Chase Woolard

1.1K posts

Chase Woolard banner
Chase Woolard

Chase Woolard

@ChaseWoolard

Building startups. Ripping life

San Francisco Katılım Haziran 2015
1.9K Takip Edilen580 Takipçiler
Chase Woolard
Chase Woolard@ChaseWoolard·
@MoFromYYZ Love this. Congrats on a huge milestone!If you're going to hire more SWEs here in SF, would love to have you check us out fonzi.ai
English
0
0
0
5
Mo
Mo@MoFromYYZ·
Today we're announcing Shepherd's $42M Series B — and I want to share what we're actually building. Commercial insurance underwriting works the same way it did 30 years ago. Broker emails a submission. Underwriter manually keys data across a half-dozen tools, cross-references loss runs, pulls comparable accounts. A great underwriter handles twenty accounts a month. We've spent four years building the intelligence layer that changes that. We're months away from the first fully agentic submission in commercial insurance. A submission arrives by email. The system reads it, enriches it, prices it, and returns a quote. No human intervention. A year from now, this industry will be unrecognizable. None of this happens without the underwriters who pushed us to build something actually useful, and the investors who saw the vision before it was obvious. Thank you to Justin Smith-Lorenzetti and Intact Private Capital for leading this round, and to Costanoa Ventures and Spark Capital for doubling down again. shepherdinsurance.com/blog/the-road-…
Mo tweet media
English
14
6
103
12.9K
Chase Woolard
Chase Woolard@ChaseWoolard·
@vmelnikova_en Moved here 10 years ago with 2 kids under 5. Now older, my kids couldn't imagine living anywhere else. Don't bail!
English
0
0
1
200
Victoria Melnikova
Victoria Melnikova@vmelnikova_en·
I moved to SF one year ago with my 1-year-old. It’s by far exceeded my expectations, but it’s mad expensive with a kid
Victoria Melnikova tweet mediaVictoria Melnikova tweet media
English
29
3
242
20.4K
Chase Woolard
Chase Woolard@ChaseWoolard·
I love building in SF. I love this moment we're having here. So many people left here, riding hype trains and buzz cycles to warmer climates or that one east coast city only to flock back chasing the new AI gold rush. Its also really cool that everyone who stayed here through some bleak times are getting to ride this wave. Where's that taking us? Who knows, but my guess is it'll still be being built here in SF. Anyhow, here's a random photo I took from the beach this Sunday with the family. SF rocks. If you aren't here, get here. P.S. If you're at a startup and hiring engineers in SF or if you're an engineer working at a startup, hit me up and let's chat.
Chase Woolard tweet media
English
0
0
2
41
Chase Woolard
Chase Woolard@ChaseWoolard·
Everyone thinks the job market is awful for SWEs but it's really a tale of two markets under 1 umbrella. Big tech is using the power of AI to reduce headcount but startups have an urgent need to hire people to use token budget and maximize scale. Bottom line, if you're an entrepreneurial SWE who is leveraging AI effectively, you're going to have startups thirsting after you for the foreseeable future.
English
0
0
0
36
Drew Tuma
Drew Tuma@DrewTumaABC7·
San Francisco making history today First time on record we’ve ever had four consecutive days of highs 84°+ in Winter All year we average only seven 84°+ days Temperature records go back to 1874
English
44
153
1.7K
74.7K
Chase Woolard
Chase Woolard@ChaseWoolard·
@Raelthy Deep South born, professional life in NYC and SF, love SoCal more than anywhere else but home.
English
0
0
1
836
Rae
Rae@Raelthy·
Men from SoCal and the deep south have an easygoing way about them that the high-strung neurotic yankee and midwesterner can only ape. It's a feature of the climates.
English
56
110
2.3K
111.8K
Don
Don@donatelli2026·
question for the tech bros: what's the best way to find a girlfriend in San Francisco?
Don tweet media
English
173
3
193
608.7K
SpaceSquid
SpaceSquid@sfspacesquid·
SF dudes say taste is important and then go line up for Salt n Straw in Hayes instead of going to hometown creamery
English
65
43
1.4K
94.4K
Chase Woolard
Chase Woolard@ChaseWoolard·
@VCBrags The amount of early founders who don't understand basic US HR law is wild. I see it constantly both online and with in person comms.
English
0
0
12
568
FinancialFreedom
FinancialFreedom@FinFreedom414·
Imagine you had to choose your life at age 40: Option A: Single. No kids. $10M net worth. Travel anywhere. Total freedom. Quiet house. Quiet holidays. Option B: Married. 3 kids. $1M net worth. Drive a Toyota. Chaos every morning. Loud house. Full dinner table. Be honest, which life are you choosing?
English
16.8K
439
10.8K
4.4M
The Random Recruiter
The Random Recruiter@randomrecruiter·
Remote workers crawling to their laptop at 8:59 AM
English
227
3.9K
59.7K
2.6M
Chase Woolard
Chase Woolard@ChaseWoolard·
@MXGRyan Neither Vince nor Cole have eyes in the back of their helmets.
English
1
0
4
267
Chase Woolard
Chase Woolard@ChaseWoolard·
@michelleefang I'm hosting the AI engineers event tomorrow night. Come out and say hi!!!
English
0
0
0
127
Michelle Fang 🌁
Michelle Fang 🌁@michelleefang·
If you're new or looking to get more connected to SF tech: bookmark these 53+ irl events 🗓️ A list of what's happening this week (March 2 - March 9) ⬇️
English
4
9
146
30.2K
Chase Woolard retweetledi
Alyssa Krejmas
Alyssa Krejmas@alyssakrejmas·
A friend took this this morning. Wow.
Alyssa Krejmas tweet media
English
32
108
2.4K
32.7K
Chase Woolard
Chase Woolard@ChaseWoolard·
@andruyeung I have 80 companies hiring just IC swes right now in my portfolio. Lots of startup SWE jobs. Brutal if you're in big tech tho.
English
0
0
0
13
Andrew Yeung
Andrew Yeung@andruyeung·
The best way to get a job at a tech company now is to build one of your own and hope to get acquired.
English
61
29
410
16.3K
joyce
joyce@henloitsjoyce·
@jeffdfeng why does a yc company have L5 engineers (or, giving them any levels at all)
English
4
0
35
3.4K
Jeff
Jeff@jeffdfeng·
Spoke with several YC founders planning to lay off all engineers below staff/principal — basically everyone under L5. This only became viable after Opus 4.5 in December. The Block layoffs are a signal: the floor just collapsed. If you’re early in your career, the next few years are everything. Your edge will be how well you integrate AI into the value you create. The fastest learners are about to compound at absurd rates.
jack@jack

we're making @blocks smaller today. here's my note to the company. #### today we're making one of the hardest decisions in the history of our company: we're reducing our organization by nearly half, from over 10,000 people to just under 6,000. that means over 4,000 of you are being asked to leave or entering into consultation. i'll be straight about what's happening, why, and what it means for everyone. first off, if you're one of the people affected, you'll receive your salary for 20 weeks + 1 week per year of tenure, equity vested through the end of may, 6 months of health care, your corporate devices, and $5,000 to put toward whatever you need to help you in this transition (if you’re outside the U.S. you’ll receive similar support but exact details are going to vary based on local requirements). i want you to know that before anything else. everyone will be notified today, whether you're being asked to leave, entering consultation, or asked to stay. we're not making this decision because we're in trouble. our business is strong. gross profit continues to grow, we continue to serve more and more customers, and profitability is improving. but something has changed. we're already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly. i had two options: cut gradually over months or years as this shift plays out, or be honest about where we are and act on it now. i chose the latter. repeated rounds of cuts are destructive to morale, to focus, and to the trust that customers and shareholders place in our ability to lead. i'd rather take a hard, clear action now and build from a position we believe in than manage a slow reduction of people toward the same outcome. a smaller company also gives us the space to grow our business the right way, on our own terms, instead of constantly reacting to market pressures. a decision at this scale carries risk. but so does standing still. we've done a full review to determine the roles and people we require to reliably grow the business from here, and we've pressure-tested those decisions from multiple angles. i accept that we may have gotten some of them wrong, and we've built in flexibility to account for that, and do the right thing for our customers. we're not going to just disappear people from slack and email and pretend they were never here. communication channels will stay open through thursday evening (pacific) so everyone can say goodbye properly, and share whatever you wish. i'll also be hosting a live video session to thank everyone at 3:35pm pacific. i know doing it this way might feel awkward. i'd rather it feel awkward and human than efficient and cold. to those of you leaving…i’m grateful for you, and i’m sorry to put you through this. you built what this company is today. that's a fact that i'll honor forever. this decision is not a reflection of what you contributed. you will be a great contributor to any organization going forward. to those staying…i made this decision, and i'll own it. what i'm asking of you is to build with me. we're going to build this company with intelligence at the core of everything we do. how we work, how we create, how we serve our customers. our customers will feel this shift too, and we're going to help them navigate it: towards a future where they can build their own features directly, composed of our capabilities and served through our interfaces. that's what i'm focused on now. expect a note from me tomorrow. jack

English
130
101
1.9K
584.5K
Chase Woolard retweetledi
Brycent
Brycent@brycent·
San Francisco is incredible
English
28
4
124
18.1K