This Week in Startups
This Week in Startups

Culture | Scaling Your Startup S2 E7: 15five’s David Hassell & Balloon’s Amanda Greenberg | E1221

Two CEOs join to talk about intentionally creating and maintaining a workplace culture that delivers high performance. First, 15five's David Hassel shares how to build culture at scale (1:49), then Balloon's Amanda Greenberg shares a process to help leaders navigate hybrid work (26:00). To

Featured Speakers

Jason Calacanis HostDavid Hassel Guest

Topics Discussed

Episode Summary

Executive Summary: In this episode of Scaling Your Startup, hosts David Hassel (15.5) and Amanda Greenberg (Balloon) discuss building high-performing cultures and navigating hybrid work. David presents a five-step framework for intentional culture design, emphasizing values, habits, and measurement. Amanda offers a six-part question framework to address hybrid challenges like trust, group dynamics, and spontaneity. The roundtable covers political speech at work, compensation fairness, productivity metrics, and loyalty. Key takeaways: culture must be led by design, hybrid work requires deliberate communication, and compensation models are shifting toward value-based pay.

Main Topics: Building a High-Performing Culture (Priority: 5/5): David Hassel outlines a five-step process: clarity of foundation (mission, values, principles), over-communication, hiring/firing based on values, instituting habits/rituals, and measuring engagement. He stresses that culture must be designed and led by the CEO, and that values should be actionable and few (e.g., 15.5 reduced from 10 to 4). Hybrid Work Framework (Priority: 5/5): Amanda Greenberg presents a six-part framework of questions to ask teams about culture, group dynamics, spontaneous interaction, trust, team cohesiveness, and structure. She emphasizes that hybrid work is here to stay and requires deliberate leadership to level the playing field between in-office and remote employees. Political Speech at Work (Priority: 4/5): A debate on allowing political discussions in company Slack channels. David and Amanda advocate for acknowledging events and focusing on principles over politics, while Jason warns of the dangers of text-based communication. They agree that leaders should model empathy and take heated conversations offline. Compensation and Negotiation (Priority: 4/5): Discussion on geography-based pay, no-negotiation policies (e.g., Reddit, Coinbase), and fairness. David argues for a clear compensation philosophy, while Amanda notes systemic biases in negotiations. Jason shares his career-path approach to attract and retain talent. Productivity and Performance Evaluation (Priority: 3/5): Remote work has exposed true output, reducing manager bias. David advocates for objective metrics and reinventing performance reviews. Amanda notes increased meetings (35% more) and the need to measure output fairly. Jason emphasizes tracking metrics and charts to identify high and low performers. Loyalty and Career Development (Priority: 3/5): David introduces the 'zone of genius' concept to help employees find their strengths, increasing retention. Jason discusses cross-training to eliminate single points of failure and creating clear career paths. Amanda links loyalty to operating in one's zone of genius.

Key Arguments: Culture must be intentionally designed and led by the CEO; it cannot be left to chance (David). Values should be few, actionable, and lived daily; over-communicate them to avoid cynicism (David). Hybrid work requires deliberate questions to teams across six areas: culture, group dynamics, spontaneity, trust, cohesiveness, and structure (Amanda). Political speech at work is risky, especially in text; leaders should acknowledge events but avoid debate, focusing on principles (David, Amanda). Compensation should be based on a clear philosophy; geography-based pay is evolving, and no-negotiation policies can reduce bias but may limit flexibility (David, Amanda). Remote work reveals true productivity; managers must use objective metrics and avoid bias toward in-office employees (David, Jason). Loyalty is fostered by helping employees find their zone of genius, providing clear career paths, and cross-training to reduce dependency (David, Jason).

Data Points: Employee desire for flexible remote options: 73% - Amanda cites this statistic to support hybrid work demand. Leaders considering redesigning office for hybrid: 66% - Amanda mentions this to show organizational shift. Workers craving more in-person time: 67% - Amanda uses this to highlight the need for deliberate connection. Increase in meetings during remote work: 35% - Amanda notes this as a challenge of remote work. 15.5 Glassdoor rating: 4.9 - David shares this as evidence of their strong culture. 15.5 employee growth: 30 to 70 to 200 - David describes scaling from 30 to 200 people while maintaining culture. Core values reduction: 10 to 4 - David explains they reduced values to make them actionable. NetSuite survey on visibility: 93% - Ad segment claims increased visibility after switching to NetSuite. Top 1% engineer performance multiplier: 10x - David references Reed Hastings' philosophy on paying top of range.

Pivotal Quotes: "The best time to plant a tree was 20 years ago, the second best time is now." — David Hassel: On the urgency of starting culture design early in a company's life. "Flexibility unlocks creativity and innovation. And ultimately, it makes people feel more fulfilled and happy." — Amanda Greenberg (quoting Matt Mullenweg): Closing her segment on hybrid work, emphasizing the opportunity of flexibility. "You can't control culture, you can only influence it." — David Hassel: Explaining that culture emerges naturally and must be steered, not controlled.

Implications: Founders must intentionally design culture from day one, using values and rituals. Hybrid work demands proactive communication and trust-building. Compensation models are shifting toward value-based pay, and performance evaluation must rely on objective metrics. Leaders should foster loyalty by helping employees find their zone of genius and creating clear career paths.

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About This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

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