Proposal Specialist Job in Toronto, ON at Cloudworks

Job Description

Cloudworks is one of North America’s fastest growing technology services companies specializing solely in cloud and hyper-automation advisory and implementation services. With experience across Oracle, Ultimate, Workday, Microsoft, ServiceNow, Google, UiPath RPA we can help your business quickly and effectively take advantage of these cutting-edge technologies.

Why work with us

People – We are passionate about fostering a culture where people thrive. Our hiring process is very thorough to help ensure potential candidates are top talent, a good fit, and giving candidates a chance to understand if Cloudworks is a right fit for them too!

Teamwork – We strongly believe in the power of success through teamwork. Working at Cloudworks you will feel an integral part of a high-performing team where all team members are accountable to each other. Together we support but also push each other to achieve great results for our clients.

Investment – Unlike many consulting companies which rely on a semi-annual or annual performance review cycle, we believe in investing in our staff through feedback which happens much more in real-time. We seek to help everyone understand and develop their strengths and capabilities, relying on an individual’s own motivations to drive results.

Perks – Work from anywhere: our employees can work remotely from their home office or can use one of our centrally located offices. Our full-time employees are provided with a comprehensive benefits package, retirement plan, unlimited vacation, a gym membership allowance, and reimbursement for internet & phone.

Proposal Specialist

Cloudworks has an immediate opportunity for a Proposal Specialist. We are looking for your unusual balance of creativity, style, attention to detail, and business acumen! If you have a minimum of 5 years’ experience coordinating and writing proposals, we want to hear from you!

Work you’ll do

Cloudworks needs thought leaders like yourself to help pave the way for our cross-functional teams to deliver high-quality proposals. Your responsibilities will include:

Manage the end-to-end proposal process from building templates to content submission

Facilitate touchpoints with proposal response teams and follow-up on outstanding deliverables

Prepare professionally written responses to proposal documents that specifically address customer requirements while positioning for success; ensure compliance, accuracy, timeliness, and incorporate key win-themes throughout our responses and client communications

Research the customer to understand their environment, politics, limitations, pain points, and other factors that will translate to a response that wins

Manage proposals to meet customer deadlines and manage communications with key stakeholders to ensure milestones are met

Review final proposal collateral for quality, format, and content for adherence to the firm’s brand standards

Ensure timely delivery of differentiated and outstanding proposals (upload or print material)

Multitask ongoing proposals; collaborate with multiple proposal teams simultaneously

Write, review, and maintain standard content used for proposals including resumes, project case studies, and standard company information

Own, maintain, and drive traffic to Qvidian, our tool for assembling proposals and repository for standard firm content, resumes, project case studies, and other collateral

Leverage content from proposals to build PowerPoint decks for oral presentations

Occasionally support other client deliverables such as Statements of Work, Kick-off decks, marketing content, etc.

Monitor proposal posting services to assess and identify the right opportunities for consideration and pursuit by our practice

Create reports for Business Development team to analyze the quality of data in HubSpot and helps update datapoints

Support ad hoc requests from the Business Development and Marketing leads to support company-wide initiatives


For this role, we are looking for candidates who have the following:

Experience working on private & public sector proposals, across industries and geographies (Canada and the USA)

Experience in professional services (management consulting, legal, architectural, engineering, and accounting firms)

Experience with any of the following would be considered a strong asset:



Office Timeline

Designing visually appealing documents while following brand guidelines (Word, PowerPoint)

Submission portals: MERX, Biddingo, Bonfire, BidsUSA, etc.

Working knowledge of Oracle, UiPath, and/or ServiceNow systems


University Degree

Minimum of 5 years of experience writing and coordinating proposals

Professional business acumen with excellent communication skills

Advanced computer skills in Microsoft Office, especially Word, PowerPoint, Excel, and SharePoint

Near-obsessive attention to detail and quality

Creativity (in both writing style and graphical/visual ability) to present ideas in a creative, clear, and engaging way

Highly organized with the ability to meet tight deadlines and adapt to changing needs

Ability to use discretion and independent judgment when dealing with customer issues and ambiguous situations

Ability to work independently with minimal supervision


Our offices are in Toronto, Mississauga, Calgary, and Kansas, but we are open to candidates from across Canada and the U.S.A. as we give our staff the flexibility to work remotely.

We thank all applicants; however, only those being considered will be contacted. At Cloudworks we are an equal opportunity employer committed to an inclusive recruitment and selection process. If you require accommodation or need this job posting in an accessible format, please contact us at [email protected]

About the Company

Company: Cloudworks

Company Location:  Toronto, ON

Estimated Salary:

About Cloudworks