Vibescaling Podcast Episode 2: Raphael Parker, CRO @ Mandolin | How He Built Segment's GTM Engine from 0 to $100M
Episode Description:
Raph Parker is Head of Revenue at Mandolin, an AI company transforming healthcare operations.
Before Mandolin, Raph was the first go-to-market hire at Segment, helping scale the company from seed to its $3.2B acquisition by Twilio.
He then served as Chief Growth Officer at New Front Insurance, taking another company from seed to unicorn (with an IPO likely on the horizon).
He started his career as a corporate lawyer, then biked around the world for 2 years before stumbling into tech sales.
He joined us to talk about the psychology of early-stage selling, how to create social proof when nobody knows you, what to look for in a CEO, and why you should compete at the shallow end of the gene pool.
Also, shout out to our awesome sponsors for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day.
Discussed in this episode:
- The three types of founders who start companies - and why you want to find the third bucket
- Why "strong ideas, lightly held" is a critical trait in early-stage leaders
- The three things you're optimizing for in your career: cash, equity, or career/talent development
- Prospect theory for salespeople: how people make decisions on risk vs. reward (and why being rationally beneficial isn't enough)
- The real motivation behind every buyer: people just want to get promoted
- How to use informational asymmetry to "hack" social proof when you only have two customers
- Flipping the script to start a sales call
- Turning the intro into something that works in your favor: the "I bet my career on this" framing
- Why nobody believes a case study & what to do instead
- Why prospects open up when they realize you talk to way more of their peers than they do
- PMF in AI is obvious right now - here's what to look for instead
- "Compete at the shallow end of the gene pool": why the least sexy industries offer the biggest opportunities
Episode Highlights:
(00:00) From Big Law to BDR: Raph's Unconventional Path into Sales
(09:00) How to Evaluate CEOs: The Three Types of Founders
(18:00) Prospect Theory: Why Early-Stage Selling is About Risk, Not Features
(24:00) Creating Social Proof When You Only Have Two Customers
(29:00) The Sales Call Hack: Flipping Informational Asymmetry
(33:00) The "Bet My Career On It" Intro That Changes Everything
(36:00) Why Nobody Believes Case Studies (And What Prospects Actually Want)
(42:00) Hiring Early Sales Reps: The First Class to Greyhound Test
(50:00) Distribution vs. Product: Why Great Ideas Fail
(58:00) Compete at the Shallow End of the Gene Pool
About VibeScaling Podcast:
The VibeScaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, partner @ VibeScaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.
No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.
About VibeScaling:
VibeScaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.
Where to Find VibeScaling: