Crossing the enterprise chasm

Crossing the enterprise chasm requires sustained investment over multiple years - it’s not a quick sprint but a marathon requiring ongoing work and maintenance

Four key areas enterprises demand:

• Control (admin features, permissions, security)
• Visibility (audit logs, usage analytics)
• Compliance (GDPR, SOC2, encryption)
• Automation (APIs, integrations)

The transition requires building two parallel streams:

• Continue developing core product features for end users
• Build enterprise-grade capabilities for IT admins/buyers

Major benefits of crossing the chasm:

• Higher revenue per customer
• Better retention rates
• Expanded market size
• Increased product defensibility
• More predictable sales cycles

Common challenges:

• Engineers prefer building core features over enterprise capabilities
• Hard to motivate teams for “unsexy” backend work
• Complex integration with legacy systems
• Large surface area for potential bugs
• Requires deep customer research with enterprise admins

Key recommendations:

• Start with identity/SSO integration
• Build APIs and webhooks for automation
• Focus on security and compliance early
• Ensure proper financing/runway before starting
• Prioritize based on future customers, not just current leads

Failed enterprise transitions often lead to competitors overtaking market share by serving enterprise needs better (e.g. Microsoft Teams vs Slack)

Success requires maintaining focus on both individual users and enterprise capabilities simultaneously rather than completely shifting focus