Job Description
Day to Day:
This role is a rare opportunity to architect AI driven transformation within one of the most complex and high stakes proposal environments in the country. As Director of Proposal Development & AI Automation, you will modernize the end to end RFP response process by replacing manual, fragmented workflows with intelligent automation, standardized content libraries, and data driven accountability.
You will be matrixed across two high impact teams — Proposal Development (a team of six technical writers) and EMS Innovation & Rural Health Transformation — while influencing without authority across finance, legal, compliance, clinical operations, and other key functions. This is a true zero to one build for someone who thrives in ambiguity and wants to leave a lasting mark on a mission driven healthcare organization.
Approximately 80% of the role focuses on transforming large, complex government proposal operations through automation, AI, and data driven workflows. The remaining 20% supports rural health and EMS transformation initiatives tied to federal funding.
This is a senior, hands on individual contributor role responsible for designing and implementing scalable systems where manual processes exist today. Success requires strong technical execution, exceptional writing ability, and the ability to influence across a highly matrixed environment.
We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.
Required Skills & Experience
• Bachelor’s degree in business, Healthcare Administration, English, Information Systems, or related field
• 8–10 years of experience in proposal development, automation, or program management within healthcare
• Hands on experience implementing AI, automation, or workflow tools; strong technical aptitude.
• Proven background in proposal development, technical writing, or content operations specifically in healthcare, with government contracting as a complementary plus.
• Ability to write and operate confidently within healthcare terminology and regulated environments.
• Exceptional communication and the ability to drive alignment without direct authority.
• Experience leading complex, cross functional initiatives; strong program and project management capability.
• Strong skills in Microsoft Word, Excel, PowerPoint, and SharePoint; Salesforce and Microsoft Copilot experience preferred.
• Exceptional written communication and mastery of English.
Nice to Have Skills & Experience
• MBA or advanced degree
• Experience supporting enterprise growth, transformation, or innovation initiatives
Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.