Sales Development Representative

Chamelio · Boston

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Sales Development Representative - Boston, MA

About Us

Chamelio is revolutionizing legal tech with an AI-powered Legal Intelligence Platform trusted by some of the world's fastest-growing companies. We help in-house legal teams accelerate negotiations, reduce risk, and unlock institutional knowledge through automated workflows.

We've raised $36M to date, including a $26M Series A in September 2026 led by Entrée Capital, with participation from Work-Bench, Emerge Ventures, and Bright Pixel Capital. Work-Bench and Emerge also led our seed round.

The Role

Can you stand out from the pack? If you've got a real hunger for sales, a desire to learn, and the drive to own your territory, let's talk.

The Sales Development Representative is a critical function on the Chamelio sales team. You'll generate leads and build new pipeline by opening conversations with General Counsels, legal ops leaders, and in-house legal teams at our top target accounts. You'll follow up on marketing-generated and event leads, re-engage conversations that went quiet, and move prospects through discovery.

This isn't a dial-for-dollars job. Legal buyers are sharp, busy, and allergic to generic outreach, so success here comes from research, judgment, and outreach that's personal, not blasted. You'll work directly with our founding team to sharpen messaging and shape how legal teams discover Chamelio.

We promote from within. SDRs at Chamelio have a clear growth path into closing roles.

What You'll Do

• Pipeline generation: Generate new customer introduction calls through proactive outbound by phone, email, and LinkedIn, with outreach tailored to each account.

• Re-engagement: Activate marketing-qualified and event leads one-to-one, and revive conversations that went cold so Account Executives can stay focused on active deals.

• Quality over quantity: This is a relationship-driven role, not a high-volume dialer. We measure success by pipeline progression, account engagement, and deal quality, not raw activity counts.

• Multi-threading deals: Partner with Account Executives early in the sales cycle to engage the full buying committee: General Counsel, legal ops, procurement, and the business teams legal supports.

• Know the buyer: Master the Chamelio value proposition and understand each organization's legal workflows, business drivers, and pain points. Speak like someone who's been in-house.

• Field and community: Represent Chamelio at legal conferences, industry events, and local in-house legal community gatherings to build long-term relationships.

• Process and territory: Follow a clear qualification process, build territory plans with sales and the founding team, and keep every touchpoint accurate in our CRM.

What You'll Need

• Sales experience: 1+ years in sales, ideally outbound B2B SaaS, or another customer-facing background such as support or customer success. You've prospected your own leads.

• Unscripted judgment: You operate independently without a script and lean on business judgment over raw activity volume.

• Account ownership: A proven track record of owning accounts and driving multi-touch follow-through across long deal cycles.

• AI fluency: You build modern AI tools into your prospecting and daily workflow to work smarter and scale outreach.

• Domain curiosity: Genuine curiosity about legal work, in-house legal teams, and how GCs and legal ops leaders buy.

• Communication: Exceptional written, phone, presentation, and interpersonal skills.

• Grit: Strong time management, comfort in a fast-changing startup, and a competitive streak that shows up as follow-through, not just talk.

• Education: Bachelor's degree or equivalent experience.

Bonus Points

• A background in law, legal ops, or legal tech. A major advantage.

• Experience selling to General Counsels, legal ops, or other in-house legal stakeholders.

• Hands-on with SDR tools like Salesforce, Nooks, ZoomInfo, LinkedIn Sales Navigator, Clay, and 6sense.

Why Chamelio

• Be the first. You'll be one of Chamelio's founding SDRs, with the opportunity to shape how we go to market, set the outbound standards, and build the sales development playbook.

• Build a category, not just a product. We're challenging how an entire industry thinks about legal technology.

• Real ownership, real impact. Your ideas won't get buried in layers of management. You'll have the freedom to build, experiment, and execute.

• A company on the rise. We're a fast-growing, VC-backed AI startup with ambitious plans and a product that's changing how legal teams work.

• Great people, zero corporate nonsense. We're ambitious, a little crazy, and serious about building something exceptional. We work hard, have fun, and enjoy the ride.

Equal Opportunity

Chamelio is an equal opportunity employer, committed to building a diverse and talented team. We do not discriminate on the basis of race, sex, religion, color, national origin, gender, gender identity, sexual orientation, age, marital status, veteran status, medical condition, disability, or any other characteristic protected by applicable law. We welcome candidates from all backgrounds.

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