Chief Executive Officer - Stealth Startup

Overview

Unusual Ventures is seeking a strategic, visionary, and execution-driven Chief Executive Officer (CEO) to lead a portfolio company's overall direction, growth, and success. The CEO will set the vision, drive business performance, build a strong leadership team, and create long-term enterprise value through a category-defining B2B software company.

About Unusual Ventures:

We lead pre-seed to Series A investments in enterprise software startups across infrastructure, developer tools, security, AI/ML, and data, with a focus on supporting founders as they journey from insight to product-market fit. Our expert team of operators works alongside our founders on everything from positioning to recruiting to enterprise sales, leveraging decades of practical experience to improve your odds of success.

Key Responsibilities

• Define and communicate the company's vision, mission, and long-term strategy
• Drive overall business growth, ARR expansion, and enterprise market penetration
• Build, lead, and mentor the executive leadership team (CTO, VP Product, VP Sales, VP Engineering, etc.)
• Make high-level strategic decisions on product roadmap, GTM motion, partnerships, and capital allocation
• Represent the company to investors, board members, enterprise customers, and external stakeholders
• Lead fundraising efforts, investor relations, and capital allocation across institutional rounds
• Own design partner and early enterprise customer relationships through the zero-to-one phase
• Establish company culture, values, and leadership principles
• Monitor performance metrics (ARR, NRR, CAC payback, pipeline coverage) and ensure execution against goals
• Identify new opportunities for innovation and competitive advantage

Requirements

• 15+ years of leadership experience at enterprise software or B2B SaaS companies, with prior executive-level roles
• Proven track record of scaling an enterprise software company or business unit (ideally from sub-$10M to $100M+ ARR)
• Strong business acumen across product, technology, and enterprise go-to-market functions
• Experience selling, building, or operating in complex enterprise sales environments (six- and seven-figure ACVs, multi-stakeholder deal cycles)
• Experience with venture fundraising, investor relations, and board management at venture-backed companies
• Demonstrated ability to lead high-performing teams across engineering, product, and GTM
• Exceptional communication, decision-making, and leadership skills

Nice to Have

• Prior experience as a CEO, Founder, or founding executive at a venture-backed enterprise software startup
• Operating experience at companies in Unusual's core investment areas: cloud infrastructure, developer tools, cybersecurity, AI/ML platforms, or data infrastructure
• Track record building category-defining products serving technical buyers (engineering, security, data, platform teams)
• Experience navigating early-stage enterprise GTM (design partners, founding AE hires, first $1M-$10M ARR)
• MBA or advanced technical degree (CS, engineering)