What We Learned at Unleash 2025 and Boston

There are two types of people at Unleash: the ones excitedly swapping sequencing tips—and the ones muttering "outbound is broken" while clutching their third cup of coffee.

This year, our Bearworks crew—Albert Wang (CEO), Ahmed (Head of Sales) and Stefan Lugo (BDR)—made the trip to Florida for Outreach's big event. We went in curiously. We came out with more questions, a few answers, and a clearer sense of where outbound is headed.

Here’s a behind-the-scenes look at what stood out, what we’re thinking about, and why a low-key dinner in Boston might’ve been just as meaningful as the mainstage.

1. Sequencing Is Smart. Strategy? Still a Work in Progress.

Albert summed it up in one line:

"Sequencing is sophisticated now. But GTM analysis? Still catching up."

That tracks. The tools are slick—auto-routing, lead scoring, the works. But figuring out who you should actually be reaching out to, and in what order, still feels like guesswork for a lot of teams.

Big orgs like Amazon are moving slower than you'd think. Lots of caution around sending data to vendors, even if the tools promise gold.

The vibe? Everyone wants to be more efficient. Nobody wants to risk it.

2. Everyone’s Talking AI. Most Are Just Cleaning Up Their CRM.

There was no shortage of AI buzz, but also a refreshing amount of honesty. The most common answer to "Where are you using AI?" was: "We're using it to clean up our CRM mess."

It hit home. That’s been a big focus for us at Bearworks too—using AI to detect bad numbers, personalize voicemails, coach reps in real time. No gimmicks. Just stuff that helps your team stop spinning its wheels.

When Outreach demoed their AI forecasting, it wasn’t a surprise—it was validation. The tide’s turning toward practical, not flashy.

3. Jade Simmons Gave Everyone Whiplash (In the Best Way)

Amid all the dashboards and data talk, Jade Simmons took the stage. And then she owned it.

Piano keys, punchy advice, energy that didn’t let go.

Stefan was impressed:

"Wow. What an amazing display of showmanship and engagement. The message? Don’t be afraid to step outside the box and do your thing."

She reminded a room full of optimizers that originality still matters.

4. From Florida to Boston

After Unleash, we hosted a quiet dinner in Boston—just some of our clients, friends, and partners. No slide decks. No product pitches. Just good food, eye contact, and a lot of real talk.

Elle from our team said it best:

“Building genuine connections takes time, but is way more fruitful.”

Albert brought up something we’d heard at the conference, too: “Change management is hard. You’ve got teams sitting on thousands of sequences. People are curious about AI—but they’re just as nervous.”

The dinner wasn’t designed to convert. But it might’ve done more for trust than any booth could’ve.

Final Thought: Tech Is Evolving, But the Best Conversations Still Happen Off-Stage

Unleash reminded us that while everyone’s racing to automate, the real challenges haven’t changed much. People want clarity. They want tools that help. And they want to feel like someone understands the mess they’re working through.

If you were at Unleash, we hope this brings a smile or sparks a memory. And if not, we’re happy to fill you in, you can always book a meeting or...

‍