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Copyright © Bookvid Technologies, 2025

Cailen

Creator profile picture

5.0

Advisory for Companies Scaling to 100m+ ARR


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


11 others have 9 figure valuations and have surpassed 8 figures in ARR. 


9 have been acquired by companies like Stripe, PagerDuty, Hightouch, IBM, Inflection AI, Procare HR, Honycomb, 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, Intrinsic, 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)

Social

Cailen’s Sessions

30 mins

$500

60 mins

$1000


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Browse our marketplace of the world's most in-demand experts. After choosing the right expert for you, book a 1:1 video call with them. At the time of the appointment, join the live 1:1 video call, ask the expert your questions, and get personalized high-quality advice!.
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Generally speaking, most of our customers have been delighted with how much they achieved during their live 1:1 video consultations. We have over 5,000 five-star reviews and a high percentage of our customers rebook the same expert or additional experts because their experience exceeded their expectations. Our most popular sessions are 30 minutes long, but you can still get a lot done during a 15 minute session.
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Many of them have shared their desire for Bookvid's mission — to give everyone access to anyone, empowering each other to build a better world. They also love paying it forward and helping others advance in their journey. With Bookvid, they now have an easy-to-use platform that makes it simple to connect with like-mind folks like yourself, while also being compensated fairly for their time. In some cases, our experts are also donating a portion or all of their proceeds to the charity of their choice.
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