StartupOS is building toward the vision of the “one-person unicorn” — a future where human and AI employees work seamlessly together to build and scale companies.

We are developing an AI-native operating system that enables companies to deploy and manage networks of intelligent agents operating within a shared context layer, allowing them to coordinate and execute across business functions.

StartupOS is early, ambitious, and fast-moving, with leadership and team members from companies including Airbnb, Adobe, Clari, Box, and Intuit.

We operate using a “pod” model — small, focused teams aligned to specific market opportunities, built to move quickly and deliver meaningful outcomes.

This role reports directly to Ben Sardella.

The Role

StartupOS is hiring its first team of Account Executives to help build the company’s early go-to-market engine around an initial wedge product focused on venture capital and portfolio company workflows.

This is not a traditional AE role.

You will help define:

• how we sell
• how we position the platform
• what resonates with buyers
• and how we scale revenue from the ground up

The initial motion is highly relationship-driven and centered around selling into:

• venture capital firms
• family offices
• investor ecosystems
• portfolio support organizations

The platform is highly flexible and configurable, allowing customers to deploy AI-native workflows tailored to their operating model and portfolio needs.

We are looking for someone who can open doors quickly, navigate ambiguity, and translate emerging AI capabilities into clear business value for sophisticated buyers.

Why This Role Matters

We believe the next generation of companies will operate with AI workforces embedded across every function.

StartupOS is building the system that makes that possible.

This role is an opportunity to help define not only the company’s revenue engine — but the category itself.

What You’ll Do

• Build and manage relationships with venture capital firms, family offices, and adjacent investor organizations
• Generate and progress early-stage pipeline opportunities
• Lead customer conversations from first meeting through close
• Help shape StartupOS’ early GTM motion, messaging, and sales process
• Translate customer pain points into tailored AI workflow solutions
• Partner closely with leadership, product, and technical teams
• Provide direct market feedback to influence product strategy and roadmap
• Operate effectively in a fast-moving, highly iterative startup environment
• Help establish repeatable patterns for future sales hires and GTM scale

Requirements

• Experience selling into venture capital, private equity, family offices, or adjacent financial ecosystems
• Proven ability to source pipeline and close deals independently
• Strong existing network within the VC / investor community
• Ability to secure meetings and build trust quickly with senior stakeholders
• Experience operating in early-stage, resource-constrained, or highly ambiguous environments
• Entrepreneurial mindset with high ownership and urgency
• Strong consultative selling and relationship-building skills
• Ability to communicate emerging technology concepts in a practical, business-oriented way
• Comfortable operating without rigid playbooks or established infrastructure

Ideal Background

• Early-stage SaaS or AI infrastructure sales
• Venture ecosystem relationships
• Founder-led sales environments
• Experience selling workflow, automation, data, or operational platforms
• High curiosity around AI-native business models and agentic workflows

Benefits

• Opportunity to become one of the first AEs and help build the GTM foundation of the company

• Direct access to leadership and meaningful influence on company direction

• Significant autonomy to deliver on your goals

• Highly entrepreneurial environment with rapid learning and growth

• Competitive compensation package including:

• Base salary

• Commission

• Potential equity participation

• Remote-first environment with flexibility and expectation of relationship-driven customer engagement