Sales Development Representative (SDR)

Askable • Chicago, IL

36d • Remote

About The Position

Askable is seeking a high-energy Sales Development Representative (SDR) to drive new business and fuel US growth. This role involves building the outbound sales motion from the ground up, acting as the primary contact for Research, UX, and Product leaders at enterprise brands. The mission is to generate quality pipeline through strategic account selection, thorough research, effective messaging, and seamless handoffs to Account Executives. The SDR will engage in cold outbound prospecting via phone, email, and LinkedIn, as well as manage warm leads from webinars, content, events, and the Insight Exchange. This is a remote position with no travel required, and multiple SDRs will be hired to build this function collaboratively.

Requirements

• SDR/BDR experience is preferred, but comparable outbound experience (inside sales, recruiting, fundraising, or similar) is also valued.
• Comfortable with cold outbound prospecting, including using the phone, navigating gatekeepers, and tailoring pitches to senior stakeholders.
• Strong communication skills, able to capture attention with relevance and conduct crisp qualification calls.
• Ability to research accounts, identify key stakeholders, and engage multiple contacts within an organization.
• Proven track record of meeting booking targets with consistent activity and outcomes.
• Proficiency with sales tools such as HubSpot, LinkedIn Sales Navigator, and sequencing tools (e.g., Lemlist, Outreach) or the ability to learn them quickly.
• Data-driven approach, comfortable analyzing personal performance metrics to identify what's working and why.

Nice To Haves

• Experience selling into enterprise accounts and multi-stakeholder buying committees.
• Experience selling to Product, Design, UX, Insights, or Research teams.
• Familiarity with SaaS workflows and longer enterprise sales cycles.

Responsibilities

• Build and own target lists, including companies, personas, and buying signals for outbound prospecting.
• Execute multi-channel cadences (phone, email, LinkedIn) to initiate conversations.
• Conduct in-depth account research and mapping to understand account needs and identify buying committee members (economic buyers, champions, influencers).
• Work warm and inbound leads from marketing activities to quickly convert interest into qualified meetings.
• Manage pre-event outreach and post-event follow-up for events to convert interest into meetings.
• Qualify leads based on fit and intent, assessing pain points, stakes, urgency, stakeholders, and process.
• Generate high-quality discovery meetings for Account Executives with comprehensive context, notes, and agreed-upon next steps.
• Contribute to playbook building by A/B testing messaging, analyzing conversion rates, and sharing insights from the field (objections, patterns, ICP insights, competitive intel).
• Maintain CRM hygiene in HubSpot to ensure frictionless handoffs and accurate reporting, using data to improve meeting quality.

Benefits

• Competitive base salary
• Commission with uncapped upside
• Generous PTO
• Askable Days (one day off per month)
• Great Health Insurance
• 401k Matching
• Potential for future international opportunities (travel/training in London and Australia offices)

What This Job Offers

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