2.4: How to Use Conversational Sales as a CDR, SDR, and AE (Tate Knapp)

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This is a podcast episode titled, 2.4: How to Use Conversational Sales as a CDR, SDR, and AE (Tate Knapp). The summary for this episode is: <p>The typical B2B sales cycle has <em>a lot</em> of conversations. Think about it: you have that first inbound (or outbound) conversation, the conversation that takes place once the meeting is booked, and all the conversations that happen between various stakeholders before the contract is signed.</p><p><br></p><p>Tate Knapp, one of Drift's account executives, is no stranger to any of these conversations. Tate has been at Drift for over four years, and in this time he's been a chat development representative (CDR), a sales development representative (SDR), and now he's an account executive (AE). </p><p><br></p><p>In this episode of Conversation Starters, Tate explains how Conversational Sales has helped him succeed in each of these roles. He shares his favorite first messages to send as a CDR, his favorite outreach method as an SDR, and the topics he makes sure to always cover in his first meeting with a new prospect.</p><p><br></p><p>Whether you're just starting out in your sales career, or you're well-tenured, Tate provides examples of how Conversational Sales fits into every part of the sales cycle.</p><p><br></p><p>Like this episode? We'd love it if you could leave us a ⭐️⭐️⭐️⭐️⭐️⭐️ review! And make sure to subscribe, so you never miss an opportunity to learn more about starting conversations in the Revenue Era.</p><p><br></p><p>You can connect with Sammi on Twitter @sammireinstein and @DriftPodcasts and Tate on LinkedIn.</p>

Sammy Reinstein: Hey, this is Sammy Reinstein, and you're listening to Conversation Starters. On this show, we talk all about bringing conversations back to B2B marketing and selling, because if there's one thing we know about doing business in the revenue era, it's that the best customer experience wins. Through the power of our own conversations with drifters, customers, and special guests, we'll learn how to deliver a sales and marketing experience that puts the buyer first. Let's get into it. Good morning, Elizabeth.

Elizabeth: Good morning, Sammy. Happy summer.

Sammy Reinstein: I'm so glad it's summer.

Elizabeth: I am too. I'm also hoping that anyone following along on the videos are watching us get progressively tanner, hopefully.

Sammy Reinstein: Tanner, and for me, blonder. Hopefully you're seeing that, because I was pale last season.

Elizabeth: Yeah. We both were. Yeah. Comment below if you're noticing if we're getting tanner or hair is getting blonder. Unrelated to any of that, yesterday I came into work and opened my Google calendar, as I do every day, and I had a meeting booked towards the end of the day that I hadn't accepted, but I just said Elizabeth and whoever. I was like, did I just forget that I set up like a meet and greet or something? I click on it and I'm like, no, I've never heard of this company. Whatever, so I just ignore it. Two hours later, so I've already received the invite, I then get an email that's like, hello, would you like to talk before our meeting to understand your pain points? We think how this podcast program could help solve problems. First of all, the product was nothing that I needed or would solve none of my problems. Two, I was like, you already sent the invite. Shouldn't you know my pain points before you go outreach like this? It was kind of creepy, because I was also like, how are you just putting time on my calendar? I know because they have the book the meeting link, but still.

Sammy Reinstein: That's crazy.

Elizabeth: I didn't respond and I ignored the invite, and then I got a follow- up email an hour after the meeting that was like, I see the time didn't work for you. Want to talk again? I was like, you've done nothing to earn my trust to warrant a meeting.

Sammy Reinstein: Wow. That is a bad sales experience.

Elizabeth: It was a very bad sales experience, and honestly, I think one of the worst I've experienced. Yeah. It just made me appreciate the mission of conversational sales so much more. Whenever things like that happen, I'm just like, I totally understand the selling pain points and why you should sell like you like to be sold to, which is not that way if you're trying to sell to me.

Sammy Reinstein: Yeah. Well, today we have someone coming on the podcast who knows a thing or two about conversational sales. Today I'm bringing on a close friend and fellow drifter, Tate Knapp. Tate has been a conversation development rep, CDR, a sales development rep, SDR, and an account executive at Drift. Needless to say, he knows a thing or two about creating a good sales experience, and you might have seen him on the sales certification or Conversational Sales Certification in Insider. If you haven't taken that certification, I recommend checking it out. We'll link it in the show notes. In this episode, Tate is going to share some of the sales tips he's learned along the way being a CDR, SDR, and AE, and he's going to share some of his favorite methods of outreach and how to continue a great conversation with a buyer. Enjoy. Tate, thank you so much for coming on Conversation Starters.

Tate Knapp: Hey, Sammy. I'm so happy to be here. Big, huge fan of the pod. I listen to it on my walks home from the gym sometimes. Would've been on my commute if we were still in the office, but I'm fully remote over here, but I'm so excited to talk to you today, Sammy. Thanks for having me.

Sammy Reinstein: I'm so excited to talk to you. I know. I used to listen to podcasts all the time on my commute, and now that I don't have a commute, I've been listening to it on a walk. I've been committing myself during the day to go on a walk and listen to a podcast, and it's been so helpful.

Tate Knapp: I love that.

Sammy Reinstein: Well, Tate, you're somewhat of a legend.

Tate Knapp: Where do we begin?

Sammy Reinstein: Where do we begin? At Drift, you've been at Drift for, what, like four or five years?

Tate Knapp: I just hit my four year last week.

Sammy Reinstein: Wow. In those four years, you have had many roles and you have gone through a lot of different types of sales roles, which I would love to hit on today. I think you specifically will have a really great outlook because you've been at one company doing different roles in sales, so you've really seen all parts of this process. I want to pick your brain today and learn a little bit more about the differences between those roles, what got you comfortable in those roles, and then the transition themselves. To jump in, can you just give a little bit of background of your time at Drift and what those roles were?

Tate Knapp: Yeah, absolutely. Thank you for the intro, by the way. I've been at Drift for four years and I've started my career at Drift. Started as an intern when I was in college and worked my way up the sales ladder throughout my trajectory here. My first role in sales at Drift was a CDR. I was the first CDR on the team, which was awesome to not only do it for the first time, but also help from an operations perspective. Then I transitioned over into the SDR team, started on the mid- market segment, and then moved up to the enterprise SDR segment, and then transitioned over into the account executive world on our growth segment back in September. Worked my way up the sales ladder, have used Drift in all those different settings and all those different day in the lives. It's all been very different in terms of how I leverage the platform, and I'm excited to talk about it today.

Sammy Reinstein: Yeah. You mentioned that you were the first CDR, which we call a chat development rep. What was the need there? Why did we start the chat development rep team?

Tate Knapp: Yeah, totally. For any business with a website that sees a decent amount of website traffic, who's using chat on their website, obviously whenever a visitor lands, they're going to engage with that bot and have that automated conversation. We identified an opportunity, in addition to having that automation on the website, maybe back that automation with a set of humans who can jump in for those more stale conversations after the visitor starts to fizzle out and try to pick them back up. We saw that as an opportunity to drive more conversations that we otherwise may have missed. It started with an experiment and it turned out to really prove strong results, and the team has been going for about three and a half years now and consistently contributing to our pipeline and revenue as a business.

Sammy Reinstein: That's so cool. You started as an experiment, you were the first one, and then you sort of graduated from CDR to SDR. What are the main differences between those roles of chat development rep and sales development rep?

Tate Knapp: Yeah. I'll start by saying that one way that the CDR role is so unique and the reason that I really like it is that it's a great way to drive pipeline for talent for the business. It's a great starting point for any young professional trying to get into sales, because you learn so much in that setting. It's a really fast way to get on the front lines, have strong conversations, interact with buyers in every segment in all different types of companies, and it really kind of gives you that framework and that those baseline skills that you need going into an SDR and into an AE position. The key difference is, as a CDR, again, chat development rep title that we created here at drift and that a lot of our clients have actually adopted and used in their own organizations, but the CDR role consists of a team who does prospecting and engages with prospects in all segments of our business only through live chat. The key outcome is to drive these conversations and ideally book qualified meetings for the appropriate salesperson, and of course, the majority of these conversations are not necessarily with hand raisers or folks who are ready to bite, but generally inbound folks who have some brand awareness and are actively on the website Now, of course, everybody listening probably understands what an SDR is. Of course, sales development rep, synonymous with business development rep. The idea there is to, in our organization specifically, our SDRs work with two account executives each. They own their entire book of business within a specific segment and they are delivering hyper- tailored and personalized cold outbound campaigns toward those target accounts and key buying personas. In terms of a measurement standpoint, the North Star Metric for our SDR team is to generate qualified sales opportunities and pipeline for the business.

Sammy Reinstein: Yeah. CDR is really about being super human, right? The bot will pass off something to a CDR or maybe a CDR will see that someone is looking for something in chat and they're like, hey, I'll jump in here and I'll get them what they need, or I know that this person is working with this person, so maybe I'll tag them in. It's like adding that element of the human relationship. Do you think that's important in a chat strategy? People have maybe bot only. What is your opinion on having bot only and then also the salesperson?

Tate Knapp: Yeah, it's a great question. I want to start by taking this back to basics and say that just the presence of any real time conversation on your website is a massive evolution of the way that we sell and market our brands. That's still an amazing inaudible. Just putting even a blank live chat on the website, or especially an automated bot with tailored conversations, or with a human behind those, all three of those strategies are incredibly important and can contribute to a lot of value because of the way that we as buyers like to engage with the business today and the way that we anticipate our buying experiences to go. Whether you just have a bot or there's a bot with human interaction, both of those are great strategies. The chat bot works so well because it is driving a dynamic experience across the website using these tailored conversations that are specific to each buyer's journey. Adding a human there is another way to do it and add even more real time engagement and to especially pick up those conversation with folks who maybe have dropped off a little bit or veered in a different direction or stopped engaging with the bot. Both work incredibly well. Adding humans is always a way to put a team behind it, begin with the bot and tee up those high opportunity conversations, but when you add a salesperson, it can take it to the next level.

Sammy Reinstein: Yeah. I'm sure you saw a lot of different types of conversations come through in chat, buyers at different stages of exploration and what they know about Drift, and then also people who are coming and we're a chat bot company, so maybe playing a little bit with the chat bot, but what was your favorite or best way to engage with a website visitor as a CDR?

Tate Knapp: Yeah. I think so many things go into driving a successful conversation. I think that the big headline here and what I hope that you take home with you, if you're ever in a scenario where you are using live chat to drive conversations at the top or middle or bottom of funnel even, the most important part is to tailor your approach to fit and to match that specific buyer's journey. That's what marketers care about, and this is a great way to pull that into the sales world. The reason that old school live chat, where it's just support and it's all reactive doesn't work is because it's so generic and it's like a static experience that's not different for each different visitor. The reason that conversation of marketing works so well is because they can be hyper personalized. Things that you're going to want to pay attention to are like, how did the visitor come to the website? What ad did they click on to come to the website? There's so much detail within a single advertisement. A certain product that it's advertising, or maybe it's an event, or it has specific messaging toward a specific persona. These things all matter because whatever that messaging was is what made that visitor click. What page are they looking at? What URL are they spending a lot of time on? How familiar are they with your product? Have they ever spoken to an account executive in the past? Have they used us in a past life? There's so many different factors that all contribute. If you can reference all those different data points, then that's going to be crucial and you're going to be able to really personalize the conversation. My favorite way to do it is just being hyper- tailored and really tweaking the way that I would speak to someone, almost like I would with a friend or a coworker. Everyone that you speak with as a salesperson, you should take a different technique and it's important to pay attention to all of those different attributes.

Sammy Reinstein: Yeah. I think that's a really important lesson no matter what role you are in sales, whether you're an SDR or you're a closing rep. Being timely and relevant is always going to make the buyer feel better and like you're personalizing to them and their needs, and everyone wants to feel special at the end of the day.

Tate Knapp: Yeah. Right. Exactly. There's so many times... the CDR role, it's a hard one. I always say that being a CDR and SDR is the hardest job you can have in sales, but there were so many awesome highlights to being in that position because buyers are just blown away by that type of interaction and it can feel good to make somebody's day or even just give them an answer to their question. Folks are usually pretty appreciative of that support.

Sammy Reinstein: Yeah. I'm sure it's a lot of nos or closed doors or whatever that may be, but when you get that yes or you get someone that's super appreciative of your outreach and the time you took, that must feel amazing.

Tate Knapp: 100%. Yeah. That's what I say a lot. In terms of the growing pains between the transition from being focused on chat as a CDR and then moving into the SDR role, there are so many more wins as a CDR. It's a little bit more inbound, folks on the website probably have a little bit more higher intent than someone that you're reaching out to or calling cold. There are less wins as an SDR, but they're a little bit more sweet because it takes a little bit more effort and you're really hunting them down from the tip top of the funnel. You're exactly right.

Sammy Reinstein: Yeah. That's an interesting point. When you were CDR, it was all inbound, right? Everyone was on the website and you were talking to them in chat. Then when you moved to an SDR, you were introducing a lot more outbound sales tactics into your day to day. What did that shift in responsibilities look like and what were those outbound tactics that you found yourself having to pick up and use in your day to day?

Tate Knapp: Yeah, definitely. You said it well. As a CDR, you are booking meetings and engaging with prospects through one channel, which is live chat. Once I got promoted to the SDR team, once one makes that transition, you're now going from juggling one channel to every single sales channel. Specific to Drift, we're using LinkedIn, we're using Drift Video, live chat still, email, cold calls, Zoom, and other different mediums, so learning the tech and learning best practices for a whole plethora of channels in addition to the one that you've already mastered is probably the biggest learning curve. I'll also say that the SDR role is a lot more strategic. You get the chance to work with an account executive. The whole point of the sales ladder, I think, is to equip reps and young talent with a new skillset whenever they get promoted to get them ready to become a closing account executive or a closing seller, so having that relationship with the AEs and owning a specific book of business allows you to learn how to prioritize accounts, analyze where high opportunities are and execute on that in a partnership with someone who's a little bit more tenured.

Sammy Reinstein: Yeah. We do have an episode coming out with Gabby and Amanda very soon, who is an SDR and an AE who worked together, and they talk about the relationship between the SDR and AE, but Tate, in your own opinion, what is important in that relationship? What are you making sure that you're communicating to your AE, and now that you are an AE, what do you feel is really important that's coming from an SDR?

Tate Knapp: Yeah. One of my favorite things to do with my AEs back when I was on the enterprise SDR team was do an account prioritization exercise with them. What we would do is leverage data from Drift and from other resources to identify within our book of outbound target accounts, who's heating up a little bit? Who's Googled a certain keyword that's specific to our product or who's visited the website? Then we would take it a step further and dig in and say, who are our key personas? Who do we really want to engage from this book? We would do this weekly and just set a big goal for ourselves of let's try to get two of these 10 accounts this week. We made a really strong, very tightly aligned game plan together. That worked so well for us. We were always aligned. We were always on the same page and it was really helpful to have that perspective of someone who had been a seller for a month longer than I had at the time and had so much experience, so that helped contribute to a lot of my success as an SDR.

Sammy Reinstein: Yeah. When you had that account that you were like, I want to break into this account so badly, they would be such a good fit for Drift, what was your preferred method of communication? What would you go to first in terms of your outreach?

Tate Knapp: Really good question. I can talk about video all day. We use Drift Video here, which is obviously a tool within the Drift platform specifically for sellers. It's a video prospecting solution where you can record videos of your face, your screen and your face, or just your screen and send them to prospects. Now, the best part about Drift Video, in my opinion, is that... I guess two things. When you paste it anywhere, when you paste that video, it unfurls with a gif preview of the video, so they're super attention grabbing. Then second favorite part is that when any of your prospects watch that video, the rep will actually get a notification in real time while they're watching it and you can click it and jump in and engage with them in real time. I would say that video contributed to probably 70% of my meetings as an outbound SDR. I put them in almost every single email campaign that I was sending. I was super nimble and jumping into all of those conversations whenever I got a notification, and it worked super well for me.

Sammy Reinstein: Do you have any video tips for someone that's maybe not used video in their outreach before? Is there anything that worked really well for you when you were sending videos?

Tate Knapp: Definitely. I could talk about video all day. There's totally different tactics to it. One of my favorite, something that keeps it so fun is that you can get so creative. I guess in terms of tips, the first time you ever record a video, it's going to take you a while. When I joined the SDR team and they told me that I was going to have to record prospecting videos, I was scared. My first time doing it, I think I did 30 takes just for one 60 second video, because it can be a little awkward listening to yourself talk and looking at yourself while you're talking. It took a lot of takes. After about a week of doing it, it's muscle memory now. I crank them out in one take and ship them right out. I would say that know that there is a learning curve. Trust the process. Reps and sets is the mindset. You will get better as you go. The reason that I think it's so fun and that it works so well is because you can always try something new. Our team is constantly experimenting with new video strategies. To name a couple, maybe you do a screen share over your target prospect's LinkedIn profile and you have your face in the corner and you have a big wave, and that's the gif that appears when you paste it in email. That's going to catch their attention, or maybe you'll screen share their website and walk through a preview demo experience of how your platform could work for their business. There are a lot of fun ways that you can do it. They almost always resonate because video still is a generally new channel for prospecting.

Sammy Reinstein: Yeah, it's so funny. I had an episode with Gong last season and we specifically talked about how hard it is to listen to yourself, like listen back to yourself. Especially with this podcast, I have such a hard time listening back and hearing myself and I'm like, Sammy, why did you say that? It's so important to go back and listen and learn, and hopefully you won't make those same mistakes twice. Like you said, after making a lot of videos and doing those reps and sets and putting that time in, now you're just a pro at making a video and sending it right out.

Tate Knapp: 100% agree with that, Sammy. That's why I say thank you to Gong for allowing the 1. 5X speed playback. It makes it a little less painful. It kind of ripped the Band- Aid off a little faster. That's my technique.

Sammy Reinstein: Tate, I want to talk now about your transition from SDR to AE. We have CDR to SDR, and even before that, which we could talk about in another podcast, you were actually a customer advocate too on the support team helping customers with all of those needs. Customer advocate to CDR, CDR to SDR, and now you are an account executive, which I'm sure is a very different set of responsibilities from those previous roles. What was it like getting into that AE position, and is there any piece of advice you can give to SDRs to help boost themselves into that AE position?

Tate Knapp: Absolutely. What I tell to... we have a great bridge program internally where we promote our top performing SDRs on a pretty frequent basis, and it's proven to be very successful in terms of quota attainment, right out of the gates, which has been so awesome to see. I talk to a lot of rising SDRs whenever they're going through that promotion bridge process. The best advice that I give them for that immediate transition is for your first three, four weeks, just pretend you're still in SDR. Just prospect as hard as you were when you were in SDR, because if you can build a solid pipeline before you're busy and swamped working a ton of active deals, you will be in an incredible spot right out of the gates. I think that my SDR background and my CDR background has been a huge asset for me in my career as an account executive, because I've learned how to prospect. Again, it's like one of the hardest parts of sales. I have taken those best practices that I built for myself and that I learned from my team while I was an SDR into the world of an AE. Of course, I have a lot less time to prospect in this role, but I continue executing on those principles and being creative with it. That helps build pipeline and puts you in a really good spot.

Sammy Reinstein: Yeah. Yeah. Our last season was about starting conversations and this season is all about continuing conversations, and it's sort of like your career has been in two seasons. Your first season of that was starting conversations with buyers. How can I engage them? How can I get them to book a meeting? Now this chapter of your career is really like, how do I continue that great work that is happening from the CDR, SDR perspective and now closing those deals? I'd love to hear a little bit more about continuing the conversation. Once that meeting is booked, what does that first meeting look like? How are you making sure that you're leveraging all of that great information in that first meeting that you're having with a buyer?

Tate Knapp: Yeah. Great point. This is a core principle of sales, and another reason why having that foundation in a top of funnel prospecting role is so important. Back when I was a CDR actually, my manager at the time, who had a sales background really ingrained in me, and I'm so grateful for this lesson, that the outcome of every conversation, of course we use the framework, engage, understand, recommend, the biggest outcome kind of falls into that understand part of the framework there, which is to identify the pain of the prospect. Whether this is a live chat conversation where you're going back and forth, or it's a cold call as an SDR, or it's a discovery call as an account executive. The biggest outcome is to identify the pain point, because you're not going to have a successful sales cycle and you can't sell something unless you're prescribing a solution that's going to solve some major pain point, some goal that's worth investing and solving for a specific buyer. I'll put it into a real life example here, because this actually was a little bit of a sales lesson for me recently. One of my good friends is actively apartment hunting in New York City, which for anyone who's ever apartment hunted in New York City knows that's potentially more complicated than a tech evaluation, but she lives in the city now. She's actually uptown. She's been here for about two years and great neighborhood, great apartment, but it's super far from where she works. We had been apartment hunting online, and of course I'm just helping. I'm on the sidelines. I just am an apartment hunting junkie and apparently can't get enough of real estate, so I'm just helping her out kind of going through the process. We're looking online, we're looking at the market, searching for different units. We reached a point where we were my friend was like, I don't know if it's worth it. It's so much work to move. It's such a headache. It's so expensive, whatever. A couple weeks later we go on a couple tours with her realtor and the realtor, I sat back in awe because I was just so impressed with her sales skills. She kind of held a discovery conversation when we were walking from one unit to another. My friend and I had kind of been feeling a little bit down. We were saying, it's too much work. Maybe we shouldn't, but the realtor helped put everything into perspective once she started digging for that pain point. Throughout that conversation, my friend was able to admit, living uptown, it's so far from my office, I've been late to work a couple times. I'm spending so much money on Uber. It's impacting my savings. All my friends are downtown. It's so much travel. There's all these negative consequences that came to the forefront not only for the realtor, but also for us, and the realtor used those pain points, those anecdotes from my friend and kind of attached them to every apartment that we looked at. It kind of put everything into perspective. Now, my friend hasn't made a decision yet, but 99% sure she's going to be moving downtown. From the realtor's perspective, incredible way of selling. Finding that pain point really gave the deal legs and reignited that need and that urgency for my friend to make that transition downtown. In a real world perspective, that's how it sounds. I was super scared of the word find pain when I first started in sales, because I was just a little bit confused by it, but it's so true. The most successful sales people are able to identify that challenge and use that challenge to recommend a solution that's going to solve it.

Sammy Reinstein: Yeah. That is such a good real life example of finding pain outside of the B2B space, and it's all true. Even if I'm going through and shopping or I'm looking for a car or whatever that is, when I'm going and looking for something, there is a pain or a need that I'm feeling. I can talk myself out of anything. I'm very good at that, so having someone there also talking me through what is the benefit, there's the pain and then there's the benefit, and then there's the recommendation. Having that advisor there, the realtor was acting as an advisor to your friend, and now they're probably going to go through and get that deal.

Tate Knapp: Yes. Selfishly, I'm excited a little bit.

Sammy Reinstein: Yeah. You get your friend closer to you too. I'm sure you were also...

Tate Knapp: Yeah. I was a big influence too, but that's a really good point. Being consultative is so important too. You need to be able to articulate as a seller what the positive outcomes are going to be from making the decision, and that will help you articulate your solution and why it matters and why it's so important. That's another big thing to learn. A big transition from being in SDR and moving into an account executive position, there's a lot more of a verbal component to it. Of course, you have the opportunity to make cold calls and you have those quick conversations on the phone, or you can record videos, which is a great way to practice your talk track, but building executive presence and learning how to public speak and have live verbal conversations is one of the biggest learning curves too. I think that our SDR team did a really great job of giving us public speaking opportunities throughout our tenure on that team to get us comfortable in front of a group, comfortable pitching a solution. I think that's something that's really important. It's a big learning curve for most reps when they get promoted, so I was really grateful for our team for giving us coaching and workshop and role play exercises as SDRs because it helps me a lot when I came into this seat.

Sammy Reinstein: Tate, thank you so much for coming on the podcast. Before I let you go, is there any other tips that you want to leave our listeners on engaging target accounts or just generally moving throughout these sales roles?

Tate Knapp: Yeah. For anyone who's in a prospecting seat now, once you become an account executive, you'll kind of realize, wow, every single negotiation and every single step in the sales process is just another prospecting conversation. You're always trying to maintain urgency, maintain momentum in the deal, maybe reengage with the prospect who's slowed down in their evaluation. It's all different outbound campaigns essentially, or inbound campaigns. It's all conversations that all have a CTA and an outcome. By mastering that skill in your position as a development representative is so critical because it's one of the most prominent elements of a closing sales position. I also think just throughout these conversations, my motto is always give, give, give value, value, value. Make all of your interactions as valuable and customer centric as possible. That's what's ultimately going to win you the deal or the meeting or the opportunity in the end.

Sammy Reinstein: Tate, if people want to connect with you, where can they do that?

Tate Knapp: Yeah. You can find me on LinkedIn. I believe the URL is \tateknapp, T-A- T- E K- N- A- P- P. Would love to connect with anybody. Any sellers who just want to chat and talk, feel free to send me a note and anyone who's interested in Drift, you can find me right there on LinkedIn or over email or through the podcast, but really appreciate you having me, Sammy. This was really fun.

Sammy Reinstein: Of course. Well, on a personal note, Tate, you're one of my favorite people to talk to about this stuff. You're just so knowledgeable in all parts of the sales process, so thank you so much for coming on the podcast.

Elizabeth: Obviously we made it very clear in the podcast episode that we love Tate. We may be a little biased there, but objectively, the man does know a lot about sales and had a lot of tips for every stage in the buying journey. I really hope our listeners got as much out of it as we hope you did, no matter where you are in your sales career.

Sammy Reinstein: We also mentioned a lot of resources in this episode, the Conversational Sales Certification, book of sales openers, and we will link all of those in the show notes so you can refer back to them.

Elizabeth: If you have any great selling tips you want to share with us, feel free to comment below.

Sammy Reinstein: Thanks so much for listening to Conversation Starters. If you liked this episode, please leave us a six star review by clicking the link in the show notes and hit subscribe so you never miss another one. You can connect with me on Twitter @ sammyreinstein, and follow all of our shows at Drift Podcasts.


The typical B2B sales cycle has a lot of conversations. Think about it: you have that first inbound (or outbound) conversation, the conversation that takes place once the meeting is booked, and all the conversations that happen between various stakeholders before the contract is signed.

Tate Knapp, one of Drift's account executives, is no stranger to any of these conversations. Tate has been at Drift for over four years, and in this time he's been a chat development representative (CDR), a sales development representative (SDR), and now he's an account executive (AE).

In this episode of Conversation Starters, Tate explains how Conversational Sales has helped him succeed in each of these roles. He shares his favorite first messages to send as a CDR, his favorite outreach method as an SDR, and the topics he makes sure to always cover in his first meeting with a new prospect.

Whether you're just starting out in your sales career, or you're well-tenured, Tate provides examples of how Conversational Sales fits into every part of the sales cycle.

The Highlights:

  • (5:25) Tate’s 4-year journey with Drift
  • (6:31) Why Drift created a chat development rep team
  • (7:36) The difference between a chat development rep and a sales development rep
  • (10:03) How to balance bot-only chat vs. looping in a sales person 
  • (11:54) Tate’s favorite way to engage a website visitor as a CDR
  • (15:45) The shift from inbound to outbound responsibilities Tate experiences as he moved from a CDR to an SDR
  • (17:23) The most important aspects of the SDR <> AE relationship
  • (18:44) Tate’s preferred method of outreach as an SDR
  • (19:59) Drift Video tips
  • (23:08) Tate’s experience transitioning from SDR to AE
  • (25:10) What Tate’s first meeting with a new account looks like
  • (31:10) Final sales tips from Tate

Learn more about Conversational Sales

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The Drift Book of Sales Openers

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