Aug 15, 2023 · 57m · saastr
10 Things Top CROs Wish They Knew Early in Our Careers with CRO Justworks
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Justworks Chief Revenue Officer Robert Lopez and seasoned sales executive Brendan Cassidy share ten foundational revenue leadership lessons and answer audience questions on scaling SaaS go-to-market motions, recruiting elite talent, optimizing RevOps, and sustaining unit economics.
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 7.4 Guest teaching 0.1 Guest disagreement 0.5 Jason pushing back 0.2
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:32 Cassidy reframing rep appetite for feedback
Cassidy pushes back slightly when Lopez asserts top performers crave hard feedback, clarifying that while they might not like or crave it, they step up the most.
Hardest push from Jason ▶ 19:49 Lopez on rejecting fictitious executive hiring modelsLopez pushes back against passive agreement in leadership, insisting sales leaders must challenge unrealistic tops-down financial models created by first-time CFOs.
Biggest teaching moment ▶ 13:43 Lopez educating on the ideal RevOps candidate profileLopez explains the unique advantage of sourcing RevOps from analytical former sales reps, offering a hiring framework that Cassidy admits he had never heard articulated before.
Jason holds their own ▶ 29:58 Cassidy on risk-averse executive due diligenceCassidy leverages deep executive experience to explain why elite CROs start candidate diligence from a position of 'no' and how founders misjudge sales recruitment.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Tip 1: Always Be Recruiting (ABR) | 7 | 0 | 0 | 0 | Robert Lopez introduces the concept of 'Always Be Recruiting' with practical tactical advice from Justworks' early days. Brendan Cassidy builds on this smoothly, affirming that leadership recruiting is a multi-year discipline. | |
| Tip 2: Building a Diversified Demand Generation Strategy | 8 | 0 | 1 | 0 | Lopez warns against over-relying on inbound marketing, advocating for multi-channel diversification including partner channels. Cassidy strongly reinforces the risk of single-threaded demand generation. | |
| Tip 3: Payback Period and True Customer Acquisition Cost | 7 | 0 | 0 | 0 | Lopez emphasizes factoring hidden costs into CAC and cohort-based payback calculation. Cassidy adds context on the escalating costs of outbound SDR models. | |
| Tip 4: Investing Early in Revenue Operations Infrastructure | 8 | 1 | 0 | 0 | Lopez makes the case for hiring RevOps extremely early, advocating for hiring former reps with analytical backgrounds. Cassidy strongly endorses this specific profile as high-value and uncommon advice. | |
| Tip 5: Long-Term Incentives and Book of Business Compensation | 6 | 0 | 1 | 0 | Lopez presents a controversial model of compensating reps on a cumulative net book of business to ensure retention and quality deals. Cassidy completely agrees with the incentive structure. | |
| Tip 6: Replacing 'Can't' with Solutions in Early-Stage Leadership | 7 | 0 | 1 | 1 | Cassidy details why sales leaders must eliminate 'can't' and bring concrete solutions to founders. Lopez provides nuance by highlighting the necessity of pushing back against unrealistic rep-driven financial models. | |
| Tip 7: Maintaining Professional Boundaries and Accountability | 7 | 0 | 2 | 1 | Cassidy explains the necessity of maintaining professional boundaries and holding reps accountable. Cassidy gently adjusts Lopez's phrasing that reps 'crave' rough feedback, noting instead that they step up. | |
| Tip 9: Prioritizing Raw Talent Over Brand Resumes | 8 | 0 | 0 | 0 | Cassidy argues that pedigreed resumes often fail in early-stage startups where grit and raw drive are needed. Lopez shares a case study of hiring a relentless former stockbroker who succeeded without prior SaaS background. | |
| Tip 10: Conducting Thorough Startup Due Diligence | 8 | 0 | 0 | 0 | Cassidy details how top sales leaders perform rigorous diligence starting from 'no' before taking startup roles. Lopez and Cassidy discuss how the startup sales community cross-checks founder claims. | |
| Audience Q&A: GTM Evolution and Product-Market Fit Signals | 7 | 0 | 0 | 0 | Audience member Wen asks about Justworks' GTM evolution and product-market fit signals. Lopez and Cassidy explain ICP geographic focus and leveraging landmark referenceable logos like Trello. | |
| Audience Q&A: Executive Hiring Sequence and PLG Integration | 8 | 0 | 1 | 0 | Audience member Ryan asks about executive sequencing beyond the sales leader. Cassidy insists on hiring a demand-generation-focused marketing leader, while Lopez highlights pairing sales-led and product-led growth. | |
| Audience Q&A: RevOps Pipeline Stages and Channel Strategy | 8 | 0 | 0 | 0 | Audience member Rahul inquires about RevOps pipeline stages and CS channel involvement. Lopez details defining binary stage criteria and managing CS-driven referral loops rather than complex channel distribution. |
Statements from this episode (22)
Cassidy: Justworks has an imminent IPO coming
“I mean, obviously Robert's got an IPO, imminent IPO at some level for JustWorks coming.”
Lopez: Direct executive outreach to candidates carries far more weight than recruiters
“The power it holds when like a founder, a CO, CO, RCRO, like reaches out directly to a candidate just holds so much more weight.”
Cassidy: VPs of Sales must know their initial hires before accepting jobs
“If you're a VP of sales and a, you know, you go to a startup or a growth company, you should have a good idea about who the people that you want to hire before you actually take the job. And if you don't, then you probably did something wrong.”
Lopez: Channel strategy requires a multi-year investment to see returns
“The challenge of channel is it takes a really long time to pay off. And so it's like a multi-year investment and, but it's just something that's like tough to see the return early on.”
Cassidy: Startups cannot scale on single-threaded top-of-funnel GTM strategies
“You're not going to get where you want to go on the backs of, you know, sort of a single threaded go to market strategy or top of the funnel strategy.”
Lopez: SEM and SEO only work today for high-value products
“And the SEM SEO game is like become so expensive to make it, unless you have a really high value product and you can spend the amount of money.”
Cassidy: Outbound SDRs cost $1,000 to $2,000 per qualified meeting
“And if somebody told me, I'm not sure how accurate is, but it seems accurate, you know, on average, like with an outbound SDR, it's like basically like a thousand, you know, somewhere between a 1002 thousand dollars cost per sort of qualified meeting.”
Lopez: Hired sales ops specialist as fourth team member
“I hired my first three reps and like the fourth hire I made was a sales ops person.”
Lopez: The best RevOps hires are analytical former sales reps
“Some of the best folks are people who maybe sat in a seat and they were a rep. Right. But they have an analytical mind and like maybe they, you know, studied economics or math or something like that.”
Lopez: Justworks pays tenured sales reps a percentage of their customer book
“And so we implemented these mechanisms where as a wrap, you can, after certain tenure thresholds, you can start making a percentage on your book, net of expansion, net of turn.”
Lopez: Push back on fictitious rep-driven models from first-time CFOs
“It's like the fictitious rep driven financial model that first time CFO like builds. I was like, oh, if you hire 50 reps, like you're gonna be good. And that's where you need to push back. Right. And it's like, how do you build like a bottoms up driven model, …”
Cassidy: Do not shy away from hiring highly ambitious AEs
“Some people shy away from that because they think it'll sort of drive, have them sort of unfocused off of like, well, I don't want somebody dreaming about being a VP of sales when they're an account executive today. But in my experience people with that kind o…”
Cassidy: 90% of first startup VPs of Sales turnover within 12 months
“I think there's some statistic that like, 90 plus percent of first VPs of sales hired at a startup turnover inside of 12 months or less than 12 months.”
Lopez: Startups do not need sales hires with prior software experience
“Sometimes when I see companies like, oh, we need software experience. It's like, you don't need software experience. You need somebody that, like, has the ambition and the drive and the will, and like, you can train. It's your responsibility as a VP of sales t…”
Cassidy: Top VPs of Sales and CROs are tremendously risk-averse
“The most in-demand people, VPs of sales and CROs are tremendously risk averse. Most people don't understand this, right? They're not gonna put their, lean their chin out for you, most likely. And so they're gonna do their due diligence really starting at no, r…”
Lopez: Justworks expanded geographically only after achieving market-level profitability
“And then we would start looking at geo and we would have these like markets that once they became profitable, Then we would go to our next market, right? And so we would look at it at a market by market profitability level, and that's how we would double down.”
Lopez: Early customer logos must be recognizable brands respected by ICPs
“Yeah, but I think it's like specifically logos that your ICP knows and respects, right? Because like, oh, if they're using this product, then like, oh, it's pretty good. There's like those proof points where it's not just some company that nobody knows and lik…”
Cassidy: Startups should hire a demand-gen leader before a sales leader
“I would say most companies are probably higher, like a marketing leader, right? Like, you know, before sales leader, I mean, obviously in a startup, being able to hire a marketing leader, that's, that is an expert in driving sort of like top of the funnel, rig…”
Lopez: Very few software products can succeed on PLG alone
“Cause everyone talks about product-led growth, sales-led growth. Like, I believe like you gotta have a marriage between the two, like very few products can exceptionally execute. Like PLG well, but like if you have the two that are married, like some buyers, l…”
Lopez: Sales pipeline stages must be binary customer actions, not rep opinions
“I think that, I mean, one of the things that I think a lot of companies fail at is like, they have their, like, they build their stages and their stages are kind of like rep dependent. So it's like, oh, like a rep says, oh, I'm interested the next stage. It's …”
Cassidy: Startups should hire dedicated partner roles earlier to diversify demand
“I definitely think leaning into the partner, A partner sort of specific role earlier is like sort of a reality now. It's a smart thing to do because, you know, everyone's looking for, you know, a way to diversify, like I think Robert talked about, or diversify…”