GTM Crossroads Podcast Ep #01: Optimizing Email Deliverability
In the first episode of GTM Crossroads, RevPartners CEO Brendan Tolleson sits down with OutboundSync Founder Harris Kenny, and Octave Co-founder and CEO Zach Vidibor to explore the shifting landscape of go-to-market strategies with a focus on email deliverability.
They discuss the impact of AI on sales outreach, the importance of clean infrastructure, and how targeted messaging can improve engagement.
Check it out! 👇
5 Minute Rundown:
The Reality of Go-To-Market Today: It’s Harder Than Ever
Brendan kicks off the episode with a reality check: the GTM landscape has shifted. While the market says selling is easier than ever, the reality is that winning is harder. Every company is going to market, it’s just a question of how well they’re doing it. Most teams are struggling because they’re playing by outdated rules.
The Death of Mass Email: Why Your Cold Outreach is Failing
Harris dives into how email providers like Google and Microsoft have rewritten the rules of outbound. The high-volume, brute-force approach of the past doesn’t work anymore as AI-powered spam filters are smarter, stricter, and more unforgiving.
Sales teams blasting generic emails aren’t just getting ignored, they’re getting their entire company’s domain flagged. Harris explains why this crackdown is happening, how email filters have evolved, and why outdated tactics are a one-way ticket to the spam folder.
Doing More is Over. It’s Time to Do Better
Zach calls out the old sales mindset that prioritized activity volume over precision. The predictable revenue era led to a culture of “send more emails, make more calls, book more meetings”, but that playbook is now dead.
Instead of blasting cold emails, sales teams need to be precise, use AI, and personalize at scale. Zach explains how better data and segmentation allow sellers to work smarter, not harder. The future of outbound is less noise, more relevance, and sniper-like targeting.
The Real Risks of Bad Outreach: It’s Bigger Than You Think
Most sales leaders don’t realize the hidden dangers of bad deliverability. Harris breaks it down: if a rogue sales rep spams too many people, it’s not just their emails that get blocked, it’s the whole company’s domain. That means customer invoices might not send, support emails could get lost, and even internal logins for business software could fail.
This isn’t just a sales problem, it’s a business-wide risk. Companies need to take email hygiene seriously before it tanks their ability to function.
Winning in the New GTM World: What Smart Teams Are Doing Now
Zach paints a picture of how modern GTM teams are evolving. The old method—high-volume, brute-force outreach—is outdated. The new approach? Precision targeting, clean data, and AI-driven personalization.
Teams that invest in secondary domains, smart sequencing, and targeted messaging will cut through the noise and win faster. Zach and Harris explain why the companies that adapt will dominate their category, while those stuck in the past will be left behind.
Stop Guessing. Start Growing.
This episode proved more activity isn’t the answer, smarter strategy is. The BowTie Model eBook shows you which revenue lever to pull—Volume, Conversion, Retention, or Deal Size—to actually move the needle.
