Where Go-to-Market Leaders Solve for Growth, Scale, and Efficiency.
The GTM landscape is evolving fast. Rising acquisition costs, misaligned teams, and broken revenue engines are forcing leaders to rethink their strategies. GTM Crossroads brings together RevOps experts, CROs, and GTM innovators to tackle real challenges and deliver actionable insights.
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From Hiring Scrappy Teams to Rethinking AI Pricing | GTM Crossroads #11
Industry experts Brendan Tolleson, Zach Vidibor, and Harris Kenny discuss how AI tools like HubSpot’s Breeze AI impact business strategy, startup hiring, and company culture, offering insights for scaling teams.
21 May 2025TRANSCRIPT
Navigating CRM Choices: HubSpot vs Salesforce | GTM Crossroads #10
In this episode, the hosts explore key aspects of building a tech startup, including choosing the right CRM, developing a product-led growth motion, and refining pricing strategies. They share 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.
Chapters:
01:42 - Exploring CRM Options for a PLG Motion
03:25 - Choosing Between HubSpot and Salesforce
06:14 - The Real Differences in Lead Objects and Data Models
10:00 - Stripe Frustrations and Subscription Complexity
12:09 - Why Pricing Changes Can Unlock Growth
14:06 - Simplifying Metrics to Drive Conversions
16:52 - Psychology Behind Pricing Models
18:25 - How Pricing Affects Sales Conversations
20:02 - Navigating Market Uncertainty and Macroeconomic Impact
22:13 - How Changes in the Economy Affect Startups
25:38 - What to Monitor When Markets Shift
27:31 - Opportunities to Scale Without Constraints
30:57 - Making AI Useful Beyond the Hype
32:52 - Why Human Plus AI is the Real Solution
33:34 - AI Adoption is Still Hard Even with Tools
Mentions:
Tobi Lütke (https://ca.linkedin.com/in/tobiaslutke)
Carter Gibson (https://www.linkedin.com/in/cartergibson)
Shopify (https://www.shopify.com)
Clay (https://www.clay.com)
Segment (https://segment.com)
ChartMogul (https://chartmogul.com)
bill.com (https://www.bill.com)
Pardot (https://www.salesforce.com/marketing/b2b-automation/)
Marketo (https://business.adobe.com/products/marketo.html)
LinkedIn (https://www.linkedin.com)
CNBC (https://www.cnbc.com)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
9 May 2025TRANSCRIPT
Navigating the Pricing Landscape in SaaS | GTM Crossroads #09
In this episode of GTM Crossroads, Brendan, Harris, and guest host Rob dive into the evolving landscape of pricing strategy in SaaS and services. They unpack the real-world implications of usage-based pricing, the role of buyer psychology, and how to position value clearly without causing confusion.
The conversation highlights the power of retention, the difference between experience and impact, and how long-term relationships often lead to business returns years later.
They also explore the trade-offs between capturing value and driving adoption, the limitations of results-based pricing models, and why traction often matters more than perfection. The episode wraps with a look at RevPartners' new DIY product, built to serve the SMB segment with speed, autonomy, and best-in-class RevOps frameworks.
Chapters:
Pricing That Keeps You Up at Night – 02:22
The Three Eras of Pricing Strategy – 04:37
DIY, Self-Service, and Perceived Value – 07:02
Value Metrics and Speaking the Buyer's Language – 10:35
RP’s Pricing and Frictionless Framing – 14:43
Experience vs Impact: What Drives Retention? – 24:04
Ruthless Prioritization and Founders’ Focus – 27:12
Can Results-Based Pricing Work? – 32:25
Democratizing RevOps Through DIY – 39:52
Mentions:
Rob Walling (https://www.linkedin.com/in/robwalling/)
Marcos Rivera (https://www.linkedin.com/in/marcosrivera/)
Donald Miller (https://www.linkedin.com/in/donaldmiller/)
Clay (https://www.clay.com/)
Instantly (https://instantly.ai/)
MicroConf (https://microconf.com/)
Smartlead (https://smartlead.ai/)
TinySeed (https://tinyseed.com/)
HubSpot (https://www.hubspot.com/)
Zapier (https://zapier.com/)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
25 Apr 2025TRANSCRIPT
The Human Side of Go-To-Market AI Can't Replace | GTM Crossroads #08
In this episode, the hosts unpack key takeaways from MicroConf, debating why human relationships remain irreplaceable in go-to-market, even as AI tools proliferate.
They share candid stories of pricing experiments (from bootstrapped constraints to consumption models), the pitfalls of ‘feature-first’ thinking, and why webinars unexpectedly work.
With insights on fake revenue trends, Tiny Seed’s funding philosophy, and the tension between PLG and partner-led motions, this conversation is a masterclass in balancing automation with authenticity.
Chapters:
MicroConf Event Recap – 00:17
Human Connection in GTM – 01:33
Pricing and Packaging Strategies – 05:22
PLG vs. Partner-Led Motion – 10:14
Technical Risk vs. GTM – 15:22
Closing Remarks & Southbound – 16:38
Mentions:
Rob Walling (https://www.linkedin.com/in/robwalling/)
Liana Patch (https://www.linkedin.com/in/lianapatch/)
Liz Christo (https://www.linkedin.com/in/lizchristo/)
Tiny Seed (https://tinyseed.com/)
MicroConf (https://www.microconf.com/)
Southbound (https://www.southbound.show/)
Clay (https://clay.run/)
Smartlead (https://www.smartlead.ai/)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
5 Apr 2025TRANSCRIPT
The Power of Omni-Channel Outbound and Product Data| GTM Crossroads #07
In this episode of GTM Crossroads, the hosts discuss their personal experiences with spring activities, transitioning into a reflection on their business performance in Q1 and strategies for Q2. They explore the importance of hiring, the shift towards API integration and first-party data, and the growing need for omni-channel marketing strategies.
The conversation also delves into transforming email marketing from a transactional approach to a more relational one, emphasizing the significance of customer experience and relationship building in today's business landscape.
Chapters:
Q1 Reflections and Q2 Priorities – 04:48
Hiring and Scaling at Octave – 06:58
Partner-Driven Growth and Focus at Intro CRM – 07:08
Sales Process Improvements and Moving Upmarket – 09:11
Using Product Data and Signals for Sales Assist – 11:37
The Rise of Omni-Channel Outbound – 15:08
Email as a Private Ad Network and Programmatic Strategy – 17:51
The Evolution of Messaging and Brand Experience – 23:51
Applying B2C Lessons to B2B GTM Strategy – 25:47
From Transactional Funnels to Continuous Relationships – 27:33
Mentions:
Derek Rahn (https://www.linkedin.com/in/derekrahn)
Intro CRM (https://www.introcrm.com)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
28 Mar 2025TRANSCRIPT
What the LinkedIn Crackdown Means for GTM Strategy | GTM Crossroads #06
In this episode, the hosts discuss the recent ban of Apollo and Seamless from LinkedIn, exploring the implications for sales tools and prospecting strategies. They share personal anecdotes, including baking adventures, and emphasize the importance of adapting to LinkedIn's evolving landscape while maintaining ethical practices in data usage.
The conversation highlights the need for a balanced approach to leveraging LinkedIn as a valuable resource for sales and marketing.
Chapters:
What Happened with Apollo and Seamless on LinkedIn – 05:22
Why LinkedIn Cracked Down and the Game Theory Behind It – 07:44
The Risk of Automation and Scraping on LinkedIn – 09:57
What Revenue Leaders Should Do Differently – 14:39
Balancing Risk and Reward in Outreach Strategy – 16:58
The Ethics and Gray Areas of Data Use – 19:22
Hedging Your Strategy Across Data Providers – 22:42
How Platforms Like LinkedIn Detect Bots and Automation – 23:08
Final Thoughts on Behavior Change and Platform Strategy – 24:36
Mentions:
Brandon Bornancin (https://www.linkedin.com/in/brandonbornancin/)
Apollo.io (https://www.apollo.io)
Seamless.AI (https://www.seamless.ai)
LinkedIn (https://www.linkedin.com)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
15 Mar 2025TRANSCRIPT
The Shift from Growth Hacking to Sustainable Strategies | GTM Crossroads #05
In this episode of GTM Crossroads, hosts Rob Jones, Zach, and Harris discuss the evolving landscape of growth strategies, the importance of transparency and vulnerability in leadership, and the distinction between personalization and humanization in marketing. They emphasize the significance of storytelling in sales and explore the changing dynamics of the buyer journey and trust in the digital age. In this conversation, the speakers explore the evolving dynamics between buyers and sellers, emphasizing the importance of understanding customer needs and the role of human interaction in the sales process.
They discuss the impact of the Amazon effect on B2B sales expectations and the necessity of thoughtful friction in sales interactions. The conversation also touches on predictions for the future of sales, highlighting a shift towards marketing and customer success roles.
Chapters:
Why GTM Crossroads Exists and What It Means – 01:02
Adapting GTM Strategies to Constant Market Changes – 05:17
The Death of Nuance and the Rise of Authenticity – 06:45
The Difference Between Personalization and Humanization – 10:21
The Evolution of Buyer Trust and Sales Cycles – 17:09
The Amazon Effect and the Changing Role of the Buyer – 23:15
Why the Future of Sales is More Like Customer Success – 26:52
The Role of Thoughtful Friction in Sales Processes – 31:27
Bold Predictions for the Future of GTM – 36:34
Mentions:
Lenny Rachitsky (https://www.linkedin.com/in/lennyrachitsky)
Chili Piper (https://www.chilipiper.com)
GTM Crossroads Podcast:
Brendan Tolleson (https://www.linkedin.com/in/brendan-tolleson-hubolutionary/) – RevPartners (https://www.revpartners.io)
Zach Vidibor (https://www.linkedin.com/in/zachvidibor/) – Octave (https://www.octavehq.com/)
Harris Kenny (https://www.linkedin.com/in/harriskenny/) – OutboundSync (https://outboundsync.com)
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
In this episode of GTM Crossroads, Brendan, Zach, and Harris dive into key go-to-market strategies, emphasizing the power of intent data, market signals, and evolving data utilization. They discuss the shift from traditional outside-in approaches to more personalized inside-out strategies, highlighting the importance of understanding unique value propositions and customer needs.
The conversation also explores the balance between current capabilities and aspirational goals, the role of partnerships in driving market success, and why segmentation and trust are essential for building effective go-to-market motions. Plus, they announce the upcoming Southbound 2025 event, sharing insights on what to expect and how it will help revenue leaders refine their strategies.
Chapters:
Market Insights and Recent Learnings – 01:29
Announcing the Southbound Revenue Event – 05:33
Beyond Intent Data: How to Drive Conversions – 07:46
Inside-Out vs. Outside-In GTM Strategies – 14:19
Balancing Product Roadmap and Go-to-Market Strategy – 24:21
The Impact of Partnerships on Sales Strategy – 25:09
Educating Partners and Revenue Attribution – 29:36
Final Thoughts and Key Takeaways – 31:03
Mentions:
Endstory - https://www.endstory.com
Clay - https://www.clay.com
Smartlead - https://www.smartlead.ai
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
28 Feb 2025TRANSCRIPT
The Truth About Intent Data and How to Use It Right | GTM Crossroads #03
In this episode of GTM Crossroads, the hosts discuss various topics related to sales, marketing, and the evolving landscape of intent data. They explore the importance of community in go-to-market strategies, the role of RevOps, and the complexities of capturing and analyzing intent signals.
The conversation delves into the challenges of attribution in intent data, the distinction between demand capture and demand generation, and the significance of understanding the buyer's journey. The hosts emphasize the need for alignment within organizations and the importance of creating valuable content to engage customers effectively.
Chapters:
Weekly Highlights and Industry Trends - 00:19
The Role of Community in Go-To-Market Strategies - 03:09
The Growing Importance of RevOps in Business Alignment - 06:27
The Shift from Delight to Deliver in Customer Success - 06:26
The Evolution of Buyer Intent and Its Impact on GTM - 08:49
Breaking Down Intent Data and Its Different Types - 09:29
How Companies Collect and Analyze Intent Data - 16:00
The Debate Over Attribution and Intent Signal Value - 17:17
Demand Capture vs Demand Generation in GTM - 23:11
Challenges in Aligning Marketing and Sales with Intent Data - 24:07
Why Investing in Intent Tools Doesn’t Work for Every Business - 30:50
Want to elevate your revenue leadership game? Visit RevPartners.io (revpartners.io) for expert insights and strategies to drive customer success and business growth!
21 Feb 2025TRANSCRIPT
Crafting Sales Emails with AI and Personalization | GTM Crossroads #02
In this episode of GTM Crossroads, the hosts discuss the importance of effective email copy, market insights, and the evolution of personalization in outbound marketing. They share personal anecdotes related to Valentine's Day, explore user feedback on email strategies, and emphasize the need for brevity and relevance in communication.
The conversation also touches on the significance of data utilization and the future trends in outbound marketing, highlighting the necessity of a solid foundation in CRM systems for successful outreach.
Chapters:
Valentine’s Day Plans and Surprises - 00:17
Challenges of Scaling Email Outreach - 02:18
New Funding in Go-To-Market Tech - 04:04
The Rise of AI in Sales Development - 05:14
Optimizing Email Copy for Engagement - 08:03
Personalization Beyond First Name Tokens - 11:26
Why ICP Data Beats Public Data - 13:33
Cold Email Best Practices and Real-World Example - 15:59
The Importance of Brevity in Sales Emails - 17:59
Avoiding the Mistakes of Over-Personalization - 22:00
The Future of AI Driven Email Testing - 23:46
The Opportunity in Nurture Campaigns - 26:15
Want to level up your GTM strategy? Visit RevPartners.io (https://revpartners.io/) for more insights and resources!
In the first episode ofGTM Crossroads, Brendan Tolleson, Harris Kenny, and Zach Vidibor 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. Tune in for insights on adapting your approach to ensure effective communication with prospects.
Want to level up your GTM strategy? Visit RevPartners.io (https://revpartners.io/) for more insights and resources!
Inside a recent episode
From Hiring Scrappy Teams to Rethinking AI Pricing | GTM Crossroads #11
Published 4 Jul 2025 · Transcript excerpt
[…] Yeah, I think if we take a step back, I think it's important to understand why it would go that direction. And so if we take a macro themes, you've got technology providers moving from point solutions to platforms, and they want to own that kind of going to market journey, they're trying to get all data sources connected inside of that. And there's just a reality that like with efficiency gains from data and technology, there's going to be fewer people. And so even just from a pure like revenue, how do we continue to grow? The usage based concept makes a lot of sense. And I think all these kind of concepts around talking about data kind of are ways to kind of start to build that momentum and movement towards that. […]
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