SaaStr 803: AI, Sales + GTM in 2025/2026: This Really Changes Everything with SaaStr CEO and Founder Jason Lemkin and Owner CRO Kyle Norton
Summary
The podcast episode featuring SaaStr CEO Jason Lemkin and Owner CRO Kyle Norton centers on the transformative impact of AI on sales and go-to-market (GTM) strategies anticipated in 2025 and 2026. A key theme is the critical necessity for sales leaders, especially CROs, to be hands-on and deeply curious about AI tools, or risk obsolescence, as AI increasingly reshapes sales operations. The discussion highlights real-world AI applications, such as attention.com’s AI sales agents automating CRM updates, sales deck creation, and call scoring, which improve efficiency and accuracy for companies like BambooHR and Scale AI. The conversation extends to customer service, showcasing Intercom's Fin AI agent resolving a significant volume of tickets, thus improving customer satisfaction while reducing hiring pressures. Kyle Norton shares insights from his leadership at Owner, emphasizing the challenges of incorporating AI in SMB sales to non-traditional buyers. A cultural shift is stressed, where curiosity about AI must be a core qualification for hiring and team development, with a hard June 30 deadline given for AI tool engagement within sales teams. The speakers discuss practical leadership approaches to stay current with AI workflows, leveraging tools such as Windsurf and GitHub for deeper integration. A balance between centralized AI expertise and gradual AI fluency among sales reps is debated, reflecting operational realities. The episode underscores evolving sales profiles, advocating for sales professionals who combine people skills with technical and product expertise, epitomized by the Challenger Sales model. There is also emphasis on the necessity for superior AI quality in customer interactions to avoid negative perceptions tied to outdated 'bot' terminology. Looking ahead, the vision includes fully AI-augmented account executives built collaboratively by top AI engineers. The discussion acknowledges the immaturity of many AI tools, urging consistent, iterative investment and realistic expectations for benefits. Leadership’s role in driving adoption, managing AI-human hybrid teams, and rethinking sales workflows is underscored as essential for success in the AI-driven future of sales and GTM.
Key Takeaways
- 1Sales leadership must have a hands-on, curious engagement with AI tools to lead effectively in the modern sales environment. Jason Lemkin stresses that leaders who do not routinely use and understand the capabilities of AI risk being rendered obsolete as competitors leverage AI-driven efficiencies and insights to optimize sales operations.
- 2AI-driven sales automation, exemplified by attention.com’s platform, revolutionizes sales operations by automating repetitive tasks like CRM updates, custom sales deck generation, and cross-sell opportunity detection, thereby freeing reps to focus on selling.
- 3AI augmentation extends beyond sales into customer service, with AI agents like Intercom’s Fin resolving up to 80% of support tickets instantly, improving customer satisfaction and alleviating the cyclical hiring demands of support reps.
- 4The podcast advocates a cultural transformation in sales organizations where curiosity about AI is essential, encapsulated by a ‘tough love’ mandate that team members must demonstrate regular AI tool use or face replacement.
- 5Evolving sales roles demand a combination of interpersonal 'people person' skills with deep product knowledge and technical expertise, as characterized by the Challenger Sales model emphasizing teaching and tailoring in sales engagements.
- 6Quality of AI-driven customer interactions is paramount, as customers prefer sophisticated AI agents over mediocre ‘bots,’ with the latter being linked negatively to outdated systems and poor experiences.
- 7The future of sales professionals involves building integrated, complete AI-augmented account executives by leveraging top AI engineering talent and platforms such as OpenAI and Windsurf, moving beyond fragmented sales tech solutions.
- 8Successful AI tool adoption requires sustained, iterative investment and realistic expectation management as the AI sales tech ecosystem remains immature, necessitating ongoing development and user adaptation to generate value.
- 9The role of Chief Revenue Officers in the AI era extends to persistent advocacy, accountability, and orchestration to ensure sales teams fully leverage AI tools, integrating technical investments with cultural change management.
Notable Quotes
"So you just said two things that I think are super important. The theme of the opening yesterday was tough love. So I'm going to make a tough love statement because what you just said I think is so important: is that you as the CRO, A, are in the tools every day and you're super interested in it. You're genuinely curious. If your sales leader that you're thinking of hiring, especially that you have, is not in the tools and worse, not curious, are they going to make it today? You're cooked, right?"
"Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls even before the coffee is cold. Teams like BambooHR and Scale AI already automate their sales and RevOps using customer conversations."
"FIN can instantly resolve up to 80% of your tickets, which makes your customers happier, and you can get off the customer service rep hiring treadmill. FIN by Intercom. Named the #1 AI Agent in G2's winter report."
"Anyone on your team that by June 30 is not deeply curious, like is not pretending to use ChatGPT once a week to get recipes, your team should be both scared and a kid in a candy store. A kid in a candy store. If your team is not like, this is effing cool, right? Every week I use a new tool, right?"
"I'm hiring one to three-year tenured reps on the upslope of their career. And I don't need them to be recreating the system. They need to operate within my system and execute the methodology. But for the betterment of their career prospects, yeah, they should be trying to learn it themselves."
""If it's mediocre, no one wants to talk to a bot. I think bot, people still use this term bot. I would banish it because bot is like IVR. It just has negative connotations. The last thing I want to do when I'm ready to buy is be forced to talk to a crappy bot.""
""So I want your thoughts in general, but there's a specific bit of hubris that many folks in sales have. So many. I'm a people person, Kyle, and people like to talk to people. Now, people like to talk to the best solution architect in the world that also deployed my product, even if we don't even use it in Owner, that also helped me get going at my buddy down the street.""
""We're going to build, you and me are going to have the three best engineers out of OpenAI and Windsurf, and we're going to build a complete AE, not a partial AE. I think we could do it, and I think it's possible today. Because it's possible in Windsurf.""
""My meta advice is when the world's changing, copy someone you respect, whoever it is. It doesn't need to be that stack. It could be it, but talk to someone you respect, copy it, and then go in with five but measured expectations. Go in and do not expect magic, but do not expect it to be magical immediately. This is a commitment.""
""You can just write a prompt, run it on every single call that ever happens, stuff into a Salesforce field, get a Slack notification. And so I've pushed it so hard on so many things. Now the muscle is there for people to have an idea and go, oh, I'm just going to talk about Rebofs and building that into Momentum. It takes 20 minutes.""
""But if you're a manager and you don't have a high degree of proficiency to just default to AI automatically for any problem you're solving, then it's really difficult to think that person is going to scale with the business.""
""We’ve gone from... probably up 25 to 30% in terms of the revenue generating activity time because they don’t have to fill out CRM after. They don’t have to update the notes for the launch team. It's all done. It’s all done for them.""
""I have a great RevOps leader who is very fluent in sales and the actual go-to-market fundamentals. And I think I see this mistake where you have RevOps people investigating tools and then applying them. But then there's no thought of, okay, how does this get to a rep? How do they follow up? How does the manager then look at what's going on?""
""Clary just published this data. The top 10% of reps close 65% of deals. I know you have a world-class team, but for these one call closes, especially when the customer is more sophisticated and yours often isn't.""
""AI can't beat a good sales rep. No way. It's dumb. It hallucinates. April 2025, maybe an okay rep. April 2026, our AI is better than 80% of reps.""
Episode questions
Why is it essential for sales leaders specifically to be deeply involved with AI tools daily?
Jason Lemkin explains that sales leaders need to lead by example to drive AI adoption throughout their teams. His view is that curiosity and practical engagement with AI tools are critical to staying competitive, given AI’s transformative impact on sales workflows such as CRM updates, sales deck creation, and call scoring. If leaders don’t personally use and understand these tools, the entire sales organization risks falling behind competitors who leverage AI effectively. This deep involvement also enables leaders to better assess, guide, and motivate their teams in the AI era.
How are AI sales agents like those from attention.com changing sales operations for companies like BambooHR and Scale AI?
Attention.com’s AI sales agents automate manual, repetitive sales tasks such as updating CRM entries automatically, building customized sales decks tailored to conversations, spotting cross-sell opportunities, and scoring sales calls for quality and potential. These automations speed up sales processes and improve accuracy, freeing human reps to focus on relationship-building and closing deals. BambooHR and Scale AI serve as practical examples of companies benefiting from this automation to scale their sales and RevOps efficiently, reflecting a broader trend of AI-powered sales automation tools gaining traction in enterprises.
What cultural changes does the podcast recommend for sales teams regarding AI adoption?
Jason Lemkin emphasizes a cultural mandate where team members must be not only proficient in AI tools but also deeply curious and even excited about experimenting with new AI technologies. He suggests the team should feel both the pressure to keep up ('scared') and delight in AI opportunities ('a kid in a candy store'). Regular usage of AI tools, even for simple tasks like obtaining recipes on ChatGPT, reflects baseline curiosity. This cultural shift aims to embed continuous learning and innovation, ensuring teams stay relevant in a fast-changing AI landscape.
How does Jason Lemkin personally stay current with AI tools and integrate them into his leadership workflow?
Jason actively experiments with various AI tools and integrates them deeply into his work processes. He uses platforms like Windsurf to automate workflows, GitHub to manage repos, and lever API for hiring analytics. Moreover, he employs AI tools such as Hicksfield AI for video creation and Reeve.ai for sales design. This hands-on approach allows him to maintain credibility as a leader, evaluate AI products rigorously, and leverage AI to optimize his operations and strategic decision-making. It exemplifies the proactive mentality he recommends to his team.