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Microsoft and Shipley’s Strategic Partnership with pWin.ai: Revolutionizing Proposal Writing with AI

pWin.ai expedites Microsoft PCoE’s time to first proposal draft by 93%.


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pWin.ai reduced first proposal draft time by 93%.

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Enabled creation of proposals within 24 hours.

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Achieved uniformity in voice and style across sections.


Microsoft has a long-standing relationship with Shipley, leveraging their expertise to win numerous government and commercial contracts. Recently, Shipley partnered with pWin.ai to develop an AI tool specifically for proposal writing, integrating Shipley’s best practices. This collaboration aims to enhance the efficiency, quality, and compliance of proposal writing, addressing the needs of large-scale operations like Microsoft’s.

As Director of Proposals at Microsoft’s Proposal Center of Excellence (PCoE), Carrie Jordan aimed to make Microsoft’s proposal shop the best in the world. This case study explores her journey, the challenges she faced as she aimed to maintain high-quality outputs while scaling operations, and her eventual decision to adopt pWin.ai, the AI proposal writing technology developed in collaboration with Shipley Associates.

Carrie’s vision was clear: She wanted to revolutionize Microsoft’s proposal process to enhance efficiency and quality. Describing her role as “high pressure” is an understatement, as she was responsible for laying out guiding principles that provide direction to 65 team members that support 10,000+ proposals that Microsoft submits every year.

As ChatGPT burst onto the scene in 2022, Carrie recognized the potential of artificial intelligence (AI) and how it could transform the creation and evaluation of proposal realization. AI brought significant challenges and requirements that needed careful consideration. The partnership between Microsoft, Shipley, and pWin.ai showcases the transformative potential of AI in proposal management. By aligning technology with best practices and user needs, the collaboration has set a new standard for efficiency and quality in the industry. The integration of pWin.ai with Shipley inside has enabled Microsoft to significantly improve their proposal operations, maintaining high standards of security, quality, and efficiency. This case study highlights the strategic decisions,
technological advancements, and collaborative efforts that made the partnership successful, emphasizing the tangible benefits and impact of adopting pWin.ai with Shipley inside for proposal writing at Microsoft.

Initially, Carrie was hesitant about integrating AI into the proposal process. She realized that for AI adoption to be successful, her team needed to embrace the tool with excitement rather than anxiety. She prepared a list of key requirements that an AI solution implemented at Microsoft would have to address:

  • Automating Grunt Work: The AI tool would have to take over repetitive and time-consuming tasks, allowing her team to focus on strategic elements.
  • Adherence to Best Practices: The tool had to generate content that met the highest standards of proposal writing best practices.
  • Technological Soundness: The technology underlying the AI must be robust and reliable.
  • Security: Given the sensitive nature of proposal content, security was a critical concern, and any new tool would have to meet Microsoft standards.
  • Ease of Use and Integration: The tool must integrate seamlessly into existing processes with minimal disruption, facilitating easy change management.

After a grueling evaluation process, Microsoft’s PCoE chose
pWin.ai for several reasons:

  • Security and Quality: pWin.ai met Microsoft’s stringent security and privacy protocols with CMMC Level 2 compliance, ensuring that sensitive data remained protected.
  • Ease of Adoption: Built on Microsoft technologies, pWin.ai facilitated easier integration and user adoption.
    Shipley’s Expertise: Integrating Shipley’s methodology within the tool was critical, ensuring the quality of the output aligned with industry best practices.
  • Shipley’s Expertise: Integrating Shipley’s methodology within the tool was critical, ensuring the quality of the output aligned with industry best practices.
  • Support for Change Management: The pWin.ai team partnered with Shipley to offer weekly masterclasses to help users understand how pWin.ai fits into the end-to-end proposal process, aiding in faster user adoption.

The response from stakeholders and executives was overwhelmingly positive, validating Carrie’s decision to implement AI proactively into PCoE’s proposal writing process. PCoE’s initial use of pWin.ai expedited the time to the first proposal draft by 93%, significantly improving efficiency and team capacity to support even more bids.

The adoption of pWin.ai has not only streamlined the proposal process but also enhanced the quality of outputs, aligning perfectly with Carrie’s vision of creating the best proposal shop in the world.

The tool is set to be rolled out to Microsoft’s entire sales team, with expectations of handling an increasing volume of proposals and significantly contributing to revenue growth.

Carrie Jordan’s journey to adopting pWin.ai exemplifies how leaders can embrace technological innovation to achieve strategic goals. By addressing her team’s challenges and aligning with Shipley and pWin.ai’s goals, Carrie is transforming Microsoft’s proposal process. Her proactive approach to AI adoption paid off in terms of operational efficiency and established her as a forward-thinking leader in proposal management.

The partnership between Microsoft, Shipley, and pWin.ai showcases the transformative potential of AI in proposal management. By aligning technology with best practices and user needs, the collaboration has set a new standard for efficiency and quality in the industry. The integration of pWin.ai with Shipley inside has enabled Microsoft to significantly improve their proposal operations, maintaining high standards of security, quality, and efficiency. This case study highlights the strategic decisions, technological advancements, and collaborative efforts that made the partnership successful, emphasizing the tangible benefits and impact of adopting pWin.ai with Shipley inside for proposal writing at Microsoft.

pWin.ai empowers businesses of all sectors to win proposals faster and more easily. Our AI-powered solution integrates seamlessly with familiar tools like Microsoft Word, Excel, and SharePoint, streamlining your existing workflow without requiring disruptive changes.

pWin.ai handles the heavy lifting, generating high quality content and accelerating your journey to a winning proposal.

A leader in proposal development, Shipley helps companies win business by providing expert consultants, training programs, and culture change solutions.