Account Executive

Overview

You're selling Checksum's AI testing platform to engineering teams at companies building web and mobile apps. You'll prospect into greenfield accounts, run technical demos, and close deals with VPs of Engineering, Engineering Managers, and QA leads. This is full-cycle—you source your own leads, run the demo, handle objections about AI reliability, and close the deal.

Role Snapshot

Company Context

Stage: Early (27 employees, likely Seed/Series A)

Size: 27 employees total

Growth: Active hiring, CRO mentions "huge demand" which suggests inbound interest

Market Position: Category participant in AI testing space—competing against manual QA processes, legacy test automation tools (Selenium, Cypress), and other AI testing startups

GTM Reality

Pipeline Sources:

• 30% Inbound - Product-led interest from developers who've heard about AI testing, found them via search or community. Quality varies—some are tire-kickers, some are serious buyers with budget.
• 60% Outbound - You're hitting up companies on LinkedIn, cold emailing VPs of Engineering at B2B SaaS companies, reaching out to DevOps teams. You'll lean heavily on sequencing and social selling.
• 10% Referrals - Early customer base is small, but happy customers will refer you to their network.

SDR/AE Structure: Likely self-sourcing at this stage. With 27 employees total, they probably don't have a big SDR team. You'll do your own prospecting.

SE Support: Probably shared or no dedicated SE. You'll need to run technical demos yourself or pull in a solutions engineer when available.

Competitive Landscape

Main Competitors: Other AI testing tools (Testim, Mabl, Functionize), traditional automation frameworks (Selenium, Cypress, Playwright alone), manual QA teams, and "we'll build it ourselves" engineering teams.

How They Differentiate: Auto-healing tests (tests update themselves when the app changes), AI-generated test coverage, claim to be "always learning." They use Playwright under the hood, which is popular with modern dev teams.

Common Objections: "We already use Playwright/Cypress," "We have QA people who write tests," "AI-generated tests sound unreliable," "Too early-stage, what if you go out of business," "Our tests are fine, why change?"

Win Themes: Speed (ship 10x faster), reduced maintenance burden (tests heal themselves), comprehensive coverage (E2E + API + CI), engineering team can focus on features instead of test maintenance.

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal/Admin (25%)

Key Activities

• Prospecting: You're scraping LinkedIn for VPs of Engineering and DevOps leads at B2B SaaS companies. You'll send 30-50 personalized emails per day, run sequences, and try to get 4-6 discovery calls per week. Most ignore you. Some reply with "not now."
• Discovery Calls: You're qualifying whether they have a testing problem, who owns it, what they're using now, and whether they have budget. Half of your calls are with people who don't have authority or budget.
• Technical Demos: You're showing how Checksum generates tests, how they auto-heal, and walking through their specific app architecture. You'll get questions about edge cases, security, and "what if the AI generates bad tests?" You need to know enough about testing frameworks to sound credible.
• Navigating Procurement: After the technical win, you're chasing down finance approvals, security reviews, and contract redlines. At this company size, you're probably learning procurement processes on the fly. Deals slip because someone went on vacation or they need to wait for next quarter's budget.

The Honest Reality

What's Hard

• You're selling a new category (AI testing). Most prospects are skeptical about AI reliability. You'll hear "we'll just hire more QA people" or "we're fine with Cypress" a lot. You're educating buyers, not just feature-comparing.
• Self-sourcing is a grind. You're doing both hunter and closer work. When you're in closing mode on 3 deals, you're not prospecting, so next month's pipeline suffers.
• Early-stage means things change fast—product roadmap shifts, pricing changes, no established playbook. You're figuring out messaging and positioning in real-time. What worked last month might not work this month.
• Technical buyers are skeptical and detail-oriented. They'll ask about infrastructure, security, edge cases. If you can't answer convincingly, you lose credibility fast.
• Small company means limited brand recognition. You're selling yourself and the vision as much as the product.

What Success Looks Like

• Closing 1-2 deals per month at $30-80K ACV
• Building a pipeline of 3x your quarterly quota
• Getting technical buyers to run a POC and seeing them extend usage
• Becoming the "go-to" rep for a specific vertical or ICP as you learn what works

Who You're Selling To

Primary Buyers:

• VP of Engineering or Head of Engineering (budget holder, cares about velocity and quality)
• Engineering Managers (day-to-day pain, cares about reducing test maintenance burden)
• QA leads or DevOps leads (technical evaluator, worried about reliability and integration)

What They Care About:

• Release velocity—can they ship faster without breaking production?
• Engineering time—are their devs spending too much time fixing flaky tests?
• Test coverage—do they have blind spots that cause bugs in production?
• Maintenance burden—are tests breaking every time the UI changes?
• Integration with existing CI/CD pipelines
• Security and compliance (SOC 2, data handling)

Requirements

• 2-4 years in B2B SaaS sales, ideally selling to engineering or technical buyers
• Comfortable with technical concepts (APIs, CI/CD, testing frameworks)—you don't need to code, but you need to understand what Playwright is and why it matters
• Experience with full-cycle sales (prospecting through close)
• Okay with ambiguity and building process as you go—this isn't a well-oiled sales machine yet
• Strong prospecting skills—you'll be doing a lot of outbound to build your own pipeline
• Located where you can work closely with the team (likely SF Bay Area or remote with overlap)