Job Description

AI-first SDR (Sales Development Representative)

CaseMark (founded June 2023, Portland, OR) is an AI-driven legal workflow platform designed to streamline legal processes. We empower legal professionals with intelligent automation and modular workflows for case summaries, depositions, chronologies, and more. Our secure, enterprise class platform is designed to increase efficiency and shift focus to client relationships and strategic casework. Committed to privacy and accuracy, CaseMark is at the forefront of legal innovation.

We're building CaseMark: an AI-native legal platform with 700+ discrete "easy buttons" that solve specific legal tasks. We need an SDR who wants to build the growth engine alongside usnot just execute playbooks, but help create them.

This is an SDR role with a growth trajectory. You'll generate pipeline and qualify leads, but you'll also sit at the intersection of sales, marketing, and opsbuilding the systems and experiments that get CaseMark discovered, evaluated, and adopted by law firms and legal service providers.

What You'll Do

• Core SDR work: Prospect, qualify, and book meetings with law firms and legal service providersfocusing on task-based pain points that our easy buttons solve.
• Run rapid GTM experiments: Test and optimize channels (paid search, content, partnerships, outbound) to discover what works for legal buyers with specific task-based intent.
• Build AI-native workflows (agentic systems, MCP servers, automations) that accelerate your own pipeline generation, qualification, and conversion.
• Manage and optimize the GTM stack (Attio, Unify, Clay, Apollo, PostHog)always asking: "how can AI make this better?"
• Use AI coding assistants (Cursor, Claude Code, etc.) for lightweight automation, data enrichment, and workflow optimization.
• Help operationalize our SEO / AI discovery strategy: turning easy button landing pages into qualified inbound leads.
• Track what's working, analyze performance data, and translate insights into clear growth decisions.
• Work directly with leadership to shape the revenue engine and go-to-market motion.

What We're Looking For

• 12 years of experience as an SDR or in SDR-adjacent roles at a B2B software company (legal tech experience is a bonus, not required).
• AI-native mindset: you default to solving problems with automation, agents, and AI tools.
• Strong interest in sales systems, ad tech, marketing automation, and revenue operationsyou want to build the machine, not just run it.
• Comfortable running structured experiments with speed and precisionhypothesis, test, learn, iterate.
• Hands-on with GTM tooling, curious with data, resourceful with ambiguity.
• Some comfort codingenough to bend AI tools to your will and ship scrappy, high-impact solutions.
• Based in San Francisco (this is an in-office role).

Why Join

• $80K salary with meaningful equity and growth potential.
• Build the GTM machine from scratch at a fast-moving legal AI startup backed by top investors.
• Direct impact on growth and revenue: every experiment you run matters.
• Work at the frontier of AI-driven sales and marketingin one of the few industries where AI is genuinely transformative.
• Learn how modern legal buyers discover, evaluate, and adopt AI tools through task-specific workflows.

Salary: $60,000 - $70,000 per year

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