sales management, the role of AI in sales, and the transition from Founder-Led Sales to hiring external sales teams. Taft shares his insights on the traits of successful sales leaders, the importance of adaptability and intellectual curiosity, and the role of emotional intelligence in leading sales teams. He also emphasizes the significance of accurate and trustworthy data in sales operations.
About the Guest
Taft Love is a former Police Officer and Federal Investigator who has transitioned into a Sales Operations leader. He has built sales development operations teams for high-growth startups such as PandaDocs, SmartRecruiters, and Doxy. Taft is currently leading teams at Dropbox and also serves as an advisor and investor for various companies. He is the founder of Iceberg RevOps, a company that helps small startups transition from founder-led sales to having an in-house qualified operations team.
Key Takeaways:
● Adaptability and intellectual curiosity are key traits of successful Sales Leaders.
● Emotional intelligence plays a crucial role in leading sales teams effectively.
● Accurate and trustworthy data is essential for making informed sales decisions.
● AI has the potential to improve data accuracy and trustworthiness in sales operations.
Time Stamp
0:00 Intro
1:15 Guest Introduction
2:39 About the Guest
4:28 Terminology in Sales
6:31 Sales Enablement
7:57 Moving From Founder Led Sales
13:09 Future With A.I.
15:45 Use of A.I.
17:40 Data Accuracy vs. Data Trustworthiness
20:56 Traits of a Successful Sales Leader
22:24 Guest’s Learning Go-to’s
23:44 Guest’s Information
24:24 Outro
Rate, Review, & Follow
If you’re liking what you’re hearing, make sure you ‘follow’ the show wherever you listen to your podcasts…so you never miss an episode!
I’d also love to hear what you think, so drop us a review after you close that next deal…tell me what you’re liking, and what you want more of so I can look to cover it in a future episode.
Transcript
Intro
Hi, everyone. I'm Ben Wright, successful entrepreneur, corporate leader and expert sales coach to some of the most talented people our amazing planet has to offer. You're listening to the Stronger Sales Teams podcast, where we bring together and simplify the complex world of B2B sales management to help the millions of sales managers worldwide build, motivate, and keep together highly effective sales teams…teams who grow revenue and make their businesses actual profits.
Along the journey, we also provide great insights and actionable steps to managing your personal health. A happy and productive you is not only better for your teams, but everyone around you. So if you're an ambitious Sales Leader who wants to build the highest performing and engaged teams, Stronger Sales Teams is right where you need to be.
Ben Wright:
Welcome back to Stronger Sales Teams, the place where we provide real world and practical advice to help you develop superpowered B2B sales teams. So, today I have with me Taft Love and we've been speaking for about ten minutes beforehand and it's been great. Actually, I've learned a bit about Taft, but what we didn't speak about was that he previously was a Police Officer and Federal Investigator who's turned Sales Operations Leader. Right? So quite a cool change, right? He's gone from throwing down the law to trying to get people to follow his way, you know, gone from having lots of power to well, no power, right, as a salesperson or certainly a different type of power. But he's built sales… sales development operations team for lots of high growth startups Panda Docs, Smart Recruiters, Doxy, and those type of guys. So Taft has got a really great background outside of his police officer and investigator career. At the moment today, Taft's leading teams at DropBox. I think I've got that right, Taft. And he's also sitting on a board and advising a business that he actually founded called Iceberg RevOps, which we'll hear about in a minute. So that's all about serving high growth startups. But at the moment, if you say to Taff what's he spending his free time on? He's got a young one. We've actually got young ones, a similar age, and we were talking about sleep and no sleep and how they drive your day before. But he's also a pilot, he has a plane and he flies that on volunteer missions.
So firstly, Taft…thank you very much for taking some time today out of your for Australians, 42 odd degree Texas Day, and for Americans, 105 Fahrenheit Day. It's hot wherever you are at the moment. So tell us more before we get into it, tell us more about you, about Iceberg RevOps, about DropBox, anything you'd like to freestyle for a minute on?
Taft Love:
Yeah, absolutely. I think Iceberg is the crew that has me on podcasts, so I'll talk about them. They're a company I founded about five years ago. It started with just me. I was a Sales and Operations Leader and I helped do an implementation of outreach.io for a friend who is a VP of Sales and that led to other operations jobs for companies and that snowballed into a real business that now is doing a few million a year in revenue and we essentially help small companies go from founder selling to having an in-house qualified operations team which is much different than a Salesforce or HubSpot administrator. We bridge that gap for them, which is something that just crushes so many startups as they grow and we try to do it for about the price of the alternative which is a single Salesforce Administrator and we handle everything for them. So that's sort of the business that came out of this early consulting and now we're almost a year into having a CEO who I've brought on to run the day to day so I can focus on other things. But I'm very much active as an advisor and investor.
Ben Wright:
Great. I like it. It's that very tricky phase in a startup when you go from Founder-led sales into external sales. And that is super tough. And we might talk about that in a minute, but before we do so when I was going through RevOps site, rather RevOps term, doing a bit of research on Iceberg RevOps before getting together today and one thing that jumped out at me is just the terminology in sales just keeps changing or evolving is probably a better word. So things like sales enablement and revenue operations, lots of different terms that well, they certainly weren't around 20 years ago when I was starting selling. So can you tell me what are some of those words mean to you? And then I want to ask you about Founder- led sales, actually. But tell me, what do those words mean to you?
Taft Love:
Yeah, I think a good place to start is like what the heck is going on? So as you know, and everybody who's listening has probably heard this many times, the way people buy is changing. So the way we're selling is changing. It was not that long ago, if you remember the movie Glengarry Glen Ross. It was not that long ago that the scene I noticed was not any of the famous ones. It's when they come in with a handful of index cards and the guys want the Glengarry leads. And the takeaway from that is marketing gave a stack of leads to Sales and now Sales handles everything. And they're done. And Silos worked perfectly. And that was fine because marketing is a thin layer meant to capture interest and hand it off to Sales. And our world has completely changed. Sales lives along the whole funnel or if you like, winning by design, the bow tie that is the sort of lifecycle of a buyer. And so what has come from that is a bunch of new functions and terminology. So RevOps in my mind most of the time when people say it, they actually mean sales operations. There are plenty of companies that don't use it appropriately. In fact, we're Iceberg RevOps and we don't really do RevOps by my definition, we do a couple of pieces of Rev Ops. But a true RevOps org, in my mind, is a centralized function that owns the customer experience from start to finish. And that's a different way than most people think about it, but think about all the things that are behind the customer experience. It's how your salespeople talk to them, what systems your salespeople access in order to know what to say to the customer. It's your strategy team's data used to help decide how we're going to interact with customers in the future and what we're going to take to market. And so that's the frame I like to use today and I break it up into three; it's Systems, Strategy, Enablement. Those three things sort of roll up into RevOps, which should have a central leader that does not report into any of its client functions.
Ben Wright:
Yeah, I like to think of it as the part of the business that represents the customer…is how I look at RevOps. Yeah, cool. Okay, great. Fantastic. Sales Enablement, what does that mean to you?
Taft Love:
So, sales enablement is, I think of it as a function, that's job is to provide sellers the resources they need, and that means content, process, tools to be successful in their roles. So, true sales enablement function collaborates between all the revenue teams to enable the go to market program to interact with buyers and sell effectively. So who do you talk to? What do you say? How do you sell? Like that's Sales enablement.
Ben Wright:
Excellent. Okay, so thank you for clarifying that. We've been speaking about these terms and lots of other terms right, for quite a while, but sometimes it's nice just to take a step back and go, hey, what do they actually mean to you? So you mentioned in your introduction, and I latched onto it and so we'll talk about it now is around when does a business move from a heavy internal team focus around selling? And when I mean internal team, I mean founder led sales, if you're a startup or I mean businesses that are actually selling through people that traditionally perhaps wouldn't sell. Right. Moving from that in a business to a more of an external-led sales drive where you'll bring people in, right. So we move from that founder-led sales to a model where you hire in a Head of Sales or you hire in a gun for hire type of model. Right. So for you, when do you see that works really well? Or have you got some stories about when it hasn't worked really well? Because it is one of the most difficult decisions as a Founder and I've had to go through it absolutely one of the most difficult decisions around timing as to when you do it. So what's your experience with that? Tell us.
Taft Love:
Yeah, I think over the years I've worked with I'm probably coming on 100 companies that I worked with as Iceberg when that was just me and now as a bigger team. And first of all, there's no right answer here. There isn't much of a clear pattern in that before X revenue or Y milestone, you hire a sales team, you'll screw up. That's not necessarily the case. I think the things that companies should think about is what is in the Founder's tool belt. Are you pure engineer, all product, or do you have some sales experience? And regardless, you should do some selling, you should be the best salesperson in your company, period. And that may change later as you scale much bigger. But early on you need to know how to sell in order to run a sales program or even indirectly manage a sales program. And you also asked about things that haven't gone well. I see one mistake that happens over and over and over again, and this is startups. And I mean that term very broadly. Early companies, they don't have to be a tech startup, but this happens most often in VC funded tech startups that have lots of money and can make expensive mistakes. They tend to go hire someone who is managing a team that looks like the team they want to have in one or two or five years. And I see this over and over and over again and it's really hard to dissuade an early Founder from this path. But it's a little bit like saying, hey, you're a restaurant investor, go cook me a meal. They're two different things, they're different levels of the same function. And so what happens is we actually have a profile at Iceberg that we use to refer to these people, we call them Adrians and they are people who were five levels above how the sausage was made at a big company, think a Cisco, an Oracle, a GE or whatever. And they come down late in their career and join a startup and that's their victory lap. And they're going to teach these kids out of business and they don't know what they don't know. They don't even know how to start rolling their sleeves up. Decisions are made very, very differently at a small startup than at a big company. And over and over and over I see failure. I see analysis, paralysis, inability to do a lot of the basic functions that an early stage Sales Leader needs. And so you see this, we call it the $400,000 mistake because that's about what it's going to cost you a year to get qualified VP of Sales from a bigger company. And so it happens over and over and it's hard to avoid.
Ben Wright:
Yeah, I really like that Taft. I'd like to share at the moment. I'm going to share a story, actually. So when I had our most successful business we had, which people who listen now, it was amazing, the business we had, life changing, grew to be one of the fastest growing companies in Australia. We were actually finalists in Australian growth company awards two years in a row, got very close to winning the big prize. And one of my golden rules, one of my absolute golden rules was that any Sales Leader in our team had to sell. So there was no VP of Sales and you manage a team and you don't sell. It was you must sell. And I wasn't prepared to let go of the reins of a sales team, of our commercial sales team. We had 21 people in our sales team when we got to our largest point. I wasn't prepared to let go of that until I was convinced that any leaders we had in the business knew our business inside and out and were continuing to sell. And I always wondered if that was the right decision. Right, so we pause story there, we move ahead five years or so. So this is about five years ago and here I am starting my own business again, Stronger Sales Teams, right? Everyone who's listening knows what that is. And towards the end of last year, I'm still helping teams, but I hadn't been direct selling myself for about two years. It's the longest break I'd ever had from really direct selling. And the comment came out in a meeting, “Ben, you're irrelevant”. My first reaction was, how dare you? How dare you say that? Ego bruised. But then an hour later, I don't realize, okay, why have they said that? Why have they said I'm irrelevant? And I realized quickly that it was because I'd actually stopped selling. So I'd lost touch. And that word touch is the most important part, is the more senior you get in your career, it's important, it's fantastic, it's lovely and it's natural life, right? The best sales people will often move into great roles, great leadership roles, but they won't always. And for me, what resonates really strongly now with that decision that if you're going to sell in a team, if you're going to lead a team, you have to be selling, is that you have to have touch. And when you haven't carried the bag, when you haven't worn the rubber off your shoes for quite a while, that's when you end up losing touch. So for me, I absolutely fundamentally agree. If you're going to move from Founder-led sales to VPs or senior roles, the most important thing is that they are in there ready to roll their sleeves up. They're not going to teach business, they're going to learn and relearn business and build it themselves. So, yeah, absolutely agree with that.
So what we're also hearing now though is, hey, for salespeople, your sales enablement is getting easier or your sales process is getting easier or your engagement with customers is getting easier because AI will do it all for you. AI is the future, right? We're going to streamline everything and AI is going to kill customer relationship building period, right? What do you think about AI? And look like I'll flag this early.
I've been reading Tafts through his social media and there's lots of stuff in LinkedIn here. So I'm looking forward to what he's going to say here.
Taft Love:
So let me preface this with I can't tell the future. I'm not an expert on AI. This answer may not hold up five years from now, but I can tell you what I see right now, which is that AI, as far as I can tell, two things are true. One is just like RevOps, it's misused constantly. How many times have marketing companies co-opted the term AI to describe something that's just using a statistical model, just an algorithm? There are so many apps out there where they're said to be AI and they're really not. So first of all, that adds a bit of confusion. There's a little fog there because of that. And honestly, I think it has no meaningful impact today. And there are LLMs, there are some really interesting stuff happening. There are some ways that I think AI is having and will have a bigger impact. For example, somebody told me the other day, a buddy of mine has a small real estate startup and he's using GPT four chatbot to text people. And it's doing a good job of having conversations and informing people about what he's doing. That's a really cool use case. That's one isolated, interesting place. But outside of things like that, it feels a lot like a novelty that hasn't really found its place.
Ben Wright:
Okay, so that's interesting. So six months ago or nine months ago, when someone said I'm irrelevant, the I word that got used with me, one of the things that I did was I went out and went on a really heavy learning process, right? Or let's call it optimizing or tweaking of my skill. And one of the things I did do was spend a significant amount of time looking at technology. I'm going to call it technology rather than AI or machine learning or anything else. And for me, what was really evident was that we can use technology now to streamline the back of house. Absolutely no question. Salespeople. What technology is doing is allowing people to spend more time in front of customers. So if you're not using tech to reduce your workload at the back of house, then I think you're missing out. The other thing that I found, and call it AI, or call it modernization, again, I don't mind, is that for me, it was really helping me sharpen what I was saying. So if I had a topic that I wanted to talk through or something I wasn't certain about, I'd use AI to wordsmith that I'd use it almost as a sounding board to go back and forward. So it was like having a free colleague who wasn't quite as lateral in their thinking. Absolutely not. But they were able to provide me a different perspective, which I think from a sales point of view is really important. Right. Particularly when you're dealing with customers who are a complex selling cycle.
Okay, so I'm hearing from you. You're not sure where it's going to end up. Have you used it yourself for anything that's been successful yet?
Taft Love:
No, and I can tell you I've played around with it quite a bit. I've used some of the sort of available online mechanisms for playing with the OpenAI APIs. And I found it interesting, I found it cool. It has not yet risen to the level of something other than novelty for me. I also found places where it struggled when I thought it wouldn't, and I wouldn't yet trust it to take over for me, interacting with people, things like that. But what I'm looking forward to is seeing different ways outside of LLMs that AI is going to be deployed. So one of the first things I think that's going to be interesting is to see how some of the operations functions that look at data will be transformed by AI. I think that's probably the first place where it's going to start having a meaningful impact. You have companies like Clari who I don't actually know if they really leverage AI or not. They've used the term AI for years on their website and in all their marketing. Maybe it's AI, maybe it's not. I don't even know the actual definition. But my suspicion is a lot of these companies are leveraging just statistical models, not artificial intelligence. But once somebody builds a model that can tease human level insights out of large sets of data, that's when I think we're going to be using AI in a way that is meaningful, isn't a novelty or just a silly hack.
Ben Wright:
Yeah. Interesting you talk about the D word data or data, right. Depending on what your approach, your language approach is. For me, that's a real hot topic. And as I was reading up about you, one of the things that really struck me was you spoke about data accuracy versus data trustworthiness, which I think is pretty relevant in terms of AI. So what's your read on that? What's your read on perhaps AI? Let's start with AI and data accuracy and trustworthiness, and then we'll go from there.
Taft Love:
I guess it would be important to sort of talk about that distinction. So let's look at this through the frame of a report. Let's say a Salesforce report. You run a Salesforce report. That's a good straw man for data generally. So you run a Salesforce report. It is always accurate unless there's a bug in Salesforce and it's literally pulling in things or excluding things that you don't mean to exclude. It is accurate. Every search you do on a database is accurate. Now, trustworthy is a totally different concept. Trustworthy is, can I make good decisions based on what this data is telling me, or is it likely to mislead? So something I've told our clients over the years, and this is where the name Iceberg came from, is this concept of how there are levels of things that must be right in order for the report, the one thing above the surface to actually be trustworthy. Your report is not accurate if the filters, the actual way the report is set up is inaccurate.
If below that, the way you're capturing data is not an ideal mechanism for capturing data. Below that are people who are capturing that data, doing what you expect of them. And then below that is your enablement actually asking them to do the right thing. If any one of those things are broken, you do not have accurate data. Where I'm totally speculating here. I don't know, I might be an idiot, but I can imagine a future where, with access to sufficient outside data, AI could gut-check some of the things in your data set. Just random example here is what's stopping us from scanning data and looking for blank spots in data, so that an AI tool with access to Clearbit and zoom info and a bunch of other data sources could probably do a much better job than a human or a developer at finding ways to patch empty spots in data and make sure that your data is accurate or normalize industries across five different data sources because no two data sources have the same industry list and so it's an absolute Charlie Frank as they say in your system, when you have 100 different pick list values representing 30 industries. And I think there's a place for AI and data in terms of cleanliness and trustworthiness. And I imagine that there are much, much bigger ways it'll be used that I haven't even considered. But that's just an easy one off the top of my head.
Ben Wright:
Yeah, right. And for me, I think this is going to be one of the biggest challenges that we see coming out of the use of technology very broadly over the coming years, making sure your data is both accurate but trustworthy. And for me, I'm a huge proponent of very simple sales metrics, and you dive deep when you need to, right start, high start, really short, sharp, simple. In fact, I use three. With all the sales teams I work with, we use three and only three. And then from there, when one of those levers is off, we dive deep. Right. Because it builds a level of trustworthiness in your data when you're actually looking at the three things every time. Alright, so we're going to change just change our angle a little bit. It's a forming tradition here in the business, is we work a lot with Sales Leaders and a lot of Sales Leaders and Leaders in general actually listen to our podcast. You've been around a while. All right, you've founded businesses, you've worked with big businesses, you've worked for on consulting for big businesses. What are some of the traits you see in successful Sales Leaders? Can you give me two or three of the ones that you really commonly come across?
Taft Love:
Keeping in mind that most of my experience is small and mid-sized startups. I mean, even Dropbox, I would say is mid size company at this point. One is adaptability. The people who do not come in with the belief that the Playbook they've had success with in the past will continue to be successful. I mean, to put it your way, like, they are irrelevant if they're out of touch, if they're not adaptable. And another is intellectual curiosity. Lifelong learners tend to be the best. I think there's a tight relationship there between adaptability and willingness and the desire to constantly learn. Another one is high EQ.
Specifically a deep desire to understand what makes people tick, because so many of the skills can be learned relatively quickly but the ability to lead a team and a program and multiple teams I think is such an important piece of that success. There is knowing what levers to pull at a human level to get the potential out of someone because it matters. Even if you think of people as cogs in a machine, you're just wrong. Every person needs a unique approach.
Ben Wright:
Okay. Two really good things, adaptability and your levels of EQ. So when we talk about EQ, one of the key drivers in EQ is learning. Right. For me, the people that have high levels of EQ are constantly learning. This is the second tradition we try and ask guests is what are your personal learning go-tos? So, when you're trying to fill your cup, what are you looking to learn on?
Taft Love:
So, when it comes to learning, I've really been leaning into YouTube lately. I've found it a really helpful resource. I think it's just a mature enough platform that there's tons of great stuff on it. And as a visual learner, it's really helpful for me to see things. And then outside of that, the traditional stuff, books, blogs in our world in RevOps, there are few books that actually are particularly helpful once you get deep into it. So it's another reason that a non-traditional source like YouTube has been really helpful.
Ben Wright:
Yeah. Excellent. Okay. And certainly that is in line with the statistics and the learning programs that I see. We've actually just completed a really large market research project and what came out of that was that video learning is becoming more and more popular. So, yeah, great to see someone that's a Leader in their industry is actually using it too. Gives some validation to statistics. Right. They're all nothing until you see that, so excellent. Well, we've talked about some great stuff today and we've talked about technology and AI. And what does AI mean? Right? Is it real or is it not real? We've talked about sales founder-led sales versus bringing in the hired guns to lead sales teams. We've talked about successful Sales Leaders. Right? Some really great stuff. So thank you. I've actually really enjoyed it today. Not that I don't ever enjoy a podcast, but I've particularly enjoyed it today. So. Thank you, Taft. So for everyone out there, reminder you can find Taft, obviously through Iceberg RevOps. Where else can people get in touch with you if they'd like to hear more about you, Taft?
Taft Love:
Yeah, the best way to get in touch with me is through LinkedIn. And if you send me a LinkedIn request, just note the podcast. So I know you're not going to blind pitch me like the thousand other people who have reached out to me, but yeah, connect with me on LinkedIn and I'd love to chat with anybody out there who's interested.
Ben Wright:
Awesome. Fantastic. And if you do go to LinkedIn, make sure you check out what Taft sees as a gamble when you don't go to Vegas. But you do have to go through an airport, right? I'm going to let everyone jump on there and see if they can find it themselves. Fantastic. Excellent. Well, thank you very much for your time today and for everyone out there.
Until next time, keep living in a world of possibility and you'll be amazed by what you can achieve.
Thanks, everyone. Bye for now.
Outro:
Want to be kept up to date with any of our free materials to help you build the best sales teams possible? Well, the easiest way you can do so is to follow us on your favorite social media channel. We're @StrongerSalesTeams on most of them and if you DM us ‘Stronger’, we'll send you right back some great resources to help you build your superpowered sales team. If you'd like a little more help, please get in touch directly and book a free discovery call with me. I run a limited number of these sessions and they're free for my podcast listeners. I'd love to help you out. Until then, see you next week for another podcast of Stronger Sales Teams.
E31 What is Sales Enablement and Why All the Fuss with Taft Love
