Who We Are
Checksum.ai is a high-growth, startup revolutionizing software testing with AI-powered, self-healing QA automation . We are backed by start up studio super{set} whose co-founders have over $1B in exists including Microsoft and Salesforce. Our platform eliminates the need for manual test maintenance by automatically generating and adapting tests based on real user behavior. Engineering teams can now release faster without sacrificing quality —and our traction proves it: we’ve grown ARR 100% in the last six months.
Why Join Checksum?
✅ Explosive Growth – tripled ARR in the past 9 months, selling into a booming market.
✅ Cutting-Edge AI – Work with leading engineering teams adopting AI/ML-driven DevOps solutions.
✅ Fast Sales Cycles – Strong inbound motion and a high-velocity pipeline.
✅ High Impact – Work directly with our co-founders to shape GTM strategy.
✅ Well-Funded & Backed by Experts – Supported by Super{Set} , a top-tier startup studio with multiple successful exits.
This is a hybrid position based in our San Francisco office 4x a week.
What You’ll Do
- Own the full sales cycle from prospecting to close, working with net new customers and expansion accounts .
- Partner with the co-founder and founding AE to refine our sales playbook and scale the GTM motion.
- Sell directly to engineering leaders (CTOs, VPs of Engineering, QA leaders) at high-growth startups and enterprises.
- Develop and execute a repeatable, high-velocity sales process in a fast-moving startup environment.
- Collaborate with product, marketing, and engineering teams to refine our messaging and influence roadmap decisions.
Who You Are
- 5+ years of closing experience in B2B SaaS, preferably in DevOps, QA, AI/ML, or technical tools .
- Strong track record of exceeding quota in a high-growth startup (pre-Series B preferred).
- Experience selling to technical buyers (CTOs, VPEs, engineering teams).
- Proficiency with structured sales methodologies like MEDDICC, SPICED, or GAP Selling .
- Excited to work in an early-stage, fast-paced environment where playbooks are still being built.
- Bonus: Prior experience selling QA automation, DevOps, or AI/ML solutions .
What We Offer
- Competitive OTE: $250k-$300K.
- Equity – Be a key player in an early-stage startup with significant upside.
- Strong inbound pipeline – You won’t be starting from scratch.
- Catered lunch 5 days a week in our San Francisco office (hybrid flexibility available).
- A fast-moving, collaborative team that values execution over ego .