You are the Product Growth Analyst at a B2B work management software platform with a strong self-serve funnel and expanding enterprise business. The company added 120,000 new workspace signups last quarter, but only 34% of new workspaces complete the core setup flow within 7 days, while 90-day workspace retention for activated cohorts is 41%. Leadership is debating whether to push harder on short-term activation by simplifying onboarding, adding more templates, and aggressively prompting users into quick wins, or to invest more in longer-term habit formation through better team collaboration setup, recurring workflows, and cross-functional use cases. The tradeoff matters because faster activation could lift trial-to-paid conversion from 8% to 10%, but some past onboarding shortcuts increased early conversion while reducing 6-month retention by 3-5 points.
How would you decide where to optimize between short-term activation and long-term retention, and what strategy would you recommend?
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