Using the Norwegian case of an integrated welfare and employment service organisation, this study examined how organisational factors of this far‐reaching, street‐level agency have affected frontline workers’ opportunities to provide individualised services to users with complex needs. The article reports on two different policy and organisational settings: frontline workers as ‘generalists’ in a ‘national employment policy context’, and frontline workers as ‘specialists’ in a policy context that emphasises ‘empowering the local level’. Findings suggest that the generalists in the study did not experience an opportunity to utilise the flexibility available to them in selecting suitable measures, nor did they develop user‐specific knowledge. The article argues that caseworker specialisation can create more room for discretion and professional knowledge about users and which measures should be applied, thereby improving the opportunity to tailor services in a ‘one size fits all’ organisational context.