Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162

1. 0:00 – 0:52

   Intro

   1. AKAshley Kelly0:00

      I would say you wanna look for anyone that has about six months of experience. Does not have to be in sales development. My favorite hires that I've ever made are people that actually come from recruiting. They're super organized. On an inbound side, if you found someone that's ever worked in a call center, again, that's, that's another really good profile. I actually am very bullish on sales development. I think it's the third pillar within the go-to-market function, and I think that it can stand alone. The SDR is kind of the bridge between marketing and sales.

   2. HSHarry Stebbings0:26

      Ready to go? Ashley, I am so excited for this. So first, thank you so much for joining me today.

   3. AKAshley Kelly0:45

      Yeah. Thank you for having me. Um, I've been following along for, for a little while now, and just feel very honored to be on, uh, the 20 Sales Podcast.

2. 0:52 – 1:52

   Journey into Sales

   1. AKAshley Kelly0:52

   2. HSHarry Stebbings0:52

      That is very, very kind of you. I, I always love to start with kind of Ashley, the love of sales. I think it's often a moment. When did you realize that you loved sales and that this was what you wanted to do as a career and for life?

   3. AKAshley Kelly1:03

      I actually started my career working for NASCAR, which is probably, um, a topic for, for a whole nother day. But, uh, world of sales, I started as an SDR at Zenefits. Um, I, very truth be told, I did not know what an SDR was. I thought I was going to be doing demos, uh, in person with, with customers. I was clearly very wrong about that. Um, but I, I ended up falling in love with the top of funnel. Um, SDR to me is just such a special, um, role that is, you know, both pipeline building but also career development at the same time. And so I stayed on the side of, of the sales funnel, and, uh, within three years of Zenefits, I left as a director. And then, uh, since then, I've built out sales development orgs at different tech companies out of the Bay Area, so, um, Lever, Brex, and now Ripley. So, I guess you could say I'm a lifer for, for sales

3. 1:52 – 3:39

   The Role of SDRs in Sales

   1. AKAshley Kelly1:52

      development.

   2. HSHarry Stebbings1:53

      SDRs, traditionally is thought of as like, uh, respectfully, a grind and fricking hard. Career development? Like, talk to me about that element.

   3. AKAshley Kelly2:02

      I would say the top AEs and best leaders that I've ever worked with have started their, their careers as sales development reps. So, we do a lot of, uh, I've always done this at all the, uh, all the companies I've been at, um, but we do a lot of promotion from within. So we promote, uh, SDRs into the account executive role, um, account management, um, into implementation. In fact, if you look at my org today, about a third of my SDR managers have actually come from the SDR role internally. So it's definitely a, uh, you know, career trajectory for, um, for salespeople.

   4. HSHarry Stebbings2:33

      I love that. So when we look at the incredible different companies that you've worked at and all that you know now, what do you know now that you're like, "You know what? It'd be really helpful if Ashley had known that going into the first Zenefits SDR role"?

   5. AKAshley Kelly2:47

      What I know now is that sales is very unpredictable. Um, it can really test your patience, um, and your sanity. (laughs) And so staying even keeled is really important. Um, and so what I think I learned was just focusing on the things that I can control day in and day out, and really two of those things are, are, are attitude and effort. And I think too frequently do people allow noise and, um, excuses to, to funnel in, um, into whether they're, you know, whether they're an individual contributor or a sales leader or anything. But, you know, if you're gonna be working for a startup that moves quickly, like, you have to be able to, um, pivot, to cha- and be adaptable to change. Um, and all of that really does come down to the things that you can control, which is your attitude and effort. And like, to me, those are what I've learned over the years as like the recipes of success.

   6. HSHarry Stebbings3:32

      So funny. On, I think SDRs and I, I think fundraising is the same, which is like, you've gotta go from rejection to rejection with no loss

4. 3:39 – 5:09

   Cold Calling in Sales

   1. HSHarry Stebbings3:39

      of enthusiasm.

   2. AKAshley Kelly3:40

      Exactly.

   3. HSHarry Stebbings3:40

      You mentioned cold call. I just wanna go straight to it. I mean, is cold calling still a thing? Like, is outbound still a thing in this way? Like, really? Are we not past that, Ashley?

   4. AKAshley Kelly3:48

      Oh my God, that's, it's like a trigger, it's a trigger for me. I, I think you know that. Outbound is definitely still a thing. I have, uh, over 200 of them that would, uh, definitely prove otherwise, uh, or, or prove, or prove what I'm saying, um, accurate. And so, I think outbound is definitely changing. Um, but everything in sales is always changing, right? And I think if you're still doing the same thing that you were six months ago, you're not going to be successful. So, to say that like outbound or SDR is dead is like a little dramatic.

   5. HSHarry Stebbings4:18

      How is outbound changing?

   6. AKAshley Kelly4:20

      I don't really wanna age myself, but when I first started doing outbound in, in sales, I've been, used a phone book, right? Uh, it, there's always different evolutions of, of outbounding. Then we moved into having, um, email automation. Like, I didn't have that when I was doing outbound, uh, sales, and that's just been the last few years. And then video prospecting became the, the next cool thing to do with outbounding. And now we have AI. And so I think there's, um, always going to be evolutions within outbound, but at the end of the, end of the day, like, to me, the most important thing to remember is that there's no silver bullet. And I think where companies make a lot of these mistakes is that they get excited about the, the new shiny object, and they kind of follow it like sheep, and then they put all their eggs in one basket. And, uh, that's wh- when outbound and SDR starts to fail, is they, they take their eye off of the fundamentals of what makes it succ- successful to begin

5. 5:09 – 6:19

   Outbound: AI and the Infinite Spam Dilemma

   1. AKAshley Kelly5:09

      with.

   2. HSHarry Stebbings5:09

      The thing I worry about, I, like, I actually like outbound, and I think it's a craft when done really well. Um, the challenge that I have is like, with AI and a lot of the tooling that will allow for outbounding at scale infinitely, I worry that we'll have just much less appreciation for it, because you'll be able to send millions of emails, and the supply will be infinite. And so everyone will be like, "Ugh, block, block, block and too much noise."

   3. AKAshley Kelly5:34

      I agree with that. I think I've, I've probably been one of the sales leaders that's been the most hesitant to adopt to AI. I do think where it will help SDRs though is eliminate a bunch of the busy tasks. And so like, the hardest part about being an SDR is, um, the, the, the little details that you have to pay attention to all day every day, and that could be...... cleaning and scrubbing your accounts, making sure you have the right contacts, the right phone numbers to make those cold calls effective, the right emails so that you have deliverability. And so I think AI can actually help just make that easier and, and free up more of an SDR's time to where they can focus on more personalization and LinkedIn connects and all the different channels, um, that really require a human outside of AI. So I think there's a lot of leveraging that can happen there.

6. 6:19 – 12:45

   Should SDRs Roll into Marketing or Sales?

   1. AKAshley Kelly6:19

   2. HSHarry Stebbings6:19

      I'm interested, when we think about like SDR accountability or where it sits, should SDRs roll into marketing or should they roll into sales do we think?

   3. AKAshley Kelly6:30

      I have my, my honest answer, but I'll give you two of those, two other ones first because I think there is different schools of thoughts on this. And really, it really could be either. I've actually done both. So I've been in orgs that have reported to marketing, um, currently in one that reports into sales. They have different use cases, so I think, um, if you're a heavy inbound org for SDR, um, there's a lot more science to it. Um, and being really tightly aligned with the team that's driving the funnel, um, is where you have, um, that feedback loop that is so important. And so when you think about an inbound funnel, um, you're thinking about what we call leads we call MQLs, right, that are coming through and then having to convert those into an SQL, which is essentially a demo set for, for an AE. And like the, like I said, the feedback loop for the quality and the volume of those leads is so important. And I think, um, if, if again, if you have a big inbound org reporting to marketing, that makes it so much easier to do. Um, now if you have a big outbound org, there's more of like an art to sales development at that point. You have to be a lot more proactive in the way that you're engaging cold accounts, um, you need to be able to educate them on a product they probably have no idea even exists or pain points that they don't even know that they have. Um, so it's, it's much more of a sales motion, um, and so I, I think that's where it's more successful rolling into sales. And as I mentioned, um, we do a lot of promotion from within. So sales development reps want to be account executives, and so if they're already in the sales org, it makes it that much easier for, for them to learn from AEs, um, and to really, like, progress in- into their sales career.

   4. HSHarry Stebbings8:04

      Can I just ask Ms. Kelley, uh, I feel like I'm a student raising my hand here.

   5. AKAshley Kelly8:08

      (laughs)

   6. HSHarry Stebbings8:09

      Uh, (laughs) uh, but you mentioned there about kind of when it's a heavy inbound model and actually that MQL to SQL, should they not be, like, a pretty good hit? Like, if there's a big difference between MQLs and SQLs, aren't the MQLs not doing their job very well?

   7. AKAshley Kelly8:22

      It's a fair point. Um, I would say it's the different types of MQLs and where they convert. So you have, like, your high intent ones, which are a demo request or someone that's clicking contact us, like, yes, that, that should have a higher hit rate. Um, but if it's lower intent, like they've just downloaded content, they might not actually be, like, ready to be in a buying motion or to be speaking to a, to a, uh, a salesperson. So we do see different conversion rates across different types of MQLs, but that's why it's important to be tied very closely to your marketing team so you can talk through those. So it's like, how do we actually get more demo requests coming through our funnel than people just clicking on a white paper?

   8. HSHarry Stebbings8:55

      Okay, so heavy inbound model, we're like, "Mm, SDRs can sit under marketing." And then a outbound model, they sit under sales?

   9. AKAshley Kelly9:03

      Yeah, but then my real answer is, um, neither. I think, uh, I actually am very bullish on sales development, if you can't tell, and, uh, I think it's the third pillar within the go-to-market function and I think that it can stand alone. And so, um, while I report into our CRO, uh, at Rippling, like, the relationship that we have is really SDR is kinda the bridge between marketing and sales, and so all of inbound and outbound sits underneath, um, underneath my org. But we are, we work very tightly with marketing to run ABM campaigns and just strategic, um, outreach for our, our tier, you know, one and tier two accounts, and then same thing partnering with sales, making sure, are we targeting the right accounts that you can actually close that are gonna be, going to become revenue and not just fit our top of funnel model. So, um, that's my bullish answer is that I think, uh, it'll be the third pillar.

   10. HSHarry Stebbings9:53

       How does that sit in structures then? Like, I think people like to think of, like, org structures with different functions. Like, when we say it's a different pillar, like, how does that actually look and how should we actually think about it- that as founders building businesses?

   11. AKAshley Kelly10:06

       Probably depends on the scope of your, of your CRO. Um, and so for us that, that's how it works is I report into the CRO. Marketing does not report into the CRO, so I guess you could technically say that, like, it is still within sales. But I think it's really how you define the relationship internally of how those three teams actually partner and go to market, um, as opposed to I think a lot of companies view SDR as, as more like order takers, um, and I think it's super important to give SDR orgs like the autonomy and the, um, ability to, to, to really, um, build their own strategy and execution.

   12. HSHarry Stebbings10:40

       Do you think AEs should be responsible for their own needs as well, or do you think they can solely rely on SDRs given how good you are, Ashley?

   13. AKAshley Kelly10:47

       (laughs) I've only seen AEs prospect successfully a handful of times, it's always the top AEs. So I think, um, I think it should always be an option, absolutely. Um, I think if you can drive the right volume and the right quality of pipeline to an AE, an AEs time is better used closing and not prospecting.

   14. HSHarry Stebbings11:06

       Which company that you've worked at was best in SDR?

   15. AKAshley Kelly11:10

       Rippling, we're talking about now, of course. (laughs) Um, no seriously, the, um, well a lot of the reason I came to Rippling was because of how, um, how incredible the inbound org was and what marketing had built, and then, uh, the ability to come in and help build and scale outbound, um, on, on this side. And now bridging those two together, I truly feel like we have, you know, one of the best SDR orgs in the world. Uh, the volume that we're able to crank out while also supporting, um, not just new logo sales but we also dive into, uh, product, we also are in, uh, the customer base helping with cross, cross-sell and up-sell, and then you add all of our different regions internationally, um, and different segments too, it's probably the most complex SDR org, um, I've ever, I've ever led. We support about 31 different functions across the business.

   16. HSHarry Stebbings11:57

       This is so confusing. You do cross-sell and up-sell? Like, this is, like, verging on account management meets customer success. Like, how do we think... Like-... are, are we not just crossing a load of functions now?

   17. AKAshley Kelly12:08

       Well, I mean, it depends on and where you, again, think where an AE or AM's time is best suited. And so when you have SDR resources that are able to go into, into the database and be able to find the customers that w- we are able to cross-sell. I mean, we have so many different products, um, we have the luxury of being able to do that. Um, and it works from, you know, a CAC paybacks perspective and so, uh, aga- it's very unique but it is, uh, you know, we're a 350 person SDR org, so we- we, uh, we're, we're an army. (laughs)

   18. HSHarry Stebbings12:37

       Th- 350?

   19. AKAshley Kelly12:38

       Yeah, between leaders and SDRs, yeah.

   20. HSHarry Stebbings12:41

       Fuck.

   21. AKAshley Kelly12:42

       (laughs)

   22. HSHarry Stebbings12:42

       Wow. Well done. Uh, uh, that really is an army.

7. 12:45 – 29:24

   SDR Hiring: Who, What, When & How

   1. HSHarry Stebbings12:45

   2. AKAshley Kelly12:45

      (laughs)

   3. HSHarry Stebbings12:45

      Um, I do wanna get to, like, hiring these people now. We mentioned a little bit beforehand in terms of your hiring in Dublin, and you mentioned that it's like 350. How many have you hired in your time, Ashley?

   4. AKAshley Kelly12:54

      800 SDRs, I think, in the last decade probably, across all d- all different companies. Yeah, I'd say Zenefits was the big one with, that we did about 250, and then now, uh, Rippling obviously with, uh, ab- about 350. And 200 of those have been just within the last year. So we've been on a hiring tear, I would say. And that's, again, across all different regions, you know, types of things. It's not just-

   5. HSHarry Stebbings13:17

      Mm-hmm.

   6. AKAshley Kelly13:17

      ... your traditional inbound/outbound, so.

   7. HSHarry Stebbings13:19

      Okay, let's start. What-

   8. AKAshley Kelly13:21

      (laughs)

   9. HSHarry Stebbings13:21

      ... in terms of s-

   10. AKAshley Kelly13:21

       I don't sleep. (laughs)

   11. HSHarry Stebbings13:23

       In terms of ... When's the right time to hire your first SDR? If you have a founder coming to you, should they hire, like, a, a, an SDR first or should they hire a head of sales first who can bring with them SDRs?

   12. AKAshley Kelly13:34

       I would probably hire a, like, junior AE, someone that has done the prospecting but also knows how, how to close, and someone that can be, um, in the weeds and helping build out the process and scale. I'll give an example. When I, um... Well actually, I think I'm a bad example for it 'cause... So this is, like, the opposite. When I was at, when I was hired at Brex, I came in at the director level. But I would not suggest doing that for your first hire because you need someone that is going to be able to create the sequences, do the cold calls themselves. And I did all that stuff, I was willing to do that, but you gotta find the right person (laughs) that's going to, you know, have that title but's also willing to do the grind that you said that it is. And then once that you can start proving out that it works, um, and you get a little bit of traction, that's when you can start hiring some, some additional SDRs. And those SDRs can, can have less experience, but I do think your first hire should be someone, um, like, not fresh outta college and definitely not their first SDR role. And I think that's, um, another w- another e- place where, where companies fail is they think that they can just plug someone in and they're gonna go know what to do, and it's, i- i- it's a lot, it's actually a little bit more complicated th- than that.

   13. HSHarry Stebbings14:41

       Should the founder always be the one to build out the first sales playbook?

   14. AKAshley Kelly14:44

       Yeah. And if not the founder, um, someone that, uh, is either high up in marketing or in sales if you ha- like, I guess it depends on how big the company is, but, uh, in my mind, a founder should always be the, the main seller, um, definitely the main storyteller, right? And that's how you create the content that you need to build your sales playbook is what is the vision, like, what are we solving here and what are we building and being able to translate that into something that works for prospects.

   15. HSHarry Stebbings15:10

       So you're an angel in my hypothetical company.

   16. AKAshley Kelly15:12

       (laughs)

   17. HSHarry Stebbings15:12

       And I'm like, "Great, we need to hire SDRs, okay?" I have no idea how to hire SDRs. I, I, I... This, this is not a hypothetical situation when I say I've never hired an SDR. So, uh, how do I structure the hiring process for an SDR? And what would you advise me as granular and as specific as possible? 'Cause I don't know.

   18. AKAshley Kelly15:33

       I would, from a profile standpoint, I would start there. Again, this depends on, like, the state of your org, how much, like, enablement or manager support you have. But typically, I would say you wanna look for anyone that has about six months of experience, does not have to be in sales development. My favorite, um, hires that I've ever made are people that actually come from recruiting that wanna make the transition into tech sales. And a lot of that is because they're super organized, they're making calls all day to people who are probably not in the market, just like a prospect is not in the market, right? And they're having to sell. Now, they're selling something different but they have that rhythm. And, and that's super important. I'd say, um, on an inbound side, if you found someone that's ever worked in a call center, again, that's, that's another, um, really good profile. I'd say the hardest part about SDR is the, is the cold calling and there tends to be a lot of resistance with that. It's much easier to hide behind sending emails, right? And so if you find people that have already built their confidence and found their voice over the phone, like, you've, you've, you've launched miles ahead of, like, the first hurdles that you're gonna run into when it comes to skills, um, for an SDR.

   19. HSHarry Stebbings16:41

       Okay. So interview process. What questions do I ask in this process to understand whether you're a potentially good candidate?

   20. AKAshley Kelly16:50

       So this is an interesting one because when you're interviewing salespeople, you can actually ask, like, "What was your quota attainment? What's the biggest deal that you've ever sold?" Right? Like, there's ex- like, you ask for, um, experience and it's, like, the complete opposite for sales development because you're, um, having to interview for traits and skills that are intangibles almost, right? Or stuff that they've learned in school or just having grown up and, and life experiences. But, um, I usually bucket them into, into three different categories, so the first being coachability, um, and ability to navigate change. So do they take feedback well? So, you know, are they, um, when their, when their manager is, is critiquing them, like, uh, do they appreciate that, do they have, like, a growth mindset, right? So the, the coachability-

   21. HSHarry Stebbings17:32

       How, how, how do you know that in an interview? 'Cause everyone says they're coachable.

   22. AKAshley Kelly17:36

       Um, so the navigate change and coachability, like, I've, I've, um, specifically had a question that said, "Tell me a time that you, that you failed at something and that you were given feedback, and how did you react to that and how did you implement that feedback?" So asking, like, some very straightforward tough questions and, and expecting them to give examples, and, and sometimes the examples are silly, right? It's like, um, my teacher got mad at me because I didn't turn in my assignment at the right time or something. But as long as they can think on their feet and not be afraid to show that they have failed before, because I think that's the big thing is, like, it's okay to fail, you're going to fail in sales, like, absolutely, especially in your first one. So, you know, like, "Give me an example of when that's happened and, and when you were coached and how you, how you, um-"... implemented that feedback.

   23. HSHarry Stebbings18:17

       Okay, so coachability and implementation of feedback, one.

   24. AKAshley Kelly18:20

       And then the next one I would say is, um, like motivation factors, so what, what gets them up in the morning every day.

   25. HSHarry Stebbings18:27

       What do you find is a good answer to that? Because I ask this of founders, and I don't find it leads to much substance. What, what d- what should we look for?

   26. AKAshley Kelly18:36

       I like two answers, one being money motivated, (laughs) which means like they're, like basically they'll, you know, I don't wanna say do anything to be successful, but like failure really isn't an option for them. Um, and then the other would be, which this was my answer as I was always interviewing, is I wanted to be a VP of sales development. Um, so I wanted the growth and I wanted the title and the recognition, and that is something that always motivated me. And so, um, I think it's just interesting to hear how people answer. Part of that is you can ask, like, "Why sales?" And I'll tell you the worst answer you can get is when someone tells you, "Well, because my dad or my mom was in sales and they think I'd be good at it." And I'm like, "Oh, God," like, you have no idea what you were signing up for, so, like, you have to really want it. And so I think there's, like, you know, some triggers. And again, after hiring 800 people, like, I, you kinda figure it out very quickly who, um, who has the grit within them that can, um, actually be successful in this type of role. And then the last thing would be organization skills. I can't tell you, like, how many different tools and tabs and things that an SDR has to click through all day every day, and if they let things slip through, through the cracks, um, that's... I mean, every minute matters, so the more that you can be organized, uh, you'll, you'll be more successful.

   27. HSHarry Stebbings19:49

       Again, how do I tell in an interview? I'm terribly unorganized. I have an EA, thank God, otherwise I wouldn't be a- anything. Uh, but I would tell you that I'm very organized.

   28. AKAshley Kelly19:59

       I mean, I ask how, and one of the answers I expect is like, "They live and die by their calendar," right? And again, a lot of these people could be coming out of, um, out of school or i- in a type of role that relies on organization, but answering like, you know, "I have, I have calendar blocks." That's a big thing for SDRs to be successful is they'll block off their calendar for different times that are dedicated to, to calls, dedicated to scrubbing their accounts, dedicated to personalizing emails. And so if someone is very type A in the sense that they are, you know, live and die by their calendar, they're, they're more likely to be successful.

   29. HSHarry Stebbings20:30

       Do people admit to being money motivated?

   30. AKAshley Kelly20:33

       Yeah, of course. We're in sales. (laughs)
8. 29:24 – 33:07

   Onboarding New SDR Hires

   1. AKAshley Kelly29:24

      too.

   2. HSHarry Stebbings29:24

      Has the way that you hire SDRs changed over time? You've mentioned hiring 800. When you think about the early days of hiring SDRs compared to now, how has it changed?

   3. AKAshley Kelly29:34

      It's funny you say that, because pre-COVID I probably never would have hired a, uh, an SDR that had SDR experience. I would have preferred to hire people fresh out of school, um, that we could, you know, really, like, mold and grow into the role. My fear back then, not anymore, but my fear back then was that SDRs, I would have to break a lot of their habits and then, you know, reteach them our ways at, at, at our company and our process. Um, also, there's, was always the thought of, well, if you've been a SDR, you know, for a year and you haven't gotten promoted yet, one, why? Two, are you gonna be willing to sign up to be a SDR for another year at our company, 'cause again, it's a grind. Um, but that was kind of a red flag back pre-COVID. Now, we have so many different tech layoffs that are happening left and right, there's... One of the first orgs to go typically is SDR. And so, there's a lot of good talent that's out there that has, has had previous experience that just kind of got the short end of the stick d- going, going through these RIFs. And so, um, it has changed quite a bit that now we hire more people that are coming from the SDR role, um, because there's more talent out there that's available.

   4. HSHarry Stebbings30:36

      People always say, "Mm, if you're part of the RIF-"... you aren't one of the good ones. Is that fair?

   5. AKAshley Kelly30:42

      Well, it's 'cause pre-COVID I would have said that, yeah. But now it's like, I've, I've hired these people, I've seen them do a great job. I think you probably have to just really trust your gut and trust your interview process, um, do some back channeling if you can. I think, you know, a lot of these companies we see top A- AEs and leaders that have been cut too, and there's kind of, you know, you can start to know people's reputation and get feedback from people on, on whether people were good or not.

   6. HSHarry Stebbings31:06

      What are the biggest hiring mistakes that you've made when it comes to hiring SDRs?

   7. AKAshley Kelly31:11

      This is really bad, um, when, uh, we were- when I was at Cenefits, I was a new manager. I think I had 35 reps reporting to me, which is already a- a terrible thing that was happening. Um, but we had huge hiring goals, and I remember we hired people off of just 30-minute phone screens, and that was it. So, it was a true, like, just needed to get butts in seats as fast as possible, and clearly, like, the, the takeaway was like, "Oh my gosh," like, didn't spend enough time on the quality of interviews, um, making sure we had the right talent that was coming through, and really, like, the buy-in from the candidate too is they're probably like, "Really? I just got a job off a 30-minute phone screen?" Um, a- and so, it was a h- that was probably my biggest m- mistake across the board.

   8. HSHarry Stebbings31:57

      (laughs) That is a-

   9. AKAshley Kelly31:59

      I know. I feel like I'm in therapy now telling you this (laughs) .

   10. HSHarry Stebbings32:02

       ... I wanna move to, like, the onboarding side now. So we've got these amazing SDRs. As you mentioned, they- you said you often quite liked them at a school. How on earth do we onboard SDRs effectively, Ashlee?

   11. AKAshley Kelly32:16

       One thing that's very unique, I think, to the way I've always built teams is I have my reps on the phone by week two. So, you've got, yeah, working their books and on the phone by work- by week two. So kind of learning a lot of, like, trial and error, uh, maybe it's 'cause that's, like, my style of how I like to learn. I'm also very cognizant that not everyone learns the same way, but what I've found over, over the years, like, I think the old, like, Yelp model is they kept them with like a different team for a month or so, and then they would finally join the floor, they're not producing until month three, and boom, boom. And so, when I just look at my cohorts of when we're hiring people, it's like, "How do I just get them, um, producing sooner?" And a lot of that was like, "Let's give them their books sooner." And so, when they're learning how to scrub accounts and identify the right contacts and use the different systems and tools to put them in sequences, they need their actual accounts to be able to do that.

9. 33:07 – 45:10

   Effective Onboarding Strategies for SDRs

   1. AKAshley Kelly33:07

   2. HSHarry Stebbings33:07

      So I was like, week one then, what are we doing in week one to make them ready for week two calls?

   3. AKAshley Kelly33:13

      So, week one is, um, like, company onboarding, uh, heavy focus on, like, our product, focused on, um, our competitors, things like that. Week two is more about how to do the SDR job, so, here are the different systems and tools that we use, which is, like, Sales Navigator, ZoomInfo, all that fun stuff. We use Outreach, which is, um, the email sequencing tool, and so teaching them how to actually do that, and then towards the end of the week is when we give them their books and they can actually start doing the job. Now, I don't expect them to do the job at full scale (laughs) in, you know, week two or week three. But we give them ramping goals. So, um, they're on a ramping quota as well, so it actually takes them until month four to be on full ramp. But every month leading up to that, they do have some sort of quota so that they learn that muscle, that they, like, build their pipeline, and so it's kind of like, uh, compounding baby steps.

   4. HSHarry Stebbings34:05

      When you say some sort of quota, does that mean they should be closing dollars in month one?

   5. AKAshley Kelly34:10

      No, no. They don't... No, so they won't be closing deals at all. So month one, uh, they're on... Well, we just changed this, hold on. So like a full month's quota if they're fully ramped is eight S2s a month. So on month one, it's like, two, and then the next month it's four, the next month it's six, and then they're on eight. So it builds up to that.

   6. HSHarry Stebbings34:28

      How do you think about good numbers to set? This sounds awful. Forgive me for it. Uh, you're like, "Four? That's one a week." Like, that's an awful lot of time for one S2. Like, how do you... (laughs)

   7. AKAshley Kelly34:45

      So, you're not wrong, you're not wrong. Trust me. Par- Parker, my CEO, says the exact same thing to me, "You're not wrong." But no, the reality of outbound is that it takes time for these things to compound and to start actually yielding results. So, when you start sending- when you start working an account or a contact, on average it takes about two weeks for a sequence to start actually being effective. And so you're not really getting responses until, you know, what I just said, they, they don't even start working them till their second week. Third week, they're putting them in sequence typically. It takes two more weeks for them to start getting like the real responses and start building that, and they're not even doing it at full capacity yet. So, it takes time for this to, like, compound. So that- that's- that's the main- the main reason why. But, um, to answer your question more specifically from like a data and science, uh, standpoint is that we look very heavily at our account S1 conversion rate and account S2 conversion rate, and we look at that monthly.

   8. HSHarry Stebbings35:35

      Well, I'm- I'm so sorry. Account S1 is what and account S2 is what?

   9. AKAshley Kelly35:39

      So the mi-

   10. HSHarry Stebbings35:40

       I feel like I'm like, James Bond.

   11. AKAshley Kelly35:42

       So if I give you, let's say, 100 accounts, right? And you are working, let's call it, 10 a day, I wanna look at, when you start working those 10 accounts, how long does it take for one of those to become a stage one opportunity and a demo? And- and what is the conversion of that cohort? Because that's how we know where- where to set a lot of our targets for S2s is because we know how much we can convert these accounts into opportunities.

   12. HSHarry Stebbings36:07

       I got you. Okay.

   13. AKAshley Kelly36:08

       There's a science and a method behind the madness, I promise.

   14. HSHarry Stebbings36:11

       How- how does the targets differ on ACV? And what I mean by that is, like, if we're doing, like, I don't know, PLG, kind of PLG but with expansion, uh, but it's like small ACVs coming in, 5 to 20K ACVs versus big 100K ACVs.... does that differ our expectations on stages and what should qualify?

   15. AKAshley Kelly36:34

       It doesn't change stages of what would qualify. It would change quotas that we would set for people. So the lower the ACV, the higher number of S2s you actually need to be producing, right, because it has to make sense from a CAC payback perspective. And so we do a lot of work. I mean, this is what my rev ops team focuses on all day, every day. And we make sure that the production of the SDRs is per rep production and they are hitting the number of S2s that they need to because it has to make sense, uh, in the finance model. And so we look at, um, not only number of opportunities that are being, uh, assigned to the, to each AE but, uh, win rates, ACVs, and then to your point, any sort of, like, product, um, attach rates that could be, like, uh, in addition to those, which actually alway- obviously helps the CAC.

   16. HSHarry Stebbings37:20

       This is so much fun. So okay-

   17. AKAshley Kelly37:21

       (laughs)

   18. HSHarry Stebbings37:21

       ... so fully ramped... Uh, no, it really is great. Fully ramped, so with, like, four months? Is that when we expect to be totally productive?

   19. AKAshley Kelly37:29

       Yeah. And we see some people sooner, absolutely, but, like, four months is, like... From a m- modeling perspective, like, that's what we expect is four months.

   20. HSHarry Stebbings37:36

       How quickly do you know if you've made a mis-hire?

   21. AKAshley Kelly37:39

       Month two.

   22. HSHarry Stebbings37:41

       Month two?

   23. AKAshley Kelly37:41

       Month two. And it's, it's not even usually based off of the S2 performance. It's usually based off of their ability to master the KPIs that are, that come before that. So how many calls are they making a day? How many emails? We expect a certain amount of c- accounts and contacts getting into sequence. And so there's a lot of inputs that get to those, uh, S1s and S2s, and if they're not able to do the inputs, like, that's a huge red flag, right? Like, there's... And that's either, it goes back to what I said before, that's either, like, effort or, like, there's, there's a reason it's not happening. It's, it's, it's not, you know, hard, hard to accomplish those things.

   24. HSHarry Stebbings38:16

       Do you really see the difference between good and great very early?

   25. AKAshley Kelly38:19

       Yeah.

   26. HSHarry Stebbings38:21

       What are the signals of good and great very early? Is it just, like, in first and out last and just giving it the, uh, time and effort, or are there other signals that really...

   27. AKAshley Kelly38:30

       For people in office, yes, and people that are, like, have a good pre- like, presence on the floor and everything, making their calls at their desk versus going and hiding in a, in a, in a, uh, phone booth, you know, out of fear is one easy one. I personally love when, and I meet with all the new hires when they first start, I do, like, a welcome, um, thing with them. In fact, I'm doing one today. And I always tell them, "My calendar's open. Like, come find time with me. Like, let's, let's meet, talk. I'm happy to help." Um, and the ones that immediately put time on my calendar, I swear, are the ones that end up being successful. And it's not because of anything I did, like, at all. (laughs) It has to do with, like, their proactiveness and the fact that they actually give a shit about their career and they, and they want to, um, you know, meet with a VP and see what they should be doing in order to stand out. And, like, those are the ones that tend to be top performers.

   28. HSHarry Stebbings39:13

       How do you manage morale when they're not hitting? When it's just, uh, maybe it's a hard market, maybe people aren't buying. I don't know why, but people are just down. How do you manage morale?

   29. AKAshley Kelly39:25

       It's hard. Once morale hits, it's one of the hardest, um, holes to dig out of, for sure. And, you know, with an org as big as ours, like, not every team is, is humming at 100% all the time. Like, we, you know, there's ebbs and flows of different teams, different, for different reasons. Um, but I think it's, like, one, you have to, like, wrap your arms around them. You need to get, like, very close and, like, make them under- like, make them understand that, like, you are here to help them be successful. Um, and then really hyperfocus on the basics, so going back to those inputs, like, "Let's celebrate the small wins. Did you get to your 70 dials today? Great job. You connected with how many people? Awesome. You had a conversation with the CEO? How did that go? Let me hear the g- let me hear the recording and I'll give you some feedback on it." So it's like, it's getting as close as you can to the business and as close to as you can to the, to the, the people, um, and just working on improvements day in and day out. Um, it's one of the hardest things to overcome though. Uh, we also try and do fun spiffs and offer, like, you know, rewards and competitions and stuff where it might not be based off of, like, the S2s, which is, like, the monthly goal, but there's daily and weekly ones that you can win. Again, it's all compounding, um, things that build.

   30. HSHarry Stebbings40:29

       What would be an example of that? 'Cause I like actually shorter term goals. There's a brilliant Tim Minchin speech and he says, you know, "Americans are to blame for our big dreams. We should have short term micro ambition that we chase with passion." And I like that a lot.
10. 45:10 – 47:27

    When Good SDRs Go Bad

    1. AKAshley Kelly45:10

    2. HSHarry Stebbings45:10

       How do good SDRs go bad? I know that sounds strange but you mentioned it being quite a short life cycle in terms of people often on an SDR for long. How do good SDRs go bad?

    3. AKAshley Kelly45:20

       I think one of the, um, traits that I look for also that I don't think I mentioned is, like, um, overcoming adversity. And so I think, uh, when someone faces failure in the SDR role, are they able to identify why did they fail last month? What do they need to do differently this month, uh, to get back on track? Are they using the resources around them with their managers, um, their peers, really looking at their own data and seeing where, you know, what worked, what didn't before, um, and where things fell off? And if they can make it back on track, th- they're good. Where they, where they go to die is where they can't identify those things, they don't want to identify those things, um, and then they're just kind of in this, like, slump for, for the foreseeable future. Um, the other thing is maybe they don't want to be in sales. That's something huge that, um, happens in SDR. You know, you, you think you wanna go into sales, you do the SDR role and then you're like, "Oh my god, this is terrible." And that happens a lot, and I've... and that's a lot of the reasons why our, um, uh, promotion path is not just to AE. There's different routes where people can go across the, across the business because my commitment to them is, you know, if you're, if you're a good contributor to the team, you're positive, at least performing the best that you can, like, we will put, we'll put you into a different type of role. Um, it's not necessarily a promotion but it could be a lateral move. But, you know, we wanna keep good people that we can trust in our, in our company regardless.

    4. HSHarry Stebbings46:40

       When you think about, like... actually (laughs) this is a hard one. When you think about, like, what you are today as a leader, how do you think you most need to improve?

    5. AKAshley Kelly46:50

       Probably time management when it comes to all the different functions that I, that I run. I always laugh saying that my brain feels like a pinball machine, um, where it's bouncing from, like, you know, my team, my SDR team that, uh, goes after the channel side of the business is totally different than my SDRs that are in the UK going after direct business or global over here, and it's like... So there's just a lot of different moving pieces. It's what I love about my job and about Rippling that we're able to, to, you know, build this type of, um, complex org, but I, I need to do a better job of managing my time so that I can effectively be present for all of those different things, um, and also hire the right leaders to take over those

11. 47:27 – 48:44

    Cultural Differences in Motivation Methods

    1. AKAshley Kelly47:27

       different things.

    2. HSHarry Stebbings47:28

       I'm intrigued. Does your motivation methods need to change dependent on geography? And what I mean by that is, like, I think people in the UK are very different to Americans (laughs) in many respects, and you kind of have to cater to the different cultural psychologies. Do you find that?

    3. AKAshley Kelly47:44

       I'm learning that, absolutely, yes. Um, I've been in, uh, Dublin three times in the last, like, two and a half months, uh, because it is new to me. I'd never been there before, and so I think for me it's a, it's a go and see exercise for me to understand that at the ground level because if I sit here being an American and, you know, try and put all of my playbooks on them and all my, you know, ideas that are so great, uh, it's never gonna work. And so building that trust, um, and understanding that the different cultural differences is super important.

    4. HSHarry Stebbings48:13

       Yeah. No, I, I totally agree. Going international is one of the hardest though. Um, okay, totally get you. Do you make them spend any time in customer support? I find that a really interesting lesson.

    5. AKAshley Kelly48:24

       We don't. Um, I think that is interesting, um-I would say the, what, what I typically do though is I do hire people into the inbound role, and then we move them into outbound after about six months. And so while that's not customer support obviously, it is like warmer conversations where they learn a little bit more before going into having to pitch

12. 48:44 – 53:43

    Quick-Fire Round

    1. AKAshley Kelly48:44

       cold.

    2. HSHarry Stebbings48:44

       Okay, listen. I wanna move into a quick fire, 'cause otherwise I could talk to you all day. Uh, so I say a short statement, you give me your immediate thoughts. Does that sound okay?

    3. AKAshley Kelly48:51

       Okay.

    4. HSHarry Stebbings48:52

       Okay, so what have you changed your mind on most in the last 12 months?

    5. AKAshley Kelly48:56

       That maybe AI can help my team be more efficient. (laughs)

    6. HSHarry Stebbings49:00

       (laughs) Well, you've got seven months left to make that New Year's resolution-

    7. AKAshley Kelly49:03

       (laughs)

    8. HSHarry Stebbings49:03

       ... so don't worry. You've still got time.

    9. AKAshley Kelly49:05

       (laughs)

    10. HSHarry Stebbings49:05

        Uh, what sales tactic has died a death?

    11. AKAshley Kelly49:08

        Sadly, the handwritten notes. That was something I used to love doing when I was in sales, but I feel like not a lot of people are in the office anymore, and so it might be more of a waste of time than it used to be, and I think it's died out.

    12. HSHarry Stebbings49:22

        D- are you not in the office with your team?

    13. AKAshley Kelly49:25

        I'm not, no. I'm in Dallas. My teams are all around the world, and so it's actually easier for me to hop on a flight and zip to all the different offices, which I do about once a month.

    14. HSHarry Stebbings49:34

        Everyone's like, "Sales remote, that's the one that's so hard. That's the one that doesn't work remote." What do you say to them?

    15. AKAshley Kelly49:40

        It's easier in person, that's for sure. Um, we pivoted about nine months ago, I wanna say, and started hiring in-office more, and you do see the in-office SDRs perform much higher than, than the ones that are remote, especially for outbound just because there's so many learning sitting next to each other, like literally shadowing each other's, you know, computers, seeing where people are clicking around, hearing calls on the floor. Um, so I, I definitely prefer in-office, but for me, like, if I was just in one of the offices, it wouldn't matter. I would still have to travel to all the other ones monthly.

    16. HSHarry Stebbings50:08

        What advice would you give to someone who's starting a new role as an SDR tomorrow?

    17. AKAshley Kelly50:14

        To go find the top performer on the team and shadow them and copy every single thing that they do, um, and then from there add your own little secret sauce and figure out, like, what your expertise are. I think too many, n- too many times people come in trying to reinvent the wheel, trying to make a name for themselves in a different way because they did it a different way, and really it's like, go replicate the top performer. There is, there's no asterisks in sales when, when you hit your, your quota because you mimicked a top performer, right?

    18. HSHarry Stebbings50:43

        How do the best SDRs use sales recordings to be better?

    19. AKAshley Kelly50:48

        Individual funnel metrics, so how many calls did they make, how many connects did they have, how many, uh, of the connects were they able to book demos, and being able to use data to then, uh, work with their manager or enablement on the coaching side of it, so leveraging the science and the art of sales development.

    20. HSHarry Stebbings51:09

        What would you most like to change about the world of SDRs?

    21. AKAshley Kelly51:12

        The stigma around it. Um, I'm so sick of hearing what's dead and what's not. Um, I think every market and industry is just very different. Uh, I take it personally just because I'm so bullish on SDR when they say that it's dead, so I think just the stigma around it.

    22. HSHarry Stebbings51:27

        What advice are SDRs often given that you think is bullshit?

    23. AKAshley Kelly51:32

        Actually, so there's one where AEs push back a lot saying that they... the SDR needs to go do more qualification and needs to go, um, you know, warm the deal up more for them. And I think, uh, to me that's BS because if I'm a, if I'm a good AE, I wanna take any conversation that someone at one of our top accounts is willing to have and I wanna be that person having that conversation versus an SDR that we, you know, really haven't trained or coached to have those conversations quite yet.

    24. HSHarry Stebbings51:56

        Yeah. I get that. Um, tell me, what's the kindest thing anyone's done for you?

    25. AKAshley Kelly52:01

        Hire me. (laughs) Um, no, but I would say hiring me and giving me the autonomy and trust. Um, I've been really lucky, um, to have amazing bosses that have, like, allowed me to create the environment of where me and my team can be successful, and that doesn't happen everywhere, and I think that's also a lot of reason why SDR orgs aren't, aren't successful is their executive leadership and, like, the buy-in at the, at the exec level is not there, um, and you need that. And so I guess, like, I don't know if that's kindness or not, but I think that is what I'm, like, most grateful for.

    26. HSHarry Stebbings52:35

        Who is the best boss you've worked beneath?

    27. AKAshley Kelly52:38

        Oh my gosh, don't make me answer that.

    28. HSHarry Stebbings52:41

        (laughs) What? That's allowed.

    29. AKAshley Kelly52:43

        Okay, so I work for Plank now, absolutely love working for Plank, um, and then Sam Blonde was the, was the other, um, boss at CRO that I worked with and those are the two that I think of, of most frequently when, uh, that have helped grow and develop my career.

    30. HSHarry Stebbings52:57

        Which one?

Episode duration: 53:43