My Framework For Picking Windsurf: 5 Tips To Choose Your Next Home Run GTM Opp

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Company selection is critical in tech GTM careers. It's not just about money.  It's about career leverage. The harsh reality? If you don't have Dropbox, Slack, Stripe, Mongo, Snowflake or a handful of other names on your resume, you're climbing uphill compared to those who do.  Great logos create a virtuous cycle of opportunities and talent networks for the next big thing.

Because I got into tech a bit later in my career (I’m 34, having switched into tech/GTM at 29), in my most recent job hunt, I was actively focused on finding a hockey stick growth company. Six weeks into my time at Windsurf - whether speaking to eager C-Suite execs at Fortune 100 companies, breaking annual targets in a quarter, and shipping industry-defining new features at a record velocity - this truly feels like generational company potential.

Dozens of folks have reached out over the last few weeks and asked, “how did you pick Windsurf?” Here's my framework for evaluating and picking the right AI startup in this noisy landscape (Chris also provided his GTMBA take a few weeks back):

1. Product-Market Fit: Listen to the Developers

Developer tools live or die by community sentiment. Instead of believing TechCrunch marketing hype, I went straight to where developers actually talk:

• Reddit threads & X posts where more and more engineers were praising Windsurf’s performance

• HackerNews discussions comparing tools where Windsurf kept winning technical arguments

• Discord channels where power users shared their workflows

With so much internet hype about competitor Cursor, I was quite nervous. These channels gave me unfiltered early signal of developer sentiment trending towards Windsurf.

One caution about online forums - be wary of over-indexing here as the loudest voices tend to be the least relevant for your target audience as an enterprise seller (think Yelp reviews.  To mitigate risk,  I interviewed multiple AEs on the team and probed deeply about where they were losing to Cursor.  While I can’t reveal specifics, I will say that those conversations sold me and it became clear that Windsurf was winning the enterprise and had clear technical levels of differentiation.  

2. Product Velocity: A Critical Leading Indicator

In an AI-powered world, product commoditization is inevitable. I've learned that exceptional startups ship at an exceptional cadence. Two things to track:

• Release frequency: I checked Windsurf’s changelog, Founder’s Twitter, and found their “Wave” releases started monthly but accelerated to bi-weekly.  

• Feature depth: Releases weren’t just UI tweaks but substantial functionality that users immediately implemented and loved.

Analyze feature quality in two ways. First watch organic customer videos like this.  Next, validate what you learn on the internet with a customer reference or outbound 2-3 customers yourself.  Ask them to rank product velocity on a scale of 1-5 and quality of newly released features on a scale of 1-5.  Probe into specifics and how perceived velocity compares to competitors.

3. Disciplined GTM Strategy 

This is where most AI startups fail. They confuse early adopter excitement with sustainable GTM motion.

CRO Graham Moreno’s interview on the SaaStr Confidential helped me understand Windsurf’s winning approach of (A) Pipeline Generation (“PG”), (B) Enablement, and (C) a culture of celebrating wins & boosting each other up.  

Pro tip: do your due diligence.  Any good CRO can sell a vision.  Get 1:1 with AEs, managers, and the CRO - probe on what these things look like Day-to-Day.  Do the stories line up across multiple people or are there inconsistencies you need to go deeper on?

4. Viral Marketing DNA

The top-performing AI companies aren’t just technically superior - they’re culturally relevant.  Again, I was quite nervous because everyone in tech seemed to know competitor Cursor, and at the time I joined, not a single of my developer friends (including those at my last company) knew Windsurf.  I knew that the only way we’d be competitive was if we had a viral marketing strategy to catch up.  Windsurf stood out with:

• A cohesive water-themed brand ecosystem with features like "Riptide" and "Cascade" and product releases called “Waves”

• Creative community engagement (the upcoming Bay-to-Breakers sponsorship is brilliant) - sign up here 

  

• Founders who were building legitimate social followings (not just posting product announcements)

5. Massive TAM 

At past companies, we ran into different TAM challenges. At one, we hit a ceiling of B2C companies with large mobile apps. At another, our focus was limited to AI and infrastructure SaaS companies.

Windsurf's developer tool approach gives the team entry points across individual developers, B2B tech, retail, financial services, and even government. This translates directly to GTM career opportunity - more customers means more sales roles, more leadership positions, and more paths to advancement.

Conclusion

I could go on about more things that caught my attention - from the hiring process, backchannels with VCs, etc.  I’ll keep it to the top 5 for this article.

A note of caution - there are only a dozen companies like Windsurf in each tech cycle. Finding them requires patience, research, and sometimes walking away from good opportunities to wait for the best ones.

For those hustling and ready to put work at the center of your life, but lacking the benefit of elite tech logos on your resume, I hope this framework helps you identify great companies.

Now that you’ve learned how to identify the opportunity, check out GTMBA’s most popular article - 5 Things I Did to Stand Out and Land Multiple AI Startup Offers

Bisous, 

Julian

Note: Opinions and commentary in this article are solely mine and do not represent the views of Windsurf in any way.