Cailen DSa's Linkedin Analytics

Founder - Vibe Scaling (Advisory Firm Supporting Founders, Execs & Employees from $0 to $100m+ ARR) Co-Creator of Silicon Sands (Private San Diego Founder/Exec/VC Network with over 200+ members) Advisory: 6 of our 60+ portfolio companies (<$20m cap when we started working with them) are either public or private decacorns or unicorns in 2025, including Dropbox, Retool, Zip, Box, Front, and Productboard 12 others have 9 figure valuations and have surpassed 8 figures in ARR. 10 have been acquired by companies like Stripe, PagerDuty, Hightouch, IBM, Checkr, Inflection AI, Procare HR, Honeycomb, and Gambling.com Focus Areas: Sales Development, New Business Acquisition (SMB, MM, Enterprise), Customer Success, Account Management, Partnerships, RevOps, Solutions Engineering, Marketing, Recruiting (technical / non-technical roles), People Operations, Compliance, Equity Strategy, Fundraising, etc. Current Portfolio: Cortex, Grain, LiveKit, SecurityPal, Lindy, Continu, Hifive, Zip, Retool, Lavender, Grit, GlenCoco, Ratio, Paramark, Loyee.io, Avoca AI, Pylon, Parcha, Siro.ai, CandorIQ, GoGo Grandparent, Render, Ozone, Quarter20, Daydream, Opine, Inductive Bio, Supio, Arcee.ai, AireXpert, Variance, LiquidText, Tome, Prospect, Daloopa, Mach9, Gather, HockeyStack, Airfold, Joist.ai, Centralize, Freeplay.ai, Ldgr, Wayfaster, Select.dev, Faliam, SubBase, Wellfound (Formerly AngelList Talent), Mastra.ai, Bluebirds.ai, Applied Labs, Solidroad, Multiple companies in stealth. Highlights: Dropbox - First GTM hire, Series A to Series C (IPO, $12B market cap) Box - First GTM hire, Seed to Series C (IPO, $5B market cap) Front - First 8 employees & Head of Sales, Seed to Series B ($1.7B valuation) Truework - First 10 employees & VP Sales, Seed to Series B ($550m valuation) RevenueCat - First GTM hire & VP Sales, Series A to Series B ($350m valuation) Retool - Investor & Advisor @ 3 employees ($3.2B valuation) Zip - Investor & Advisor @ 2 employees ($2.2B Valuation) Productboard - Investor & Advisor @ 2 US employees ($1.7B valuation) Cortex - Investor & Advisor @ 3 employees ($470m valuation) LiveKit - Investor & Advisor @ 2 employees ($110m valuation) Arcee.ai - Investor & Advisor @ 2 employees ($120m valuation) Okay Software - Fractional CRO (Acquired by Stripe) Jeli.io - Advisor to CEO (Acquired by PagerDuty) HeadsUp - Advisor to Founders (Acquired by Hightouch) Clarent - Advisor to Founders (Acquired by ProCare HR) Jelled AI - Investor & Advisor (Acquired by Inflection AI) OddsJam - Advisor to Founders & CCO (Acquired by Gambling.com)