Director of Planning Enablement at Bank of Montreal in Chicago, IL

Director of Planning Enablement Location: Chicago, IL, USA Application Deadline: 05/28/2026 Address: 320 S Canal Street Job Family Group: Wealth Sales & Service Position Overview The Director, Planning Enablement is a senior individual contributor responsible for building and executing a content strategy that equips BMO’s sales-facing and planning teams with timely, high-impact planning insights for High Net Worth (HNW) client conversations. This leader curates, creates, and deploys a cohesive planning-content ‘throughline’ across the full planning discipline—Private Banking (PB), Family Office (FO), Philanthropy, Family Governance, and Trust—to ensure consistent market positioning, best practices, and field utilization. As a member of the Planning Leadership Team, this role is a central connector between planning subject matter experts, field teams, Training & Development, Marketing, and Compliance to ensure content is accurate, approved, discoverable, and actively used in client meetings, seminars, and events. This is not a people-manager role. Success requires strong leadership through influence, excellent editorial judgment, and disciplined program execution across multiple stakeholders. Key Outcomes A best-in-class, centralized planning content library that showcases the best of BMO across PB/FO/Philanthropy/Family Governance/Trust and supports the field with client-ready tools. A repeatable content deployment model (calendar, channels, packaging, reinforcement) that increases adoption by sales-facing teams and planners. Demonstrable utilization and impact: increased field usage of planning content, stronger consistency in HNW positioning, and lift via Training & Development alignment. Key Responsibilities 1) Content Strategy & Editorial Leadership Own the planning content strategy and define the thematic ‘throughline’ that guides what is produced, when it is deployed, and how it supports go-to-market planning priorities for HNW clients. Build and manage an annual and quarterly editorial roadmap aligned to seasonal planning moments, market/legislative developments, and prioritized client needs. Solicit and translate field feedback and Planning Leadership priorities into an actionable, client-ready content pipeline. 2) Field Enablement & Content Deployment (Sales Enablement) Establish a repeatable content deployment cadence—ensuring the field receives the right content at the right time, with clear ‘how to use this’ guidance. Package content for use in client meetings (e.g., talk tracks, discovery prompts, one-pagers, FAQs, objection handling, case studies, and ‘next best conversation’ suggestions). Partner with sales-facing leaders to reinforce adoption and create feedback loops to improve relevance and usability. 3) Training & Development Alignment Align select content with Training & Development decks and enablement programming to help sales-facing teams adopt new ideas and confidently position them with HNW clients. Ensure content translates planning expertise into clear behaviors and client conversation pathways. 4) Cross-Discipline Orchestration (PB, FO, Philanthropy, Family Governance, Trust) Coordinate across the planning discipline to develop a unified content library reflecting PB, FO, Philanthropy, Family Governance, and Trust capabilities. Establish and run a governance rhythm (e.g., editorial council / intake process) to prioritize, sequence, and standardize content creation across SMEs. 5) Content Library Ownership & Knowledge Management Build and maintain the centralized content library with clear taxonomy, version control, usage guidance, and retirement/refresh rules. Track usage and outcomes (views/downloads, training tie-ins, field feedback) and adjust the roadmap to maximize utilization. 6) Annual Gap Analysis & Content Build Program Conduct an annual gap analysis to identify missing/outdated content versus client needs, market changes, and best practices. Convert gaps into a build plan with owners, timelines, and approval paths; coordinate creation with planning SMEs and partners. 7) Compliance + Marketing Partnership & Amplification Partner with Compliance and Marketing to ensure content is appropriately reviewed, approved, and distributed through approved channels, with auditability and governance. Support amplification and internal campaigns that drive content awareness and field adoption. 8) Conferences, Seminars, & Best-Practice Sharing Help market the BMO planning brand at conferences and industry events; synthesize learnings into actionable briefs and field-ready content. Facilitate planners’ seminar presentations to external audiences and leverage content for efficient, repeatable events. Share best practices, learning opportunities, and ‘what changed / what to do now’ updates to keep the planning field team current. 9) Planning Summit & Events Help lead planning and execution of the Planning Summit and other wealth planning internal/external events, including content construction, exaction, and post-event enablement packages. Qualifications Required Deep planning expertise and demonstrated experience in the HNW client space. Proven ability to translate complex planning concepts into clear, usable content for sales-facing teams and planners. Strong cross-functional leadership skills—stakeholder management, influence without authority, and program execution discipline. Preferred Advanced degree or credential aligned to senior planning roles (e.g., JD, CPA, CFA, CFP® or similar). Core Competencies Strategic editorial leadership; ability to create a coherent narrative ‘throughline’. Strong technical planning fluency and judgment for HNW relevance. Influence and execution across complex stakeholder ecosystems. Program management (roadmaps, cadences, workflows, approvals). Outcomes orientation (utilization, adoption, and measurable impact). Success Measures Content library launched with standards, governance, and measurable growth in client-ready assets; annual gap analysis completed and executed. Measurable field utilization (adoption metrics + qualitative feedback) and integration into Training & Development programming. Faster time-to-market for timely planning updates with compliant, approved amplification. Framework to capture and disseminate best practices and presentation efficiency built and implemented. Salary: $137,000.00 - $238,000.00 Pay Type: Salaried The above represents BMO Financial Group’s pay range and type. Salaries will vary based on factors such as location, skills, experience, education, and qualifications for the role, and may include a commission structure. Salaries for part-time roles will be pro-rated based on number of hours regularly worked. For commission roles, the salary listed above represents BMO Financial Group’s expected target for the first year in this position. BMO Financial Group’s total compensation package will vary based on the pay type of the position and may include performance-based incentives, discretionary bonuses, as well as other perks and rewards. BMO also offers health insurance, tuition reimbursement, accident and life insurance, and retirement savings plans. To view more details of our benefits, please visit: https://jobs.bmo.com/global/en/Total-Rewards About Us At BMO we are driven by a shared Purpose: Boldly Grow the Good in business and life. It calls on us to create lasting, positive change for our customers, our communities and our people. By working together, innovating and pushing boundaries, we transform lives and businesses, and power economic growth around the world. As a member of the BMO team you are valued, respected and heard, and you have more ways to grow and make an impact.  We strive to help you make an impact from day one – for yourself and our customers.  We’ll support you with the tools and resources you need to reach new milestones, as you help our customers reach theirs. From in-depth training and coaching, to manager support and network-building opportunities, we’ll help you gain valuable experience, and broaden your skillset. To find out more visit us at http://jobs.bmo.com/us/en BMO is proud to be an equal employment opportunity employer. We evaluate applicants without regard to race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or any other legally protected characteristics. We also consider applicants with criminal histories, consistent with applicable federal, state and local law. BMO is committed to working with and providing reasonable accommodations to individuals with disabilities. If you need a reasonable accommodation because of a disability for any part of the employment process, please send an e-mail to BMOCareers.Support@bmo.com and let us know the nature of your request and your contact information. 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