CareerPlan

Head of Mid Market Sales, North America

ChicagoFull-time$425k2026-10-15 → 2026-11-12

Core

Lead frontline managers and own the regional Mid Market number for North America, building a repeatable go-to-market engine for legal and professional services using agentic AI.

Role type

Second line leadership, regional sales head

Builds

A scalable sales motion and high-performing team for mid-market law firms

Domain

Legal tech / Professional services / SaaS

Required skills

B2B tech sales leadership, hiring and developing sales managers, scaling teams in ambiguity, implementing sales playbooks, complex SaaS selling, pipeline and forecasting rigor, executive presence

Preferred skills

Experience in early-stage high-growth environments, fluency with MEDDIC/MEDDPICC, cross-functional partnership

Technologies

agentic AI, enterprise-grade platform

Responsibilities

Hire, lead, and coach Mid Market Sales Managers; Own and evolve the NAMER Mid-Market playbook; Drive regional sales strategy and territory design; Own forecasting and pipeline health; Develop executive relationships with key customers; Partner with global leadership to localize the motion

Seniority

Senior, hands-on IC