Higher education institution career and employability services are evolving from bounded, standalone services toward being members of “connected communities”, pursuing projects in “coordinated collaboration” with a wide range of internal and external stakeholders. This has required a shift in career and employability service priorities from the traditional intensive individual career counselling and guidance, toward efforts to work at greater scale with cohorts, such as contributing to the curriculum or delivering large scale career education programs and services that work alongside it. There is a growing ecosystem of career and employability EdTech providers, with several dominant platforms offering comprehensive suites of products alongside numerous smaller niche providers. The ecosystem can be viewed as an example of wider conversations around the emergence of the ‘digital university’. This chapter will bring together conversations about the development of the digital university with conversations in the field of career guidance about the development of digital tools.