Job Description

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.

We’re looking for an entrepreneurial, technical Account Executive to join as our second sales hire , working closely with our founders to scale revenue and refine our GTM motion. This is a high-impact, high-growth opportunity to sell an innovative AI product to technical buyers while helping define the sales playbook for a breakout startup.

Why Join Checksum?

✅ Explosive Growth – 100% ARR growth in the last six 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 on-site position based in our San Francisco office 4-5x 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: $200-$350K.
• 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 3 days a week in our San Francisco office (hybrid flexibility available).
• A fast-moving, collaborative team that values execution over ego .

🚀 Join us in shaping the future of AI-powered software testing! If you're a top-performing AE ready to sell an innovative product, work closely with founders, and help build a world-class sales organization , we want to hear from you.

Apply today!

The estimated OTE $200K-$350K, with uncapped commission. This does not include the value of benefits or a potential equity grant. A wide range of factors are considered in making compensation decisions, including but not limited to skill sets, market conditions, experience and training, licensure and certifications, and business and organizational needs.

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