Context: freelancers and startups could provide each other with promising opportunities that lead to mutual growth, by improving software development metrics, such as cost, time, and quality. Niche skills processed by freelancers could help startups reduce uncertainties associated with developments and markets, with the ability to quickly address market issues (and with higher quality). This requires the associations between freelancers and startup to be long-term, based on trust, and promising agreements driven by motivations (leading to the growth of both parties). Freelancers could help startups foster innovations and undertake software development tasks in better ways than conducted in-house, if they are selected using informed decision-making. Objectives: the paper has three objectives, (1) to explore the strategies of startups to outsource software development tasks to freelancers (termed as freelancing association strategies); (2) to identify challenges in such outsourcings; and (3) to identify the impacts of outsourcing tasks to freelancers on overall project metrics. The overall objective is to understand the strategies for involving freelancers in the software development process, throughout the startup lifecycle, and the associated challenges and the impacts that help to foster innovation (to maintain competitive advantages). Method: this paper performs empirical studies through case studies of three software startups located in Italy, France, and India, followed by a survey of 54 freelancers. The results are analyzed and compared in the identification of association models, issues, challenges, and reported results arising because of such associations. The case study results are validated using members checking with the research participants, which shows a higher level of result agreements. Results: the results indicate that the freelancer association strategy is task based, panel based, or a hybrid. The associations are constrained by issues such as deciding pricing, setting deadlines, difficulty in getting good freelancers, quality issues with software artefacts, and efforts to access freelancer work submissions for reward. The associations have a positive impact on software development if there is availability of good freelancers (which lasts long for various tasks). The paper finally provides a freelancing model framework and recommends activities that could result in making the situation beneficial to both parties, and streamline such associations. Fostering innovation in startups is, thus, a trade-off situation, which is limited and supported by many conflicting parameters.
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