Stevie Case
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- RAISE Summit41 min
Cracking the ROI Code: Is Intelligence Meeting the Income Statement? | RAISE Summit 2026
May Habib, Rick McConnell, Vishal Talwar, Amit Zavery, Stevie Case, Karen Kwok
Executives from ServiceNow, Dynatrace, FedEx, and Vanta convene to assert that artificial intelligence has transitioned from a speculative technology to a foundational operational driver, citing a direct $500 million P&L improvement for ServiceNow and a 350% average ROI for Dynatrace customers. The panel emphasizes a strategic shift away from measuring technology inputs like token volume toward traditional financial metrics and outcomes such as autonomous issue resolution, while identifying a critical workforce transformation that requires reskilling 500,000 employees and adapting hiring practices for functional engineering roles. Ultimately, the discussion concludes that successful AI integration depends on establishing robust trust frameworks through AI Control Towers and data consolidation to manage shadow AI risks, positioning organizational culture and process rewriting as the primary prerequisites for future scalability.
20Sales: How to Scale a Career While Scaling a Family; Work-Life Balance; Parental Leave | E1012
Maggie Hott, Stevie Case, Renu Gupta, Lauren Schwartz, Julie Maresca, Jessica Arnold, Harry Stebbings
Six sales leaders, including Jessica Arnold, Stevie Case, and Maggie Hott, convened to discuss the dual challenges and unique advantages of balancing motherhood with high-level sales careers. The panel detailed how integrating family responsibilities fosters leadership superpowers like time efficiency and empathy while highlighting systemic barriers such as career pauses and the lack of equitable parental leave policies. By advocating for structural changes like protected quotas during leave and cultural shifts that normalize vulnerability, the group emphasized that organizational support is essential to transforming perceived work-life conflicts into competitive advantages.
Tips for Hiring Salespeople
The event outlines a strategic framework for building early sales teams, emphasizing that first hires must be intimately coupled with founders through direct observation to internalize the company narrative rather than relying on documentation. It prioritizes hiring candidates with proven ACV deal experience and a "hunter" mindset capable of navigating complex market dynamics over those with mere domain expertise. Additionally, the discussion details specific assessment techniques for identifying "grit" by evaluating a candidate's history of enduring long-term adversity and making significant sacrifices to achieve difficult goals.
How to Structure Sales Comp
The session outlines critical strategies for structuring early-stage sales compensation by prioritizing risk-tolerant hires and aligning incentives through collaborative, iterative plan development. It further details methods for maintaining team morale during market downturns via strategic transparency and the tactical use of gamified "small wins" to sustain momentum. Finally, the discussion defines effective Sales Performance Incentive Funds, illustrating their application through activity-based goals and monetary multipliers like Twilio's "Pipe Pipe Week" to drive non-routine business objectives.
Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970
Former gamer turned CEO Ciara Vanta leverages her unique background in game design and federal litigation to advocate for a sales model grounded in vulnerability, mathematical rigor, and human connection rather than traditional aggression. She advises enterprise leaders to avoid simultaneous PLG and enterprise motions, recommending instead a staggered expansion strategy that incorporates early multi-threading with finance and security stakeholders to navigate capital constraints. Vanta further emphasizes hiring for grit and curiosity while restructuring compensation to gamify pipeline activities, ultimately urging the industry to pivot toward higher empathy and authentic engagement.