Dec 15, 2022 · 30m · saastr
SaaStr CRO Confidential: Founders Fund Partner Sam Blond + Rippling VP Sales Matt Plank
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of SaaStr CRO Confidential, Founders Fund Partner Sam Blond interviews Rippling VP of Sales Matt Plank to examine the foundational go-to-market strategies, outbound tactics, and distribution playbooks that scaled Rippling from an early basement startup to a multi-billion-dollar enterprise.
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 7.2 Guest teaching 6.2 Guest disagreement 1.0 Jason pushing back 1.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:40 Rejecting generic all-in-one HR pitch framing
Matt forcefully notes that emailing buyers with standard HR and payroll messaging was completely useless and that only attacking IT provisioning generated responses.
Hardest push from Jason ▶ 5:02 Challenging standard sales hiring orthodoxySam points out the contrarian nature of hiring a VP of Sales as employee number five instead of the standard SaaS playbook of hiring two individual contributors first.
Biggest teaching moment ▶ 26:25 Building US outbound sales reps in BangaloreMatt educates Sam on Rippling's unconventional move of building a high-efficiency 15-person sales pod in Bangalore to close US-based SMB accounts.
Jason holds their own ▶ 22:15 Detailed playbook on multi-site scaling at ZenefitsSam demonstrates deep operator expertise by detailing how he and Parker restructured go-to-market targets from ten to twenty million ARR by aggressively launching secondary geographic hubs.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Rippling's Founding Vision and Basement Origins | 6 | 5 | 1 | 1 | Sam Blond contextualizes Rippling's entry into a crowded HCM market against their shared Zenefits history. Matt Plank explains Rippling's core value proposition as an employee system of record combining HCM and IT capabilities out of Parker Conrad's basement. | |
| Building the Outbound Engine from Ground Zero | 7 | 6 | 1 | 1 | Sam highlights the unconventional path of hiring a VP of Sales as employee number five rather than initial individual contributors. Matt details the scrappy early sales mechanics, from building lead lists and taking over Parker's script to setting up Outreach and Salesforce. | |
| Crafting High-Converting Cold Outreach Around IT Pain | 7 | 7 | 1 | 1 | Matt explains how focusing cold outreach on greenfield IT provisioning pains yielded high response rates compared to generic HR pitches. Sam connects this to high-converting sales methodology that hones in on distinct product differentiation. | |
| Developing Strategic Broker and Accounting Channels | 8 | 6 | 1 | 1 | Matt contrasts Rippling's early broker and accountant strategy with Zenefits' anti-channel posture, explaining how indirect influence later closes direct deals. Sam reciprocates with deep tactical examples from scaling Brex partnerships like First Republic Bank and Y Combinator. | |
| Scaling Sales Capacity and Preserving Demo Volume | 8 | 6 | 1 | 1 | Matt describes capacity planning focused on demo volume, avoiding premature headcount growth, and overcoming email deliverability challenges. Sam provides an extended anecdote detailing how late-night whiteboard goal-setting with Parker led to opening a Phoenix sales office to scale Zenefits to twenty million ARR. | |
| Unconventional Growth Levers: Pricing and Bangalore Sales | 7 | 7 | 1 | 1 | Matt breaks down non-traditional scaling mechanisms, including removing public pricing to test elasticity, cross-selling multi-product SKUs, and setting up an SMB sales pod in Bangalore. Sam synthesizes the unit economic benefits of pricing leverage and international sales offices. |
Statements from this episode (14)
Blond: Rippling was valued at over $11 billion in May 2022
“It's a company that is now valued at something like over eleven billion dollars. That was a valuation as of, like, May of this year, so this is like a fairly current valuation after a lot of the correction.”
Blond: Rippling reached hundreds of millions in ARR by late 2022
“The revenue growth, hundreds of millions of dollars of ARR and so much more, but I know that it was a lot of really hard work to get to where we are today and probably a lot of hard work left as well.”
Early Rippling had no paying customers, selling exclusively to YC startups
“And so at that point we were really just selling to YC companies. Like we had come out of the recent winter batch. And so that was really what our top of funnel was selling to other YC companies in the batch. And we were really starting from zero. I mean, we h…”
Parker Conrad hustled a free Outreach seat for early Rippling
“Parker actually convinced Riley, who was, had moved over from Zenefits to Outreach to give us, like, a free seat in the early days which was a great play because we became a big customer of theirs.”
Rippling unlocked early outbound by pitching IT automation instead of HR
“And so what, the way that we kind of described what we did to people was we basically wrote an email that was something along the lines of like, look, I'm sure that you have like you know, an automated process for like onboarding employees and managing HR and …”
Software provisioning per new hire surged from 2-3 to 20-50 accounts
“If you think back to 10 years ago when you hired a sales rep, it was like maybe two to three accounts you would set up for them. It was like, here's your email and here's your, you know, video conference tool. And today when you hire a sales rep, there are pro…”
Plank: Gusto generated huge early revenue through accounting channel partnerships
“We never had accountant partnerships when all of our competitors like Gusto, you know, had an enormous amount of their revenue in the early days came from the accounting channel.”
Plank: Expecting immediate measurable results ruins channel sales strategies
“I think one of the things that I think people make the mistake that people make or one mistake people make in channel is they expect, like they expect immediate results and they expect to be able to measure the impact of the channel, like incredibly directly. …”
Rippling schedules demos directly for reps rather than requiring self-sourcing
“I was always a big believer in, and really still to this day, like we put demos on reps calendars. We did not hire reps to be like, go out and, you know, kind of build your own pipeline.”
Blond: Zenefits started 2014 at $500K ARR targeting $10M
“Four months into Zenefits we were in 2014, our target was ten million in ARR. We started 20 14 about 500,000 of ARR.”
Zenefits doubled its 2014 revenue target to $20M ARR and hit it
“We changed the revenue target to twenty million. Like two days later, Parker couldn't keep the secret and we hit it.”
Rippling repeatedly raised early prices and removed pricing from its website
“We increased our pricing like multiple times in the early days pretty dramatically. And we, and when we did it, we actually removed it from our website as well.”
Rippling doubled revenue per customer with zero drop in win rates
“We increased pricing pretty dramatically and nothing changed. Like the wind rates didn't go down at all. You know, we just started making two, three times more per customer.”
Rippling built a Bangalore-based sales team to efficiently target US SMBs
“We built a sales team that we have today based out of Bangalore that today I think is like 15, 16 people, a director, a couple of managers. And those folks are like incredibly efficient from how, you know, compared to kind of how much revenue they close.”