Chicago-based Enterprise SDR for AI Ad Tech (Remote-First)

Pencil; Chicago, Northern (IL, KY); Hybrid; USD 60,000 - 90,000; Full time

Benefits offered by this job

25 days PTO

Remote-first

Health insurance

Wellness stipend

Parental leave

Flexible hours

Job summary

Pencil, an AI advertising platform, is looking for a Sales Development Representative to drive enterprise and mid-market growth. You will identify and qualify new leads, build pipeline, and schedule meetings and demos for our enterprise and mid-market sales teams.

You’ll generate net-new opportunities starting at $25K ACV and help scale a fast-moving, remote-first organization. Based in the Chicago area, you’ll collaborate with sales/marketing to shape outreach, using LinkedIn Navigator, Apollo,

Qualifications

• Must have 1 year of outbound sales development experience into enterprise accounts.
• Experience in SaaS, tech sales, martech or creative production is preferred.
• Strong communicator who can explain complex ideas clearly in writing and on the phone.
• Consistent, disciplined outbound across calls, email and LinkedIn.
• Comfortable in a fast-moving environment where the playbook is still evolving.
• Proficient with CRM software (e.g., Salesforce) and modern prospecting tools.

Responsibilities

• Lead Generation: Identify and connect with potential clients based on our Ideal Customer Profile. Global coverage with focus on UK and US.
• Lead Nurturing: Keep leads warm with personalized outreach sequences.
• Sales Collaboration: Work with sales to ensure leads are fully qualified and set up for success.
• Tools: Use LinkedIn Sales Navigator, Apollo and Lusha for prospecting; Salesforce to track leads.
• Targets: Hit monthly targets for qualified leads with commissions on qualified leads and closed-won deals.

Skills

Outbound sales

SaaS/tech sales

Communication

Lead generation

Prospecting

Tools

Salesforce

LinkedIn Navigator

Apollo

Lusha

Job description

Pencil, an AI advertising platform, is looking for a Sales Development Representative to drive enterprise and mid-market growth. You will identify and qualify new leads, build pipeline, and schedule meetings and demos for our enterprise and mid-market sales teams.

You’ll generate net-new opportunities starting at $25K ACV and help scale a fast-moving, remote-first organization. Based in the Chicago area, you’ll collaborate with sales/marketing to shape outreach, using LinkedIn Navigator, Apollo,