$150K to $1M ACV: The Constellation Strategy

A constellation is just a group of random stars in the sky that an astronomer connected together to create meaning. In complex enterprises, your job is to be the one connecting the dots among seemingly disconnected pieces.

This week I’ve focused on enabling and growing one of my existing customers, a $10B annual revenue publicly traded company with 15,000 employees spread across multiple acquisitions…think of this as 20 different companies inside one.   

Each division has different priorities, budgets, tech stacks, and opinions about their AI coding stack.  There’s ~200 developers who know what Windsurf is and 8,000 who don't. Of those 200, ~20 actually use Windsurf effectively.

My challenges were textbook complex enterprise:

• Siloed orgs with zero communication between teams

• Absent exec sponsor who signed the initial deal but went dark

• Enablement reluctance from time-protective engineering managers

• Multi-vendor chaos and competitive risk

• Feature gaps that block adoption in key use cases

All this said, we plan to 5x this account in 6 months with a clear strategy. Here’s how:

Step 1: Qualify Power of the Original Buying team 

I’m fortunate to have inherited this account from a stellar AE. However, within one meeting with the original buying team, it was clear that the central “Developer Productivity” isn’t going to be my champion for expansion opportunities.  We discussed a rollout plan and were met with more “we can’t do this” than “let’s do this.” For example, I asked them to compile a list of success stories from early adopters and they could only find one.  This team is going to be a coach to understand some of the org dynamics, but not champions.  Not their fault, just a reality of the decentralized org structure.

Step 2: Launch Mass Awareness Blitz

Using Lemlist, I built a 3-step LinkedIn sequence targeting every Director+ executive across all divisions.

The goal isn’t immediate meetings - I have a high connect rate because we are already an approved vendor, but most folks don’t respond.  That’s OK.  I want them in my orbit for social selling and awareness.

Step 3: Learn from Power Users

I identified the top 20 power users and slid into their Slack DMs with a simple ask: "Heard you're finding success with Windsurf. Mind sharing what's working and not working for your specific use case?"

On the “not working” front, I consistently found that they weren’t enabled properly and not using tools that already exist in Windsurf. Pointing them to the right documentation allowed me to get quick wins and build 1:1 relationships.   

On the “working” front, IC Engineers tend to think tactically, not strategically, so I had to guide them towards answers focused on business impact.  Once I had one success story that matched a very specific format of "saved X days doing Y task in Z coding language", I then sent that as social proof of what I was looking for in every subsequent DM to get many more examples with quantifiable results.  

Step 4: Build the Org Chart

I’m lucky to have a head start from the original AE who sold the deal. That said, I’m using the strategies discussed in last week’s Minimum Viable Org Chart (MVOC) GTMBA post to build out an understanding of power structures across the decentralized teams.

Step 5: Async Enablement at Scale 

Armed with power user insights, my next step is to create simple, division-specific “how to use Windsurf” docs that call out specific wins on their codebase. I’ll post this in the shared Slack channel and DM 100s of users. The key here is customization at scale - not generic enablement you could find on our website.

For every positive response, I will ask them to share the doc with their team and invite teammates to our channel. Viral expansion through value, not spam.

Step 6: Exec Trumpet Up with Data 

In parallel to Step 5, I’ll synthesize power user feedback into exec-facing content that shows concrete wins across multiple business units. Our original Executive Buyer (“EB”) didn’t seem particularly keen to meet with us, so I’m coming to him with concrete examples of real wins…inspiration and ammo to motivate him to get more people involved.

In addition to our original EB, I’ll be taking the same approach with each business unit head.

Step 7: The Feature Gap Jujitsu

A few months back, I wrote a 3-part series on how to win deals with Feature Gaps.  For this customer, I’m using the “Buyer Immaturity” approach.  I can’t get overly specific here because some readers of GTMBA work at our competitors, but I’ve identified a few power users who I’d consider more “forward-thinking” and open to experimentation.  I have success stories of these developers using a workaround to the identified Feature Gap.  Now, that I know there’s a workaround with proofpoints, I need to go challenge the laggards with the “Why Test” and offer up a compelling alternative solution.

Conclusion

As a new AE, inheriting an existing customer is awesome. Sometimes you’re given a home run. Most of the time, you get a customer that is struggling with implementation, adoption, or limited champion juice beyond the initial land. Use the roadmap above to connect the dots.

Cheers,

Julian 

P.S. - Shoutout to Hayden Hibberd and Ryan Klaus for taking initiative on our GTM tooling strategy and bringing in Lemlist.