The plays remain the same, but the rules have shifted dramatically—here’s what truly matters now. At SaaStr, after 12+ years of advising on hiring VPs of Sales/CROs, the core truth endures: about 70% of first VP Sales hires fail within 12 months. This mis-hire is the most common and costly error in B2B, often costing startups a crucial year that can mean survival or failure. That has not changed. What has evolved is AI’s transformative impact on the role of a VP of Sales/CRO in 2025 and beyond. Key trends include 36% of companies reducing SDR/BDR headcount—the steepest decline in sales functions—while AI SDRs are managing 15, 000+ messages in 100 days with 5-7% response rates, rewriting the traditional sales playbook on the fly. So what should you prioritize today? 1. **Deep AI Sales Tool Expertise:** Candidates must fluently discuss AI sales platforms (e. g. , Artisan, Qualified), conversation intelligence (Gong), AI forecasting, and wisely use ChatGPT. Avoid vague “leveraging AI” talk. Look for those with hands-on experience, able to clearly specify which tools they’d deploy or avoid in their first 90 days. 2. **Building Hybrid Human+AI Sales Teams:** The traditional SDR role is being largely automated. Your VP must know how to assign AI agents to handle 70%+ of prospecting and qualification, transition human SDRs to “AI operators, ” and free AEs to close deals. They should have managed AI-augmented teams and can explain productivity boosts realized. 3. **Data-Native Leadership:** AI success hinges on clean, well-structured data. A VP of Sales must proactively ensure CRM hygiene, data enrichment, and integration architectures to power effective AI deployment. Treat data mastery as equally important to sales acumen. 4. **Experience Selling at Your Price Point:** AI automates transactional sales well, but enterprise deals ($100K+ ACVs) still demand human skill. Ensure candidates have closed deals near your price point—no more than a 3-5x mismatch—bringing concrete examples of managing those sales. 5. **A Network of AI-Savvy Talent:** Ideal candidates bring 2-3 trusted people, including AI-native sales ops experts, ready to join.

Beware those relying solely on recruiters without an AI-literate network. 6. **Desire to Actively Sell:** Despite automation, the best VPs still want to engage customers and close deals. If their focus is only on systems or dashboards initially, it’s a bad sign. Top candidates are eager to learn your prospects and hit the ground selling. 7. **Understanding AI-Augmented Sales Economics:** They must grasp that AI SDRs cost a fraction (~$1K-$5K/month) of traditional reps (~$90K/year), handling 10x volume and boosting productivity by 47%. They should competently plan hitting quotas with leaner headcount but expanded AI tooling. 8. **Proven Hiring of Modern Sales Talent:** They’ve built teams, hiring reps who succeed in partnering with AI agents, focusing on complex selling, and interpreting AI insights. Candidates still using 2019 hiring profiles miss the mark. 9. **Resilience and Adaptability:** AI disruption has burned some sales leaders who either dismiss AI as hype or are paralyzed by past failures. Avoid those blaming tools or leadership; prefer those who learn from failed AI experiments and stay energized by innovation. 10. **Willingness to Carry Quota Initially:** Especially at early stages, your VP must be a player-coach, personally closing 20-30% of deals while building the team and processes. Reluctance to sell immediately signals a poor fit. **In summary:** The 2026 VP of Sales/CRO excels in traditional sales fundamentals and AI deployment, maintaining enthusiasm amid rapid change. They are rare but invaluable. While 8 out of 10 first-time VP Sales hires still fail, hiring the right AI-savvy leader can create a sales engine operating 3-4x more efficiently than competitors. The stakes have never been higher—and so has the potential reward. Move fast if you find this candidate.