Principal Mid-Market Account Executive

Team: Mid-Market

Location: Remote, USA

Commitment: Full-time

Workplace Type: remote

Salary:

About the Opportunity – Principal Mid-Market Account Executive:

This is a strategic individual contributor role designed for top-performing Mid-Market sellers who operate with enterprise-level rigor inside the Mid-Market segment.

As a Principal Mid-Market Account Executive, you are expected to be a business partner to your customers, a strategist within your territory, and a standard-setter within the sales organization. You bring a repeatable, insight-driven approach to winning complex deals, and you elevate those around you through your execution and thinking.

You will own a high-value Mid-Market territory and be responsible for driving durable revenue through account strategy, multi-threading, and disciplined deal execution, while also influencing broader sales excellence.

About the Team:

You’ll be a part of a high-performing Mid-Market sales team focused on driving new business growth through disciplined outbound execution and consultative selling. This is a metrics-driven, high-activity environment where accountability, coaching, and continuous improvement are core to success. The team is deeply collaborative and plays a critical role in scaling pipeline, revenue, and repeatable sales performance across the organization. 

What You’ll Do:

End-to-end ownership of a strategic Mid-Market territory with clear coverage, segmentation, and whitespace strategy.
Delivery of predictable, high-quality revenue across new business and expansion.
Forecast accuracy at a high confidence level (commit discipline, low variance).
Elevation of team standards through informal leadership, deal collaboration, and best practice sharing.
Build and execute a multi-quarter territory strategy grounded in data, ICP alignment, and account prioritization Drive pipeline through account-based motions, executive outreach, and strategic prospecting (focused on quality and conversion, not volume alone).
Lead deep, hypothesis-driven discovery that connects business objectives to measurable outcomes.
Orchestrate multi-threaded deal cycles, building alignment across HR, TA, Finance, IT, Procurement, and executive sponsors.
Develop and execute comprehensive deal strategies (stakeholder mapping, competitive positioning, risk mitigation, mutual close plans).
Deliver executive-level narratives and business cases that quantify ROI and drive urgency.
Navigate complex procurement, legal, and security processes with control and momentum.
Identify and create expansion pathways early, positioning for land-and-expand success.
Maintain exceptional pipeline hygiene, inspection readiness, and CRM discipline
Partner cross-functionally to increase win rates and deal velocity.
Act as a thought partner and mentor to peers on deals, discovery, and strategy.
What Differentiates a Principal Account Executive:
You operate with strategic intent across your territory, not just deal-to-deal execution.
You bring consistency and predictability quarter over quarter.
You excel at executive selling and value articulation tied to business outcomes.
You proactively identify, surface, and mitigate deal risk early.
You demonstrate strong internal influence without formal authority.
You improve team performance by raising the bar on deal quality and thinking.

What You Bring:

7–10+ years of quota-carrying SaaS sales experience.
Sustained track record of top-tier performance (e.g., President’s Club, top 10–20%) in Mid-Market or Commercial segments.
Demonstrated success closing complex, multi-stakeholder deals with meaningful ACVs.
Advanced capability in territory strategy, account planning, and pipeline construction.
High level of forecast accuracy and inspection rigor.
Expertise in value-based, consultative sales methodologies (SPICED, MEDDICC, Command of the Message, or similar).
Strong executive presence with the ability to influence VP and C-level stakeholders.
Proven ability to self-inspect deals and continuously refine approach.
High ownership, strong business acumen, and disciplined execution.
Preferred Experience:
Experience selling SaaS in HR Tech, Talent Acquisition, or adjacent markets.
Experience managing platform or multi-product sales motions.
Exposure to land-and-expand strategies within Mid-Market accounts.