Apr 5, 2023 · 56m · saastr
CRO Confidential: Guild Education SVP, Go To Market Strategy, Operations & Enablement Cherishma Shah
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In this episode of CRO Confidential, host Sam Blonde and Guild Education SVP Cherishma Shah break down the core pillars, organizational design, hiring strategies, and execution frameworks needed to build a high-impact Revenue Operations function.
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 5.7 Guest teaching 3.6 Guest disagreement 0.1 Jason pushing back 0.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:01 Nuancing the default to systems hiring
Cherishma pushes back on Sam's assumption that early startups should always hire a systems-first operator, warning against copying what other companies do without deliberate intent.
Hardest push from Jason ▶ 17:46 Defending tactical systems prioritySam asserts that immediate startup pain points almost always demand technical systems fixes first before strategic partnership can be leveraged.
Biggest teaching moment ▶ 26:13 Why generalist operators outperform domain expertsCherishma educates listeners on why hiring for exact industry or customer profile fit is a mistake in RevOps compared to hiring generalists who understand cross-functional dependencies.
Jason holds their own ▶ 52:33 Algorithmic lead scoring case studySam demonstrates deep domain mastery by explaining the exact mechanics of how Brex automated rep workflows and hustle scoring to eliminate variance and 3x deal sizes.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Career Journey and Core Operator Capabilities | 5 | 3 | 0 | 0 | Sam Blond opens the episode establishing his own background moving up through sales roles and explaining why sales leaders often lack operational skills. Cherishma outlines her transition from architecture and consulting into Go-to-Market operations. | |
| Defining Revenue Operations and Its Core Pillars | 5 | 4 | 0 | 0 | Cherishma defines revenue operations across the entire lifecycle beyond traditional siloed sales ops. Sam demonstrates expertise by summarizing her pillars into systems, process, data-driven strategy, and enablement. | |
| Timing the First Operations Hire and Strategic Partnership | 6 | 4 | 1 | 1 | Sam shares benchmarks from Zenefits and Brex on hiring the first ops person at 2-8 reps and arguing for indexing on systems first. Cherishma gently nuances this view, urging leaders to be intentional about bringing in strategic thought partners early rather than defaulting to tactical systems builders. | |
| Hiring Profiles, Generalist Skillsets, and Common Pitfalls | 5 | 4 | 0 | 0 | Cherishma outlines why generalist profiles with cross-functional dot-connecting skills outperform exact industry matches. Sam validates this with examples of successful hires from non-startup backgrounds. | |
| Organizational Placement and Cross-Functional Embedding | 6 | 3 | 0 | 0 | Sam discusses his personal evolution from resisting sales ops at EchoSign and early Zenefits to mandating it as a core partner at Brex. Cherishma emphasizes that whether ops reports to the CFO or CRO, the team must be deeply embedded with functional teams as peers. | |
| Scaling RevOps, Team Structuring, and Operational Focus | 6 | 4 | 0 | 0 | Cherishma details headcount ratios versus jobs-to-be-done sizing and structuring the team into dedicated functional business partners alongside centralized specialist pods. Sam illustrates how this model successfully scaled at Brex. | |
| Measuring Operational Impact and Transformational Case Studies | 7 | 3 | 0 | 0 | Cherishma details measuring impact through clear milestone objectives and balancing execution with test-and-learn mentalities. Sam delivers an extensive masterclass on building automated lead scoring and hustle scores at Brex to triple average deal size. |
Statements from this episode (11)
Shah: RevOps differs from sales ops by spanning the entire customer journey
“That said, I think it's also important to call out that this is incremental to what is, what a traditional sales ops or marketing ops function looks like because revenue operations essentially touches multiple functions across the sales cycle, right? All the w…”
Shah: Enablement is an integral part of revenue operations
“And then finally, I would be remiss not to mention enablement. And this is something that I have seen come in and out of sometimes like a rev ops function. However, I believe enablement is an integral part of revenue operations. Because it has not just like th…”
Blond: Zenefits waited far too long to hire a sales operations leader
“At Zenefits, I pushed off hiring anyone in this function for too long. I didn't have an appreciation for it.”
Blond: Startups should hire their first RevOps leader at 2-8 sales reps
“The company is two to eight sales reps, which is maybe the range with which I would suggest making this higher, you know, any, anywhere between two and eight.”
Shah: Delaying a RevOps hire makes fixing processes far more costly
“Oftentimes what happens is when certain things get embedded in the org, changing them becomes much harder, right? And also not just an intensive, right? Resource intensive, right?”
Shah: The strongest RevOps hires are generalists, not domain specialists
“The strongest people I have seen in this role, even people who eventually become go deep in systems or enablement are generalists.”
Blond: EchoSign had zero sales ops staff at its Adobe acquisition
“And echo sign, we were like, ah, gosh, a hundred to a 150 employees or thereabouts when Adobe acquired us. And we didn't have anyone in sales ops.”
Shah: Validate sales processes manually before codifying them into software tools
“Oftentimes what you want to do is make sure you have the right process Before you put it in the system, right? Like you need to define the sales methodology before you put it in the system. You need to define like, and so what you will likely do is you will do…”
Blond: Brex boosted revenue by tying SDR compensation to revenue generated
“At Brex when we shifted the comp plan for SDR from like opportunities created to revenue generated, and the output of that was a lot more revenue”
Blond: Brex saw a 3x deal size jump from automated lead scoring
“I think the like biggest data point that we could point to was something like a three X increase in the average opportunity size, because people were going after the opportunities that generated the most, most revenue for the business in a very automated way.”