Principal Mid-Market Account Executive

Accountabilities:

• • Own and execute a strategic Mid-Market territory plan, including segmentation, account prioritization, whitespace analysis, and multi-quarter growth strategies.
  • Build a high-quality pipeline through account-based prospecting, executive outreach, strategic engagement, and disciplined opportunity development.
  • Drive predictable revenue across new business and expansion opportunities while maintaining strong pipeline coverage and exceptional CRM hygiene.
  • Lead hypothesis-driven discovery that connects customer challenges and business objectives to measurable outcomes.
  • Orchestrate complex, multi-threaded sales cycles involving stakeholders across HR, Talent Acquisition, Finance, IT, Procurement, security, and executive leadership.
  • Develop comprehensive deal strategies covering stakeholder mapping, competitive positioning, risk mitigation, mutual action plans, and close planning.
  • Deliver executive-level presentations and compelling business cases that demonstrate ROI, establish urgency, and support informed purchasing decisions.
  • Navigate complex procurement, legal, and security processes while maintaining deal momentum and control.
  • Maintain highly accurate forecasts, demonstrate strong commit discipline, and proactively identify and address risks that could affect revenue outcomes.
  • Identify expansion opportunities early and establish land-and-expand strategies that support long-term account growth.
  • Partner with cross-functional teams to improve win rates, deal velocity, customer outcomes, and overall sales effectiveness.
  • Serve as an informal sales leader by collaborating on strategic deals, mentoring peers, sharing best practices, and raising standards for discovery, account strategy, and execution.

  Requirements:

  • 7–10+ years of quota-carrying SaaS sales experience, preferably within Mid-Market or Commercial segments.
  • Demonstrated sustained top-tier sales performance, such as President’s Club recognition or consistent placement among the top 10–20% of sellers.
  • Proven success closing complex, multi-stakeholder SaaS deals with meaningful annual contract values.
  • Advanced expertise in territory planning, account strategy, pipeline generation, and opportunity management.
  • Strong forecasting and inspection discipline, with a demonstrated ability to deliver predictable results quarter after quarter.
  • Deep experience with value-based and consultative sales methodologies such as MEDDICC, SPICED, Command of the Message, or similar frameworks.
  • Strong executive presence and the ability to build credibility and influence with VP- and C-level stakeholders.
  • Excellent business acumen, strategic thinking, negotiation, communication, and relationship-building skills.
  • Ability to independently assess opportunities, identify risks, and continuously refine sales strategies and execution.
  • High ownership, accountability, resilience, and comfort operating in a fast-paced, metrics-driven environment.
  • Experience with SaaS solutions in HR technology, Talent Acquisition, or adjacent markets is preferred.
  • Experience selling platforms or multi-product solutions and executing land-and-expand strategies within Mid-Market accounts is an advantage.

  Benefits:

  • Base salary: $132,000–$165,000 per year (USD), with final compensation determined by skills, experience, qualifications, and location.
  • Additional compensation: Eligibility for performance-based bonuses, equity, or other variable compensation may apply.
  • Remote-first work environment: Flexibility to work remotely while remaining connected through virtual collaboration and regular in-person meetups.
  • Unlimited PTO: Trust-based paid time off designed to support rest, flexibility, and sustainable performance.
  • Healthcare coverage: Comprehensive medical, dental, and vision benefits for employees and their families.
  • Career development: Access to learning, training, mentorship, and professional development opportunities.
  • People-first culture: A collaborative and inclusive environment centered on accountability, customer focus, continuous improvement, and mutual support.
  • Equal opportunity workplace: Commitment to diversity, inclusion, accessibility, and providing reasonable accommodations throughout the hiring process.