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digitalNow

6 min read

digitalNow 2026 Recap: The Top 10 Takeaways for Association Leaders

digitalNow 2026 wrapped on Wednesday, October 28, at the Hilton Arlington Rosslyn at The Key, just outside Washington, D.C. Eight keynotes in three...

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7 min read

digitalNow 2026 Day 2 Recap: Outcomes First, AI Second

If Day 1 of digitalNow 2026 asked who should hold the keys to an association's AI, Day 2 answered a more practical question: once you hold them,...

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7 min read

digitalNow 2026 Day  1  Recap: Who Holds the Keys to Your AI?

Day 1 of digitalNow 2026, Sidecar's annual conference on AI and associations, opened on Monday, October 26, at the Hilton Arlington Rosslyn at The...

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2 min read

Why the Time Is Now for digitalNow

I've had a lot of roles at digitalNow over the past decade. I've been an attendee, soaking up every session I could fit into a day. I've been an...

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St. Louis Arch mid-construction on a sunny day, with two unfinished legs rising toward each other and workers on scaffolding below.

5 min read

Bottom-Up Buy-In: Why Your Frontline Staff Should Write Your Strategy

Strategy typically flows in one direction. The board sets vision. Executive leadership interprets it. Senior management translates it. Staff execute...

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Stylized racetrack with a centered stop sign symbolizing a strategic pause that boosts momentum.

6 min read

The Pause That Propels: When Associations Hit Stop to Move Forward

Most associations operate under constant addition. New programs stack on top of existing ones. Member requests become new initiatives. Strategic...

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Abstract 2×1 illustration with speech bubbles, a dinner-table silhouette, declining call-volume icon, and a glowing lightbulb, all in flowing coral, teal, and charcoal Sidecar colors.

6 min read

Stop Talking, Start Measuring: Real AI ROI from Associations

Return on investment doesn't always arrive in a spreadsheet. Sometimes it walks up to you at dinner. Sometimes it shows up as a percentage drop in...

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Sidecay Sync Podcast episode 108 cover featuring Amith Nagarajan and Mallory Mejias

21 min read

Live from digitalNow 2025: Inside the Association Evolution | [Sidecar Sync Episode 108]

Summary: Live from digitalNow 2025 in Chicago, this special edition of Sidecar Sync brings together voices from across the association world, sharing...

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digitalNow 2025 featuring a cartoon plane leaving a cartoon Chicago landscape

5 min read

The Deeper Questions digitalNow 2025 Is Really Asking

I'm sitting here on Day 3 of digitalNow 2025 in Chicago. Over the past few days, we've seen incredible sessions on implementation, infrastructure,...

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