Alejandro Dinsmore

Finding ways to live a better life through intentional work.

Founder (raised 2M in funding) | Early-stage Product Manager  (0-11M ARR) | Forbes 30u30 (not in jail)

Newsletter: https://alejandrodinsmore.substack.com/

Product Manager

Founding Product Manager - 1500% increase in Loan Volume in 2023. 

Working on B2C and B2B initiatives across the business.

Claude code’s first birthday event was a great time (well done Anthropic)!

If you work at a company that has fully adopted Claude code then you know it’s hard to understate the impact it’s having across all functions, not just engineering. 

It’s also made work a lot more fun. 

It lets me focus on the things that matter and handles a lot of the monotonous tasks, in way that is simple and addicting.

Hard to believe it’s only been out for a year. Can only imagine where things will be by claude code’s second birthday…

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Director of Content ✨ I talk about personal branding, marketing, and other things I learn along the way.

8+ years in content + marketing
operator for consistent content and partnerships.
build systems, manage production, grow distribution.
contact → jaelannalee@gmail.com

Jael Johnson

when in san francisco I guess 


LinkedIn

Strategic Partnerships & Content @ Scot Chisholm Co.

This morning we hosted Alex Bard for a Fireside Chat inside our Highland Society, along with our founder Scot Chisholm.

Alex is a Managing Director at Redpoint Ventures and former founder of Desk.com (acquired by Salesforce). He's built, sold, and invested in companies across every major tech wave since the mid 90s.

We spent most of the session on AI and what it means for founders scaling companies right now. A few things we covered:

1. SaaS is flipping from "software as a service" to "service as software." The shift isn't about making humans 10% more productive anymore. AI is actually doing the work. That changes everything about how companies are built, priced, and valued.

2. Seat-based pricing is becoming a liability. Companies like Block just cut 40% of their staff proactively, not because things were bad, but because AI made it possible. When your customers hire fewer people, your per seat revenue shrinks. The best companies are moving toward outcome based pricing tied to labor budgets, not headcount.

3. The companies that will ACTUALLY win will completely reinvent themselves. Not just bolt on an AI copilot. But like a full reinvention. The ones that don't will get passed by founders who can now build in days what used to take months.

For CEOs specifically, the game is changing. Alex made the point that he'd rather bet on someone with a steep learning slope than someone with 20 years of domain experience who isn't adapting. 

Hiring less, hiring for potential over pedigree, and treating the company itself as the product you're building.

These sessions are exclusive to our Highland Academy Society members. Founders and their teams join live, ask questions directly, and walk away with stuff they can actually use. This is the kind of room you want to be in.

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The Battle

Alejandro Dinsmore

Jael Johnson

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Alejandro Dinsmore's LinkedIn Performance

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