Who Is Checksum?

Checksum.ai is an ambitious and successful company at the forefront of artificial intelligence, using AI to automatically QA software based on real user behavior. Our AI models generate and self-heal tests with lightning speed so that engineering teams will never have to sacrifice release velocity for quality. Checksum has grown in ARR over 100% in the past quarter, and we need a seasoned, entrepreneurial, technical account executive to join our team!

This role is on-site or hybrid, based in our office in downtown San Francisco.

Why Checksum?

We are well-funded and backed by Super{Set}, a startup studio with multiple exits and highly experienced founders. In your role you will be working with everyone from hyperscaling startups to enterprise customers who are early adopters of AI tools, and you will become an expert in agentic AI/ML use cases needed by Engineering Leaders. We need someone detailed and highly organized who can ramp quickly in a fast-paced, buzzy startup. Our founding Account Executive closed multiple deals in their first quarter, and we want to set you up for the same kind of success.

Position Overview:

As a seed-stage company, we’re growing fast and looking for talented people who want to be part of something early, meaningful, and impactful. You won’t just be closing deals—you’ll be helping define our go-to-market strategy, influencing product development, and working alongside a team of brilliant, supportive, and driven individuals. We believe in teamwork over ego, and look for candidates with a results-focused mindset.

Key Responsibilities:

• Identify, qualify, and engage with potential customers - from initial contact, to demo, to contract negotiation and close - with net new customers as well as existing accounts.
• Partner closely with the cofounder to close deals, refine the customer buying journey, and help shape the GTM team at Checksum.
• Collaborate on, develop, and execute sales strategies to meet and exceed revenue targets.
• Maintain a deep understanding of our products and effectively communicate their value to potential customers.
• Collaborate with product, marketing, and solution engineering teams to positively impact customer success.

Qualifications:

• Proven experience in an account executive role at a SaaS-based startup, preferably pre-Series A.
• Superior communication and interpersonal skills with a customer-centric mindset.
• Ability to work independently and collaboratively in a fast-paced environment, with a ‘Get Shit Done’ mentality.
• Out-of-the-box thinker with a driving urge for success.
• Experience selling QA automation, DevOps, or highly technical tools to engineering leadership.
• Demonstrable sales process (MEDDICC, SPICED, GAP Selling) that you have leveraged to close six-figure deals.
• Bonus: Experience selling AI/ML tools, or a deep desire to learn about AI/ML tools.

What We Offer:

• A realistic, achievable quota that is still highly ambitious in a market category that is currently exploding in growth.
• Strong inbound lead generation with fast sales cycles.
• A chance to be a key player in an early-stage startup with significant growth potential.
• Direct partnership with the cofounders, offering insights and experience in scaling a company.
• Competitive compensation and benefits, including base salary and equity
• Catered lunch 3 days a week in-office.

The estimated base salary range for this position is $125k to $200k with a 50% base and 50% commission variable, $250K-$400K OTE. 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.