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
  


• (07:51 ) - - Why product marketing is the foundation of great B2B marketing
  


• (09:28 ) - - The importance of positioning and messaging in a competitive market
  


• (11:37 ) - - How Trinity rebuilt UserGems’ website for free before joining the company
  


• (12:54 ) - - Negotiating your role and setting the foundation for marketing
  


• (14:30 ) - - Why marketing should own SDRs and outbound prospecting
  


• (16:11 ) - - The early days of building demand gen at UserGems
  


• (17:49 ) - - Differentiation and positioning in a crowded market
  


• (19:54 ) - - Aligning marketing with product teams and company vision
  


• (23:08 ) - - Developing ICP and refining target accounts
  


• (25:53 ) - - Why outbound was the first major pipeline driver for UserGems
  


• (27:43 ) - - Transitioning from a startup to a growth-stage company
  


• (29:58 ) - - How UserGems runs ABM at scale
  


• (32:12 ) - - The AI shift in outbound marketing and its impact
  


• (35:24 ) - - AI for sales outreach and improving outbound efficiency
  


• (38:48 ) - - Why Trinity was initially skeptical about AI in outbound
  


• (41:31 ) - - Cutting spend while increasing pipeline with AI-driven outbound
  


• (44:15 ) - - The role of brand and inbound marketing in a demand gen playbook
  


• (46:27 ) - - Why traditional inbound marketing didn’t work for UserGems
  


• (48:13 ) - - Creating engaging demand gen campaigns
  


• (50:08 ) - - Final takeaways

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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