20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Ashley Kelly
I would say you want to 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, 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. SDR is kind of the bridge between marketing and sales. This is 20 sales with me, Harry Stebbings. Now 20 sales is a monthly show. Where we sit down with the best sales leaders in the world to discuss.

Harry Stebbings
Their tips, tactics and strategies to scaling. The best sales teams. Today, we dive inside the sales machine that is rippling one of the fastest. Growing tech companies in Silicon Valley, now with a $12 billion valuation. And joining us is Ashley Kelly, VP of global sales development at rippling.

Before rippling, Ashley played a crucial role in scaling Brexit outbound sales from $2 million to over $300 million in ARR and has hired over 800 sdrs during. Her time in some of the best tech companies, including leather and zenefits. But before we dive into the show today, Clay helps the best GTM teams uplevel their data enrichment and outreach workflows. It consolidates 75 plus data enrichment tools into one credit based marketplace, letting you search multiple tools at once for contact info, company details, and more. They've tripled data coverage and quality for large Silicon Valley companies versus using one or a few tools like Zoom info at a tiny fraction of the cost.

Clay even lets you use AI to do unstructured research. Ask it to visit a list of websites and summarize pricing. Decide if a company is b two b if it's SoC two approved, or anything you can think of. Finally, based on that research, you can use clay to auto generate personalized email lines for each lead on your list. Everything syncs to your CRMs like Salesforce, your email Sander like outreach, and even your database.

Like Snowflake, Clay helps GTM teams across Ramp, vacada, Intercom, Sandoso and many others go from campaign to execution in seconds. They have dozens of free templates and GTM resources. Visit clay.com Harry today and get started with Clay and talking about incredible companies like Clay, let me tell you about airbase. Have you ever wondered why spending company money is so broken? Employees want to follow the process, but they're confused and frustrated.

It takes forever to get anything approved it's so tedious to get anything paid, and folks in procurement, finance and other stakeholders are just as frustrated too. Duplicate spend, unauthorized contracts, surprise vendors, late invoices, missing receipts and documentation. It just doesn't end altogether. It makes suspending feel out of control, wastes time and money, and increases risk. It shouldn't be this hard.

It doesn't have to be. Arbase makes it easy Airbase is the only procure to pay software that beautifully combines enterprise with employee friendly ease of use. It orchestrates upstream intake requests all the way through to the downstream processing of invoices, expense reports, credit card transactions, transactions and reconcile that seamlessly in your ERP. Replace a complex maze of tools, forms, emails and spreadsheets with an interconnected, collaborative platform. Stop uncontrolled spend.

Make it easy for employees to follow the process. Put stakeholders in the loop. Close your books faster. Keep suppliers happy. All this and more is possible with airbase.

To learn more, head over to airbase.com 20 vc Airbase procure pay close and speaking about game changers with Airbase, you need to check out our next sponsor. Is expense management a painful chore? Sounds like you use concur. Its time to switch to Brex. Brex automates and accelerates spend management with easy to use corporate cards, travel, expense management and bill pay all on one AI powered platform, Brex makes it easy to boost efficiency and compliance enterprise wide and free up your managers, employees and accounting team for higher impact work.

Don't let concur slow you down. Top companies from startups to enterprises are using Brex to manage spend with greater efficiency, accuracy and speed. We're talking DoorDash. Robinhood, airtable and countless other industry leaders ready to join them. Switch to AI powered span management@brex.com.

Speaker C
Dot, you have now arrived at your destination. Ashley, I am so excited for this. So first, thank you so much for joining me today. Yeah, thank you for having me. I've been following along for a little while now.

Ashley Kelly
I just feel very honored to be on the 20 sales podcast. That is very, very kind of you. I always love to start with kind of actually 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?

That's a good question. So I actually started my career working for NASCAR, which is probably a topic for a whole nother day, but world of sales. I started as an SDR at zenefits very. Truth be told, I did not know what an SDR was. I thought I was going to be doing demos in person with customers.

I was clearly very wrong about that, but I ended up falling in love with the top of funnel. SDR, to me, is just such a special role that is, you know, both pipeline building, but also career development at the same time. And so I stayed on this side of the sales funnel, and within three years of benefits, I left as a director. And then since then, I've built out sales development orgs at different tech companies out of the Bay Area. So lever, Brex, and now Ripley.

Speaker C
Sdrs traditionally is sort of, like, respectfully a grind and fricking hard career development. Talk to me about that element. Yeah, I would say the top AE's and best leaders that I've ever worked with have started their careers as sales development reps. I've always done this at all the companies I've been at, but we do a lot of promotion from within, so we promote sdrs into the account executive role, account management into implementation. In fact, if you look@my.org today, about a third of my SDR managers have actually come from the SDR role internally.

Ashley Kelly
Definitely a career trajectory for salespeople. I think SDRs and I think fundraising is the same, which is like, you've got to go from rejection to rejection with no loss of enthusiasm. You mentioned cold call. I just want to go straight to it. I mean, is cold calling still a thing?

Speaker C
Like, is outbound still a thing in this way? Like, really? Are we not past that? Ashley? Oh, my God.

Ashley Kelly
That's. It's like a trigger. It's a trigger for me. I think, you know, that outbound is definitely still a thing. I have over 200 of them.

That would definitely prove what I'm saying accurate. And so I think outbound is definitely changing. Everything in sales is always changing. Right. 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. And now we have AI, and so I think there's always going to be evolutions within outbound. But 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 new shiny object, and they kind of follow it like sheep, and then they put all their eggs in one basket. That's when outbound and SDR starts to fail, is they take their eye off of the fundamentals of what makes it successful to begin with.

Speaker C
I actually like outbound and I think it's a craft when done really well. The challenge that I have is like with AI and a lot of the tooling that will allow for outbounding at scale infinite. I worry that we'll have just much. Less appreciation for it because you'll be. Able to send millions of emails and.

Harry Stebbings
The supply will be infinite. And so everyone will be like, oh, block, block, block, and too much noise. I agree with that. I think 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.

Ashley Kelly
And so, like, the hardest part about being an SDR is 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 free up more of an SDR's time to where they can focus on more personalization and LinkedIn connects and all the different channels that really require a human outside of AI. So I think there's a lot of leveraging that can happen there. I'm interested, when we think about like.

Speaker C
SDR accountability or where it sits, should sdrs roll into marketing or should they roll into sales, do we think? I have my honest answer, but I'll give you 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.

Ashley Kelly
So I've been in orgs that have reported to marketing, currently in one that reports into sales, they have different use cases. So I think if you're a heavy inbound.org for SDR, there's a lot more science to it. And being really tightly aligned with the team that's driving the funnel is where you have that feedback loop that is so important. And so when you think about an inbound funnel, if 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 an AE. And like I said, the feedback loop for the quality and the volume of those leads is so important.

Again, if you have a big inbound.org reporting to marketing, that makes it so much easier to do. 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. 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. It's much more of a sales motion.

I think that's where it's more successful rolling into sales. And as I mentioned, 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 them to learn from AE's and to really like, progress into their sales career. 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?

Speaker C
Like, if there's a big difference between MQLs and SQLs, aren't the MQLs not doing their job very well? It's a, it's a fair point, 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 should have a higher hit rate, 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 salesperson.

Ashley Kelly
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? Okay, so heavy inbound model, we're like, SDRs can sit under marketing and then an outbound model, they sit under sales. Yeah, but then my real answer is neither. I think I actually am very bullish on sales development if you can't tell.

And I think it's third pillar within the go to market function. And I think that it can stand alone while I report into our CRO at rippling. The relationship that we have is really SDR is kind of the bridge between marketing and sales. And so all of inbound and outbound sits underneath my. But we work very tightly with marketing to run ABM campaigns and just strategic outreach for our 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 going to become revenue and not just fit our top of funnel models. So that's my bullish answer, is that I think it'll be the third pillar. How does that sit in structures then? I think people like to think of, like, all structures with different functions. When we say it's a different pillar, how does that actually look, and how should we actually think about that as founders building businesses?

I think probably depends on the scope of your, of your CRO. For us, that that's how it works. I report into the CRO. Marketing does not report to 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, teams actually partner and go to market, as opposed to. I think a lot of companies view SDR as more like order takers. And I think it's super important to give SDR orgs, like, the autonomy and the ability to really build their own strategy and execution. So do you think a 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?

I've only seen A's prospect successfully a handful of times. It's always the top AE's. I think it should always be an option. Absolutely. I think if you can drive the right volume and the right quality of pipeline to an AE, an AE's time is better used closing and not prospecting.

Speaker C
Which company that you've worked at was best in SDL Ripley. The volume that we're able to crank out while also supporting not just new logo sales, but we also dive into product. We also are in the customer base helping with cross sell and upsell. It's probably the most complex sdr.org I've ever led. We support about 31 different functions across the business.

This is so confusing. You do cross sell and upsell. This is like verging on account management meets customer success. Are we not just crossing a load of functions now? Well, I mean, it depends on and where you, again, think we're an AE or AMS time is best suited.

Ashley Kelly
And so when you have SDR resources that are able to go into the database and be able to find the customers that we are able to cross sell, I mean, we have so many different products. We have the luxury of being able to do that. And it works from, you know, a CAC payback perspective. And so it's very unique. You know, we're a 350 person sdr.org, so we're an army.

Harry Stebbings
350. Yeah. Between leaders and sdrs. Yeah, that really is an army. I do want to get to, like, hiring these people.

Speaker C
Now, we mentioned a little bit beforehand in terms of your hiring in Dublin, and you mentioned that, like, 350. How many of you hired in your time? Ashley? 800 strs. I think in the last decade, probably across all different companies.

Ashley Kelly
Yeah, I'd say zenefits was the big one. With that, we did about 250. And then now rippling, obviously, with about 352. Hundred 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. Okay, let's start. When's the right time to hire your first SDR? If you have a founder coming to you, should they hire, like, an SDR first or should they hire head of sales first who can bring with them sdrs? 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 in the weeds and helping build out the process and scale. I'll give an example. 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 got to find the right person that's going to, you know, have that title, but also willing to do the grind that you said that it is. And then once that you can start proving out that it works and you get a little bit of traction, that's when you can start hiring some. Some additional sdrs. And those sdrs can have less experience. But I do think your first hire should be someone, like, not fresh out of college and definitely not their first SDR role.

And I think that's another place where. Where companies fail is they think that they can just plug someone in and they're going to go know what to do. And it's actually a little bit more complicated than that. Should the founder always be the one to build out the first sales playbook? Yeah.

And if not the founder, someone that is either high up in marketing or in sales. If you have, like. I guess it depends on how big the company is, but in my mind, a founder should always be the main seller. 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 more prospects. So you're an angel in my hypothetical company, and I'm like, great, we need to hire sdrs. Again, I have no idea how to hire strs. This is not a hypothetical situation.

Speaker C
When I say I've never hired an SDR, how do I structure the hiring process for an SDR? And what would you advise me? As granular and as specific as possible, because I don't know from a profile. Standpoint, I would start there. And again, this depends on, like, the state of your, how much, like, enablement or manager support you have.

Ashley Kelly
But typically I would say you want to 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, that want to 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 that's super important. I'd say 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'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 launched miles ahead of, like, the first hurdles that you're going to run into when it comes to skills or an SDR. Okay, so interview process. What questions do I ask in this process to understand whether you're a potentially good candidate? 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 like, you ask for experience and it's like the complete opposite for sales development because you're 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 life experiences. But I usually bucket them into three different categories.

So the first being coachability and ability to navigate change. So do they take feedback well? So, you know, when their manager is critiquing them, like, do they appreciate that? Do they have like, a growth mindset? Right.

Speaker C
How do you know that in an interview? Because everyone says they're coachable. So the navigate change in coachability. Like, I've 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, and how did you react to that and how did you implement that feedback? So asking like, some very straightforward, tough questions and expecting them to give examples and, and sometimes the examples are silly, right.

Ashley Kelly
It's like 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. It's okay to fail. You're going to fail in sales, like, absolutely. Especially in your first one.

So, like, give me an example of when that's happened and when you were coached and how you implemented that feedback. Okay, so coachability and implementation of feedback. One and then the next one I would say is like motivation factors. So what, what gets them up in the morning every day do you find. Is a good answer to that?

Speaker C
Because I asked this of founders and I don't find it leads to much substance. What should we look for? I like two answers, one being money motivated, which means, like, basically they'll, you know, I don't want to say do anything to be successful, but, like, failure really isn't an option for them. 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. So I wanted the growth and I wanted the title and the recognition.

Ashley Kelly
And that is something that always motivated me. And so 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 are 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, you kind of figured out very quickly who has the grit within them that can 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, every minute matters.

So the more that you can be organized, you'll be more successful. Again, how do I tell in an interview? I'm terribly unorganized. I have an EA, thank God. Otherwise I wouldn't be at anything.

Speaker C
But I would tell you that I'm very organized. 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 school or in a type of role that relies on organization. But answering like, you know, I have, I have calendar blocks.

Ashley Kelly
That's a big thing for sdrs to be successful is they'll block off their calendar for different times that are dedicated 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. Do people admit to being money motivated? Yeah, of course.

We're in sales. They do. I'm surprised. I thought it's kind of like a taboo subject where it's like, it feels dirty to be like, yeah, I'm into the money. I think that's a UK or european thing.

I think in the states hiring, like, absolutely. People have no problem saying that they are money motivated. That is fantastic. I'm thrilled. So now we've kind of got those kind of three core traits.

Speaker C
Is that in one meeting? Is that in two meetings? Just help me understand, like, do we do a test? Do we do a role play? Yes.

Ashley Kelly
We'll have a hiring manager that has a phone screen. Then we do, you know, two to three actual panels. What used to be in person, sadly, is now over. Zoom in this new modern world, but essentially an in person interview. We do.

We do role plays and we do an email assessment, actually. And for me, both of those are equally important. I don't expect someone to nail the role play. Right. They don't work for us.

They haven't gone through our training program or anything like that. But if someone gives you feedback on the role play and then you do the role play a second time, if you're not implementing that feedback, then you're clearly not what we talked about earlier, coachable. Right. You're not implementing the feedback. And so it's a, it's a way to, like, test it live.

Speaker C
What is the role play? Is it like, pitch us rippling? How do you structure that? How long do you give them just talk me through that. Yeah, I've done a few different ones, like, you know, the traditional, like, elevator pitch.

Ashley Kelly
So I give them a scenario where it's like, hey, you're in the elevator, you bump into a director of HR. You see that they're going to a conference, they're talking to their peer. How do you bump in and talk to them about what rippling does and offer? That's an interesting one to do. How often do they do it?

Speaker C
Well, I mean, again, this is not a company that they've worked for before. This is your company that they're coming in news, they don't know all the product nuances. They don't know everything that you know. How often do they do it? Well, I'd say about 50% of the time.

Ashley Kelly
But again, it's like I'm not looking for them to nail the pitch. I'm looking for the manager that's interviewing them to give them feedback, saying, hey, your tone sounded like this, or you should have asked more upfront questions about this. And then for them to do it a second time and to actually add those couple pieces in to me is a good, good sign of someone that I'd be willing to take a bet on that we can actually coach and develop into the role based off of, you know, all the trainings and things that we've built over the years. So we have that elevator pitch. You got 60 seconds.

Speaker C
Go pitch this key account. The other one you mentioned was the email test. I haven't. This is very exciting. I haven't had this before.

What is an email test? So what we want to see their writing skills, right? A lot of the times we are booking demos over email, we have sequences and we have templates that we use. But when you get an objection, it's really important to make sure, just like the active listening on a cold call, that you can actually actively read. And so are you actually taking the content that the prospect is responding to?

Ashley Kelly
Are you mirroring their language? Are you able to actually respond in a short, cohesive way to actually continue the conversation, engage and book a demo? So that's one example. We also do cold email outreach as well. So the Whyu, why now framework that I grew up with, I still think it is, like, super valuable.

And so, again, being able to be relevant with your information of why you're reaching out to a company, why you're reaching out to that Persona specifically, and seeing someone connect those dots in their email is a good sign that they will be a good sdR. Where do they fuck up more on the role play or on the email. Email is getting a lot tougher because of AI. Okay. So there's another reason that I'm a little hesitant with AI, because they could use that and send over the email and like, we don't know if it was actually them that wrote it or if they use chat, GPT or something.

Speaker C
But does it matter? That's an interesting one. The output is the same. Like, maybe. Yeah, that's a good, that's a really good point.

Ashley Kelly
Maybe it doesn't matter. And they're being resourceful and they're using tools that, that are gonna make them a better SDR. Yeah, I would give them more credit for that. Like, great. You can probably do more scale and if I didn't know, it's probably pretty good.

That's actually a really good point. I will take that back. That's a good point. Yeah, I think that'd be great. Okay, that's super interesting.

Speaker C
Do you find sdrs are like really wanting to engage with AI tools or not? Is that fair? I think a handful of them do, yes. One thing about tools in general with, with my SDR is like, I usually rely very heavily on them because they are the ones who are in the weeds all day, every day, and, like, they're trying to make their lives easier, too. And so when they come to me with a tool that they think is going to help them with their job, I'm like, all right, let's check it out.

Ashley Kelly
I'm way less inclined to be the one that's going to go look at the tools. And so I rely very heavily on my reps and their, their inputs of what they think is going to help them. We just started using clay to help with personalization, and that's been like very recent. So I'm excited to see not only how it's like, impacted our numbers, but how reps are liking it, too. So we've done email tests, we've done role play.

Speaker C
We want to give this candidate the job, actually. It got no idea how much to pay them, Ashley. And how much should be in terms of actual salary versus bonus, how we should structure that. Can you help me understand the actual financial package? Yes.

Ashley Kelly
So finance package will be determined based off of geo location. So we have different markets that are more expensive for cost of living. So those are a little bit higher of a total OTe. But as far as the comp structure, we do a 70% base salary and then we do 30% based off of their variable, which is tied to their quota. And so their quota is based off of what we call stage two opportunities.

So basically, a demo has been held by an AE. The AE has decided, yes, this is a director hire within one of our Personas. It's something that can actually be a customer of ours. We have next steps that we're going to continue the conversation and we're going to try to make them a customer. And then the AE moves that into stage two, and that's when an SDR gets their credit for it.

And then each team, segment, function, line, whatever you want to call them, they all have different quotas based off of the tam and types of roles that they do. You think that's right? And what I mean by that is like, it doesn't actually. It doesn't wrong about it. You tell me.

Harry Stebbings
It doesn't actually tie to revenue. It's a fair question. But in taking a step back, your entire financial model should add up to revenue. Right. Let me take actually a step back.

Ashley Kelly
You can actually. I have done this before. I have put strs on a revenue model, and we did, we moved SDR onto revenue. But there's very few companies and very few examples of when it actually works. The reason it worked at Brax was we were highly transactional.

Our deal cycle was, you know, two to three weeks, and it was GMV based. It was a consumption based on what was being spent on the card. Very different than an ARR model, which in most SaaS companies is longer deal cycles, and SDRs aren't in the role that long, and they need to have more transactional focus on their goals. And so that's why we do monthly s, two s. I will say the pros of when it works.

So when it worked at Brex, we were able to three x the referring revenue that SDR has brought in within six months. So, trust me, I've done it. I've seen it work. There's also times that I don't think it works, and where I'm not a proponent of it for right now, where we're at rippling, I think at some point we will have teams where absolutely it makes sense, but it has to be what you're solving for. And I think a really good example of that is the volume of demos versus the quality of them.

And once you start getting too much volume with not enough quality, that's when you have to improve the threshold of what you're comping sdrs on. The other thing at Brex is once we started comping them on revenue, the s two s absolutely tanked. So there weren't enough demos and at bats because people were hitting quota at the revenue side, and we weren't giving enough at bats or demos over to the AE's. And any sort of finance model that's kind of how you build it is based off of how many opportunities that account executives get. It's funny.

Speaker C
It's. What is it? Show me the incentive, and I'll show you the outcome. And by the way, there is zero questioning of me on sdrs to you. It's a fair question, and I get asked it all the time.

Ashley Kelly
And trust me, there's times where I'm like, shoot, should we do it on this team? Because this team, you know, has a bunch of volume that's happening right now. You have to ask yourself, like, what are you solving for? And obviously, we're all solving for revenue, but it's the means to the ends that matter, too. Has the way that you hire sdrs changed over time?

Speaker C
You've mentioned hiring 800. When you think about the early days of hiring sdls compared to now, how has it changed? It's funny you say that, because, pre Covid, I probably never would have hired an SDR that had SDR experience. I would have preferred to hire people fresh out of school 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 our company and our process.

Ashley Kelly
Also, there was always the thought of, well, if you've been in SDR for a year and you haven't gotten promoted yet, one, why? Two, are you going to be willing to sign up to be an SDR for another year at our company? Because, again, it's a grind. 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 is a lot of good talent that's out there that has had previous experience that just kind of got the short end of the stick going through these riffs. And so it has changed quite a bit that now we hire more people that are coming from the SDR role because there's more talent out there that's available. People always say, if you're part of the riff, you aren't one of the good ones. Is that fair?

Well, it was a pre Covid, I would have said that. Yeah. But now it's like, 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.

Do some back channeling if you can. You know, a lot of these companies, we see top AES and leaders that have been cut, too. You can start to know people's reputation and get feedback from people on whether people were good or not. What are the biggest hiring mistakes that you've made when it comes to hiring sdrs? We were, when I was at benefits, I was a new manager.

I think I had 35 reps reporting to me, which is already a terrible thing that was happening. But we had huge hiring goals. And I remember we hired people off of just 30 minutes phone screens, and that was it. So it was a true, like, just needed to get butts and seats as fast as possible. And clearly the takeaway was like, oh, my gosh.

Didn't spend enough time on the quality of interviews, 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 of a 30 minutes phone screen. That was probably my biggest mistake across the board. I feel like I'm in therapy now telling you this.

Speaker C
I want to move to, like, the onboarding side now. So we've got these amazing sdrs. You said you often quite like the man of school. How on earth do we onboard sdrs effectively? Ashley, 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.

Ashley Kelly
So kind of learning a lot of, like, trial and error. What I found over the years, like, I think the old, like, Yelp model, was 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 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. Week one. Then what are we doing in week one to make them ready for week two calls? So, week one is, like, company onboarding, heavy focus on, like, our product, focused on 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, zoom info, all that fun stuff. We use outreach, which is 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 in, you know, week two or week three, but we give them ramping goals.

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

No, no, they don't know. So they won't be closing closing deals at all. So like a full month quota, if they're fully ramped, is eight s two s a month. So on month one, it's like two, and then the next month is four, the next month is six, and then they're on eight. So it builds up to that.

Speaker C
How do you think about good numbers to set? This sounds awful. Forgive me for it. Like four, that's one a week. That's an awful lot of time for one s two.

Ashley Kelly
So you're not wrong. You're not wrong. Trust me. 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, we start working account or 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 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 compound. That's the main reason why.

But to answer your question more specifically from like, a data and science standpoint, is that we look very heavily at our account to s one conversion rate and account to s two conversion rate, and we look at that monthly. I'm so sorry, account to s one is what an account s two is what. So if I give you, let's say at 100 accounts, right, and you are working, let's call it ten a day, I want to look at when you start working those ten accounts, how long does it take for one of those to become a stage one opportunity in a demo? And what is the conversion of that cohort? Because that's how we know where to set a lot of our targets for s two s is because we know how much we can convert these accounts into opportunities.

Speaker C
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, plg, but with expansion. But it's like small acvs coming in five to 20k acvs versus big 100k cv's, does that differ our expectations on stages and what should qualify? Yes, well, it doesn't change stages of what would qualify. It would change quotas that we would set for people.

Ashley Kelly
So the lower the acv, the higher number of s two s 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 rebops 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 s two s that they need to because it has to make sense in the finance model. And so we look at not only number of opportunities that are being assigned to each AE, but win rates, acvs, and then to your point, any sort of like product attach rates that could be in addition to those, which actually obviously helps the CAC fully ramped. So we're like four months, is that when we expect to be totally productive? Yeah. And we see some people sooner.

Absolutely. But like four months is like, from a modeling perspective, like that's what we expect is four months. How quickly do you know if you've made a mis hire? Month two. And it's not even usually based off of the s two performance.

It's usually based off of their ability to master the KPI's that come before that. So how many calls are they making a day? How many emails? We expect a certain amount of accounts and contacts getting into sequence. And so there's a lot of inputs that get to those s one s and s two s.

And if they're not able to do the inputs, like, that's a huge red flag. Right. 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 not, you know, hard to accomplish those things.

Speaker C
Do you really see the difference between good and great very early? Yeah. What are the signals of good and great very early? Is it just, like, in first and outlast and just giving it the airtime and effort, or are there other signals that really. For people in office, yes.

Ashley Kelly
And people that are, like, have a good prep, like, presence on the floor and everything, making their calls at their desk versus going and hiding in a bone 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 thing with them. In fact, I'm doing one today, and I always tell them my calendar is open.

Like, come find time with me. Like, let's. Let me talk. I'm happy to help. 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. It has to do with, like, their proactiveness and the fact that they actually give a shit about their career and they want to, you know, meet with the 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. How do you manage morale when they're not hitting? When it's just.

Speaker C
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? It's hard.

Ashley Kelly
Once morale hits. It's one of the hardest holes to dig out of, for sure. And, you know, with an.org as big as ours, like, not every team is humming at 100% all the time. Like, we. You know, there's ebbs and flows of different teams, different for different reasons, 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 understand that, like, you are here to help them be successful and then really hyper focus on the basics. So going back to those inputs, like, let's celebrate the small wins. Did you get your 70 dialys a day? Great job.

You connected with how many people? Awesome. You had a conversation with the CEO. How did that go? 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 you as you can to the people and just working on improvements day in and day out. It's one of the hardest things to overcome, though. We also try and do fun spiffs and offer rewards and competitions and stuff where it might not be based off of the s choose, which is the monthly goal, but there's daily and weekly ones that you can win. Again, it's all compounding what would be. An example of that?

Speaker C
Because 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. I do too.

Ashley Kelly
And that's why I love SDR is it's a daily function. Like you could be, I could have a rep right now at the 22nd and they're not even close to target, but we still have at least six days of selling that we can like make an impact on this month and they could get to their quota still. And so that's the cool part about SDR. Like sales is very different, right? Like it takes, can take months for deals to progress.

But an example of it. We've done a lot of spiffs that are what I'll call a fast start. And so we'll want people to get, you know, halfway to their quota by week one of the month. And so then they're like already pacing and set up for the rest of the month. So anytime we do a spiff, it's always tailored around how, what the end goal is.

Right? Like what any incentive should be. We also do a lot of call blitzes. We have paired people up together. We've done competitions where regionally, like we'll have, you know, west coast versus east coast.

Whoever, you know, has the most dials with the most connects, gets put into a raffle and then we draw the raffle and they win money. There's a lot, we did march Madness. Like, there's a lot of creative, like fun things that you can do, too. And that's the best part about SDR, is like, these teams are fun. They want to have a good time.

And again, back to when we said, like, they're making hundred calls and getting told no all day. It's like the more fun you can make it, the better. So I'm, for my sins, kind of a marketer in many ways. I love content and I think content is, you know, the superpower. Like, you think SDRs is the superpower.

Speaker C
Marketing and content should sell you entirely to contract signing if done well, but I'd be pissed. If I was an SDR and people didn't know our brand, I'd be like, you, marketing team didn't do your job. And that would have helped me a lot in the process because it's much easier if you send me an email and I'm like, oh, rippling. Yeah, great. I've heard about you.

Is there tension between SDR and marketing? I wouldn't say there's tension between it. I'd say there is a lot of opportunity still in the ABM world for teams like SDR and marketing to partner better together. It's a muscle we started about last year. We do a lot of direct mail campaigns which help, you know, kind of warm up the awareness with the prospect before an SDR will call in and start doing emails.

Ashley Kelly
Content, I think is really nice, actually, for sdrs, it's really easy to send, like, a white paper over something to them that they, you're kind of putting the ball back in their court, and then that way you're able to follow up with them later because you did what they asked. So I think those are all super important LinkedIn ads, making sure that market. I don't know why sdrs aren't way more effective. Sorry, I'm going off on one. But, like you choose your ICP, start a podcast interviewing the world's biggest and best in that ICP.

Speaker C
If I worked for you, this is what I'd do. You give me a segment, I'll start a podcast interviewing the biggest, I don't know, Chros in software companies. Between 505,000 people. And now I have a reason to twice a week meet the biggest Chros. What an unbelievable lead funnel I'm getting.

And I'm hired. Harry, you're hired. That's great. We haven't doubled in podcasts, but I will say events, now that those are back, have actually been very successful. And I also think it depends on who your Persona is.

Ashley Kelly
Hr people love, love going to events. And so we've had a lot of success at the last couple shrm events we've been to. I do want to go back. You know, you mentioned at the start. 350 now on your SDR team.

Speaker C
What are the break points in scaling an SDR team to that stage? You definitely need the right senior leaders. I would say one of the most challenging things has been the international piece. We just move so quickly, and by the time I wake up and I'm talking to my team in Emea, it's like they only have a couple more hours left in the day that they're working. And like, we miss out on a day all the time.

Ashley Kelly
And so we're a heavy slack culture, which is good, so we can, you know, get messages to each other that are important as fast as possible. But I'd say that's been the biggest muscle that I'm learning is how to, you know, in a dispersed, that big of a disperse in geographical time zones, being able to still run as fast as we always have. 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?

I think one of the traits that I look for also that I don't think I mentioned is overcoming adversity. And so I think 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 to get back on track? Are they using the resources around them with their managers, their peers, really looking at their own data and seeing where, you know, what worked, what didn't before and where things fell off and if they can make it back on track, they're good. Where they go to die is where they can't identify those things.

They don't want to identify those things. And then they're just kind of in this, like, slump for the foreseeable future. The other thing is maybe they don't want to be in sales. That's something huge that happens in SDR. You know, you think you want to 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 that's a lot of the reasons why our promotion path is not just to AE. There's different routes where people can go across the business, because my commitment to them is if you're a good contributor to the team, you're positive and at least performing the best that you can. Like, we will put you into a different type of role. It's not necessarily a promotion, but it could be a lateral move.

But, you know, we want to keep good people that we can trust in our company. Regardless. When you think about, like, what you are today as a leader, how do you think you most need to improve? 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 where it's bouncing from, like, you know, my team, my SDR team that 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 build this type of complex. But I need to do a better job of managing my time so that I can effectively be present for all of those different things and also hire the right leaders to take over those different things.

Speaker C
I'm intrigued because your motivation methods need to change dependent on geography. And what I mean by that is I think people in the UK are very different to Americans in many respects, and you kind of have to cater to the different cultural psychologies. I'm learning that, absolutely, yes. I've been in Dublin three times the last, like, two and a half months because it is new to me. I'd never been there before.

Ashley Kelly
And so I think for me, 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 try and put all of my playbooks on them and all my, you know, ideas that are so great, it's never going to work. And so building that trust and understanding that the different cultural differences is super important. Going international is one of the hardest, though. Do you make them spend any time in customer support? I find that a really interesting lesson.

We don't. I think that is interesting. 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 cold. Okay, listen, I want to move into a quick fire because otherwise I could talk to you all day.

Speaker C
So I say a short statement, you give me your immediate thoughts. Does that sound okay? Okay. Okay. So what have you changed your mind on most in the last twelve months?

Ashley Kelly
That maybe AI can help my team be more efficient. Well, you've got seven months left to make that New Year's resolution, so don't worry if you still got time. What sales tactic has died a death? 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.

Speaker C
Are you not in the office with your team? 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. 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? It's easier in person, that's for sure. We pivoted about nine months ago, I want to say, and started hiring in office more. And you do see the in office sdrs perform much higher than the ones that are remote, especially for outbound, just because there's so many learnings sitting next to each other, literally shadowing each other's computers, seeing where people are clicking around, hearing calls on the floor.

Ashley Kelly
So 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. What advice would you give to someone who's starting a new role as an SDR tomorrow? To go find the top performer on the team and shadow them and copy every single thing that they do, and then from there, add your own little secret sauce and figure out, like, what your expertise are?

I think too many, 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's no asterisks in sales when you hit your quota because you mimicked a top performer. Right. How do the best sdrs use sales recordings to be better?

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

Speaker C
Glad I asked that one. That's a good one. What would you most like to change. About the world of sdrs? The stigma around it.

Ashley Kelly
So sick of hearing what's dead and what's not. I think every market and industry is just very different. 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. What advice are sdrs often given that you think is bullshit, actually?

So there's one where AE's pushed back a lot, saying that the SDR needs to go do more qualification and needs to go warm the deal up more for them. And I think, to me, that's B's, because if I'm. If I'm a good AE, I want to take any conversation that someone at one of our top accounts is willing to have, and I want to 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. Tell me, what's the kindest thing anyone's done for you? Hire me?

No, but I would say hiring me and giving me the autonomy and trust. I've been really lucky to have amazing bosses that have 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 successful is their executive leadership. And, like, the buy in at the exact level is not there, 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. Who is the best boss you've worked beneath? Oh, my gosh. Don't make me answer that. What?

Speaker C
That's allowed. Okay, so I work for plank now. Absolutely love working for plank. And then Sam Blonde was the other boss CRO that I worked with. And those are the two that I think of most frequently that have helped grow and develop my career.

Which one? I'm not answering that. You can. Matt's coming on the show, and we've had Sam on the show, so it's equal. Ask them who their favorite sales development leader was.

I'm not getting an answer, am I? Okay, help me out here. Ten years time, where does Ashley want to be then? I will be a chief sales development officer. I think that sales development will sit at the executive level within ten years.

I love it. Ashley, thank you so much for putting up with my meandering. I love this. This has been fantastic. Good.

Ashley Kelly
Well, I've had fun, too. Thank you so much for having me on. And hopefully some people got to learn a little bit more about sales development and either, like, some high level or tactical stuff they can walk away with. So much fun there with Ashley. And if you want to watch the.

Harry Stebbings
Full episode on YouTube, you can, of course, find it by searching for 20 vc. That's 20 vc on YouTube. But before we leave you today, let me tell you about Clay. Clay helps the best GTM teams uplevel their data enrichment and outreach workflows. It consolidates 75 plus data enrichment tools into one credit based marketplace, letting you search multiple tools at once for contact info, company details, and more.

Theyve tripled data coverage and quality for large Silicon Valley companies versus using one or a few tools like Zoominfo at a tiny fraction of the cost. Clay even lets you use AI to do unstructured research. Ask it to visit a list of websites and summarise pricing. Decide if a company is b two b if its soc two approved, or anything you can think of. Finally, based on that research, you can use Clay to auto generate personalized email lines for each lead on your list.

Everything syncs to your CRMs like Salesforce, your email sander like outreach, and even your database. Like Snowflake, Clay helps GTM teams across Ramp, Vacada, Intercom, Sandoso and many others go from campaign idea to execution in seconds. They have dozens of free templates and GTM resources. Visit klei.com Harry today and get started with clay and talking about incredible companies like Clay. Let let me tell you about airbase.

Have you ever wondered why spending company money is so broken? Employees want to follow the process, but they're confused and frustrated. It takes forever to get anything approved. It's so tedious to get anything paid. And folks in procurement, finance and other stakeholders are just as frustrated too.

Duplicate spend, unauthorized contracts, surprise vendors, late invoices, missing receipts and documentation. It just doesn't end altogether. It makes suspending feel out of control, wastes time and money, and increases. It shouldnt be this hard. It doesnt have to be.

Arbase makes it easy. Airbase is the only procure to pay software that beautifully combines enterprise with employee friendly ease of use. It orchestrates upstream intake requests all the way through to the downstream processing of invoices, expense reports, credit card transactions and reconcile that seamlessly in your ERP. Replace a complex maze of tools, forms, emails and spreadsheets with an interconnected collaborative platform. Stop uncontrolled spend.

Make it easy for employees to follow the process. Put stakeholders in the loop. Close your books faster. Keep suppliers happy. All this and more is possible with airbase.

To learn more, head over to airbase.com 20 vcairbase Procure Pay close and speaking about game changers with Airbase, you need to check out our next sponsor. Is expense management a painful chore? Sounds like you use concur. It's time to switch to Brex. Brex automates and accelerates spend management with easy to use corporate cards, travel expense management and bill pays all on one AI powered platform, Brex makes it easy to boost efficiency and compliance enterprise wide and free up your managers, employees and accounting team for higher impact work.

Dont let Concur slow you down. Top companies, from startups to enterprises, are using Brex to manage spend with greater efficiency, accuracy and speed. Were talking DoorDash, Robinhood, airtable and countless other industry leaders ready to join them? Switch to AI powered spend management@brex.com. Dot as always, I so appreciate all.

Your support and stay tuned for an incredible episode with the one and only Reid Hoffman on Monday.

20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Primary Topic

Episode Summary

Main Takeaways

Episode Chapters

1: Introduction

2: The Role of SDRs

3: Hiring and Training SDRs

4: Utilizing AI in Sales

5: Compensation and Career Development

Actionable Advice

About This Episode

People

Companies

Books

Guest Name(s):

Content Warnings:

Transcript