Senior Manager, Proposal Strategy, Content & Enablement

Ainsworth Inc•Mississauga, ON

79d•CA$90,000 - CA$120,000•Hybrid

About The Position

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.

Requirements

7 to 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.

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.