Head of Mid Market Sales, North America

Chicago · 4+ years experience · Full-time · Hybrid · Posted Oct 15, 2026

At a glance

This is a second-line leadership role responsible for leading frontline managers and owning the regional Mid-Market sales number for North America. The role involves building a world-class team, scaling a repeatable go-to-market engine, and defining the sales motion for legal and professional services.

Hire, lead, coach, and develop a team of Mid-Market Sales Managers across North America.
Drive accountability for net new logo and expansion ARR targets.
Own and evolve the NAMER Mid-Market playbook, including ICP, segmentation, and qualification methodology.
Implement and maintain a rigorous sales operating cadence, including onboarding, enablement, and coaching.
Drive regional sales strategy, including territory design and coverage models.
Own NAMER Mid-Market forecasting and pipeline health.
Hire, coach, and retain top managerial talent to build a leadership bench.
Partner with global leadership to ensure consistent methodology while localizing for NAMER buyer behavior.
Develop executive relationships with high-value Mid-Market customers.
Work cross-functionally with marketing, solutions engineering, legal, and customer success.

10+ years of B2B tech sales experience.
4+ years hiring, managing, and developing sales managers or senior individual contributors.
Demonstrated success leading a regional or multi-market sales organization in a high-growth, early-stage environment.
Track record of selling complex software to enterprise or mid-market clients using consultative, value-based methodology.
Experience building or scaling a sales playbook in a fast-growing SaaS environment.
Fluency with pipeline and forecasting rigor.
Exceptional communication and executive presence.
Genuine passion for Harvey's mission and interest in AI transformation of knowledge work.