Enterprise Sales Development Representative (SDR) - Pencil

Some of the world's biggest brands already run their advertising on our AI platform. We're moving fast—want to help us build the pipeline that gets us there?

Due to the location of our client and target customer base, this position requires you to be based in the Chicago, Illinois area. Being locally based is important to support effective prospecting, client engagement, and relationship building within the market.

About Pencil

At Pencil, we've built the operating system for AI-made advertising—the platform that aggregates every major AI model so creative and marketing teams go from brief to finished asset without stitching tools together themselves. 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 major global brands like L'Oréal, Unilever, Bayer, Diageo, and more with enterprise-grade legal, security, and procurement rigor.

We're backed by The Brandtech Group, a $4B marketing technology company that also owns Oliver and Jellyfish, giving us the scale and reach to work with the world's largest advertisers.

Role Overview

We are looking for a Sales Development Representative (SDR) with a genuine enthusiasm for AI to drive our enterprise and mid-market growth. In this role, you'll identify and qualify new leads, build pipeline, and schedule meetings and demos for our enterprise and mid-market sales teams. You'll play a key role in bringing net-new clients to Pencil, working deals starting at $25K in annual contract value.

Key Responsibilities

• Lead Generation: Identify and connect with potential clients based on our Ideal Customer Profile. This role covers global markets, with a focus on the UK and US.
• Lead Nurturing: Keep leads warm and engaged with personalized outreach sequences for accounts not quite ready to buy, ensuring they convert when timing aligns.
• Sales Collaboration: Work hand-in-hand with our sales team to ensure every lead is fully qualified against our BANT framework. Help shape account strategy and setup for success.
• Sales Tech Stack: Use LinkedIn Sales Navigator, Apollo, and Lusha for prospecting and contact data, and Salesforce to track leads, organize activity, and record key insights.
• Performance Targets: Hit monthly targets for qualified leads. Earn commission on qualified leads with additional commission on closed-won deals.

Requirements

• 1+ year of outbound sales development experience targeting enterprise accounts. Proven ability to navigate complex organizations, multi-thread across stakeholders, and secure meetings with senior buyers.
• Industry Experience: Background in SaaS, tech sales, martech, or creative production, or a strong understanding of how global brands purchase advertising. Ability to speak the language of marketing, procurement, and brand leaders.
• Strong Communication: Clear, persuasive, and confident verbal and written communication skills.
• Outbound Discipline: Consistent multi-channel outreach across calls, email, and LinkedIn, balancing volume with tailored craftsmanship.
• Adaptability: Comfortable in a fast-paced environment where playbooks evolve, and proactive about contributing to process improvements.
• Tech Proficiency: Hands-on experience with CRM software (e.g., Salesforce) and modern sales intelligence tools.

Benefits

• 25 days PTO plus public holidays
• Remote-first working model with access to offices in London (The Shard) and New York
• Private health insurance / medical cover
• Monthly stipend for wellness, fitness, and professional development
• Enhanced parental leave policies (birth, adoption, or surrogacy)
• Flexible working hours