Simran Duggal is VP of Sales at Juicebox, an AI-native recruiting platform where she leads GTM across three functions and 18 direct reports. She spent five years at Webflow as one of its early enterprise reps, building an enterprise motion on top of a product-led base, and came up before that in enterprise B2B SaaS. She got there by accident: a founder-track master's at Waterloo (Business, Entrepreneurship & Technology) put her in a room with brilliant early-stage technologists who had no idea how to commercialize, and she realized selling was the craft she wanted to build.
In this conversation, she and Chris get into the learnings from scaling PLG into enterprise, the traits she screens for when hiring sellers in the AI era, and why the old sales playbooks no longer apply.
Discussed in this episode:
- Why loving a product and buying it are two different things, and how a pipeline of fans inflates your forecast
- Selling to users vs. buyers, and to marketers vs. developers
- The number one trait she screens sellers for: mental resiliency
- Hiring "spikes" over generalists to raise the whole team's ceiling
- Scrapping the job title to hire in the AI-native era
- The mock discovery call and the feedback round that actually decides it
- Why personalization is about the buyer's problem, not their alma mater, and why the phone call still converts
- How the best talent leaders are becoming business strategists
- Why she believes the universal sales playbook is dead
Timestamps:
(0:00) Background: from Waterloo's founder track to sales
(4:34) Founder mistakes: conviction pointed the wrong way
(5:31) Webflow: joining as an early enterprise rep
(6:22) Two-engine companies: why she wanted PLG + sales
(7:27) The downside of selling on a PLG base
(10:30) User vs. buyer: what Webflow got wrong
(11:57) Marketers vs. developers: the art of vision casting
(15:46) Webflow as a GTM talent factory
(19:28) Hiring spikes: elevate everybody, raise the bar
(20:58) The number one trait: mental resiliency
(23:18) The mock discovery call
(24:52) The feedback round that decides it
(27:14) Reading a career: running toward vs. away
(28:42) Leaving Webflow, betting on AI-native
(33:06) Why recruiting: the Juicebox thesis on people
(40:24) Talent leaders as business strategists
(43:33) Outbound that works: pick up the phone
(46:24) The AI tools she can't work without
(50:05) The sales advice Simran thinks is dead
(51:42) How to actually get Simran’s attention
About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM 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 CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.
Where to Find Crew
LinkedIn: linkedin.com/company/crewgtm
YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg
Newsletter: withcrew.blog
Website: withcrew.ai
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