Musings of a Seasoned Proposal Writer: From Handwritten Drafts to AI-Powered Precision 

By: Chip Schaller, Chief of Capture and Proposals at AutogenAI

Proposal writing has undergone a remarkable transformation over the past 30 years, evolving from a manual, paper-heavy process into a strategic, tech-driven function. With each technological advancement, shifting market dynamic, and evolving stakeholder expectation, the industry has adapted—demanding greater agility, precision, and insight. 

Looking Back: The Early Days of Proposal Writing 

My journey as a proposal writer began with drafting grant proposals for my college, leading me to a Washington, DC-based nonprofit, and eventually into the defense contracting sector. In those early days, proposal development was a solitary and labor-intensive craft—meticulously built from scratch using handwritten drafts, hardcopy binders, and physical color reviews. “Cut and paste” was often literal, involving scissors and glue. Tools were limited to basic word processors and desktop publishing software like PageMaker. 

Collaboration was a challenge. Long email chains, late-night calls, and physical war rooms were the norm, with proposal sections taped to walls to refine structure and flow. Compliance checks were painstaking manual processes, and meeting deadlines required sheer endurance and meticulous attention to detail. 

The Digital Shift: A Game-Changer for Proposal Management 

The arrival of digital tools revolutionized proposal writing. Computers, the internet, and specialized software brought newfound efficiencies—automated compliance checks, collaborative writing platforms, and sophisticated data analysis tools. The process became more dynamic, enabling faster responses and better alignment with client needs. 

Today, cloud-based platforms streamline version control, AI-driven tools like AwardGen™ accelerate content creation, and remote collaboration enables global teams to work in real time. What once required couriers delivering proposal binders can now be accomplished with a single click, fundamentally changing how we operate. 

What Remains Constant—and What Lies Ahead 

Despite these advances, the core principles of proposal writing remain the same: understanding the customer, crafting compelling value propositions, and ensuring compliance. However, AI is revolutionizing the how—enhancing data analysis, optimizing content, and enabling faster, more strategic responses. 

As AI levels the playing field, it is also transforming client expectations. Organizations now expect highly tailored, solution-oriented proposals that address their unique challenges with precision. Proposal teams are adapting by leveraging AI-driven insights to craft high-value solutions with minimal reliance on subject matter experts, ultimately increasing speed and strategic alignment. 

The Call to Action: Embracing the Future 

Proposal writing is no longer just a tactical function; it’s a strategic discipline at the intersection of marketing, sales, and technology. The challenge now is to embrace AI tools effectively and continuously refine our approach to stay competitive. 

Whether you’re a seasoned professional or new to the field, the question remains: How will you adapt to the next wave of change in proposal writing?