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The lean startup approach (LSA) is extensively utilized by early-stage entrepreneurs, with “pivot” serving as a key pillar. However, there is a research gap concerning the boundary conditions impacting LSA and pivot decisions, especially when addressing societal challenges, as in the context of transformational entrepreneurship. In this regard, the healthcare sector, further compounded by a lack of research on startups and scale-ups, presents an embraced opportunity to provide multiple contributions for both theory and practice.

The present investigation employs a grounded approach to explore the experiences of the co-founders of a fast-growing Italian e-health startup. A narrative strategy was employed to organize conditions and evolving strategic action/interactions into three different pivoting phases of the startup – before the pivot, its enactment and aftermath – with primary and secondary data collected over a period of one year.

Pivoting in digital healthcare unfolded as a liminal experience marked by factors such as high regulation, multiple stakeholders, technological and symbolic ambivalence, resource-intensive demands and institutional actors acting as pathway pioneers, leading to an information overload and unforeseeable uncertainty to manage. These factors challenge entrepreneurs' ability to attain optimal distinctiveness, presenting the paradoxical need for vertical flexibility for scaling up.

By uniquely illuminating the sector’s constraints on entrepreneurial phenomena, this study provides a valuable guide for entrepreneurs and institutional actors in addressing societal challenges.

This study introduces a process model of transformational information crafting when pivoting, highlighting the role of entrepreneurs' transformational stance and platform-mediated solutions as engines behind strategies involving information breaking and transition, preceding knowledge-driven integration strategies.

This study aims to develop theory on the process toward digital service innovation (DSI) and to generate insights into how companies deal with the rising complexity associated with DSI, both inside and outside of the organization, through organizational learning and alignment.

After purposeful sampling, in-depth, longitudinal case studies of three manufacturers are presented as illustration. Per case, multiple semi-structured interviews are conducted, and insights are validated through rich additional data gathering. Each company's DSI pathway is reconstructed with critical incident technique. Next, using systematic combining, a middle-range theory is developed by proposing a theoretical frame concerning the relations between DSI maturity, learning and alignment.

The authors posit that, as companies gradually develop and progress toward DSI maturity, they deal with a rising degree of complexity, fueling their learning needs. Companies that are apt to learn, pass through multiple cycles of learning and alignment to overcome specific complexities associated with different DSI stages, with each cycle unlocking new DSI opportunities and challenges.

The study applies a stage-based view on DSI combined with complexity management and organizational learning and alignment theory. It offers a theoretical frame and propositions to be used by researchers for future DSI studies and by managers to evaluate alternative DSI strategies and implementation steps.