Green Eggs & Ham: The AE’s Guide to Deal Resurrection

In 2020, I made a career switch into tech sales.  My roommate at the time - who had done door-to-door start-up sales - warned me of the emotional rollercoaster ahead.  Despite his warnings, I went all in.  

When I accepted my first sales gig, my roommate gave me a welcome gift: Green Eggs and Ham.  At first, I thought he was trolling me.  But the story of Sam-I-Am's relentless persistence - with a myriad of creative approaches to get someone to try something they initially found repulsive - was inspiring.  

Over the past 5 years, I’ve hit roadblock after roadblock on enterprise deals.  Every time I get stuck, I re-read Green Eggs and Ham to remind myself that there’s a workaround.  Below are three deal resurrection stories that would make Sam-I-Am proud.

The $1M Feature Gap Workaround @ Windsurf

Context: Within my first two weeks at Windsurf, I landed a meeting with the Chief Engineering Officer at a Fortune 500 SaaS company.  After 2.5 months of multi-threading across the organization, we finally got the thumbs up to PoC.  

Roadblock: Our product did not work on their core repo set-up and thus we could not run a PoC.  

Sam-I-Am Moment: Instead of walking away, we offered an alternative.  First, to get internal support, I built a business case showing >$10M at risk across multiple AEs and accounts with the same product blocker.  Then I came back to the prospective customer with a proposal - test Windsurf on another repo while we build support for their core repo.  Like the character in Green Eggs and Ham, they tried and loved what they tested.  

Result: $1M land forecasted for Q3 with $5M+ expansion potential.  This feature build has also unblocked another $500K+ land in my book of business.  

Biking to Urgency @ Branch

Context: As a newly promoted AE at Branch, I inherited a publicly-traded QSR account I broke into initially as an SDR.  I had 10+ stakeholders aligned and pushing for Branch.

Roadblock: We were stuck in limbo without a compelling event.  MSA was sitting in their legal queue with no urgency and no updates other than “we need uncapped LoL.”  

Sam-I-Am Moment: I knew my Champion loved biking.  During PTO in LA, I called him up to invite him to go on a bike ride.  We ended up doing a 25-mile bike ride and grabbing lunch.  During those several hours, we went deep on his CTO’s and Chief Legal Officer’s concerns.  We created a plan to get me CEO access.  Within 1 week of that CEO meeting, the MSA redlines were turned around.  

Result: Largest company deal of the quarter, leading to winning our new logo SPIFF.  

The Risky Pushback & International Trip @ Metronome

Context: I met with a well-known Infrastructure SaaS company that was a perfect ICP fit for Metronome - they priced based on compute hours and needed billing system flexibility to launch new SKUs rapidly.   

Roadblock: They had already talked to a competitor and were fixated on our “missing” invoicing capability and declined a next step via email.

Sam-I-Am Moment: I took a risky bet, challenging their email and copying in our Product team.  The psychology worked and they agreed to meet with our Product team, which led to a PoC.  Knowing we were behind in the evaluation to the competitor, we took a second bet and flew our lead Solutions Architect to London to run the PoC live onsite and win on the partnership side.  

Result: Ultimately, we walked away from the deal - there were too many feature gaps.  We were now a Series B company and could no longer win deals the way we had during Seed/Series A stage - by winning on the partnership side and building every custom feature a prospect asked for.  While we made a business decision to walk away, we built strong relationships with their SVP Engineering who I still regularly connect with.  

Conclusion

One thing new AEs and SDRs get wrong is how to approach persistence - the key is to be creatively persistent.

Sam-I-Am didn’t just keep asking about green eggs and ham in the same way. He offered different scenarios, different contexts, different angles. Each “no” gave him data to refine his approach.

In enterprise sales, your job isn’t to overcome objections - it’s to find the scenario where your solution makes sense.  Next time you hit a major roadblock, channel your inner Sam-I-Am.