Making the Most of Every Opportunity with Tonni Bennett

[00:01:23] So what’s, um, let’s start with, you know, kind of tell me your story. How’d you get into how’d you get into sales? 

[00:01:30] Tonni: [00:01:30] Well, like a lot of people, it was an accident. I was pre-law set to go to law school, realized they had a lot of student debt and shouldn’t do that. A mentor of mine. I was a VP of sales at a division of UPS and encouraged me in that direction.

[00:01:46] Um, I didn’t know much about sales. I was really bad at it at first, but it was a job in a way to pay down some school debt. And over time I realized, especially as I got into a really interesting role at a startup. [00:02:00] How fun and interesting sales really could be and how much it’s about problem solving and helping versus pushing a, which was my previous perception.

[00:02:10] So, uh, sort of accidental, but, uh, started at UPS and got a great base there. 

[00:02:17] Brad: [00:02:17] So, so once you, what’s your, so what was your next position after, after UPS? Is that when you stepped into Terminus? 

[00:02:23] Tonni: [00:02:23] No, actually I had a short stint at a company called JobServe. I was moving to Atlanta right before I got married.

[00:02:32] Uh, it was a, a job board, um, online job board in, in Atlanta. Um, that was a bit of a stepping stone to getting a role at Pardot in sales. So when I joined the Pardot team, I think I was in the first 50 employees. They had just won best place to work in Atlanta. Uh, had a lot of momentum and kind of exciting buzz.

[00:02:54] Um, I joined as an AE and that’s really where I [00:03:00] fell in love with sales, the experience of working with people who were in their twenties, who all were really authentically themselves on the phone with their customers. And like we just talked about the UPS sale was. Kind of hard to wrap your mind around because I wasn’t selling a thing.

[00:03:16] And what really helped me to make some big strides forward in my, uh, sales acumen was having a software that tangibility of it really helped me to sink my teeth into. How to sell something and really perfecting the art of a discovery to understand, needs to point to features, to show in a demo. Uh, so you know, when the business, and so that role was really crucial to me discovering how much.

[00:03:46] I enjoyed the sales profession, um, and just kind of helped me take things to the next level and build more. 

[00:03:54] Brad: [00:03:54] So when you were, so Pardot is interesting you because you’re in Atlanta, we’re in Indianapolis, [00:04:00] Exact Target ends up. Buying part out and then gets purchased by Salesforce. Um, just real quick.

[00:04:06] Can you tell us about that, that story? Cause I know that it was, uh, a wild ride that David had started part, uh, you guys were, were scaling up. Um, could you just sort of take us back a little bit? 

[00:04:21] Tonni: [00:04:21] You know, part how it was such an incredible, uh, utopia. Everybody got along and were friends and the benefits and perks, uh, it was such a neat place.

[00:04:34] And I didn’t realize part of the reason that. Part I, uh, the part that founders could treat us to all of these things was because they had mostly bootstrapped the company off of another business. David had, had given him some runway. And so, um, it was a really special place. And the technology, you know, I joined right as marketing automation was starting to take off.

[00:04:55] So it was a really cool time to be there. Um, when we got acquired, I [00:05:00] had never been through that. So I was pretty nervous. And the experience was actually really wonderful, Exact Target leadership. As virtually everyone I’ve met from Indianapolis, they were just really nice kind people. The business was very people focused similar to how part of that was.

[00:05:17] And so there was a really good matchup of cultures. Um, they kind of let us operate as a separate business unit. And so we still had things running almost as they had been, but with some extra firepower, extra budget for marketing and a bunch of sales reps on the Exact Target side now passing us leads.

[00:05:37] So, um, that, that integration was actually pretty successful. And I imagine a big reason why they acquired. Uh, acquired Pardot was to be acquired by Salesforce. So in the second one, second acquisition happened, that’s where everything started to change. The Salesforce culture was quite different and structure was quite different than what we had experienced.

[00:06:00] [00:05:59] And so that changed things quite a bit. Um, After that acquisition. 

[00:06:04] Brad: [00:06:04] Yeah. So I did. So this is exciting. I didn’t realize that you were one of the first 50 employees at Pardot, um, which, you know, like, as I mentioned, it’s interesting to hear kind of your, your perspective. Um, well, what’s fascinating about this conversation.

[00:06:19] I think, you know, one kind of how you guys positioned yourself in the market, but to sort of knowing where that you, that you moved into Terminus then eventually at Twilio, is that you have these really kind of three different. Um, business experiences and they’re all different. And I think they all probably teach you something specific that you’ve learned at each stage.

[00:06:42] So I’d love to sort of learn to, to understand, you know, Hey, once you transitioned from Pardot, what was the next step? And then what’d you feel like you learned there? And then on where you’re at today. 

[00:06:54] Tonni: [00:06:54] Once the Salesforce acquisition was complete and we went through the process of really [00:07:00] changing things over at the time I was young and stubborn and I loved, um, a lot of the benefits I had gotten and the, really the flexibility and freedom of working for a startup.

[00:07:11] So I followed a previous manager who still remains a mentor of mine to People Matter. Um, unfortunately didn’t stay there along, came back home to Atlanta and worked for SalesLoft. Uh, Kyle Porter. They used to share an office with us that part-time. So I knew him pretty well. Uh, reached out, told them I might be interested in leaving People Matter.

[00:07:34] He said, Hey, if you want a spot at SalesLoft, come on over. So I was one of the first eight sale sellers at SalesLoft. 

[00:07:42] Brad: [00:07:42] So is this pre, this is pre email then, right? Are they still selling the data tool? 

[00:07:47] Tonni: [00:07:47] Yes, they were still selling the data to at the time actually, we had just released, we had just launched cadence and we’re just starting to sell it at the time we had one or two sellers just focused on that product.

[00:08:00] [00:07:59] And by the time I left, we were all starting to sell it. Um, I was really happy there. They continue to do really well. I’ve been really excited, uh, to continue to follow a SalesLoft. Um, I had planned to stay was happy there, but the opportunity to build the sales team at Terminus came along. And so it was something I couldn’t pass up.

[00:08:20] Um, so then at Terminus was when I joined as the Director of Sales, myself, and one other sales person sold the first million dollars for Terminus until I was able to build out a team. Step out of the player coach role, uh, and just, you know, focus on building that team, uh, moved into the VP of Sales role and help scale the business to 20 million in recurring revenue.

[00:08:43] Brad: [00:08:43] You feel like you learned, so you’ve made this transition from salesperson to, um, VP or player to coach. Uh, what was the hardest thing about making the transition from player to coach? And what’s the one thing that you feel like you learned in that scenario? 

[00:08:58] Tonni: [00:08:58] It’s it’s a totally [00:09:00] different role. It’s a totally different job.

[00:09:02] So it’s definitely a big transition. Um, I think the biggest learning early on part of what motivated me early on, I’ve always been kind of a builder and like to figure things out. Uh, I got really excited about the opportunity of building a team. And then as you start to grow that team, you realize the importance of the actual team.

[00:09:23] It’s not about you or how much you are excited to build and tinker it’s about. Um, finding a way to attract great people, keep them motivated and happy. All the dynamics of managing people and personalities and having to have hard conversations and disappointing conversations, uh, looking somebody in the eye and telling them that something’s not working.

[00:09:49] Um, there’s a lot about that. That was a. Uh, led to a lot of good learnings. 

[00:09:57] Brad: [00:09:57] Moving from the [00:10:00] player role to the coaching role. Um, obviously. There’s some really big transitions. You got to have hard conversations. Not that you’re not having hard conversations with clients, but you’re having it with people that you work with on it on a day-to-day basis.

[00:10:14] And you’re trying to build a, you’re trying to build a growing software company with all its complexities.

[00:10:19] Tonni: [00:10:19] I mean, it was just going to say one of the biggest things that I definitely learned very quickly in that role and yeah. Um, have, have tried and will always take with me is, um, sometimes you want to avoid having an uncomfortable conversation or let something slide.

[00:10:37] But inevitably it gets worse when you do that. It is far better to address something early, make sure you’ve, you know, let it sit for a little while, have done your homework, have clear data points. Uh, you don’t want to be quick to criticize without. Really understanding, but making sure that you are being direct and honest and giving people the chance to explain or to [00:11:00] talk through their perspective on it, uh, doing that stuff early and really staying in touch with people, even when it’s uncomfortable.

[00:11:07] I think that was a really important skill to learn. And I say skill because it can be learned by anyone, but even when you learn it, it’s something that you can not exercise well. So it’s like a discipline. You have to continually exert.  

[00:11:21] Brad: [00:11:21] Well, I think there’s something, you know, when you, as you’re saying that, I’m thinking the word, you know, you’re keeping the dignity of your sales reps and team and how important that is to building a good culture, um, having the tough conversations, but, but, but allowing there to be good, healthy interaction that, so you’re not tearing, not tearing people down.

[00:11:43] Tonni: [00:11:43] Absolutely. 

[00:11:44] Brad: [00:11:44] Um, okay, so you’re, so you have the, you moved from player to coach. Um, you guys have crazy, crazy revenue growth, and then you make a pretty big transition. Right? 

[00:11:58] Tonni: [00:11:58] Well, I had my daughter who [00:12:00] just recently turned two, so I had my daughter, I was out on maternity leave, uh, right about the point where we hit that 20 million mark in about four years.

[00:12:11] And. Ended up taking a step back and doing some consulting for awhile. So after my daughter, I didn’t go back to Terminus. I did some consulting with mostly local companies, but I also worked a little bit with Scaled, which is a great, um, consulting group led by Jake Dunlap, uh, who was really good on LinkedIn.

[00:12:33] If you’re looking for any support on the sales side and, um, So I did some work with him. I did some work on my own. I was debating whether or not I wanted to start my own business doing that sort of thing full time and spend a year just trying to figure out, um, how to make sense, this crazy experience I had just had.

[00:12:55] I had been running, I had really been sprinting for four years. That’s one thing about a startup that’s [00:13:00] tough is every day is an important day. Um, I would get out of bed every morning, feeling like if I didn’t bring my a game today, it would impact the team. It could impact the business. So there was a constant level of stress of this X million dollar number is on my head and I am the one responsible for getting there.

[00:13:17] Right. Um, there was, and that’s exciting and motivating, but it was just a sprint. And so. Taking some time to step back, really think about what parts of that experience were invigorating and exciting. What parts have become draining and exhausting, and then figuring out who am I as a mother and what does that mean for my life moving forward and for my work-life moving forward, um, it was.

[00:13:44] Really a time to reflect while continuing to learn. So I got to work with some really incredible companies and really great startups in Atlanta. Um, learn about different businesses in sales motions, work through some pretty complex problems. Uh, I [00:14:00] enjoyed that very much, but ultimately decided that, um, I don’t like to be my own boss.

[00:14:06] I like working for entrepreneurs. I don’t want to be an entrepreneur. And so I started trying to figure out where my new home would be. I talked to about 50 different companies throughout that year, and there are lots of interesting opportunities, but nothing really felt right. And when I started talking to Twilio, I really thought the company was going to be too big.

[00:14:30] And I, my role, my title was VP. Um, I knew the title wouldn’t be the same. And so I really had to do some self-reflecting to figure out what do I really like and enjoy what do I want to do and how much do things like title even matter. And ultimately what I decided was the things that I really loved about the startup world is getting to build, uh, getting to build a team and work with people and help them get better at their craft.

[00:14:58] Um, [00:15:00] this role at Twilio had. To help, uh, grow this new market segment. So we were just spinning off a mid-market segment and I would be joining to manage the East coast and build up the team. Uh, so it had the building of a startup, but without as much of the early stage stress and pressure, and to work under really tenured and experienced leadership, the VP that I roll up under.

[00:15:26] Spending 13 years at Salesforce and some time at companies before has so much wisdom. I’ve learned so much from him already. And so it was just, you know, I think if I had gone straight from Terminus to something new, I don’t know that I would have been open to this role, but in again, really reflecting on strengths areas where I wanted to grow more and what I really wanted in a job, it actually ended up being a really good fit.

[00:15:54] Brad: [00:15:54] Um, so, so the one thing that sort of strikes me is the, you know, a [00:16:00] lot of people that we sell to, particularly on the sales side, I know the titles are important and you took a step down, you know, from, from title or this could be perceived that way, but you seem to have found yourself in a place that you’re really happy.

[00:16:16] Tonni: [00:16:16] Yeah look, it’s not even comparable, right? A VP again, my, my boss who’s a VP has like, you know, 25 plus years of experience building and scaling sales orders. Uh, the comparison isn’t the same. And so I very quickly was able to get over that. What’s more important is, is the role challenging, is it satisfying?

[00:16:39] Am I learning something new? Um, am I in a business where there’s incredible growth potential? Twilio to me was such a big company. And now that I’m in it, it’s so funny. Our CEO constantly says we’re still at day one. There’s so much in store for Twilio. And so to think about that, like Twilio still sees itself as a startup and still sees itself [00:17:00] as, you know, a young, early stage company.

[00:17:02] And so. Uh, it’s still again, has those elements of early stage and building and figuring it out. Uh, and so I don’t think title matters whatsoever. And the other thing I’d say in some ways, my scope has reduced. But I wouldn’t say the level of responsibility has reduced. I mean, I’m still responsible for pretty much about as much revenue as I was at Terminus.

[00:17:25] And there was a lot of freedom within this role to really be entrepreneurial with my region, with my part of the business. Yes. And so, um, yeah, it’s, it’s really exciting. 

[00:17:38] Brad: [00:17:38] So, this is a fascinating conversation and I’m gonna, I’m going to go back to something you said early, early on, um, you talked about moving from a solution sale to a software sale.

[00:17:50] So as you move from UPS and then into your, into your role at part on that, you finally had something that you could point to. Can you talk a little bit about [00:18:00] the difference. Um, from the about selling as a service or maybe a complex product that has lots of, uh, different avenues versus selling a software.

[00:18:12] Tonni: [00:18:12] Absolutely. So stepping into Twilio for anyone who doesn’t know, I mean, Twilio has a suite of communications or what we call now, customer engagement, API APIs. So, um, If you ever called or texted your Uber or Lyft driver, if you’ve ever changed your flight with Delta, you’ve used Twilio. Um, we power some incredible brands and do some really powerful things, but a lot of people don’t really understand all the things that Twilio can do.

[00:18:39] Um, we don’t have a tangible out of the box solution and early in my career, that was really hard to wrap my brain around at ups. Having that tangible software. For a number of years, uh, really helps for things to click. So now I could go back and do something like this and look, the sale is, is very [00:19:00] different.

[00:19:00] And Twilio in particular, we have a very unique, uh, selling motion or business doesn’t really work like other businesses. There’s a lot of things that make it unique, including the fact that customers can just come and use Twilio and don’t have to speak to a salesperson. There’s no gate to just using the product and moving forward without any support. So there’s a number of things that make our sale complex, but to your point, yeah. Without having something to demo. I can’t rely on a demo to get you interested or excited. I really have to understand what are you trying to build? Why is it important to your business?

[00:19:34] What outcome are you trying to drive with this? Oh, by the way, what are you planning to do in the next five years? And could Twilio power any of that as well? Could we be. A strong long-term partner to power multiple parts of your business. Um, so the conversation is a lot more of a business conversation about what someone’s trying to achieve and linking use cases and then products to it.

[00:19:58] Now, sometimes of course, we’ll [00:20:00] start with the developer has already midway through building a project. We may start off more tactical, um, just build trust when some early business. But then usually we’re trying to see who else in the business, what else might you be working on that we could partner with you on?

[00:20:15] So it’s, I don’t know if I really answered your question, but it is a very different type of sale.  

[00:20:20] Brad: [00:20:20] Now transitioning a little bit, I know in kind of getting into, you know, the, the adversity piece of the podcast here. This has been a tough year, I think for everybody, um, even companies that have had a lot of growth, um, have still had to handle the curve ball.

[00:20:38] Um, what’s that been like for you, you and your team at Twillio. And then what are some of the tips that you would want to highlight, um, to other people who were kind of in the middle of this. 

[00:20:51] Tonni: [00:20:51] Well, first at Twilio is really fortunate and to be in a great position as our CEO, Jeff says all the time we were made for a time like [00:21:00] this, not that we’re in any way, happy that this craziness has happened this year, but Twilio enables digital or remote experiences.

[00:21:08] So we can power you to drive deeper customer engagement. Through digital channels, even when you’re remote. So Twilio as a whole, we’ve certainly have had certain industries that have decreased spend, but we’ve had a lot of new tele-health and, uh, just virtual use cases pop up. Twilio is doing really well as a business, I would say in mid-market and in my region, in the Southeast, that one of the challenges that we face is.

[00:21:40] A lot of the bread and butter of Twilio customers have been the Uber, the Lyft, Airbnb and Twilio works with a lot of non-traditional companies too. But our region is a little greener. We’re doing a lot of work to figure out how do we sell to logistics and, uh, insurance companies in the [00:22:00] Southeast who aren’t as used to building out their own solutions.

[00:22:04] And so it has been a challenging. A year for my team to really sink our teeth into a greener territory and figure out what parts of what Taleo has done really well today apply. And where do we need to adjust a little bit to make sure that we are being relevant to our audience here? Um, how do we best leverage partners to help support that?

[00:22:28] And so I think our team has had our. Had her own challenges. 

[00:22:34] Brad: [00:22:34] So talk to me a little bit, so, so I’m curious on something that you sort of skipped over a few times, and now we’re talking about, um, kind of green areas or new opportunities. Talk to me a little bit about the lead generation process when you don’t have a product, because I think generally services are difficult to sell when you can, when you can say, yeah, we do that.

[00:22:55] We do that. We do that. It’s hard to get somebody focused. [00:23:00] On, as it pertains to the lead generation. Right. So you think about the historic lead generation SDRs. Um, you worked at sales off your, a Terminus, so you’re obviously going after a group of clientele with a kind of predetermined problem that you think they have, and you’re presenting a solution what you’re selling today.

[00:23:18] And particularly as you introduce services, Um, it’s not like that. So you have any, just talk about that whole process, because there’s a huge, if you’re listening and you’re selling software or you’re thinking about selling services or you’ve done either, they’re different. So can you talk about the differences and how you generate leads or think about generating leads in a service-based business?

[00:23:37] Tonni: [00:23:37] Totally different. Um, at Terminus, we are mostly an outbound shop. We had like two SDRs to one AE at a period of time. We are the total opposite business model. So, I mean, Trulio went public with maybe five salespeople. The model was inbound. The company was growing like crazy, just from developers, understanding the vision of controlling their own [00:24:00] roadmap, being able to build what they wanted, how they wanted.

[00:24:04] Uh, not being dependent on out of the box software. And so we had a lot of people coming to us and we still do, um, now that we are growing our sales or we are of course pushing more outbound and it is very tricky. I wouldn’t say we have a fully repeatable model because to your point. Because everything at Twilio has to be built, depends on what requirements are there needs to be.

[00:24:32] If not a project, at least an initiative that we can hook onto. So maybe a business has a digital transformation initiative or are tasked with reducing or increasing efficiency, I should say, in their contact center. There has to be something active that they are willing to spend budget on in order to engage with Twilio, which makes it really tricky to reach outbound to people.

[00:24:55] And there going to be a little bit of luck in again, do they have something ongoing that we can [00:25:00] attach ourselves to? So the outbound motion is first off, really trying to identify accounts that have a lot of potential because Twilio has so many solutions. Uh, the more potential use cases we could think about a company having, the more opportunities I have, if I can get them on the phone to figure out a way we could work with them.

[00:25:21] So we’re, we’re trying to identify companies that have a lot of potential with Twilio, and then it’s. Trying to hit on a theme, we think would be relevant, especially vertical base. So if you’re in healthcare, you’re probably thinking about deepening patient experience at a time when I can’t actually get together with my patients as much, bring them into an office in person.

[00:25:42] So how do I simultaneously do more digitally while deepening customer relationships, uh, doing so efficiently where I don’t need to double my contact center. And so those are the types of. Things that might get, um, someone’s attention in healthcare to speak with us. And then the [00:26:00] use case could be telehealth.

[00:26:01] It could be some sort of patient engagement platform. It could be a number of other things. So we have to hit on bigger picture themes and business challenges that we believe a company might be thinking about.

[00:26:17] Brad: [00:26:17] Okay. So I didn’t mention it at the beginning of the show, but I had brought Tonni on because she had had a significant impact in a, in a former guest Morgan Ingram, who you, who you may know, he had to stay at Terminus. He’s a, a talking head and somebody that you would know in the sales space. Tonni had a very big impact on him while she was his. VP of Sales. And so I wanted to have her on the show. I’d heard her talk on Jim Brown’s, um, podcast on Sales Tuners. I was really impressed with, with her, with her story. Um, and the thing that sorta hopped out at me, as she’s talking about [00:27:00] this, this transition, it was kind of this unsaid. The thing that she didn’t say is what popped out is that she had built she’s really built her career.

[00:27:09] On these really strong relationships and these relationships have moved her from one position to another, and then she talked about what she didn’t talk about, but it was pretty obvious that, that she had built some really strong alliances that have impacted where she had been and where she is, and most likely where she’s going.

[00:27:29] But she also talked about, um, opportunities and, and seeing how those opportunities like really. Seeing them for what they are as they come in. Sometimes you have to step back to go forward and you have to think differently about the opportunities in front of you. And I think that’s the one thing that I heard in her story is as opportunities have come her way, she’s been able to really reflect, you know, have some self-awareness around what she’s really good [00:28:00] at.

[00:28:00] And since she has that type of self-awareness, she’s able to really look at an opportunity for what it is and what it could be. And I think that’s the one thing that I got out of this, uh, interview this afternoon is if you know yourself well, then you can look at opportunities for what they really are and what they could be versus what you think they might be.

[00:28:19] And so that was a great, it was a great show, great podcast. I’m so grateful that she was on this afternoon. And I think you guys are going to love it and enjoy it. And as always, if you want to get more of these great stories and great content and great takeaways go to monsterconnect.com/podcast.

[00:28:37] You can download the content. You can also like us and give us a five-star review on Apple Podcasts. And until next time don’t let what you can’t do interfere with what you can. [00:29:00]