Sales Development Representative - Chicago, IL (Ansarada)

DatasiteChicago, IL
$51,600 - $85,300Hybrid

About The Position

This is an outbound sales role where you own top-of-funnel for our Deals product — the platform of choice for M&A, capital raising, insolvency, and private equity. You’ll generate and qualify pipeline across AMER, working hand-in-hand with AEs, Marketing, and Digital Growth. AI is how you’ll do more of the right work, with less noise. The role leverages AI for prospecting, outreach, call preparation, and lead qualification to make informed calls rather than cold calls. The company is Datasite, which includes associated businesses like Blueflame AI, Grata, and Sherpany, all focused on facilitating economic value creation and defining the future for business growth.

Requirements

  • Experience in a sales or client-facing role.
  • Strong interest in building a career in tech sales, specifically in M&A and corporate finance.
  • Commercially sharp, curious about the industry, and hungry to develop fast.
  • AI fluency: use LLMs (ChatGPT, Claude, Gemini) daily.
  • Ability to generate real output using AI for prospecting lists, outreach sequences, call prep, and objection handling.
  • Understanding of where AI provides an edge and where human instincts and energy are crucial.
  • Willingness to share what works and continuously seek improvements.
  • Hunter mindset: enjoy the chase and building relationships from scratch.
  • High-impact communicator with strong verbal and written skills, comfortable engaging senior stakeholders.
  • AI-curious by default, always looking for better, faster ways.
  • Metric-driven and outcome-focused.
  • Fast learner who shares wins and lessons.

Responsibilities

  • Generate and qualify pipeline by prospecting across email, phone, social, and live chat.
  • Run outbound campaigns and convert engaged leads, utilizing AI for research and personalization.
  • Deliver high-quality, well-qualified opportunities to the AE team.
  • Build awareness and relationships within focus accounts, driving education and engagement.
  • Join in-person meetings with key accounts to support relationship-building and revenue growth.
  • Identify expansion signals and share them with the wider pod.
  • Use Salesforce to track activity, manage pipeline data, and keep information clean and current.
  • Work cross-functionally with Marketing, Digital Growth, and AEs to sharpen campaign targeting and follow-up.
  • Share effective strategies, including AI prompts and call openers.

Benefits

  • Maxwell Leadership Program
  • Book budget and time to learn and grow
  • Real AI development: tools, training, and space to build workflows
  • Subsidised health insurance
  • Generous paid leave (parental, birthday, community, anniversary)
  • Flexible hybrid model: 3 days in office & 2 days remote
  • Competitive compensation
  • Employee benefits
  • Health insurance (medical, dental, vision)
  • Retirement savings plan
  • Paid time off
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