Checksum AI, Inc.
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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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.
#J-18808-Ljbffr