Founder Festival: Gordon Wintrob's Profile

Welcome, Gordon Wintrob

This profile has not been claimed and data may not be accurate.

Founder79

82nd percentile

Investor23

68th percentile

Combined

#219 on Leaderboard

2x YC founder who sold Newfront to WTW for $1.3B and StackLead to LinkedIn

• Professional:YC W2018 Serial Founder Unicorn Founder Acquired 2 Exits Raised $200M+500+ Employees Angel Investor

Credibility

this founder typical founder (50th pct)

Operator · 90th percentile

Current Co-Founder and CTO of Newfront Insurance.
Y Combinator alum — StackLead (W2014) and Newfront (W2018) were both YC-backed companies.
Both Newfront and StackLead were co-founded with partners.
Wikidata entity exists (Q137671346) identifying Gordon Wintrob as an American technology executive and co-founder of Newfront.

Relationship Matrix

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Founder score

99%Current Co-Founder and CTO of Newfront Insurance.
99%Y Combinator alum — StackLead (W2014) and Newfront (W2018) were both YC-backed companies.
98%Past Co-Founder and CEO of StackLead, acquired by LinkedIn in 2014.
97%Both Newfront and StackLead were co-founded with partners.
95%Newfront was acquired by Willis Towers Watson (WTW) for up to $1.3 billion, and StackLead was previously acquired by LinkedIn.
95%newfront.com ranks #421,861 on the Majestic Million (global domain prominence).
90%Wikidata entity exists (Q137671346) identifying Gordon Wintrob as an American technology executive and co-founder of Newfront.
85%GitHub account identified as gwintrob, linked from public sources.

Investor score

92%Publicly identified as an angel investor with confirmed investments in companies including Rillet, Sensible, and Ascend.
88%Has made 5 active investments per CBInsights, with the latest in Rillet (Seed, July 2024).
65%Approximately 3 years of angel investing experience, with earliest tracked investment around 2022.

What you likely need

You're at a rare inflection point post-Newfront exit, with the credibility, capital, and network to move fast on whatever comes next — but the right rooms matter more than ever. Festival events that connect you with YC alumni, insurtech operators, and early-stage investors will help you decide whether to launch, fund, or both. You'd also benefit from deliberate spaces to decompress and think out loud with peers who've navigated similar post-exit transitions.

Would you attend these IRL Festival events?

We will tune and customize your Founder Festival experience to make sure you get invited to the events that would be most valuable to you.

introsA YC W2014/W2018 alumni founder dinner to reconnect with batch peers, surface potential co-founders, and pressure-test early ideas for your next venture before anything is public
wellbeingA post-exit founder dinner for founders who've recently closed $500M+ acquisitions to share hard-won lessons, decompress, and think clearly about what to build — or fund — next
fundraisingA micro-fund and syndicate formation roundtable with YC-pedigreed angels who've formalized 5–15 angel checks into named vehicles, to map out LP sourcing and deal flow infrastructure
positioningAn insurtech AI operator dinner with founders and execs building in the $900B commercial insurance market to workshop where the next 10-year wedge is after Newfront's brokerage model
fundraisingA pre-seed term sheet dinner with YC-affiliated angels and scouts who back repeat YC founders on idea alone, designed for W2014/W2018 alumni ready to announce their next company early
introsA roundtable with founders who've closed enterprise distribution partnerships through acquirers like WTW, Marsh, and Aon to map replicable playbooks for your next insurtech or AI venture
positioningA positioning workshop for technical founders with 7+ years of operator experience in regulated industries, focused on turning proprietary AI insights into credible public thought leadership on platforms like Substack and LinkedIn
hiringA happy hour for MIT EECS and top-CS-pedigree founders actively looking for technical co-founders, where open-source projects and AI tooling demos serve as the conversation starter