Pros
Talented individuals across teams, especially among peers
- Opportunity to learn quickly in an unstructured environment
- Exposure to multiple functions (sales, onboarding, retention, support)
Cons
Compensation structure lacked transparency. The role was presented with a base salary, but in practice operated as a quota-dependent structure where earnings were contingent on hitting targets, without clear communication upfront.
- No sales infrastructure at launch. No dialer, no real CRM discipline, and no consistent tracking of activity or performance for a founding sales team.
- Constantly shifting expectations. KPIs, responsibilities, and priorities changed frequently without clear direction.
- Role ambiguity. SDRs were expected to perform full-cycle sales, onboarding, retention, and customer support simultaneously.
- Lead quality issues. Outreach was primarily directed at competitors’ existing users, many of whom had already tried and rejected the product.
- Lack of cross-functional alignment. Sales, marketing, and customer support operated in silos, often sending conflicting messages to customers.
- Product-market fit challenges. Retention issues were known internally but not addressed at the root, creating friction in sales conversations and onboarding.
- Culture of optics over execution. Emphasis on narrative (“bullish on sales,” “VIP experiences”) without the systems to support those initiatives.
