Sales Development Representative (USA)

Askable • Chicago, IL

13d • $55,000 - $65,000

About The Position

We’re seeking a high-energy, outbound-focused Sales Development Representative (SDR) to hunt for new business and fuel our US growth.
You’ll be the first point of contact for Research, UX, and Product leaders at enterprise brands. Your mission is to build a high-quality sales pipeline through cold calling, email, and social selling. While your main goal is booking discovery meetings for our Account Executives, you’ll also leverage our in-person and virtual events, like Insights Exchange Dinners and webinars, as powerful ways to open doors and engage top-tier prospects.

Requirements

• Outbound experience: Experience as an SDR/BDR is preferred, but we also value comparable outbound experience (inside sales, recruiting, fundraising, or similar).
• Cold outbound confidence: You are comfortable picking up the phone, navigating gatekeepers, and tailoring your pitch to senior stakeholders.
• Track record: You have hit targets for meetings booked and can demonstrate consistent activity and outcomes.
• Sales tools: Comfortable with HubSpot, LinkedIn Sales Navigator, and sequencing tools like Lemlist or Outreach (or you can learn fast).
• Data-driven: You like digging into your own numbers to understand what’s working and why.

Nice To Haves

• Experience selling into enterprise accounts
• Experience selling to Product, Design, UX, Insights, or Research teams
• Familiarity with SaaS workflows and multi-stakeholder deals

Responsibilities

• Outbound Prospecting: Execute multi-channel cadences (phone, email, LinkedIn) to identify and qualify new business opportunities.
• Pipeline Generation: Own the top of the funnel by booking high-quality discovery meetings and demos for the Sales team.
• Strategic Outreach: Use Askable’s events (dinners, meetups, webinars) as strategic "ins" to engage hard-to-reach stakeholders and drive RSVPs that lead to sales conversations.
• Playbook Optimization: A/B test messaging, monitor conversion rates, and iterate on sequences to stay ahead of the curve.
• CRM Management: Maintain pristine data in HubSpot and our sales stack to ensure seamless hand-offs to Account Executives.

Benefits

• Competitive base salary + commission:
• Base: $55,000 to $65,000 (depending on experience)
• OTE: $85,000 to $95,000, with uncapped upside for high-quality results.
• Generous PTO + Askable Days: One Friday off each month, just for you.
• Great Health Insurance & 401k Matching
• International opportunities: Potential travel / training at to London and Australia offices

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed