Intro

In this episode, Dave sits down with Trinity Nguyen, CMO at UserGems, to discuss her journey from first business hire to CMO, the role of product marketing in B2B, and how AI is transforming outbound sales. Trinity got started at UserGems’ by building their first website for free, then got hired as Head of Marketing and has shaped the company’s ABM strategy and demand generation playbook.

Dave and Trinity cover:

1. Why every startup should hire a product marketer
2. How to develop a strong vision and align with product teams
3. Scaling outbound with AI-driven ABM and sales engagement

Timestamps

• (00:00) - - Intro to Trinity
• (07:41) - - Why product marketing is the foundation of great B2B marketing
• (09:18) - - The importance of positioning and messaging in a competitive market
• (11:27) - - How Trinity rebuilt UserGems’ website for free before joining the company
• (12:44) - - Negotiating your role and setting the foundation for marketing
• (14:20) - - Why marketing should own SDRs and outbound prospecting
• (16:01) - - The early days of building demand gen at UserGems
• (17:39) - - Differentiation and positioning in a crowded market
• (19:44) - - Aligning marketing with product teams and company vision
• (23:50) - - Developing ICP and refining target accounts
• (26:35) - - Why outbound was the first major pipeline driver for UserGems
• (28:25) - - Transitioning from a startup to a growth-stage company
• (30:40) - - How UserGems runs ABM at scale
• (32:54) - - The AI shift in outbound marketing and its impact
• (36:06) - - AI for sales outreach and improving outbound efficiency
• (39:30) - - Why Trinity was initially skeptical about AI in outbound
• (42:13) - - Cutting spend while increasing pipeline with AI-driven outbound
• (44:57) - - The role of brand and inbound marketing in a demand gen playbook
• (47:09) - - Why traditional inbound marketing didn’t work for UserGems
• (48:55) - - Creating engaging demand gen campaigns
• (50:50) - - Final takeaways

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more.