Enterprise Sales Development Representative (SDR)

Some of the world's biggest brands already run their advertising on our AI platform. We’re moving fast and need help building the pipeline that gets us there. This position requires you to be based in the Chicago, Illinois area to support effective prospecting, client engagement, and relationship building within the market. At Pencil we’ve built the operating system for AI‑made advertising—a platform that aggregates every major AI model so creative and marketing teams can go from brief to finished asset without stitching tools together. Our mission is to make AI the default in advertising without replacing creative people, and we’re leading that shift today, running production at scale for brands such as L’Oréal, Unilever, Bayer, Diageo, and more, with the legal, security, and procurement rigor enterprise clients require. Backed by The Brandtech Group, a $4 B marketing technology company, we have the scale and reach to work with the world’s largest advertisers.

Responsibilities

• Lead Generation: Identify and connect with potential clients based on our Ideal Customer Profile, covering global markets with a focus on the UK and US.
• Lead Nurturing: Keep leads warm and engaged with personalized outreach sequences for prospects not yet ready to buy.
• Sales Collaboration: Work hand‑in‑hand with the sales team to fully qualify every lead against the BANT framework and help shape the best engagement strategy for each account.
• Tools: Use LinkedIn Sales Navigator, Apollo, Lusha, and Salesforce for prospecting, contact data, and lead tracking.
• Targets: Hit monthly targets for qualified leads and earn commission on qualified leads, with additional commission on any that convert to closed‑won deals.

Requirements

• At least 1 year of outbound sales development experience into enterprise accounts, with experience navigating large organizations and multi‑threading across stakeholders to secure first meetings with senior buyers.
• Experience in SaaS, tech sales, martech, creative production, or a genuine curiosity about how the world’s biggest brands create and buy their advertising.
• Strong communication skills—able to explain complex ideas simply and confidently, both in writing and on the phone.
• Consistent, disciplined outbound activity across calls, email, and LinkedIn; treats the pipeline as a numbers game and a craft.
• Comfortable in a fast‑moving environment where the playbook is still being written, and eager to help improve it.
• Proficiency with CRM software (e.g., Salesforce) and modern prospecting tooling.

Benefits

• 25 days PTO plus public holidays.
• Remote‑first work model with access to offices in The Shard (London), New York, or the ability to work anywhere in your home country.
• Health insurance / private medical cover.
• Monthly stipend toward wellness, fitness, and learning & development.
• Enhanced parental leave policies for birth, adoption, or surrogacy.
• Flexible working hours.