Regional Director, Field Engineering, Healthcare

CursorYesterday

Location

San Francisco

Type

Full Time

Salary

USD 200,000 – 280,000

Level

Manager

Role

Manager

Posted

Jul 8, 2026

Full TimeManager

The role

Summary

Regional Director, Field Engineering at Cursor leads a high-impact pre-sales Field Engineering team focused on the healthcare vertical, managing technical discovery, demonstrations, and proof-of-concept evaluations for enterprise healthcare accounts. This hands-on leadership role combines technical fluency with people management, requiring deep expertise in healthcare-specific compliance requirements (HIPAA, data governance) and the ability to position Cursor as the leading AI-native development platform for regulated environments.

What you'll do

Lead and Develop Field Engineering Teams: Build, manage, and scale a high-performing team of Field Engineers supporting enterprise healthcare opportunities. Establish clear performance expectations, career development paths, and coaching frameworks that enable team members to excel in complex technical evaluations and pre-sales engagements.

Drive Technical Pre-Sales Motion: Partner closely with Sales leadership and Account Executives to design and execute high-quality technical discovery sessions, product demonstrations, and proof-of-concept projects tailored specifically to healthcare buyer requirements and organizational constraints.

Establish Healthcare-Specific Best Practices: Develop standardized methodologies and frameworks for enterprise evaluations that account for healthcare-specific regulatory requirements including HIPAA compliance, data governance protocols, legacy systems integration challenges, and healthcare IT procurement dynamics.

Serve as Technical Escalation Point: Manage complex customer evaluations and high-stakes enterprise deals requiring senior technical guidance and executive presence. Provide strategic counsel on healthcare-specific implementation challenges and competitive positioning within regulated environments.

Recruit and Onboard Field Engineering Talent: Source, hire, and successfully onboard Field Engineers with healthcare domain expertise or regulated-industry experience. Design comprehensive onboarding programs that transfer product knowledge, healthcare compliance frameworks, and customer engagement best practices.

Serve as Voice of the Field: Synthesize customer and prospect feedback from field interactions to inform Product Management and Engineering roadmap priorities. Communicate customer pain points, competitive insights, and market trends to internal stakeholders to drive product strategy alignment.

Ensure Successful Customer Transitions: Facilitate tight handoffs between pre-sales and post-sales teams to ensure seamless customer onboarding, adoption enablement, and long-term success. Maintain customer relationships through critical early implementation phases to maximize expansion opportunities.

Maintain Product and Market Expertise: Stay deeply versed in Cursor's product capabilities, AI-native development platform differentiators, technical roadmap, competitive positioning, and healthcare industry trends. Continuously update knowledge to effectively advise customers and guide team selling strategies.

What we look for

Technical

AI-Native Development Platform ExpertiseDeep understanding of AI-assisted coding tools, machine learning-powered development environments, and how AI technologies integrate into modern software development workflows. Ability to articulate AI capabilities to non-technical healthcare stakeholders and developers alike.

Healthcare Compliance and Regulatory KnowledgeDemonstrated expertise navigating HIPAA regulations, data governance frameworks, healthcare IT security standards, and compliance requirements specific to health systems, payers, and healthcare software vendors. Experience evaluating vendor compliance postures.

Enterprise SaaS Architecture and IntegrationSolid understanding of enterprise software architecture patterns, API integrations, cloud deployment models, and healthcare legacy system integration challenges. Ability to assess technical fit and implementation complexity for healthcare enterprise environments.

Pre-Sales Methodology and Deal StrategyProficiency in discovery methodologies, proof-of-concept design and execution, value-based selling frameworks, and deal strategy development. Experience translating buyer technical requirements into tailored evaluation approaches.

Solution Architecture and Technical DiscoveryAbility to conduct thorough technical discovery sessions, architect proof-of-concept solutions, evaluate system fit, and present technical findings to stakeholders. Experience designing evaluation frameworks that de-risk enterprise buying decisions.

Education

Bachelor's Degree in Computer Science, Engineering, or Related FieldFormal education in computer science, software engineering, information systems, or related technical discipline. Provides foundational technical knowledge and credibility in technical pre-sales conversations.

Healthcare or Life Sciences Background (Preferred)Academic or professional certification in healthcare administration, health informatics, regulated industry compliance, or related healthcare-specific discipline strengthens candidacy for the role.

Experience

4+ Years Pre-Sales LeadershipMinimum four years of direct experience leading Field Engineers, Solutions Architects, Sales Engineers, or similar pre-sales teams in enterprise software environments with demonstrated track record of building high-performing organizations.

Healthcare or Regulated Industry ExposureSignificant professional experience in healthcare, health tech, pharmaceutical, financial services, or other highly regulated industries. Direct engagement with healthcare system procurement, compliance evaluations, and buyer decision-making processes.

Enterprise Sales CollaborationProven ability to partner effectively with Sales teams, Account Executives, and sales leadership while maintaining technical credibility, integrity, and customer trust. Experience balancing sales velocity with technical diligence.

Customer-Facing Deal ManagementDemonstrated comfort operating in high-pressure enterprise deal environments with complex stakeholder dynamics. Experience guiding teams and customers through multi-month evaluations involving multiple decision-makers and technical requirements.

Healthcare Buyer ExpertiseDirect experience navigating healthcare buyer environments including health systems, payers, and healthcare software companies. Understanding of healthcare procurement processes, compliance requirements, security evaluations, and organizational decision-making structures.

Skills

Required skills

Technical Leadership and MentorshipAbility to lead, coach, mentor, and develop technical professionals. Demonstrated success building high-performing teams, providing career development guidance, and fostering a culture of excellence and continuous improvement.

HIPAA Compliance and Healthcare SecurityDeep expertise in HIPAA regulations, healthcare data governance, PHI protection protocols, and security standards. Ability to guide teams and customers through compliance evaluation processes and communicate security postures effectively.

Enterprise Sales Process and MethodologyMastery of enterprise sales methodologies, discovery frameworks, qualification criteria, and deal strategy development. Experience navigating complex multi-stakeholder buying environments and translating technical requirements into sales strategies.

Solutions Architecture and Technical DesignAbility to design comprehensive proof-of-concept solutions, conduct technical evaluations, assess system fit, and create implementation roadmaps. Experience translating business requirements into technical specifications.

Executive Communication and PresenceStrong verbal and written communication skills with ability to engage effectively with developers, systems architects, CTOs, and healthcare IT leadership. Professional executive presence in high-stakes negotiations and customer meetings.

Startup Operations and Rapid Organization BuildingComfort operating in fast-moving startup environments with ambiguity and changing priorities. Ability to create organizational structure, establish processes, and build scalable team infrastructure from the ground up.

Customer Discovery and Value AlignmentSkill in conducting deep customer discovery, identifying customer pain points, understanding business drivers, and positioning solutions for maximum value. Ability to uncover hidden requirements and guide customers to optimal buying decisions.

Cross-Functional Collaboration and InfluenceDemonstrated ability to partner effectively across Sales, Product Management, Engineering, and Customer Success functions. Skill in influencing without direct authority and building consensus across diverse organizational perspectives.

Nice to have

AI and Machine Learning Platform ExperienceFamiliarity with AI-assisted development tools, large language models, machine learning operations, or AI-powered productivity platforms. Understanding of emerging AI trends in software development and their business applications.

Healthcare Software Vendor ExperienceBackground working at healthcare software companies, health tech startups, or healthcare IT vendors. Direct experience with healthcare customer acquisition, vendor selection processes, and healthcare-specific market dynamics.

Advanced Degree in Technical FieldMaster's degree in Computer Science, Software Engineering, Healthcare Informatics, or related technical discipline. Additional certification in healthcare compliance, information security, or regulatory affairs strengthens candidacy.

Healthcare System IT Leadership RelationshipsEstablished relationships with healthcare IT leadership, CIOs, and technology decision-makers within health systems, payers, or healthcare software organizations. Network that supports territory expansion and customer introductions.

Product Management or Engineering BackgroundPrior experience in product management, engineering management, or technical architecture roles. Direct software development or systems design background enhances credibility with technical buyers and team members.

Market Research and Competitive AnalysisExperience conducting competitive analysis, market research, and competitive positioning exercises. Ability to identify market opportunities and position products against competitive alternatives effectively.

Compensation & benefits

Salary

USD 200,000 – 280,000 (annual)

Stock options

Available

Benefits

Equity Compensation

Participate in Cursor's equity upside as an early-stage AI developer tools company. Opportunity to build significant long-term wealth through stock options aligned with company growth and market success.

Competitive Health Insurance

Comprehensive health insurance coverage including medical, dental, and vision benefits. Access to preventative care and wellness programs supporting physical and mental health.

Flexible Work Arrangements

Flexible work location and schedule supporting work-life balance. Ability to work remotely or in-office based on role requirements and personal preferences, with consideration for customer-facing responsibilities.

Professional Development

Investment in continuous learning through conference attendance, training programs, and professional certifications. Annual professional development budget supporting skill development and industry expertise advancement.

Unlimited Paid Time Off

Generous unlimited paid time off policy enabling flexible vacation and personal leave. Commitment to supporting work-life balance and preventing burnout in fast-paced startup environment.

401(k) Retirement Plan

Access to tax-advantaged 401(k) retirement savings plan with company matching contributions. Support for long-term financial security and retirement planning.

Parental Leave

Comprehensive parental leave program supporting both maternal and paternal leave. Commitment to supporting employees during major life events and family growth.

Wellness and Mental Health Benefits

Mental health support including therapy access, meditation programs, and employee assistance programs. Commitment to supporting holistic employee wellbeing in high-pressure sales environments.

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