In the tenth episode of GTM Crossroads, RevPartners CEO Brendan Tolleson sits down with OutboundSync Founder Harris Kenny, and Octave Co-founder and CEO Zach Vidibor to discuss the key aspects of building a tech startup, including choosing the right CRM, developing a product-led growth motion, and refining pricing strategies.
They also get into the real-world challenges with tools like Stripe, discuss how market uncertainty influences decision-making, and examine how AI can be used effectively to scale operations.
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Outbound isn’t the top growth driver, but it’s still critical, especially when signup alerts from tools like Octave hit Slack and prompt action. Cold mass emails aren’t cutting it in a world of inbox fatigue and generic AI outreach.
GTM teams need smarter signals, personalized touchpoints, and a clearer handoff between product interest and pipeline conversion.
PLG startups don’t need to default to Salesforce for enterprise deals. HubSpot can support both product-led growth and high-touch motion when configured properly.
It’s not about which CRM has the right features, but rather understanding how to model lifecycle stages, lead objects, and usage signals inside a single system without splitting tech stacks.
Stripe looks polished, but managing SaaS subscriptions under the hood is a mess. Miss one step in your deal structure or co-sell flow, and it creates churn flags you can’t undo.
Stripe isn’t built for the nuance of ARR/MRR reconciliation or flexible contract workflows, and when things go sideways, the admin pain is real.
Changing one metric transformed Octave’s sales cycle. Moving from ambiguous event counts and feature gates to a dead-simple usage metric, email volume, led to faster closes, higher conversion from the pricing page, and less confusion on calls.
The takeaway: charge for what users already understand, and the entire GTM engine runs smoother.
When the market gets shaky, the smartest move is to go back to fundamentals. Instead of chasing trends or throwing tools at the problem, winning teams get laser-focused on retention, pipeline health, and customer fit.
GTM success in this environment means spotting real buying signals, tightening messaging, and doubling down on what’s working, especially when the hype around AI and automation can easily distract.
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Check out our webinar with Clay on how to streamline your GTM efforts by unifying fragmented data, enriching contact records, and automating workflows directly into HubSpot. 👇