152: Ben Orenstein - How to Stand Out When Applying for a Job at a Small Company

What It Covers

Ben Orenstein and Adam Wathan share hiring insights from small company founders' perspectives, covering application strategies, interview tactics, and how candidates can demonstrate competence while reducing perceived risk for resource-constrained startup teams.

Key Questions Answered

• •Application quality over quantity: Submit deliberate, customized applications instead of mass-applying to hundreds of positions. Read job postings carefully, follow instructions exactly, and reference specific requirements in your response to demonstrate attention to detail and genuine interest.
• •Derisk yourself as a candidate: Small company founders fear bad hires intensely. Demonstrate competence upfront by doing small amounts of actual work—analyze their product, suggest improvements, or share a relevant code commit with trade-off explanations rather than linking to your entire GitHub profile.
• •Showcase cross-functional abilities: Highlight skills beyond the core job requirement—developers with design sense, anyone with strong writing ability, or side projects completed independently. Small teams value generalists who can execute across domains without constant oversight or specialized departmental support.
• •Create your own opportunities: Email founders directly with specific project proposals showing first-day work completed, potential business impact, and execution plans. Many hires at small companies never had job postings—demonstrating initiative and alignment with company goals can create positions that didn't previously exist.