Jan 3, 2023 · 37m · saastr
SaaStr CRO Confidential:Hiring a Great VP of Sales Today Sam Blond + Former Lattice CRO Dini Mehta
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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 CRO Confidential, host Sam Blond and former Lattice CRO Dini Mehta examine the critical strategies for hiring high-impact sales leaders while providing an actionable career progression playbook for sales professionals aspiring to executive leadership.
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 1.0 Jason pushing back 1.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:30 Challenging the domain expertise requirement
Dini reframes conventional hiring biases by arguing that domain ignorance actually fuels creativity and innovation over recycled playbooks.
Hardest push from Jason ▶ 5:30 Dismissing big-company startup unit excusesSam flatly rejects founder rationalizations about hiring leaders who merely ran internal business units at massive incumbents like Salesforce.
Biggest teaching moment ▶ 29:40 Deconstructing management readiness metricsDini educates listeners on why raw top-performer quota attainment is insufficient for leadership without consistency and peer perception.
Jason holds their own ▶ 17:15 Laying out the hypergrowth sourcing playbookSam demonstrates deep operator expertise by detailing his exact systematic framework for sourcing high-performing sales directors from top-tier startups.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| The Macro Landscape and Surge in Sales Leadership Hiring | 7 | 3 | 1 | 1 | Sam outlines a clear framework of common hiring traps including domain experience fixations and misjudging company scale. Dini reinforces these insights with observations on resume logo pattern-matching. | |
| Evaluating Sales Leaders: Functional Fit and Values Alignment | 4 | 5 | 1 | 1 | Dini explains how founders should balance functional requirements with operating style and cultural alignment. Sam actively listens and prompts deeper exploration into candidate evaluation. | |
| Structuring Go-to-Market Milestones and Strategic Success Criteria | 5 | 5 | 1 | 1 | Sam asks for granular definitions of success criteria beyond top-line revenue targets. Dini responds with clear operational milestones like geographic segmentation and multi-product transitions. | |
| Candidate Sourcing: The Hypergrowth Startup Playbook | 8 | 1 | 1 | 1 | Sam shares his personal sourcing playbook, outlining a spreadsheet method to target directors who scaled rapidly inside top unicorn startups like Zenefits and Rippling. | |
| Dini Mehta's Unconventional Career Journey to CRO | 3 | 4 | 1 | 1 | Dini shares her career progression from non-sales roles to Quantcast, Drawbridge, and Lattice. Sam listens attentively, drawing parallels to shared midwestern roots. | |
| Career Advice for Sales Reps: 18-Month Increments and Promotion Criteria | 5 | 6 | 1 | 1 | Dini articulates her 18-month career increment strategy and breaks down three promotion pillars: consistency, peer perception, and coaching adaptability. Sam acknowledges the depth of her process. | |
| Sam Blond's Framework for Sales Career Progression | 8 | 1 | 1 | 1 | Sam delivers a masterclass on career progression based on his leadership at Brex, emphasizing company quality over OTE, effort and attitude, and aiming for top leaderboard rank. |
Statements from this episode (11)
Blond: Startups are seeking sales leaders despite early 2023 macro layoffs
“And one thing that is counterintuitive in this environment of layoffs and slow to hiring is that I'm actually seeing more companies looking for a sales leader.”
Blond: Startups should not prioritize domain experience when hiring sales leaders
“There are only so many really amazing sales leaders that exist to begin with. And if you limit your candidate population to a very small domain, like let's just say property tech or something like that, how many unbelievable property tech sales leaders are the…”
Blond: Founders must prove success with individual contributors before hiring VPs
“The more, Common path here is hire a couple individual contributors, make them successful, then hire a sales leader to scale the team.”
Mehta: Enterprise sales leaders face a massive adjustment at SMB startups
“If you are an SMB business hiring for someone that's done multi-million dollar deals at great startups, it's gonna be a huge adjustment. Can it be done? Sure. But that's not the most natural path.”
Mehta: Early startups should hire second-in-command leaders over seasoned VPs
“Someone that's seen it, seen the journey from the early, early millions to hundreds of millions, but they weren't in the seat. They were close to the seat. They were the second in command or third in command. And so is that level the one you want or is it, you…”
Blond: Zenefits AEs became revenue leaders for Rippling, Gong, and TripActions
“Zenefits alone produced as starting as AEs, the head of revenue at Rippling, the head of revenue at Gong, the head of revenue at Modern Health, the former head of revenue at TripActions, like all of these came out of Zenefits alone”
Blond: Hiring promoted leaders from hypergrowth startups yields zero hiring misses
“I'm not aware of a single miss I, I've seen tons of misses on, we hired from a big company. I haven't seen a single miss where we hired from the hottest tech startup of the sort of last generation. We hired somebody that grew their career there to come in and …”
Mehta: Lattice had 800 customers and 30 employees in 2018
“I joined, you know, we were 800 customers, single digit in revenue, 30 folks, In 2018”
Mehta: Lattice promoted 40 percent of its sales management team internally
“40% of my management team at Lattice was promoted from within.”
Blond: Early-career sales reps should optimize for company quality over OTE
“First is, like, solve for the quality of company and not OTE especially earlier in your career.”
Blond: Hitting sales quota just places reps in the top 70 percent
“Philosophically, the advice that I give to folks is you want 70% of the team over quota. And so if you're defining your success by being your by being over quota, what you're effectively saying is I'm going to be in the top 70%. And that's not that good. There…”