Senior Account Executive

HeyMilo AI

$100K — $150K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience in enterprise sales, preferably with SaaS products.
  • Proven track record of exceeding sales quotas consistently.
  • Experience handling complex sales cycles including negotiation and closing.
  • Strong ability to communicate technical concepts to non-technical audiences.
  • Comfortable working in high-pressure, fast-paced environments.
  • Previous success selling AI-driven solutions.
  • Strong understanding of customer workflows and hiring processes.

Responsibilities

  • Manage the entire sales process from prospecting to closing deals.
  • Engage with multi-stakeholder buying groups across various departments.
  • Demonstrate the superiority of the product in competitive scenarios.
  • Lead discussions with high-level executives at various company sizes.
  • Identify and analyze customer challenges to present tailored solutions.
  • Collaborate with internal teams to ensure successful implementation and customer satisfaction.
  • Act quickly and effectively to capitalize on market opportunities.

Benefits

  • Work with a cutting-edge, category-leading product.
  • Opportunity to shape sales strategies in a growing market.
  • Collaborative work environment across different functional teams.
  • Engagement with high-profile clients ranging from mid-market to Fortune 100.
  • Performance-driven culture that rewards excellence and results.
Full Job Description
What You Will Do
  • Own the full sales cycle-prospecting, discovery, demos, solutioning, negotiation, and closing.
  • Run complex 5- and 6-figure deals with multi-stakeholder buying groups across HR, TA, Operations, IT, Compliance, and Finance.
  • Sell a category-leading product by demonstrating how HeyMilo outperforms competitors in accuracy, speed, fraud detection, and real-world complexity.
  • Lead strategic conversations with executives across staffing agencies, BPOs, and mid-market to Fortune 100 corporates.
  • Diagnose workflows and hiring pain points to drive urgency and ROI-focused decision-making.
  • Collaborate cross-functionally with Product, Engineering, and Customer Success to ensure smooth handoffs and long-term customer success.
  • Execute with speed, precision, and ownership to help capture market share in a rapidly growing category.


Who You Are
  • A top-performing AE who consistently exceeds quota and holds themselves to elite standards.
  • A true full-cycle seller capable of independently running outbound, discovery, demo, solution design, negotiation, and close.
  • Experienced navigating complex 5- and 6-figure SaaS deals and presenting to senior leaders.
  • A clear, confident communicator who can simplify technical concepts and speak credibly to executives.
  • Highly competitive with a strong internal drive to win and outperform alternatives.
  • Thrives in a high-growth, fast-moving environment where urgency, ownership, and excellence are the baseline.
  • Have sold agentic AI capabilities to organizations previously
  • Curious, product-minded, and comfortable understanding integrations, data flows, and real-world hiring operations.
  • Customer-obsessed and committed to delivering outcomes-not just closing deals.

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