Senior Manager, Proposal Strategy, Content & Enablement

Ainsworth Inc; Mississauga; Hybrid; CAD 90,000 - 120,000; Full time

Benefits offered by this job

Comprehensive health, dental, and medical benefits

RSP matching

Generous vacation

Service milestones and peer recognition

Employee Discounts and Incentives

Job summary

A leading multi-trade services company in Mississauga is seeking a Senior Manager, Proposal Strategy & Content Enablement to drive proposal initiatives. The role combines strategic leadership with hands-on execution, overseeing content quality and effectiveness. Desired candidates have 7-10 years of experience in proposal management and demonstrate excellent leadership and communication skills. The position offers a salary range of $90,000 to $120,000, along with comprehensive benefits and a hybrid work model.

Qualifications

• 7–10+ years of experience in proposal management, sales enablement, or related roles.
• Proven ability to lead through influence and dotted-line relationships.
• Strong strategic judgment combined with willingness to execute tactically.
• Experience operating as a player-coach in lean or high-impact environments.
• Excellent communication and stakeholder management skills.

Responsibilities

• Central point of leadership and alignment for proposal content.
• Provide strategic guidance, standards, and frameworks to teams.
• Track and communicate impact through metrics.
• Support tactical execution during peak demand.

Skills

Proposal management

Sales enablement

Content strategy

Leadership

Communication skills

Job description

If you thrive in a team-oriented workplace that challenges your skills, to drive your career development, embraces diversity and rewards innovation, with competitive pay and great employee programs, join the GDI Ainsworth team today!

Job Summary

The Senior Manager, Proposal Strategy & Content Enablement serves as the strategic owner and connective leader for proposal content and strategic response initiatives across the organization. This role combines hands-on execution with enterprise-level leadership, providing direction, alignment, and enablement to proposal, business development, and operational sales teams through both direct and dotted-line engagement.

With one direct report, this role functions as a player-coach, accountable for outcomes, prioritization, and forward momentum—while actively contributing to tactical deliverables where needed to ensure quality, speed, and impact.

Key Responsibilities

• Act as the central point of leadership and alignment for proposal content, strategic responses, and proposal enablement across the business.
• Provide strategic guidance, standards, and frameworks to proposal, BD, and operational sales teams.
• Ensure proposal efforts align with enterprise priorities, value propositions, and go-to-market strategy.
• Own the implementation, scaling, and optimization of proposal software across the business to improve proposal effectiveness, efficiency, and consistency.
• Define the vision and roadmap for proposal technology and content systems.
• Drive use of standardized language, templates, and reusable content.
• Partner with Sales, Marketing, Operations, and IT to integrate proposal tools into broader workflows.
• Track and communicate impact through metrics such as cycle time, content reuse, and response quality.
• Own proposal and content outcomes, including quality, effectiveness, and strategic impact.
• Manage intake, prioritization, and sequencing of proposal initiatives and technology enhancements.
• Make informed trade-off decisions to focus on high-value opportunities.
• Maintain momentum and resolve obstacles across initiatives.
• Contribute directly to strategic proposals, executive summaries, and win themes.
• Support tactical execution during peak demand or high-stakes pursuits.
• Provide real-time coaching and quality oversight.
• Oversee governance and evolution of proposal content and response assets.
• Ensure content is current, compliant, reusable, and aligned to strategic messaging.
• Develop standardized narratives, value frameworks, and proposal best practices.
• Translate complex SME inputs into clear, compelling proposal content.

Qualifications

• 7–10+ years of experience in proposal management, sales enablement, content strategy, or related roles.
• Proven ability to lead through influence and dotted-line relationships.
• Strong strategic judgment combined with willingness to execute tactically.
• Experience operating as a player-coach in lean or high-impact environments.
• Excellent communication and stakeholder management skills.

The salary range is $90,000 to $120,000 per year. Actual salaries will vary based on factors such as education, experience, knowledge, skills, and abilities, as well as alignment with market data. The base salary is just one component of Ainsworth’s total compensation package, which also includes additional rewards and benefits such as short-term incentives and health insurance, among others.

This posting is for an active and current vacancy; interested applicants are encouraged to apply as soon as possible.

Why work at GDI Ainsworth?

Benefits

GDI Ainsworth is growing at an unprecedented rate and to help attract and retain top talent, we provide benefits on your first day with us. We offer a wide variety of benefits including the following:

• Benefits: Comprehensive health, dental and medical benefits, including wellness supports, RSP matching and generous vacation
• Rewards: Service milestones and peer recognition plus Employee Discounts and Incentives
• Flexibility: Hybrid working models, where applicable
• Diversity: An inclusive organization that embraces diversity and belonging; work in a great team atmosphere with future potential for promotion within company

While we appreciate all applications we receive, we advise that only candidates under consideration will be contacted.

GDI Ainsworth is committed to building a diverse and inclusive workplace. Qualified designated group members are encouraged to apply as any reasonable accommodation of qualifications will be considered as per our Accommodation Policy, available upon request.

GDI Ainsworth is an integrated multi-trade company, offering end-to-end services and solutions for all asset maintenance and refurbishment requirements of our customers. We are continually striving to create better and more advanced products as well as provide the highest quality service. We are rapidly growing and need talented professionals to help drive our vision at becoming the best multi-trade company in the country! Join us…. Make a difference.