Jun 11, 2025 · 31m · saastr
5 Ways AI Has Already Changed B2B Sales Forever with Perplexity's CBO Dmitry Shevelenko
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At SaaStr Annual, Perplexity CBO Dmitry Shevelenko and host Sam Blonde discuss how artificial intelligence is fundamentally transforming B2B sales, enterprise productivity, and go-to-market strategies. They emphasize that execution speed, AI-driven discovery, and lean sales models are redefining modern competitive advantage.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 6.2 Guest teaching 3.5 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:09 Reframing the future around invariants
Rather than predicting new features, Shevelenko flips the prompt to focus on what will not change, asserting that human inquiry and curiosity remain the core bottleneck.
Hardest push from Jason ▶ 28:40 Pushback on unnecessary transactional sales repsBlond challenges standard B2B sales motions, arguing that forced calls with transactional reps add negative value compared to automated self-serve AI workflows.
Biggest teaching moment ▶ 13:18 The 80 percent expert workflow frameworkShevelenko outlines an actionable framework for utilizing AI to complete 80 percent of specialized tasks like contract review before consulting specialists.
Jason holds their own ▶ 10:39 Outlining automated GTM demand generation stepsBlond demonstrates deep domain expertise by detailing how AI models should score accounts, layer intent signals, and prescribe targeted outreach strategies.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Speed as the New Competitive Moat | 4 | 2 | 0 | 0 | Host Sam Blond introduces the session and guest Dmitry Shevelenko after an initial clip and ad read. The dynamic is introductory and cordial as Dmitry shares his career background and the mission of Perplexity. | |
| AI-Driven Meeting Preparation and Founding Timing | 6 | 3 | 0 | 0 | Blond explains how he used Perplexity directly to prepare the interview agenda, framing the broader question around GTM applications. Shevelenko elaborates on speed as a moat and explains how market timing made Perplexity viable. | |
| Live Discovery Demos and Rapid Prototyping | 5 | 4 | 0 | 0 | Blond highlights time savings in sales discovery prep, and Shevelenko offers a tactical technique of doing real-time screen-share discovery queries with prospects. Shevelenko also describes rapid prototyping tools like Cursor and Perplexity Projects. | |
| Automating Demand Generation: Lead Scoring and Intent Signals | 8 | 1 | 0 | 0 | Blond takes the lead, breaking down a three-step demand gen playbook using models for lead scoring, intent signal overlays, and targeted outreach cadences. He asks Shevelenko how larger organizations can apply these capabilities. | |
| The 80% Expert Model for Enterprise Efficiency | 4 | 6 | 0 | 0 | Shevelenko educates listeners on the 80% expert mental model, illustrating how cross-functional professionals can triage legal contracts and generate personalized proposals before looping in human specialists. | |
| Disrupting Commodity Sales and Prioritizing Trust | 8 | 2 | 0 | 0 | Blond details his direct experience testing SaaStr's sales bot and how its transparent downselling built trust. Shevelenko builds on this point, explaining that trust is the core scarce asset for AI products. | |
| Objective AI Pipeline Reviews and Expanding Context Windows | 8 | 3 | 0 | 0 | Blond describes the flaws of traditional subjective sales rep pipeline reviews and advocates for AI-driven transcript and email analysis. Shevelenko adds context regarding expanding token windows and output fidelity. | |
| The Future of AI: Inquiry Skills and Proactivity | 5 | 6 | 0 | 0 | Blond asks Shevelenko what the AI landscape will look like in 12 months. Shevelenko provides a nuanced answer focusing on what will remain invariant—inquiry skills and curiosity—alongside proactive rather than reactive intelligence. | |
| Unified Go-to-Market Platforms and Lean Sales Teams | 7 | 5 | 0 | 0 | Blond predicts unified GTM platforms replacing fragmented tools, enabling technical founders to lean on AI. Shevelenko shares Perplexity's own metric of supporting 5,000 enterprise customers with only five sales reps. | |
| Removing Sales Friction, Compliance Roles, and Perplexity APIs | 7 | 3 | 0 | 0 | Blond discusses unnecessary human friction in transactional sales, while Shevelenko highlights security and compliance as lingering areas requiring human reps. Shevelenko reveals Blond's startup uses Perplexity APIs, and they close out warmly. |
Statements from this episode (22)
Sales Teams Should Use AI for Discovery Before Meetings
“Every question that you would ask in a meeting with some, you know, third party and an external party, you can be asking those questions of perplexity of different AIs in advance, right? So the, there's no excuse to not be informed. You should not actually be …”
Sam Blond Is Building a Stealth End-to-End Revenue Platform
“I'm also the founder of a startup that's in stealth. That's an end to end revenue platform.”
Shevelenko: Speed Is the New Competitive Moat
“Speed is the new mode, right? So the one, if there's one takeaway, you have no excuse to not be moving faster, right? And really, you now have these superpowers at your fingertips.”
Perplexity Would Have Failed If Founded Six Months Earlier or Later
“If we had, you know, we got lucky with timing. If we had founded the company six months before we did, GPT-III would not have been good enough, the equivalent of it, at that point in time, and we wouldn't have been able to create that initial magical experienc…”
Related Questions Are Perplexity's Most Popular Product Feature
“One of the most popular features in the product are the related questions that we show below the answer.”
Perplexity to Launch Projects Feature for Building Mini-Apps
“We're going to have the ability to build many apps and perplexity soon, or something's going to get announced called projects.”
AI Reduces Early Startup Prototyping From Weeks to One Hour
“To quickly visualize different concepts and get feedback on them, that should no longer take a week, a month. That's like an hour. And you should be constantly running through your head. You know, how can I do in one hour, what used to take a day? In one day, …”
Sales Teams Must Adopt AI for Demand Gen to Stay Competitive
“These three different steps here, score my database for me, overlay intent signals on top of my score database. And then tell me what I should do to break into these accounts based off of the information that exists in these scores and intent signals. Models a…”
AI Brings Non-Specialists to 80% Expert Level in Unfamiliar Fields
“I think one mental model is to assume that using a tool like perplexity and other AIs, you can get to 80% of an expert level in a lot of fields that, you know, are not your profession, right?”
Dmitry Shevelenko Uses Perplexity to Pre-Screen Contracts Before Legal Review
“Instead of immediately kicking over to the lawyer, I run it through perplexity and I prompt, I ask, Hey, what are the likely issues here? And what should I actually discuss with my counsel?”
Shevelenko: AI delivers 80% first drafts without replacing human judgment
“You should never then just take that output and immediately hit send. That's not, I think that's, it's not about replacing human judgment and oversight. It's about saving you that time to get to the 80% quality first draft and then making sure you're applying …”
Sam Blond Predicts AI Will Fully Automate Transactional Sales
“Transactional sort of commodity like sales will be disrupted in ways that support has been disrupted, where more and more revenue will be generated from just pure models, converting website visitors to revenue without the sales touch. And I think that will con…”
Shevelenko: Trust Will Be the Scarce Asset of the Agentic Internet
“And trust will be the scarce asset of the agentic internet.”
Sam Blond: Traditional CRM Forecasts Are Fundamentally Wrong Due to Bias
“The only problem is it's entirely wrong. And, you know, you have like a sales rep that is adding their own like subjective Experience about the account. Like they may want to influence the sales manager to think that the deal is going to close, or they may be …”
Shevelenko Predicts AI Context Windows Will Continue to Expand Reliably
“The one thing that you can rely on in terms of the direction of AI progress is the context windows will expand, right? You'll be able to feed more into the prompt and get a useful output right now.”
LLM Output Quality Deteriorates at Million-Token Context Sizes
“They claim million tokens, ten million tokens. When you start going up to that size of input. The quality deteriorates on the output”
Perplexity CBO: Asking the Right Questions Remains Critical as AI Evolves
“Coming up with the right questions to ask will become the critical skill, right? And you can say that's a form of like prompting, but preserving the spark of curiosity and knowing where to take the next question. That's because the answers will keep getting sm…”
Shevelenko Predicts AI Will Shift to Proactive Assistance Within 12 Months
“I think where we want to take the technology is to become a lot more proactive rather than being reactive, right? So instead of you having to always ask for the update of what's happening with this account, we're able to detect those changes that are meaningfu…”
Sam Blond Predicts Unified Platforms Will Consolidate AI Sales Tools
“I think there will be a sort of like unified platform that comes together that takes all of these sort of disparate piecemeal processes and basically combines them. So you can effectively say like, this is my TAM. I want meetings. And the output can be, these …”
Perplexity Serves 5,000 Enterprise Clients With Just Five Sales Reps
“We have around over 5000 enterprise clients for Prophexity Enterprise Pro, and we have five sellers.”