Head of Mid Market Sales, North America
About The Position
Harvey is hiring a Head of Mid Market Sales to lead frontline sales managers and own the North American Mid Market regional sales number. The role will turn early traction into a repeatable, high-performing go-to-market engine for legal and professional services. The leader will set strategy and structure while remaining close to the field on critical deals, helping define Harvey’s sales motion and customer value proposition as organizations adopt AI in high-stakes environments. Harvey’s Mid Market segment uses an “enter-lite” motion focused on law firms with 15–150 attorneys. Sales representatives manage the full cycle, from prospecting and converting net-new accounts to driving expansion. The successful candidate will lead managers and account executives based across western North America and scale the regional motion. The role also partners with global Mid Market leadership and cross-functional teams, and represents the North American segment in company planning and strategic initiatives.
Requirements
- 10+ years of B2B technology sales experience.
- At least 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 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 holding managers accountable to them.
- Exceptional communication and executive presence, with the ability to influence frontline teams and senior internal stakeholders and customers.
- Genuine passion for Harvey’s mission and strong interest in AI’s impact on knowledge work and the legal profession.
Responsibilities
- Hire, lead, coach, and develop Mid Market Sales Managers across North America, holding teams accountable for net-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 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 North American 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 align playbooks, methodologies, and compensation and accelerator structures while adapting them to North American buyer behavior and legal market dynamics.
- Develop executive relationships with high-value Mid Market customers across the region.
- Work cross-functionally with marketing, solutions engineering, legal, and customer success to deliver 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
