Head of Mid Market Sales, North America

Role Overview

This is a second line leadership role where you will lead frontline managers, build a world class team, and own the regional Mid Market number for North America. You will be responsible for turning strong early traction into a repeatable, high performing got to market engine across legal and professional services.

We are still early. That means you will operate across altitudes, setting strategy, building structure, and staying close to the field on critical deals. You will help define how Harvey shows up in the North American market, shape our sales motion, and ensure we are delivering real value to customers adopting AI in high stakes competitive environments.

We are looking for someone who has led multi team segments, hired and developed high potential sales managers, scaled teams in ambiguity, implemented a rigorous sales playbook, and knows what great looks like in complex SaaS sales.

What You'll Do

• Hire, lead, coach and develop a team of Mid Market Sales Managers across North America driving accountability for net new logo and expansion ARR targets.
• Own and evolve the NAMER Mid-Market playbook end to end- ICP and segmentation criteria, qualification methodology (e.g., MEDDIC/MEDDPICC), deal stage definitions, discounting and deal desk guardrails, and forecasting cadence, so the motion is repeatable across every manager and AE in the region.
• Implement and maintain a rigorous sales operating cadence, including seller onboarding, enablement, coaching, pipeline generation, and deal execution.
• Drive the regional sales strategy, including territory design, coverage models, and go-to-market execution across the U.S. and Canada.
• Own NAMER mid market forecasting and pipeline health, providing accurate reporting to senior leadership.
• Hire, coach, and retain top managerial talent; build a strong leadership bench across the region.
• Partner with global mid market leadership (EMEA and APAC) to keep the playbook, methodology, and comp/accelerator structure consistent globally while localizing it for NAMER buyer behavior and legal market dynamics.
• Develop executive relationships with Harvey's highest value Mid Market customers across the region.
• Work cross functionally with marketing, solutions engineering, legal, and customer success to ensure a cohesive customer experience across the region.
• Represent NAMER mid market in global planning cycles, headcount discussions, and strategic initiatives.

What You Have

• 10+ years of B2B tech sales experience, including 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.
• Strong track record of selling complex software to enterprise or mid market clients using a consultative, value based methodology.
• Experience building or scaling a sales playbook: segmentation, qualification frameworks (MEDDIC/MEDDPICC or equivalent), territory design, and deal-desk processes, in a fast growing SaaS environment.
• Fluency with pipeline and forecasting rigor: accurate stage by stage forecasting, pipeline coverage ratios, and the discipline to hold managers accountable to them.
• Exceptional communication and executive presence, able to influence both frontline teams and senior stakeholders internally and within our key customers
• Genuine passion for Harvey's mission and a strong interest in how AI is transforming knowledge work and the legal profession.

Compensation $425,000 Usd Ote 50/50

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