Two of the top sales leaders in SaaS came to SaaStr Annual to do a deep dive and AMA on what’s working (and what’s not) in modern sales organizations. Not the fluff you read on LinkedIn. The real, data-driven learnings from the trenches.
Meet Our SaaS Sales Leaders
Jeff Perry is the Chief Revenue Officer at Carta (if you don’t know Carta, they’re the $1B+ ARR leader in cap table management and fund administration). Before taking the helm at Carta 6 years ago, Jeff spent 15 years at Oracle leading both Enterprise and SMB software/hardware divisions. He also put in 4 years at Doximity building their S&B organization from scratch.
Brendon Cassidy might be the definition of “been there, done that” in SaaS sales. As co-founder of High Five, he brings 20+ years of startup sales experience. But here’s what really matters: he was the first VP of Sales at LinkedIn, EchoSign, and Talkdesk. Translation? He’s scaled sales orgs from $0 to $100M+ ARR multiple times.
The Truth About SDRs and AI in 2025
- No, AI isn’t replacing your SDR team. At $1B+ ARR companies like Carta, they’re doubling down on both inbound and outbound SDRs
- The real playbook: Use AI to make SDRs 2x more efficient, not replace them
- Segment your SDR team by product type and ICP – this is what’s working at scale
- Key learning: Your competitors talking about “full AI replacement” of SDRs? They’re mostly posturing. The data doesn’t support it.
The New Enterprise SaaS Sales Motion That’s Actually Working
- The old “rip and replace” playbook is dead
- What’s working now: Finding budget from disaggregated spend across multiple tools
- The winning pitch: Value selling focused on efficiency gains + risk reduction
- Remember: You’re not just selling to the business – you’re selling to the person. Focus on their personal pain points and career wins
Events Strategy That Actually Drives Pipeline. Here’s what’s working at Carta:
- CFO symposiums for high-ACV deals ($100k+)
- Segment events by business unit – different strategies for different ACVs
- Use existing customers as your best salespeople
- The magic ratio: 70% customers, 30% prospects at high-end events
The Sales + Legal Dance in Hypergrowth: Real Talk
- Legal can kill your quarter if you let them
- The Adobe/EchoSign story: How legal slowed down a rocket ship
- The solution: Deal desk + early legal partnership
- Key metric: Track legal review time as a KPI
The New GTM Reality: Data From the Front Lines. The data is clear:
- Marketing owning 100% of demand gen is dead
- The winning model: Trifecta approach (Sales + BDR + Demand Gen)
- At Carta: 9 trifectas across 3 business units
- The hard truth: Companies with zero marketing-sourced pipeline are dying
What’s Really Working in Account Management in 2025
- The Hunter/Farmer model? Only if you have LinkedIn-level resources
- Customer Success teams are evolving or dying
- What’s working: Integrated new business + growth + focused CS
- The efficiency play: Combine CS and support roles
The 5 Key Traits of Your Next VP Sales (That Actually Matter)
- They’re probably not from Oracle (unless they built something from scratch there)
- They’re likely risk-averse and will heavily vet your company
- They have strong references from people in your network
- They’ve scaled something from $0 to $10M+ ARR
- They understand the product-sales feedback loop
What’s Next? The Future of Sales Org Design The next 12-24 months will see:
- Further consolidation of CS roles
- AI augmentation (not replacement) of sales roles
- Increased focus on efficiency metrics
- More integrated GTM motions
And remember: Your VP Sales hire will likely make or break your company. Take the time to get it right.
