
THE FESTIVAL MORTGAGE NEEDS!
Sept 23 & 24 | International Centre, Toronto
Bring ideas. Bring your team. Build your advantage.
BIGGER EVENT.
BETTER FORMAT.
BOLDER AMBITION.
The Canadian Mortgage Summit is becoming something bigger. MortgageFest Canada is the is the festival the industry has been asking for – two full days, two stages, 2,000+ brokers, lenders, executives, and innovators, and a format built for people who want more than a conference.
Bigger event. Bigger ambition. September 23–24 at the International Centre, Toronto. Come ready to do business, have the conversations that matter, and leave with more than you came with.

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InsuranceFest was a ‘wow’ experience – after more than 600 conferences, I’d rank the networking and social interaction on the Santa Monica Pier in my top five.
INSURANCEFEST AT A GLANCE
Network Like You Mean It
1,000+ insurance leaders, founders, and innovators in one place. Brokers, MGAs, agencies, insurers, InsurTechs. From C-suite to NextGen, they’ll all be on the pier.
Join the Conversation
60+ industry voices you actually want to hear from—from Aon to Marsh McLennan to InsurTech founders. Interactive sessions across every zone where you’re invited to jump in, ask what you really want to know, and steer the discussion. This isn’t sit-and-listen; it’s speak up and be heard.
Hands-On Marketplace
30+ exhibitors and interactive InsurTech demos you can actually touch and test. A buzzing marketplace of ideas, solutions, and collaborations where you discover new tools, products, and partners to tackle your biggest challenges.N ot just watching — finding what you’ll take back to your work.
Discussion Table Real Talk
50+ exclusive, 1-hour Discussion Tables for senior brokers and decision-makers. Small-group, facilitated conversations on Cyber, Digital Transformation, Construction, and E&S where everyone leans in, swaps war stories, and pressure-tests ideas in real time.
Bring Your Crew
Team experiences and group sessions designed so your whole organization goes back energized with shared insights and new connections. Build your own festival lineup as a team, join collaborative workshops together, tackle live challenges side by side, and turn the pier into your offsite — complete with shared moments, fresh ideas, and stories you’ll still be talking about back at the office.
Festival Energy on the Pier
From sunrise yoga to sunset sets, food trucks, cocktails, and ocean air — the pier turns every coffee break into a moment.
- Summit Stage
- Insights Stage
- Expo & Networking
The main stage. Big ideas, bold voices, the conversations the whole industry wants to have. Where the market is heading, how underwriting is shifting, what it takes to win when competition is tighter. The renewal wave, AI, private lending, client trust — all of it, in one room.
This is where the real work gets done. Hands-on sessions with people who've been exactly where you are — leave with a framework you'll actually use, a decision made, or a next step you can act on straight away. Tax structuring, succession, fraud risk, lead generation. Practical and immediate.
Two days on the floor with 2,000+ of the people who matter most to your business. Dive into our all new surprise experiences, find the conversations you didn't know you needed, and leave with relationships that do something.
WOMEN
IN MORTGAGE SUMMIT
Running alongside Day 2 of MortgageFest Canada, Women in Mortgage Summit Canada is a dedicated one-day event bringing together 500+ women across the industry – brokers, lenders, executives, and emerging leaders.
A high-energy day of influential speakers, candid conversations, and powerful networking built to advance the women shaping Canada’s mortgage future.

WHAT ATTENDEES ARE SAYING




KEYNOTE SPEAKER
JESSICA HOLMES
Taking to the stage on Day 2, Jessica is opening the event with something this industry doesn't hear enough of: an honest, relatable, and deeply human conversation about how to actually keep going when the market is brutal, the pressure is relentless, and you're running on fumes.
World reknown is a comedian and motivational speaker. She has brought the house down, opening for giants such as Ellen DeGeneres, Jerry Seinfeld, and Oprah Winfrey. She performed at Just For Laughs, The Second City, and starred in the comedy series The Holmes Show and Royal Canadian Air Farce.
Funny, candid, and closer to home than you'll expect. Day 2 starts here.
SESSION HIGHLIGHTS
What Brokers Are Getting Wrong Right Now — And What It's Costing Them (Summit Stage)
A candid, no-filter look at where deals are being lost unnecessarily, where client trust is quietly eroding, and where brokers are unintentionally creating friction with lenders. Small adjustments. Big impact on approvals, conversions, and relationships.
AI + the Broker Advantage - Winning the Complex Deals (Summit Stage)
Automation is already moving clean, straightforward files through without a broker. This panel gets honest about where AI is reshaping deal flow, where human judgment still wins, and exactly how top brokers are staying essential — and ahead — in an increasingly automated market.
How to Protect Your License When Deals Go Wrong (Insights Stage)
Fraud is getting smarter, more digital, and harder to detect — and AI-generated documents are raising the stakes for every broker. Real cases, real legal exposure, and a live Q&A on the grey-area situations brokers are actually facing right now.
Why Deals Get Approved (or Rejected): Inside the Underwriter’s Decision Process (Summit Stage)
Every broker has had a deal declined and wondered what actually happened. This session pulls back the curtain on how underwriting decisions are really made — beyond the guidelines — and what you can do differently at the file level to improve approval speed, reduce conditions, and win more business.
HIGHLIGHT SPEAKERS
Jodie Kaufman Davis
Jodie Kaufman Davis is the Group Co-President of H.W. Kaufman Group and a member of the company’s Board of Directors. A leader in developing and executing company strategy and management-driven initiatives, Jodie advises on best practices and expertise to drive the company’s global growth strategy.
As part of her leadership role, Jodie serves as Vice Chair, Atain Insurance Companies and oversees RB Jones, the Kaufman subsidiary that serves as a destination for highly specialized insurance solutions.
She is also responsible for all Kaufman companies outside North America.
Jodie was previously named to the Insurance Business Global 100 and Business Insurance Women to Watch.
Outside of the workplace, Jodie is a board member of the Young Presidents’ Organization (YPO) Motor City chapter, a Director on the Insurance Supper Club (ISC) Group Global Advisory Board and serves on the Insurance Industry Charitable Foundation’s (IICF) International Board of Governors.
She is also a member of the national board for Jewish Federations of North America as well as CLAL, an international learning organization.
Prior to joining Kaufman, Jodie worked for the law firm Dorsey & Whitney where she advised Canadian and U.S. companies on mergers & acquisitions, capital market financing and regulatory issues. Jodie earned a Juris Doctor degree (J.D.) and graduated cum laude from Michigan State University and received a bachelor’s degree from the University of Michigan.
Margaret Milkint
Margaret Resce Milkint is a talent strategist, inclusion champion, and evangelist for talent innovation, transformation, and excellence, serving as the Global Insurance practice leader, a member of the Board practice and Co-Head of DSG Global's Chicago office. From CEOs to Chief Medical Officers, her expertise spans across the C-suite and boardroom.
Jen Scales
Jen Scales partners with high-powered CFOs and executives to navigate the complex world of Directors & Officers and Corporate Insurance. Through collaboration and insightful guidance, she ensures their professional and personal assets are fully protected, enabling them to lead their businesses towards sustainable growth.
Expertise:
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Crafting tailored D&O and corporate insurance solutions based on individual needs and industry risks.
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Educating and empowering leaders to understand their coverage and make informed decisions.
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Partnering with clients to achieve their long-term financial goals with clarity and peace of mind.
Jen is the founder of Confidante, Gallagher's Women CFO Network. Through intentional and intimate events, this private network cultivates a supportive and inspiring community for women leaders to connect, learn, and grow - both personally and professionally.
THEMES AT A GLANCE
Digital Transformation & Innovation
Cyber, Risk & Underwriting
Nat Cat & Climate
Regulation, Legal & Compliance
Next Gen
E&S Unfiltered
Construction & Specialty Reports
Market Capacity, M&A & Economic Headwinds
DISCUSSION TABLES
Step into action with our all-new themed discussion tables—built for leaders who want results now. These fast-paced, interactive sessions go beyond theory, delivering tactical conversations and proven takeaways you can put to work immediately.
Cyber
How do you keep up with rapidly evolving cyber policies while driving client education on emerging risks and solutions?
Digital Transformation
What are the transformational benefits of implementing AI effectively across your business?
Construction
What are the biggest hidden builder’s risks brokers and clients need to watch for, and how can you identify them early?
Excess & Surplus Lines
How do you build and maintain client trust in E&S placements, especially in a volatile market?
Cyber
How are you leveraging AI to outpace cyber threats, and what challenges are you facing in the cyber arms race?
Digital Transformation
How can brokers turn data into actionable insights that drive revenue and growth?
Construction
What strategies help brokers navigate high-risk construction projects in a tightening market?
Excess & Surplus Lines
How do you stay ahead of volatility in the E&S market and make confident placement decisions?
Cyber
What strategies have helped you convert cyber skeptics into loyal, proactive clients?
Digital Transformation
How do you design a digital-first client experience that truly delivers value and loyalty
Construction
How do you evaluate and implement jobsite technologies that deliver real value for clients?
Excess & Surplus Lines
What creative strategies help brokers secure E&S coverage when traditional markets say no?
Cyber
What digital threats are most concerning for your clients, and how are you helping them prepare?
Digital Transformation
What lessons have you learned from your digital transformation journey—both successes and failures?
Construction
How do you identify and negotiate contract clauses that can make or break a construction deal?
THEMES AT A GLANCE
Digital Transformation & Innovation
- Turning AI from hype to ROI in real brokerage workflows
- Building a digital client journey that wins (and keeps) business in a virtual world
- Choosing InsurTech and RegTech partners that accelerate real transformation
Cyber, Risk & Underwriting
- Turning cyber risk into a client‑value conversation, not a fear pitch
- Cyber crisis playbooks: who does what, when it hits
- Underwriting the next wave of cyber and personal cyber exposures
Nat Cat & Climate
- Rethinking nat cat models for a world that won’t sit still
- Helping clients understand climate‑driven pricing and coverage shifts
- Placing and structuring nat cat and climate‑exposed risks when volatility is the norm
Regulation, Legal & Compliance
- What new rules really mean for AI, cyber, and everyday brokerage workflows
- RegTech that actually simplifies audits, file reviews, and reporting
- Staying compliant on claims, E&S, and specialty without killing broker speed
Next Gen
- Career playbooks: what rising brokers wish they’d known earlier
- Mixing veteran experience with new ideas in
- Finding your lane as a NextGen broker in a consolidating, tech‑driven market
Diversity & Inclusion
- Real stories from women and under‑represented leaders on breaking through and bringing others with them
- How brokers can sponsor others, share opportunities, and use their voice even without a hiring title
- Where inclusion has changed client relationships, ideas, and outcomes – not just internal messaging
E&S Unfiltered
- Winning in a capacity‑tight, appetite‑shifting E&S market
- Designing E&S solutions for “wild risks” the standard market won’t touch
- Broker, MGA, and carrier partnerships that unlock specialty placements
Construction & Specialty Reports
- Managing construction risk under climate, cost, and regulatory pressure
- Spotting breakout niches across specialty lines before the market crowds in
- Claims and coverage lessons from large, multi‑party and specialty projects
Market Capacity, M&A & Economic Headwinds
- Broker playbooks for navigating consolidation and staying relevant
- Positioning your firm for sale, scale, or strategic partnership
- Competing when capacity, pricing, and client demand all move at once
Digital Transformation & Innovation
- Turning AI from hype to ROI in real brokerage workflows
- Building a digital client journey that wins (and keeps) business in a virtual world
- Choosing InsurTech and RegTech partners that accelerate real transformation
Cyber, Risk & Underwriting
- Turning cyber risk into a client‑value conversation, not a fear pitch
- Cyber crisis playbooks: who does what, when it hits
- Underwriting the next wave of cyber and personal cyber exposures
Nat Cat & Climate
- Rethinking nat cat models for a world that won’t sit still
- Helping clients understand climate‑driven pricing and coverage shifts
- Placing and structuring nat cat and climate‑exposed risks when volatility is the norm
Regulation, Legal & Compliance
- What new rules really mean for AI, cyber, and everyday brokerage workflows
- RegTech that actually simplifies audits, file reviews, and reporting
- Staying compliant on claims, E&S, and specialty without killing broker speed
Next Gen
- Career playbooks: what rising brokers wish they’d known earlier
- Mixing veteran experience with new ideas in
- Finding your lane as a NextGen broker in a consolidating, tech‑driven market
Diversity & Inclusion
- Real stories from women and under‑represented leaders on breaking through and bringing others with them
- How brokers can sponsor others, share opportunities, and use their voice even without a hiring title
- Where inclusion has changed client relationships, ideas, and outcomes – not just internal messaging
E&S Unfiltered
- Winning in a capacity‑tight, appetite‑shifting E&S market
- Designing E&S solutions for “wild risks” the standard market won’t touch
- Broker, MGA, and carrier partnerships that unlock specialty placements
Construction & Specialty Reports
- Managing construction risk under climate, cost, and regulatory pressure
- Spotting breakout niches across specialty lines before the market crowds in
- Claims and coverage lessons from large, multi‑party and specialty projects
Market Capacity, M&A & Economic Headwinds
- Broker playbooks for navigating consolidation and staying relevant
- Positioning your firm for sale, scale, or strategic partnership
- Competing when capacity, pricing, and client demand all move at once









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