Head of Mid Market Sales, North America

Location: Chicago Workplace: Hybrid WHY HARVEY At Harvey, we’re transforming how legal and professional services operate. By combining frontier agentic AI, an enterprise-grade platform, and deep domain expertise, we’re reshaping how critical knowledge work gets done for decades to come. This is a rare chance to help build a generational company at a true inflection point. We have strong product-market fit and world-class investor support. We’re scaling fast and defining a new category in real time. The work is ambitious, the bar is high, and the opportunity for growth — personal, professional, and financial — is unmatched. Our team moves fast, takes ownership, and is deeply committed to the mission — operating with intensity, staying close to our customers, and pushing each other for excellence. We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear judgment over perfect information, we believe simplicity is what scales, and we're never satisfied with where we are. If you want to do the best work of your career alongside people who share that drive, we'd love to build with you. At Harvey, the future of professional services is being written today — and we’re just getting started. 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. About the NAMER Mid-Market Segment Mid Market at Harvey runs an “enter-lite” motion selling to law firms with 15–150 attorneys, including many of the most prestigious speciality and boutique firms in the world. . Reps own the full cycle, prospecting into net-new accounts, converting them, and driving expansion You'll inherit a team of Mid Market Sales Managers and their AEs based across western NAMER and will be the primary owner of how that motion runs and scales across the region. 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 DEPENDING ON YOUR LOCATION, AN APPLICANT PRIVACY NOTICE MAY APPLY TO YOU. YOU CAN FIND ALL OF OUR APPLICANT PRIVACY NOTICES HERE https://harveyai.notion.site/Harvey-Candidate-Privacy-Notices-319ac3fcdd7a803bb807d5094f249922?pvs=74. #LI-BL1 Harvey is an equal opportunity employer and does not discriminate on the basis of race, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or related condition, or any other basis protected by law. We are committed to providing reasonable accommodations to applicants with disabilities, and requests can be made by emailing accommodations@harvey.ai