AI Agents Reshape Startup Hiring: Gusto, Insight Partners and Leland at Disrupt 2026
Gusto, Insight Partners and Leland leaders will examine how AI agents reshape early startup hiring, ownership and culture at Disrupt 2026 in San Francisco.
Summary
AI agents capable of multistep engineering, customer support, research, operational and sales tasks are prompting startups to reconsider whether their first 10 teammates must all be people. At the Disrupt 2026 Builders Stage session “Hiring When AI Is a Co-Founder,” Gusto CEO and co-founder Josh Reeves, Insight Partners senior vice president Michelle Johnson and Leland CEO and co-founder John Koelliker will examine how founders can divide work between humans and agents without sacrificing speed, accountability or culture. Human roles may increasingly emphasize judgment, customer understanding, relationships, strategy, ownership and directing people and machines.
Gusto combines AI with more than a decade serving over 500,000 companies across payroll, benefits, compliance, onboarding, HR and retirement. Johnson advises CEOs and CROs across North America and Europe on go-to-market strategy, revenue organizations and AI implementation, after helping Flock Safety grow from under $1 million to $90 million in ARR. Koelliker previously held product and growth roles at LinkedIn, Curated and Uber before co-founding Leland, a career and talent platform. Disrupt runs October 13 to 15 at Moscone West in San Francisco with more than 10,000 startups, investors and technology decision-makers. Passes are discounted by up to $200 until September 25 at 11:59 p.m. PT, while groups can save up to 30%.
Positives
- AI agents can complete multistep engineering, support, research, operational and sales tasks, potentially helping small startup teams move faster.
- Gusto’s experience serving more than 500,000 companies provides broad evidence of how small businesses approach hiring and AI adoption.
- Michelle Johnson helped Flock Safety increase ARR from under $1 million to $90 million before joining Insight Partners.
- Human employees may concentrate more on judgment, customer relationships, strategy, accountability and directing both people and machines.
- Groups attending Disrupt 2026 can save up to 30% on passes.
Risks & concerns
- Delegating multistep work to agents leaves founders responsible for determining who checks outputs and makes final decisions.
- Agent failures could create accountability gaps when no person clearly owns the delegated work.
- Critical responsibilities involving strategy, culture, customers and judgment may be too important to automate safely.
- AI-native staffing could make early hiring decisions harder by changing which skills and roles startups should prioritize.