Skylar moved from building products at companies like BetterUp, Justworks, and Level into venture investing, and that background shapes how she judges founders—she looks for a few deeply engaged customers over many lightly satisfied ones, pushes for more systematic, measurable ways to evaluate founders instead of relying on gut feel, and expects software to prove its value quickly rather than through a sales pitch. In AI, she looks past the hype to ask whether a startup truly owns proprietary data, workflows, or deep industry expertise, and she's known for staying closely involved with founders through the earliest, messiest decisions—like picking a cofounder or timing a raise—always ready to roll up her sleeves and help solve problems rather than just watch from the board seat.