Jan 4, 2024 · 43m · saastr
From Zero to Hero: How to Dominate Outbound SaaS Sales with Rippling and Sam Blond
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In this episode of CRO Confidential, host Sam Blond and Rippling VP of SDR Ashley Kelly break down proven strategies for hiring, structuring, compensating, and scaling high-performing outbound sales development teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 7.3 Guest teaching 2.0 Guest disagreement 0.3 Jason pushing back 0.7
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 33:21 Ashley caveats Sam's revenue-metric enthusiasm
Ashley gently pushes back on universally applying revenue-tied SDR quotas, noting enterprise deal cycles make it impractical due to 6-9 month closing timelines.
Hardest push from Jason ▶ 8:31 Ashley clarifies the director-level player-coach requirementAshley immediately reframes Sam's comment about her director-level title, pointing out she was actively cold-calling and building the sequences herself in the early days.
Biggest teaching moment ▶ 11:30 Ashley details non-traditional candidate sourcing profilesAshley educates the audience on why non-tech agency recruiters make superior early SDR hires due to preexisting cold outbound skills.
Jason holds their own ▶ 37:22 Sam details the Zenefits TAM degradation collapseSam demonstrates deep domain authority by illustrating how overhiring SDRs degrades conversion rates across an entire sales floor once reps stray from core TAM.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Tactical Early-Stage Outbound Playbook at Brex | 8 | 0 | 0 | 0 | Sam opens with an extended, detailed monologue breaking down Brex's early outbound strategy, including first-degree LinkedIn targeting, YC network leverage, champagne gifting campaigns, and San Francisco billboard placements before posing the first question to Ashley. | |
| Identifying and Sourcing High-Potential SDR Profiles | 7 | 3 | 1 | 1 | Ashley elaborates on targeting collegiate athletes, state school graduates, and previous agency recruiters for entry-level SDR roles. Sam reinforces her framework by categorizing the traits and synthesizing actionable takeaways for early-stage founders. | |
| Interviewing Methodologies and Assessing SDR Motivation | 6 | 2 | 0 | 1 | Ashley describes her candidate scorecard and core interview question ('Do you love to win or hate to lose?'). Sam validates her approach and adds nuance regarding career trajectory clarity as a key hiring signal. | |
| Establishing SDR Daily Structure and Playbooks | 7 | 2 | 0 | 1 | Ashley highlights the difference between micromanagement and structured time-blocking, warning against vanity activity quotas. Sam extends her point by advising founders to always hire two SDRs simultaneously to pressure-test processes. | |
| Transitioning SDR Performance Metrics to Closed Revenue | 8 | 3 | 1 | 1 | Sam and Ashley review the evolution of quota metrics from top-of-funnel SQOs to closed revenue at Brex. Ashley adds nuance by pointing out that revenue quotas only function smoothly when deal cycles are short (sub-30 days) rather than long enterprise cycles. | |
| Scaling SDR Capacity, Ratios, and TAM Constraints | 8 | 2 | 0 | 0 | Ashley outlines SDR-to-manager ratios (8:1) and penetration benchmarks before Sam shares a cautionary case study from Zenefits about exhausting core TAM when attempting to hire 300 SDRs in a single summer. |
Statements from this episode (15)
Brex scaled from $2M to over $300M ARR during Kelly's tenure
“Where she was able to scale the business from about two million in ARR is where Ashley joined and left it like three hundred million plus in ARR.”
Blond: 80% of Brex's revenue came from outbound sales
“About 80% of Brex's revenue came from sales outbound.”
Start outbound sales using existing networks, not cold email tools
“You do not want to start with purchasing a sequencing tool, purchasing a system that gives you contact information and blasting your ICP. I've talked about this before, but you really want to start with who you are targeting being in your own network.”
Blond: Billboards significantly increase outbound email reply rates
“The probability of people replying to an email after they had seen our billboards and knew what we did Was significantly higher than the probability of somebody who has no idea who we are or what we do replying to an email that they received.”
Kelly: Recruiters make ideal early SDR hires due to transferable skills
“And then I would say also, if you're not just hiring directly from college, if you're actually getting people that have some work experience, which I highly recommend, especially for first time hires, if you don't have systems and process in place, I've had a …”
Kelly: Candidates who drive the interview make better outbound SDRs
“If they're driving the conversation and driving more of the interview in such a junior role, if they're able to do that, like more times than not, I have a lot of faith that they'll be able to do that when talking to prospects on the phone.”
Kelly: Arbitrary SDR dial quotas lead to box-checking behavior
“If you tell a rep to make 70 dials,
Guess what they're going to make?
70 and have a very hard stop at 70.
And so eliminating like the, what I'll call this like checking the box type of activities throughout the day and like truly getting to a point where you h…”
Blond: Rippling currently generates several hundred million in ARR
“Rippling today is several hundred million dollars in AR.”
Always hire two SDRs initially to accelerate learning and benchmarking
“When you do hire your first SDR, hire two because they will be able to share learnings with one another and really accelerate the time to effectiveness because they're trying and failing, they're trying and succeeding, and then they can share both the failures…”
Top-of-funnel SDR quotas drive quantity while down-funnel quotas drive quality
“The way that I think about this is the further up the funnel you go, which sales qualified opportunity is towards the top, what you are solving for is more quantity over quality. And the further down the funnel you make the SDR performance measurement, like wh…”
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.”
Kelly: Rippling maintains an eight-to-one SDR-to-manager ratio for better coaching
“We actually are very conservative with the number of reps that report to managers, and that really helps from, like, a day-to-day coaching perspective, especially in this, like, remote environment. When managers have a little bit more bandwidth to help coach t…”
Blond: Rapidly scaling SDRs at Zenefits tanked performance of existing reps
“When we added all of these new SDRs into the mix, not only were they less effective than the more tenured existing reps, they actually made the existing reps far less successful because we had to tap into this TAM base that people were less likely to convert.”