5 Things I Did to Stand Out and Land Multiple AI Startup Offers

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Not yet announced, but I start at Codeium, the makers of Windsurf, this week.  If you haven’t yet heard of Codeium, it’s one of the fastest growing AI start-ups, competing with incumbent Githhub Copilot and fellow newcomer Cursor for market dominance in the AI coding market.  Unlike Cursor, which started with a viral PLG tech community groundswell, Codeium has been the dominant challenger in enterprise.  

In my recent job hunt, I landed interviews at every company I wanted - from LLM giants OpenAI and Anthropic to infrastructure and app layer start-ups like TogetherAI, Cursor, and Decagon.  Ultimately, I negotiated from a position of leverage to pick the right company for the next stage of my career.

Here are my top 5 unconventional tactics:

Tactic #1 - Breaking In with Customer Interviews

Context: I couldn’t break into Anthropic’s interview process despite 4 different referrals - too much demand, not enough roles. 

Approach: I researched Anthropic’s customers, found decision makers, and outbounded ~40 companies.  Four responded and took me up on customer interviews around their buying process pain points.  I synthesized the findings (using my friend Claude, of course) into a 2-page analysis of top painpoints and potential solutions, then sent it to Anthropic’s Head of Sales.  I got an interview the next day.  

Shout out to AJ Tennant @ Glean for inspiring this approach during his 20VC episode with Harry Stebbings (see prior GTMBA take).  

Tactic #2 - The “Not Now” Drip Campaign

Context: In December, I interviewed for a Founding AE role at one of the hottest AI start-ups.  After a 60 minute in-person coffee, I received the feedback: “we really like you, but we need someone with more existing technical understanding of our market for our first hire.”

Approach: Instead of walking away, I spent my winter holidays in a coding bootcamp gaining SWE experience, used their product extensively, and recorded demo Loom videos, which I sent to the COO.  They came back in February trying to convince me to renege on my Codeium offer.  

Shout out to Allen He @ Metronome for this idea.  Allen demonstrated persistence when applying to Metronome staying in touch for 6 months with relevant content, insights, and PoVs on usage-based pricing until the timing was right.

Tactic #3 - The Brand Book

Context: Hiring managers are biased.  I have 10+ yrs of professional experience, but < 5 yrs in tech sales.  Some hiring managers see my JPMorgan background as unique, but most ignore it and jump straight to my sales experience - cutting my career experience by > 50%.

Approach: Create a portfolio of work artifacts that help tell a compelling narrative with social proof.  You should selectively bring the brand book to help validate your stories (and anticipate objections).  A few ideas:

• Career Arc: Highlight key early career projects with transferable skills (especially if a career switcher like me)

• Cross-Functional Partnership: Includes quotes from peers/mentors

• Pipe Gen Strategy: Show examples of creative outbound emails

• Deal Review: 3-5 simple slides highlighting approach to key deal (e.g., break-in strategy, qualification approach, anonymized business case) 

Tactic #4: Proactive References 

Context: Competition for the best jobs is fierce.  Start-ups will typically backchannel once at the offer stage. But what if you haven’t yet received an offer?

Approach: Select a past manager who knows your strengths/weaknesses well, and has a strong external brand (title / company / personal reputation).  Draft a note for this person to send proactively to the hiring manager before your final round.  This provides an opportunity for someone to handle objections on your behalf and lets you address concerns in your final interview. Note: this is very similar to the tactic I use in deals with prospective customers, highlighted in the TIPS Framework.   

Shout out to my GTMBA partner Chris Balestras for this idea.  Chris overcame the “big company guy” bias when joining Metronome by leveraging his network and has delivered on everything and more than his reference called out.  

Tactic #5: The Gratitude Loop

Context: People invest significant time interviewing you, making introductions, and providing advice.  Show your appreciation for those who help you along the journey.  

Approach: At the end of every recruiting cycle, send notes (email, text, or video), to everyone you met, regardless of the outcome with that person.  In this last search, I sent ~100 thank you notes.   Two people I thanked after my previous job search were instrumental in bringing me to Codeium…it’s a very small tech world :) 

Shout out to my mentor Professor Craig Wortmann for this idea. He takes this to another level, writing handwritten thank you notes to thousands of people annually.  

There’s much more to landing a great offer, but these five tactics will help you stand out and build negotiating leverage.  

Bisous,

Julian

Disclaimer: I wouldn’t recommend copying Tip #1 with Anthropic GTM (it’s been done), but try it with other target companies.

Templates 👇 Want templates of materials like the Customer Interviews or Brand Books?  (A) Subscribe, (B) Like this post, and (C) Comment “template” on my LinkedIn post.