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:
- Why every startup should hire a product marketer
- How to develop a strong vision and align with product teams
- Scaling outbound with AI-driven ABM and sales engagement
Timestamps
- (00:00) - - Intro to Trinity
- (07:40) - - Why product marketing is the foundation of great B2B marketing
- (09:17) - - The importance of positioning and messaging in a competitive market
- (11:26) - - How Trinity rebuilt UserGems’ website for free before joining the company
- (12:43) - - Negotiating your role and setting the foundation for marketing
- (14:19) - - Why marketing should own SDRs and outbound prospecting
- (16:00) - - The early days of building demand gen at UserGems
- (17:38) - - Differentiation and positioning in a crowded market
- (19:43) - - Aligning marketing with product teams and company vision
- (22:37) - - Developing ICP and refining target accounts
- (25:22) - - Why outbound was the first major pipeline driver for UserGems
- (27:12) - - Transitioning from a startup to a growth-stage company
- (29:27) - - How UserGems runs ABM at scale
- (31:41) - - The AI shift in outbound marketing and its impact
- (34:53) - - AI for sales outreach and improving outbound efficiency
- (38:17) - - Why Trinity was initially skeptical about AI in outbound
- (41:00) - - Cutting spend while increasing pipeline with AI-driven outbound
- (43:44) - - The role of brand and inbound marketing in a demand gen playbook
- (45:56) - - Why traditional inbound marketing didn’t work for UserGems
- (47:42) - - Creating engaging demand gen campaigns
- (49:37) - - 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 Grammarly.
Ever have one of those weeks where you spent more time replying to Slack and email than doing actual marketing work?
You’re not alone. The average marketing team spends 28+ hours a week just keeping up with comms.
That leads to burnout, frustration, and a whole lot of performative productivity that doesn’t actually move the needle.
AI-fluent marketing teams are changing that. Grammarly’s 2025 Productivity Shift Report shows how they’re using AI to:
– Cut down on back-and-forth
– Automate content, research, and reporting
– Eliminate busywork
– Make space for strategy
We’re marketers because we love crafting campaigns, driving revenue, and proving impact – not spending all day buried in messages.
Get the report and see how top teams are making AI actually useful.
Visit go.grammarly.com/exitfive to grab it.
***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
- They give you unlimited podcast editing and strategy for your B2B podcast.
- Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
- Visit hatch.fm to learn more
