.png)
Lead company vision, strategy, and execution; drive growth, fundraising, investor and board relations; build and mentor executive team; align organization, monitor performance, and create long-term value.
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)
Similar Jobs
Artificial Intelligence • Cloud • Computer Vision • Hardware • Internet of Things • Software
Generate and qualify enterprise sales opportunities for Samsara’s SaaS products by conducting approximately 50 daily cold calls, mapping accounts, engaging executives, and building product demand. The role requires resilience, curiosity, collaboration, and the ability to learn technical concepts and use AI in daily workflows. Successful representatives may advance to closing sales roles within two years.
Top Skills:
Artificial Intelligence (Ai)Internet Of Things (Iot)Linkedin Sales NavigatorSalesforceZoominfo
Artificial Intelligence • Cloud • Computer Vision • Hardware • Internet of Things • Software
Entry-level sales role focused on responding to prospective customer inquiries, booking product demos, identifying new business opportunities, supporting Account Development and Account Executive teams, and maintaining accurate CRM records. The position includes formal and on-the-job training to develop into an outbound Account Development Representative and offers a progression path toward Account Executive.
Top Skills:
CRMInternet Of Things (Iot)SaaSSalesforce
.png)
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
Develop and manage Square’s always-on B2B content engine across social, thought leadership, customer stories, partner content, and industry narratives. Build content calendars, formats, briefs, campaigns, and AI-assisted workflows; coordinate cross-functional teams and external partners; oversee production through launch; and analyze performance to optimize messaging, formats, and distribution.
Top Skills:
Ai ToolsLinkedInSocial AnalyticsSocial Media Platforms
What you need to know about the Calgary Tech Scene
Employees can spend up to one-third of their life at work, so choosing the right company is crucial, not just for the job itself but for the company culture as well. While startups often offer dynamic culture and growth opportunities, large corporations provide benefits like career development and networking, especially appealing to recent graduates. Fortunately, Calgary stands out as a hub for both, recognized as one of Startup Genome's Top 100 Emerging Ecosystems, while also playing host to a number of multinational enterprises. In Calgary, job seekers can find a wide range of opportunities.
