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Harvey

Head of Mid Market Sales

Harvey

. Lead frontline Mid Market Sales Managers across North America .

Posted 10/15/2026full-timeChicago • Illinois • United StatesLead💰 $425,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in leading and developing high-performing sales teams in the B2B tech sector, with a strong focus on building and executing sales strategies, playbooks, and forecasting methodologies. Proven ability to drive revenue growth and establish executive relationships within the mid-market segment.

Highest-signal resume keywords
B2B Tech Sales ExperienceSales Playbook DevelopmentPipeline ForecastingTeam LeadershipConsultative Selling

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Sales StrategyTerritory DesignQualification MethodologyDeal-Desk ProcessesSales ForecastingSegmentation FrameworksSaaS SalesValue-Based SellingCoaching and DevelopmentHigh-Growth Environment Experience
Soft Skills
Exceptional CommunicationExecutive PresenceCollaboration
Industry Keywords
Mid Market SalesLegal ServicesProfessional ServicesGo-To-Market ExecutionPipeline GenerationCustomer SuccessHigh-Value CustomersNorth America Market PresenceAI in Legal ProfessionConsultative Sales

About the role

Key responsibilities & impact
  • Lead frontline Mid Market Sales Managers across North America
  • Build a world-class team and own the regional Mid Market number for North America
  • Turn early traction into a repeatable, high-performing go-to-market engine across legal and professional services
  • Set strategy, build structure, and stay close to the field on critical deals
  • Define Harvey’s North American market presence and shape the sales motion
  • Hire, coach, develop, and retain sales managers while building a leadership bench
  • Own and evolve the NAMER Mid-Market playbook, including ICP and segmentation, qualification methodology, deal stages, discounting and deal-desk guardrails, and forecasting cadence
  • Implement and maintain sales operating cadence covering onboarding, enablement, coaching, pipeline generation, and deal execution
  • Drive regional sales strategy, territory design, coverage models, and go-to-market execution across the U.S. and Canada
  • Own forecasting and pipeline health and provide accurate reporting to senior leadership
  • Partner with global mid-market leadership in EMEA and APAC on playbook, methodology, and compensation/accelerator consistency
  • Develop executive relationships with high-value Mid Market customers
  • Collaborate with marketing, solutions engineering, legal, and customer success
  • Represent NAMER Mid Market in global planning, headcount discussions, and strategic initiatives

Requirements

What you’ll need
  • 10+ years of B2B tech sales experience
  • 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, including 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, including stage-by-stage forecasting and pipeline coverage ratios
  • Exceptional communication and executive presence
  • Passion for Harvey’s mission and interest in AI’s impact on knowledge work and the legal profession
  • Currently based in Chicago or willing to relocate, and able to work from the office 3 days per week
  • Legally authorized to work in the country where the role is located

Benefits

Comp & perks
  • Equity plan
  • Comprehensive health, dental and vision coverage
  • Retirement benefits with 401k match up to 4%
  • Flexible PTO
  • Up to 4 applications to Harvey in any 30-day period
  • Eligibility to reapply after 90 days if a previous application was unsuccessful