Program

Engineering Serendipity: A smarter way to meet funders

A free, three-part workshop series from the Lenfest News Philanthropy Network

September 4, 2026

Date: Tuesdays, September 22 through Oct 6

Time: 2 p.m. ET / 11 a.m. PT

Presenter: Jake Hylton, founding executive director of LOOKOUT News

Let’s be honest: hoping for a lucky break with a program officer at the coffee break isn’t a strategy; it’s a gamble. “Engineering Serendipity” transforms the anxiety of conference networking into a calculated, high-yield operation. Inspired by the meticulous preparation of The Devil Wears Prada’s Miranda Priestly, this session dismantles the “spray and pray” approach to business cards and replaces it with a tactical playbook on playing the long game.

Back by popular demand after the 2026 News Philanthropy Summit, “Engineering Serendipity” replaces the panic of transactional fundraising with a relational strategy, teaching attendees to view funders as humans first while using rigorous preparation to ensure connection happens. 

Jake will help participants move past the elevator pitch and into the mechanics of the approach, including: how to build a pre-conference dossier using digital tools, why memorizing headshots is your secret weapon, and the counter-intuitive rules of engagement that can help generate interest in your organization’s mission. 

Each of the three workshops will focus on key operational phrases, leaving participants with a customizable prospect blueprint, hard skills in open-source intelligence, and the strategic confidence to stop chasing checks and start building relationships: 

• Sept. 22, 2 p.m. ET – The mindset: Why everything you’ve been taught about fundraising is incomplete, and why you already know how to fix it
• Sept. 29,  2 p.m. ET – The tools and the psychology: The operational system and the science of why it works
• Oct. 6, 2 p.m. ET – The engagement: What actually happens in the room, and putting it all together

Register now and learn how to turn chance encounters into meaningful, human relationships, proving that the best serendipity is the kind you engineer yourself.

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