Case Study
Instawork: Pivoting to an On-Demand Staffing Marketplace
The Problem
Instawork is a YC, Benchmark, and Google Ventures–backed startup, and I joined as its 1st employee. Our early product had some fundamental flaws — it was an inconsistent experience for both businesses and job applicants, and when we succeeded, neither side of the marketplace needed Instawork any longer. We decided to try a new approach: instead of matching applicants to businesses for jobs, we'd match them for individual shifts.
What I Did
- Identified the shift to an on-demand staffing marketplace as the path to reignite growth, and made the case to lead the company through the pivot.
- Got scrappy: built a proof-of-concept using only email, text messages, and a Google Sheet — cold-calling local restaurants on Thursday nights to see who needed a dishwasher or cook for the weekend, then hand-matching them myself as a one-person sales, billing, and support team.
- Once demand was clear, scaled up the team and worked with engineering to build the product to support the business.
- Recruited and managed a team of 12 product managers, designers, and customer support agents to build and support the new product.
- Owned the marketplace product end-to-end as it grew into the company's primary business line.
- Helped grow the company from 3 to 100+ employees and raise $28M in funding as a founding executive team member.
Doing things that don't scale: I offered to drive the worker to our first ever shift.
The Result
- The marketplace pivot reignited revenue growth and became Instawork's primary line of business.
- Grew the founding team's headcount from 3 to 100+ while raising $28M across funding rounds.