Founding Account Executive

We're Hiring: Founding Account Executive Obkio is looking for our first Account Executive to help us scale from $2M to $5M ARR over the next 12-18 months. Location: Montreal (hybrid/on-site) OTE: $240K - $280K CAD (Base: $120K - $140K) Role: Founding AE - you'll build the sales playbook from scratch ABOUT OBKIO Obkio does automated troubleshooting, not just monitoring. We automatically diagnose network issues across your LAN, your ISP, and Microsoft Teams. Our vision: expand use cases and automate even more with Insight. The result: IT pros save hours every week, enhance their game, and improve their company's network performance. MSPs can scale by managing more clients with less effort. We're the only network-first observability platform with auto-diagnostics. While ThousandEyes does cloud-first and SolarWinds does legacy, we own a unique angle that nobody else has. Current traction: $2M ARR, 150 clients, 4.9/5 customer satisfaction, 100% bootstrapped THE OPPORTUNITY This isn't for everyone. If you want corporate structure, this isn't it. But if you want to: Build a sales playbook from scratch Have direct impact on every deal you close Shape the product with your feedback Potentially lead a sales team within 12 months Capture the upside of a company scaling 3-5x in 18 months then we should talk. The timing is perfect: Teams monitoring Insight launch Q1 2026. The territory is wide open: 10,000 MSPs globally, 50K mid-market companies, zero saturation. WHO YOU ARE You're already a money maker. You close deals. But your impact is invisible in a big machine, and your career path is blocked. At Obkio, every deal you close gets celebrated and analyzed together. Your feedback shapes the product. Within 12 months, if you prove you can write a playbook and train people, you lead a team. It's YOUR path, not a vague promise in 5 years. MUST-HAVES: - Located in Montreal - Track record of hitting/exceeding quota in B2B SaaS or tech sales - Strong understanding of tech/IT buyers (you speak their language) - Complete autonomy - you identify strategies, we challenge and guide - Leadership ambition - you want to build and lead a team eventually NICE-TO-HAVES: - Experience selling to MSPs or mid-market IT teams - Knowledge of networking, monitoring, or observability space - Startup experience (comfortable with ambiguity and speed) - Bilingual (French/English) RED FLAGS: - You wait for inbound leads instead of hunting - You blame external factors when things don't work - You need structure and process handed to you - You want to stay an individual contributor forever WHAT WE OFFER Compensation: - Base: $120K - $140K CAD - OTE: $240K - $280K CAD - Equity: Leadership package after 12 months (if you prove you can scale a team) ️ Career Path: Two options are possible: 1. Build and lead the sales team (VP Sales path) 2. Stay a top-performing IC (keep maximizing commissions) We evaluate together after 6-12 months. No forced management track if it's not your thing. The Role: - Own the entire sales process from prospecting to close - Define how we sell, to whom, with what messages - Work directly with CEO on strategy - Collaborate with Product - your feedback shapes roadmap - Create the playbook that future AEs will learn WHY NOW? We're at an inflection point. Teams monitoring and Insight (auto-diagnostics) launch Q1 2026. This is our "ChatGPT moment" for network troubleshooting. If you join now, you capture the entire upside. If you wait 6 months, we'll be at $4M ARR and you'll be AE 3, not Founding. The window is 12-18 months. After that, we're either scaled successfully (and you're leading the team) or we missed the opportunity.