Head of Mid Market Sales, North America
About The Position
Harvey is hiring a Head of Mid Market Sales to lead frontline managers and own the North American Mid Market sales number. The role is responsible for converting early traction into a repeatable, high-performing go-to-market engine serving legal and professional services customers. The position combines strategic planning and team building with close involvement in the field on critical deals. The Mid Market segment uses an “enter-lite” sales motion focused on law firms with 15–150 attorneys, including prestigious specialty and boutique firms. Representatives manage the full sales cycle, from prospecting and winning new accounts to driving expansion. The successful candidate will lead existing Mid Market Sales Managers and their account executives across western North America and determine how the regional sales motion operates and scales. The Head of Mid Market Sales will set regional strategy, develop managers, establish operating rigor, and evolve the sales playbook. The role also partners with global Mid Market leadership and cross-functional teams to support a cohesive customer experience and align regional execution with global plans.
Requirements
- At least 10 years of B2B technology sales experience.
- At least 4 years of experience 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 selling complex software to enterprise or Mid Market clients using a consultative, value-based methodology.
- Experience building or scaling a sales playbook in a fast-growing SaaS environment, including segmentation, qualification frameworks, territory design, and deal-desk processes.
- Fluency in pipeline and forecasting rigor, including accurate stage-by-stage forecasting, pipeline coverage ratios, and accountability for managers.
- Exceptional communication and executive presence, with the ability to influence frontline teams and senior internal stakeholders and key customers.
- Genuine passion for Harvey’s mission and strong interest in how AI is transforming knowledge work and the legal profession.
Responsibilities
- Hire, lead, coach, and develop Mid Market Sales Managers across North America, holding the team accountable for new-logo and expansion ARR targets.
- Own and evolve the North American Mid Market playbook, including ideal customer profile and segmentation, qualification methodology, deal-stage definitions, discounting and deal-desk guardrails, and forecasting cadence.
- Implement and maintain a rigorous sales operating cadence covering seller onboarding, enablement, coaching, pipeline generation, and deal execution.
- Drive regional sales strategy, including territory design, coverage models, and go-to-market execution across the United States and Canada.
- Own regional Mid Market forecasting and pipeline health and provide accurate reporting to senior leadership.
- Hire, coach, and retain managerial talent and build a strong regional leadership bench.
- Partner with global Mid Market leadership in EMEA and APAC to maintain consistency in the playbook, methodology, and compensation and accelerator structure while localizing for North American 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 regional customer experience.
- Represent North American Mid Market in global planning cycles, headcount discussions, and strategic initiatives.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
