Windsurf Chaos & My 1st 7-Figure Deal

The last 3 weeks have been the most intense of my career.  More intense than any M&A deal or product launch I worked on at JPMorgan.  On July 11, the craziest 72 hrs in start-up history kicked off - Windsurf founders were acqui-hired by Google, I was about to be unemployed, and prospects were frantically texting me that they were pulling out of deals…Windsurf was dead ☠️. 

Yet, last Thursday, 7/31/25, a few hours before quarter-end, I brought home the largest deal of my career in what from the outside looks like a miracle.   

But this 7-figure deal was no miracle - this was a tale of grit, teamwork, creativity, and operational excellence…and involved flying out to meet Execs to save the deal.  As my VP Ben Jaderstrom put it:

I feel truly lucky to be part of such an elite GTM team with a world class product.  Below I’ve laid out how we got sh*t done when the world was crashing down upon Windsurf.  Let this be an inspiration that persistence pays off in enterprise sales. 

The Anatomy of a 7-Figure Deal

Stage 0: Outbounding

At Windsurf, AEs are expected to generate their own pipeline.  Our CRO & President Graham Moreno’s GTM scaling philosophy, derived from his days as an early GTM hire at MongoDB, starts simple: every Wednesday is “PG” (Pipe-Gen) day.  

In my first “PG-Wednesday” I landed a meeting with the Chief Eng Officer of a publicly-traded company who oversaw 15K+ developers.  While I landed this my first week, I had been working my network for 3 weeks prior to my start date to orchestrate this meeting.  

Stage 1: Discovery & Intel Gathering

That exec meeting took almost 2 months to get on the calendar after multiple re-schedules.  Rather than sit and twiddle my thumbs, I went aggressive on PG to gather intel ahead of that Exec discussion.. 

Before outbounding, I built my “Minimum Viable Org Chart”.  Strat sales is very different than SMB or Mid-Market sales.  You needed to be targeted.  

After meeting various teams, I finally engaged with their Developer Productivity team and hit my first major hurdle.  

Roadblock #1: Developer productivity had already purchased our competitor and were standoffish, punting our meetings and ignoring follow-ups.  

Unblocking Roadblock #1: We took a new approach - leaned into our expertise in AI coding and educated them on trends, proving ourselves to be thought leaders in enterprise AI.  The tone changed and they kept coming back to us for more insights (not about our product), which opened the door to product discussions and finding a wedge that our competitor did not solve for. 

Stage 2: Pilot Scoping

Pilot scoping is the most critical phase of our buying process.  When done right, this increases the likelihood of a successful pilot and champion buy-in for a larger deal with an accelerated deal cycle.    

Step 1 - Champion & Coach Building: As I highlighted in last week’s article, no champion, no deal.  For this deal, not only did we identify a very strong champion, we also had 3 strong coaches - all of whom I had texting relationships with.  Some coaches help understand org dynamics, like supporters and detractors.  Others helped navigate tactical pilot logistics.  The key to building champions and coaches was a combination of onsites (yes, in person matters!) and education on the rapidly evolving industry. Here are some tips for landing in person meetings.

Step 2 - Exec Buyer Alignment: Another critical component of Stage 2 is getting the Executive Buyer (EB) to align on scope prior to pilot commencement.  

After 2 months of calendar tetris getting in front of the EB, it finally happened. I took the call at 10PM from Barcelona, where I was attending my friend’s wedding.  It’s rare you get a shot at meeting with the C-Suite of a Fortune 500 company and I wasn’t going to miss the opportunity.  The most important part of this call was coming in with a PoV based on all the research I had conducted in discovery conversations and framing the discussion in the EB’s language (think top 3 company C-Suite strategic initiatives from earnings reports).

At this point, we had finally identified potential champions / coaches and met the EB.  Then we hit our next major hurdle. 

Roadblock #2: The EB was in and ready to pilot, but as we were scoping, we discovered a mission-critical feature gap that effectively blocked the deal.  

Unblocking Roadblock #2: Having been a Founding GTM hire at a Series A start-up previously, I’ve had extensive experience selling around feature gaps (I write about this in my 3-Part Series on Selling Around Feature Gaps).  We took a two-prong approach:

• (A) Internal Selling: We built a compelling internal business case to unlock Eng resources to fill the gap

• (B) External Options: We created 3 options, one of which included piloting existing functionality with a subset of devs and jointly collaborating in design partnership on the feature gap.

Stage 3: Pilot 

There are many MVP plays we orchestrated during the pilot, but given that competitors read GTMBA, I’ve been asked to keep details light.  TLDR: don’t be passive during the pilot - find creative ways to drive maximum engagement and gather quantifiable success.  

Stage 4: Pilot Readout & EB Sign-Off

Our pilot readout was scheduled for Tuesday 7/15. Results were looking great and I was feeling on top of the world. Then everything went to hell:

• Fri 7/11 @ 2PM: A bomb dropped about Google acqui-hiring Windsurf’s founders.  

• Sun 7/12 @ 4PM: My manager called me and said, “I can’t tell you more, but don’t panic, come to our Mountain View office…we’re in for a hell of a next 3 weeks through quarter close.”

• Mon 7/14 (AM): Cognition announces it acquired Windsurf

• Mon 7/14 (Afternoon): My champion tells me our deal is off and that the pilot readout was cancelled…rather than panicking, I give him our PoV on the acqui-hire news, and ask him to keep the pilot readout scheduled and ensure the EB is in the room

• Mon 7/14 (Evening): Ben (my VP), Henry (my RD), and I hop on flight to meet our champion and EB in person the next day.  

• Tues 7/15: Our champion proved to be a true champion in front of the EB, defending our pilot results, despite uncertainty around Windsurf.

In preparation for the 7/15 pilot readout, we worked jointly with our Champion to co-author the presentation.  One key win (and a mistake I see AEs make over and over) was framing the business case.  Rather than building a business case oriented towards a junior “Below-the-Line” (BTL) audience, it’s critical to solve executive “Above-the-Line” (ATL) business problems.  I’ll take an example from a deal I sold at Branch:  

• BTL Problem: “My priority at Mobile Product Manager is we need to increase App Installs by 70% in 2024.  Branch helps drive more app installs.”

• ATL Problem: “My #1 priority as SVP Digital Engineering is our Media Pocket thesis.  I know that omni-channel customers spend 6x more if they are also Mobile App users, and if I can increase App Installs by 70%, I can increase revenue by $XM annually against my goal of $YM.  Branch is uniquely positioned to drive organic installs by converting million of web users into app users.”

Make sure you are speaking the executive’s language.  

Stage 5: Negotiation & Paper Process

Again, I’ll keep the negotiation details light, but we grew the deal from ~$600K to >$1.5M by truly understanding this prospective customer’s needs and anchoring this to a rock solid business case focused on C-Suite top strategic priorities.  

If I were to do one thing differently in this deal it would be managing the paper process earlier.  As much as I tried to control and understand all aspects of the approval process, no one could give me a clear answer of all the items and who owned which pieces.  This resulted in needing to chase down the CEO of a Fortune 500 company in a 17-person approval chain within 24 hrs of quarter close…we made it happen with some MVP coaching from Ben and Henry.   

Conclusion

The truth about 7-figure deals is they are >50% crisis management.  Every major deal goes through “deal-killing” moments and the difference between wins and losses isn’t avoiding crisis, but rather how you respond when crisis occurs.  

Two main takeaways:

• Winning big deals takes grit: There were three major challenges we had to circumvent - an existing competitor, a mission-critical feature gap, a loss of faith in our business due to industry actions outside our control.  While each seemed insurmountable initially, we stayed calm and thought outside the box to unlock a path forward

• Winning big deals is about team sport: I could probably double or triple the length of this article going into details of how I partnered with so many amazing teammates.  My #1 Partner-in-Crime is my Deployed Engineer Sam…there’s no way I could’ve done this without him.  Beyond Sam was an entire cross-functional team of elite colleagues ranging across Founders, Engineering, Product, Marketing, GTM leadership, fellow AEs, and BD.  

As exhilarating as the past few months have been, the most exciting part is ahead.  When a company pays you >$1M, you better be ready to give them everything you have to make them wildly successful. 

Cheers,

Julian