Ashley Kelly
VP of Global Sales Development, Rippling. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
executiveoperatorfounderLinkedIn ↗rippling.com ↗
Ashley Kelly leads outbound sales development strategy and rep hiring as Vice President of Global Sales Development at Rippling. She is best known for helping scale Brex's outbound ARR from $2 million to over $300 million and managing hundreds of SDRs across Zenefits, Lever, and Brex.
Everything Ashley Kelly said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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.”
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.”
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.”
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.”
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.”
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.”
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…”
Ashley Kelly predicts sales development will reach C-suite status by 2034
“I will be a Chief Sales Development Officer. I think that sales development will sit at the executive level within 10 years.”
Kelly: Shifting SDR quotas to closed revenue tripled Brex's SDR-sourced revenue
“We more than three X what the SDR org was sourcing previously when they were on an S two quota.”
Enterprise startups with long sales cycles should avoid SDR revenue quotas
“I think when you're at a more enterprise company and it takes six to nine months for a deal to close, it's really hard to put SDRs on a revenue quota because they're really only in the role for nine months to a year and a half.”
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.”
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…”
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.”
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…”
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…”
The other half of the tape: Ashley Kelly's own voice is left out of every number here. Other people bring the name up 13 times in 5 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Matt Plank 7Sam Blond 3Jason Lemkin 2Harry Stebbings 1
Statements about Ashley Kelly, by other people (1)
Every mention by year
tap a year for its mentions
the Official SaaStr Podcast 7
20VC 6
2024 10 mentions in 3 episodes 3 per episode
- Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
- The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale with Rippling CRO Matt Plank
- Advice Every SaaS Founder Needs to Know to Scale to $100m with Sam Blond and Jason Lemkin
- every mention in 2024, scene by scene →
2023 2 mentions in 1 episode
2021 1 mention in 1 episode
One line per show, most statements first. The link opens Ashley's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | VP of Global Sales Development, Rippling | 1 | 50 | — | full record on 20VC → |
| SAASTRLEDGER | VP of Global Sales Development, Rippling | 1 | 7 | — | full record on the Official SaaStr Podcast → |