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Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles?

SaaStr

A bit more on that here : How to Cope With Long Sales Cycles But there are plenty of things that help : Hire a VP of Sales with Enterprise Experience : A great VP of Sales who’s closed deals at your price point can shave months off your sales cycle. They know how to navigate pilots, engage stakeholders early, and avoid late-stage objections.

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Is AI Penetration … Slowing Down? Ramp Says Possibly

SaaStr

Moving from AI pilots to production-grade implementations requires solving hard technical problems around data pipelines, security, compliance, and workflow integration. Price pressure is coming. Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated.

AI 281
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The Enterprise Journey: 8 Keys to Going Upmarket Successfully with Workiva’s CEO Julie Iskow

SaaStr

Focus on: Building robust security and compliance (SOC 2, ISO 27001) Automating customer onboarding/offboarding Creating enterprise-grade support processes Developing procurement relationship expertise Having clear data handling procedures 5. If one does and one doesn’t, you know it’s the person not the motion.

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Palantir’s +79% vs Bill’s -43%: The AI Divide That Defined SaaS Performance in 1H’25

SaaStr

Guidewire (GWRE): +37% YTD Insurance industry digital transformation accelerating with climate-related claims driving modernization Comprehensive P&C platform essential for sophisticated risk modeling and regulatory compliance Cloud-first approach and AI capabilities resonating with insurers modernizing operations Vertical specialization creating (..)

AI 216
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Outrun Your Competition: Best Practices for Accelerating Sales Processes

Slow-moving compliance reviews. By building a modern GTM motion that uses data, automation, and proven best practices to unlock insights, engage customers, and win faster. Longer sales cycles. Larger buying committees. Every go-to-market team knows the frustrations that come from a drawn-out sales process. How can you speed it up?

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🚀 Top 5 SaaStr Learnings from G2’s 2025 Buyer Behavior Report: You Gotta Be AI

SaaStr

The Mega-Deal Era Is Over — Enterprise deals are clustering in the $100K-$150K range The Shift : Enterprise deals are clustering in the $100K-$150K range (down from ZIRP-era budgets) The New Model : 39% of buyers prefer pay-as-you-go pricing. Lead with integration capabilities and security compliance, not just business outcomes 5.

AI Search 147
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Whatfix Mobile Review: Pricing, Features, Pros & Cons

User Pilot

But for mobile, youd want to invest in a solution that truly gets the job done, aka one that improves user engagement and retention. This way, users get the help they need, exactly when and where they need it, leading to faster adoption, reduced friction, and higher engagement from day one. Whatfix mobile pricing. moment faster.

Mobile 93