Diamond Willow Advisory isn’t your typical financial services firm. We help ambitious, mid-market businesses access the capital they need to grow, transform, or survive. Our specialty is complex corporate debt transactions—and we bring clarity, urgency, and execution horsepower to situations where others fall short.

This role anchors that promise. If you’re the person who lives for order, turns chaos into clean processes, and takes pride in spotless follow-through, keep reading.

You’ll be the operational heartbeat of our Calgary office - keeping the team organized, driving lender outreach and follow-ups, and increasingly supporting deal execution with financial models and polished lender presentations. This is for someone who prefers to perform in-office with a high-ownership, detail-obsessed mindset.

• Keep us relentlessly organized
‍Own calendars, task lists, meeting prep, travel coordination, and inbox triage for key team members. Maintain clean document management (naming conventions, checklists, trackers, data rooms, NDAs/KYC packages).

• Run our lender outreach machine
‍Research and maintain lender databases by lending type, lending size, sector, and risk profile. Build and run outreach sequences, track responses in the CRM, book meetings, and document next steps.Prep concise lender briefs ahead of calls; capture and circulate crisp call notes and action items.

• Support deal execution
‍Build and maintain checklists, close plans, diligence trackers, and reporting cadences. Assemble first-pass lender materials: teasers, exec summaries, and credit-style memos (PowerPoint/Word). Prepare data room folders and keep them current.

• Grow into financial modelling & presentations
‍Update 3-statement models, borrowing base and covenant schedules, and basic scenarios under guidance. Turn analysis into client- and lender-ready slides with zero-defect attention to detail.

• Report and improve
‍Publish weekly pipeline and lender-outreach dashboards from CRM/Excel. Spot process gaps and tighten them—templates, naming conventions, and “done-right-the-first-time” habits.

• 2 - 6 years in operations, executive admin, credit/lending administration, corporate banking support, or similar professional services.
• Meticulous, systems-driven operator: you love checklists, version control, and clean files.
• Strong writing and formatting—the kind that makes lenders and executives say “crisp.”
• PowerPoint/Word: you finish with aligned boxes, consistent styles, and airtight grammar.
• CRM: comfortable owning records, pipelines, and activity hygiene (Dynamics/HubSpot/Salesforce experience a plus).
• Professional discretion with sensitive information; high integrity and follow-through.

• Exposure to credit/lending, private credit, corporate banking, or restructuring.
• Familiarity with data rooms (SharePoint/Box/Dropbox), Adobe (PDF/X), and Canva or InDesign.

• 30 Days: You own calendars, task systems, lender lists, and basic outreach.
• 90 Days: You’re running outreach end-to-end, models are updated with supervision, and lender decks ship with minimal edits.
• 6 Months: You’re a force multiplier—anticipating needs, tightening processes, and contributing reliable analysis and presentation work across multiple deals.

• High-integrity platform that values reputation over shortcuts.
• Loyal, experienced team focused on impact, pace, and client outcomes.
• Growth path into deeper deal execution and financial analysis for those who lean in.

• Calgary-based, in office Monday–Friday (some flexibility as needed by deals).
• Competitive salary and bonus upside.