Position Title: Proposal Writer
Position Status: Hybrid, Full Time
Salary Range: $80,000-100,000
About Uwill
Uwill is the leading mental health and wellness solution for colleges, schools, and students. Utilizing its proprietary technology and counselor team, Uwill pioneered the first student and therapist matching platform. The solution offers an immediate appointment with a licensed counselor based on student preferences, all modalities of teletherapy, a direct crisis connection 24/7/365, prescription management, on-demand medical support, basic needs assistance, wellness programming, realtime data, and support. Uwill supports more than 4 million students at 500+ institutions worldwide.
About the Role
Reporting to the SVP of Customer Operations and Support, the Proposal Writer will work closely with the sales, product, and marketing teams, as well as other teams within the organization. The primary goal of the Proposal Writer will be to create documents to effectively communicate our value proposition and technical elements. Types of documentation this position will oversee include sales proposals, RFIs, RFPs, and general documentation in support of sales.
Responsibilities:
Sales RFPs and Proposals
Oversee the creation and submission of a variety of proposal materials (RFPs, RFIs, PPTs, etc.), supporting the entire lifecycle of the documentation process, from scheduling and first draft creation to submission.
Segment projects into discrete steps and establish, communicate, and manage a timeline with consideration for internal and external deadlines.
Customize all materials based on the sales strategy, incorporating appropriate brand messaging.
Generate first draft proposals by drawing from the existing content, with the end goal of establishing a comprehensive response database.
Cultivate critical relationships across the organization in various departments, including sales, marketing, product, counselor success, clinical affairs, and account management.
Build a process for win/loss debriefings to ensure that lessons learned are appropriately captured and communicated.
Manage contributor and reviewer roles according to the strategy and project timeline.
Qualifications:
Bachelor’s degree in Communications, Journalism, or a related field
Experienced writer with excellent proofreading skills (e.g., grammar, spelling, punctuation, syntax errors).
Comfort with Google Docs as well as RFP software tools
High level of proficiency in Microsoft Suite, particularly Word.
Strong organizational skills with the ability to work both independently and collaboratively while managing multiple demands.
Solid research and proposal writing experience.
Detail-oriented with a high standard of accuracy.
Demonstrated success in responding to RFPs.
Maintains a sense of urgency in driving projects to successful completion.
Exceptional verbal and written communication skills.
Highly motivated with the ability to prioritize effectively in a fast-paced environment.
Benefits:
Company-paid medical, vision, and dental coverage for the employee and family
11 paid holidays per year
Flexible paid time off
401(k) plan with company match
A team-oriented culture with a supportive supervisory team and accessible leadership team
Opportunities for advancement within our unique company
As one of the fastest-growing companies in Massachusetts, you will be challenged to build your skills and take on increasing responsibility. Our office environment is open, collaborative, fast-paced, and high-energy.
Uwill is proud to be an equal opportunity employer. We thrive because of the diversity of our employees. At Uwill, people of different backgrounds, experiences, abilities, and perspectives are always welcome. We foster an environment of mutual respect and do not tolerate any discrimination. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, sexual orientation, gender identity, disability, or protected veteran status.

Utilizing its proprietary technology and counselor team, Uwill pioneered the first student and therapist matching platform. The solution offers an immediate appointment with a licensed counselor based on student preferences, all modalities of teletherapy, a direct crisis connection 24/7/365, on-demand medical care, prescription management, basic needs support, wellness programming, realtime data, and support.
In 2025, Uwill was recognized as the #79 fastest growing private company in the US according to Inc, its second consecutive year in the top 100 (#27 in 2024). Uwill also ranked as the #1 fastest growing company in the state of Massachusetts by the Boston Business Journal (2025) and the #32 fastest growing company in North America according to Deloitte (#18 in 2024).