Bring Ryan to SKO (Aug 19-21, LA) - make the ask on his behalf and let him choose his own duration

Situation

In the 7/23 Ryan 1:1 Peter learned nobody had asked Ryan about the sales kickoff. He decided support should be represented, said he would take it to Chris Baek himself, and explicitly refused to dictate how long Ryan should attend - I am going to turn it around, I am going to support whatever you want. He called Baek the same evening and confirmed back to Ryan an hour later that Baek was on board. Peter himself attends only Thursday the 20th.

Reasoning

Peter spent his own capital rather than routing Ryan to ask, because Ryan was never going to ask for himself - Ryan told him he deliberately stays on the edge of SKO, having championed it for years, feeling last November went sideways, and consciously waving the pom-poms from the side out of respect for Lindsay and Hope running it. Peter making the call and carrying it removes the awkwardness entirely. The timing next to the comp conversation was deliberate: Peter had just told Ryan the re-leveling would not resolve his comp ask, so giving him something concrete and visible - a seat at the companys revenue moment - is a substitute form of investment Peter could actually deliver in that conversation. Handing Ryan the duration choice after naming the cost himself (three days away from a short-staffed team) treats him as the person who knows his own capacity - the same construction as the headcount exchange in the same 1:1, where Peter set the constraint and Ryan picked inside it. The stated reason also holds on its own: support needs a voice in front of sales and Ryan is the bridge between engineering and revenue.

Additional Context

Peter confirmed both the reasoning and that the placement next to the comp conversation was intentional. Ryans team is already short - Owen departing, Arsalan out for a first child. Ryan is rearranging a booked Myrtle Beach trip to his mother, made easier because SKO is in LA rather than Reno.

Observed Evidence

Fathom transcript plus three Slack messages showing same-day execution: the ask to Baek 14 minutes after the 1:1 ended, confirmation to Ryan 24 minutes later, and Ryan following up on Peters own attendance day the next morning.

Matching Patterns

Confidence Breakdown

Reasoning Depth Analysis