AI agents are reshaping the workspace, leading to drastic change of how humans work. Despite the considerable potential of human-agent collaboration both in preserving human agency and generating economic value, this paradigm remains largely absent from occupational task evaluation, hindered by the difficulty of gathering real human data and accounting for inter-human variability. We introduce CollabSkill, a framework for evaluating human-agent collaboration on real-world occupational tasks. CollabSkill pairs real human workers with AI agents on tasks matched to their occupational background, collecting data that capture the complexity of economically valuable tasks and the usage patterns of real workers. To account for inter-human variability, CollabSkill employs a Bayesian skill rating system to disentangle and quantify the skill contributions of both humans and AI agents. Drawing on over 1,500 prompts from 386 working sessions contributed by 93 human workers, our analysis yields insights on two fronts: on the agent side, rankings on CollabSkill diverge meaningfully from those of existing fully autonomous benchmarks where Codex leads, with Claude Code ranking first; on the human side, CollabSkill reveals that practical experience emerges as the primary driver of collaboration skill, with hands-on collaboration meaningfully shifting workers' AI literacy. Together, we hope CollabSkill enables the community to invest in systematic evaluation of human-agent collaboration and spurs development efforts aimed at building AI agents that genuinely augment human workers.