Jun 7, 2024 · 53m · news
Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162 · 20VC with Harry Stebbings
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In this episode of 20VC, Harry Stebbings interviews Ashley Kelly, VP of Sales Development at Rippling, to dissect the tactical playbook for building, hiring, and scaling world-class Sales Development Representative (SDR) teams. Kelly shares actionable insights on organizational design, compensation structures, interview evaluation strategies, onboarding schedules, and the future of sales development.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 21.8% of the talking time here. How this is scored →
Harry as informed peer 2.6 Guest teaching 4.0 Guest disagreement 1.1 Harry pushing back 2.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 3:48 Rejection of 'Outbound is Dead'
Ashley passionately defends outbound sales when Harry suggests cold outreach is obsolete, calling the claim dramatic and pointing to her 200+ SDRs as proof.
Hardest push from Harry ▶ 27:03 Pushback on Non-Revenue Comp ModelsHarry directly confronts Ashley on why SDR compensation is tied to stage-two opportunities rather than actual closed revenue, forcing her to defend SaaS compensation structures.
Biggest teaching moment ▶ 27:07 Masterclass on SDR Comp Models: Brex vs RipplingAshley details the nuances between transactional consumption models like Brex and long-cycle SaaS ARR models like Rippling, explaining how revenue-based comp can ruin demo volume.
Harry holds his own ▶ 24:30 Defending Candidate AI ResourcefulnessHarry counters Ashley's skepticism about AI-generated email tests by arguing that utilizing modern tools to produce strong results shows high SDR resourcefulness, forcing Ashley to concede.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Ashley's Journey into Sales Development | 1 | 3 | 1 | 2 | Harry opens with standard interview questions about Ashley's career arc. Ashley explains how SDR roles serve as internal career launchers, educating Harry on promotion pathways into AE and management roles. | |
| The Evolution and Reality of Outbound Sales | 3 | 4 | 3 | 4 | Harry challenges whether cold calling and outbound are dead in an era of infinite AI email spam. Ashley playfully rejects the premise, explaining that while methods evolve from phone books to AI, outbound fundamentals remain essential. | |
| Where Should SDRs Report: Sales or Marketing? | 3 | 5 | 1 | 4 | Harry raises his hand like a student to query why MQL to SQL conversion isn't higher if marketing is doing its job. Ashley clarifies the distinction between high-intent demo requests and low-intent content downloads. | |
| SDR as the Standalone Third Pillar of GTM | 2 | 4 | 1 | 2 | Ashley pitches her vision of SDRs acting as an autonomous third pillar of GTM bridging sales and marketing. Harry questions whether AEs should still prospect, and Ashley explains that AE time is better spent closing. | |
| Scaling a Sales Development Army | 2 | 5 | 1 | 3 | Harry expresses surprise that SDRs handle cross-sell and upsell, questioning if functions are blurring. Ashley details how 350 SDRs operate as an army across 31 business functions, and advises hiring junior AEs before first SDRs. | |
| Why Founders Must Build the First Sales Playbook | 1 | 3 | 0 | 1 | Ashley explains why founders must be primary storytellers and build initial playbooks. She highlights hiring profiles like former recruiters and call center workers for phone confidence. | |
| The Three Core Traits for Interviewing SDRs | 2 | 4 | 1 | 3 | Harry challenges how to evaluate coachability when candidates always claim to be coachable. Ashley breaks down probing for specific past failures and implementation of feedback. | |
| Testing Organization and Structuring the Interview | 3 | 4 | 1 | 2 | Harry notes cultural nuances around declaring money motivation between the UK and US. Ashley outlines calendar blocking organizational traits and live role-play feedback tests. | |
| Evaluating Writing Skills via the Email Test | 5 | 3 | 2 | 5 | When Ashley expresses hesitation over candidates using AI on writing tests, Harry smartly counters that leveraging tools to get results shows resourcefulness. Ashley admits he makes a valid point. | |
| Bottom-Up Tooling Adoption and Clay | 4 | 6 | 3 | 6 | Harry pushes back directly on SDR compensation not being tied to closed revenue. Ashley provides a comprehensive masterclass comparing Brex's transactional model with SaaS ARR models and the trade-offs on demo volume. | |
| Evolving SDR Hiring: Pre- vs. Post-COVID Strategies | 2 | 4 | 2 | 4 | Harry asks whether candidates caught in tech layoffs are lower quality hires. Ashley corrects this assumption by explaining post-COVID tech rift dynamics and backchanneling techniques. | |
| Onboarding SDRs and the Two-Week Ramp | 1 | 4 | 0 | 1 | Ashley details her aggressive onboarding methodology of getting reps on phone calls by week two. She explains how ramping quotas incrementally build compounding muscle over four months. | |
| Setting Realistic Ramping Quotas and Pipeline Compounding | 3 | 5 | 2 | 5 | Harry challenges the low quota numbers during ramping, noting that one stage-two opp per week seems very low. Ashley defends the timeline by explaining sequence lag and conversion compounding science. | |
| Adjusting SDR Quotas Based on ACV and Unit Economics | 3 | 4 | 0 | 1 | Harry asks how ACVs adjust quota expectations. Ashley outlines CAC payback math and explains that input activity metrics reveal bad hires as early as month two. | |
| Managing Morale through Micro-Ambitions and Spiffs | 3 | 3 | 0 | 1 | Harry quotes Tim Minchin on micro-ambitions to frame short-term SDR goals. Ashley describes short-cycle spiffs, fast starts, and competitive call blitzes. | |
| SDR and Marketing Alignment: ABM and Creative Funnels | 5 | 3 | 1 | 4 | Harry argues as a marketer that content should drive sales and creatively pitches setting up ICP podcast interviews as an SDR lead funnel. Ashley praises the idea and playfully offers to hire him. | |
| Scaling Challenges and How Good SDRs Go Bad | 2 | 4 | 0 | 1 | Ashley details international scaling hurdles and explains how good SDRs go bad when they fail to analyze or overcome performance slumps. | |
| Leadership Growth and Managing Global Sales Cultures | 2 | 4 | 0 | 1 | Ashley reflects on her time management weaknesses across time zones. Harry asks about managing across cultures, and Ashley discusses learning Dublin's ground-level sales culture. | |
| Quick-Fire Round and Future of Sales Development | 3 | 3 | 2 | 3 | In the quick-fire round, Harry playfully tries to get Ashley to choose between her former and current bosses. Ashley refuses to pick and boldly predicts Chief Sales Development Officers will exist within ten years. |
Statements from this episode (52)
Kelly defines the SDR role as equal parts pipeline generation and career development
“SDR to me is just such a special Role that is, you know, both pipeline building, but also career development at the same time.”
The best account executives and sales leaders start as SDRs
“I would say the top AEs and best leaders that I've ever worked with have started their careers as sales development reps.”
One-third of Rippling SDR managers were promoted internally
“In fact, if you look at my org today, about a third of my SDR managers have actually come from the SDR role internally.”
Rippling employs over 200 outbound SDRs
“Outbound is definitely still a thing. I have over 200 of them that would definitely prove otherwise or prove what I'm saying accurate”
Outbound sales fail when teams replace fundamentals with shiny tools
“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 i…”
AI will eliminate SDR busywork to enable human personalization
“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 the little details that you have to pay attention to all day, every day. And that could be. Cleaning and scrubbing your accoun…”
Inbound SDR teams perform best when reporting to marketing
“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 you're thi…”
Outbound SDR teams are more successful reporting into sales
“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…”
Sales development will become GTM's standalone third pillar
“I think I actually am very bullish on sales development if you can't tell. And I think it's the third pillar within the go to market function. And I think that it can stand alone.”
Rippling places all inbound and outbound SDR teams under one org
“While I report into our CRO at Rippling, like 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 underneath my org”
SDR teams need strategic autonomy, not order-taker status
“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.”
Rippling's SDR org supports 31 business functions
“We support about 31 different functions across the business.”
SDR Cross-Selling Works from a CAC Payback Perspective for Multi-Product SaaS
“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 C…”
Startups should hire a junior AE as their first sales rep
“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.”
A company's first sales hire shouldn't be fresh out of college
“I do think your first hire should be someone like not fresh out of college and definitely not their first SDR role.”
Founders must be primary sellers and storytellers early on
“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 …”
Former recruiters make the best tech sales development representatives
“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 marke…”
Cold calling is the hardest SDR skill
“I'd say the hardest part about SDR 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 th…”
SDR interviewing requires evaluating traits, not past sales performance
“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 y…”
Citing a parent's advice is the worst SDR interview answer
“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.”
US sales candidates freely admit to being money motivated
“I think that's a UK or a European thing. I think in the States hiring, like, absolutely people have no problem saying that they are money motivated.”
Repeating interview role-plays with feedback tests candidate coachability
“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?”
Relevancy in interview email tests predicts SDR success
“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, is a Good sign that they will be a good SDR.”
SDR candidates using AI in writing tests demonstrates resourcefulness
“Maybe it doesn't matter and they're being resourceful and they're using tools that you know, that, that are gonna make them a better SDR.”
Sales leaders should rely on SDRs to discover software tools
“One thing about tools in general with my SDR is like, I usually rely very heavily on them because they are the ones that 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 …”
Rippling recently started using Clay for outbound personalization
“We just started using clay to help with personalization.”
Rippling uses a 70% base and 30% variable SDR compensation model
“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.”
Rippling SDRs only receive quota credit when AEs advance deals
“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 step…”
Brex tripled SDR revenue in six months by compensating reps on revenue
“When it worked at Brex, we were able to three X the referring revenue that SDR has brought in within six months.”
Brex saw Stage 2 leads collapse after tying SDR compensation to revenue
“The other thing at Brex is once, once we started copying them on revenue, the S two is absolutely tanked.”
SDR teams are typically among the first departments cut during layoffs
“There's one of the first orgs to go typically is SDR.”
Rippling now hires experienced SDRs due to post-layoff talent availability
“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.”
Ashley Kelly Hired Zenefits SDRs After Only 30-Minute Phone Screens
“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.”
Ashley Kelly puts new SDRs on the phone by week two
“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.”
Ashley Kelly ramps SDRs over four months with progressive quotas
“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.”
Rippling sets fully ramped SDR quota at eight S2 opportunities monthly
“A full month's quota, if they're fully ramped is eight S twos 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.”
Outbound sales sequences take two weeks on average to become effective
“When you start working account or contact on average, it takes about two weeks for a sequence to start actually being effective.”
Bad SDR hires are identified by month two via input KPIs
“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 KPIs that come before that. So how many calls are they making a day? How many emails? We expect a certain amount of accounts and cont…”
Proactive SDRs who reach out to VPs early become top performers
“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 car…”
SDRs far behind target on day 22 can still reach monthly quota
“I could have a rep right now at the 22nd and they do not, 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.”
Rippling uses fast-start spiffs requiring 50% quota in week one
“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.”
Marketing and content alone should drive sales to contract signing
“I think marketing and content should sell you entirely to contract signing, if done well.”
SDRs should host podcasts interviewing target buyer personas to generate leads
“You choose your ICP. Start a podcast interviewing the world's biggest and best in that ICP. If I worked for you, this is what I'd do. You'd give me a segment. I'll start a podcast interviewing the biggest, I don't know, CHROs in software companies between 505,…”
In-person events are highly effective for selling to HR leaders
“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.”
Rippling offers lateral career transitions outside sales for high-performing SDRs
“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, you know, if you're a good contributor to the team, you're positive, at least performing the best that you can, like we wil…”
Imposing U.S. sales playbooks on international teams never works
“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 it's never going to work, and so building that trust and understanding that the different cultural differences is super importa…”
SDRs should start in inbound roles for six months
“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.”
In-office SDRs significantly outperform remote peers, says Ashley Kelly
“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.”
New SDRs should copy top performers completely before trying to innovate
“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 times people come in trying to reinvent the w…”
Expecting SDRs to heavily qualify leads at target accounts is bad practice
“Actually, so there's one where AE's pushed back a lot saying that they, the SDR needs to go do more qualification and needs to go you know, warm the deal up more for them. And I think To me, that's BS because if I'm a good AD, I want to take any conversation t…”