Territory Director

Clinically AI is a rapidly scaling healthcare AI company transforming how behavioral health and healthcare organizations manage clinical documentation, chart auditing, compliance workflows, and operational efficiency through artificial intelligence.

Our platform helps providers reduce administrative burden, improve documentation quality, strengthen audit readiness, and create more time for patient care. We operate at the intersection of healthcare operations, AI workflow transformation, and real-world clinical execution in a market where trust, adoption, workflow integration, and measurable outcomes matter deeply.

We are seeking multiple Territory Directors to lead regional market expansion across the Midwest, Southwest, and Mid-Atlantic regions.

This is not a traditional territory sales role focused solely on quota attainment or transactional software sales. Territory Directors at Clinically AI are responsible for building regional market presence, developing strategic customer relationships, independently conducting sophisticated product demonstrations, and helping healthcare organizations operationalize AI inside complex clinical and compliance-driven environments.

Customers are not simply evaluating software. They are evaluating whether AI can safely and realistically integrate into highly operational healthcare environments where documentation quality, reimbursement integrity, clinician burnout, compliance exposure, audit defensibility, and workflow efficiency directly impact organizational sustainability.

As a result, this role is deeply consultative, operational, and workflow-oriented.

Territory Directors are expected to independently lead live platform demonstrations throughout the sales process. This is not a sales motion where technical demos are fully owned by solutions engineers or implementation teams. Territory Directors must become highly fluent in the Clinically AI platform, behavioral health workflows, AI-assisted documentation, compliance operations, and operational transformation use cases in order to confidently guide sophisticated customer conversations autonomously.

Our demos are highly contextual, operational, and workflow-driven in nature. Territory Directors must be comfortable independently leading end-to-end platform demonstrations that connect AI capabilities directly to real-world clinical, compliance, and operational challenges within behavioral health and healthcare organizations. This includes navigating conversations around AI-assisted clinical documentation, ambient listening workflows, chart auditing and compliance operations, behavioral health documentation standards, EHR workflows and form structures, operational efficiency initiatives, reimbursement and compliance risk reduction, and broader organizational AI adoption concerns.

Successful Territory Directors are expected to operate independently throughout the sales process, including leading operational discovery conversations, conducting customized live demos, and translating complex AI functionality into practical workflow outcomes that resonate across multiple stakeholder groups. You must be comfortable dynamically tailoring demonstrations based on each organization’s workflows, documentation processes, operational pain points, and organizational structure while communicating effectively with executives, compliance leaders, operational stakeholders, IT teams, and frontline clinicians alike.

This role requires the ability to explain complex AI concepts clearly to both technical and non-technical audiences while positioning Clinically AI not simply as a software vendor, but as a long-term operational transformation partner helping organizations improve documentation quality, strengthen compliance readiness, reduce administrative burden, and create more time for patient care.

Each territory operates with a high degree of ownership and autonomy. We view territory development as a long-term market-building initiative rather than a short-term transactional sales motion. In practice, this role functions more like operating and scaling a regional business unit than simply managing a sales territory.

Initially, you will operate as the primary commercial owner of your territory: driving pipeline development, customer acquisition, executive relationships, live product demonstrations, and strategic expansion efforts. Over time, successful Territory Directors may have the opportunity to help shape regional support structures and contribute to territory scaling strategy as market penetration increases.

Our ideal customer profile includes Medicaid-funded behavioral health organizations, community mental health providers, nonprofit healthcare systems, and operationally complex care organizations where documentation quality, compliance, clinician retention, reimbursement integrity, and workflow efficiency are mission-critical.

This is a high-growth environment where priorities evolve quickly and speed of execution matters. You must be comfortable operating with autonomy, learning quickly, creating structure where needed, and maintaining momentum in a rapidly evolving market.

KEY ATTRIBUTES TO SUCCEED

• Ownership Mentality You operate with accountability and initiative, treating your territory like a business rather than simply managing a pipeline.

• Relationship-Driven Commercial Leadership You build long-term trust with executives, operators, clinicians, compliance leaders, and organizational stakeholders in complex healthcare environments.

• Consultative & Operational Selling You understand that customers are evaluating workflow transformation, operational outcomes, compliance risk reduction, clinician adoption, and organizational efficiency: not simply software features.

• Independent Demonstration Leadership You are comfortable independently leading sophisticated platform demonstrations, workflow conversations, and operational discovery sessions with healthcare executives, operational leaders, compliance stakeholders, and clinicians.

• Executive Communication You communicate clearly and confidently with healthcare executives, operational leaders, IT teams, compliance stakeholders, and frontline clinicians while adapting your communication style to different audiences.

• AI-Native Thinking You actively use AI tools in your own workflow and understand how AI can improve operational efficiency, communication, research, and workflow execution.

• Territory & Systems Thinking You think strategically about market development, customer retention, expansion opportunities, referral networks, and long-term territory scalability.

• Resilience in Ambiguity You operate effectively in environments where priorities shift quickly, systems are evolving, and structure is still being built.

• Startup Adaptability You are energized by building, iterating, solving problems, learning quickly, and helping shape organizational systems during a high-growth phase.

REQUIRED

• 5+ years of experience in healthcare technology, SaaS, behavioral health, healthcare services, or enterprise B2B sales environments

• Demonstrated experience owning pipeline generation, customer acquisition, territory growth, or strategic account development responsibilities

• Demonstrated experience independently conducting workflow-oriented software demonstrations, operational discovery sessions, and live customer evaluations without reliance on dedicated solutions engineering support

• Willingness to travel throughout assigned territory for customer meetings, conferences, relationship development, onsite evaluations, and strategic growth initiatives

PREFERRED BUT NOT REQUIRED (Nice to Have)

• Experience selling into behavioral health, community mental health, nonprofit healthcare, Medicaid-funded organizations, or regulated healthcare environments

• Experience selling workflow, compliance, documentation, operational, or healthcare technology solutions

• Startup or early-stage company experience

• Experience opening or scaling new geographic markets or territories

• Existing relationships within behavioral health or healthcare provider networks

This is a full-time territory-based position supporting regional market development across the Midwest, Southwest, or Mid-Atlantic territories. Territory Directors are expected to operate with a high degree of autonomy while remaining closely aligned with company leadership, operational priorities, and go-to-market strategy.

Clinically AI is intentional about building a high-accountability, execution-oriented culture where speed, ownership, collaboration, learning velocity, and customer outcomes matter. While much of the organization operates from our San Diego headquarters, Territory Directors serve as strategic regional representatives helping establish market presence, customer trust, and operational partnership within their assigned territories.

Compensation structure, territory scaling opportunities, and long-term regional support models may continue evolving alongside company growth and market expansion. We are seeking entrepreneurial operators excited by the opportunity to help shape both territory strategy and organizational growth over time.

We offer competitive compensation, performance-based incentives, healthcare coverage, and flexible time off. The base salary range for this role is $150,000–$220,000 annually, depending on experience, market expertise, demonstrated performance, and overall scope alignment. In certain cases, we may consider candidates outside of this range whose background, domain knowledge, or leadership experience strongly aligns with the needs of the role.

The interview process includes an initial screening interview followed by interviews focused on healthcare sales experience, workflow understanding, demonstration capability, operational judgment, relationship-building skills, AI fluency, and startup adaptability. Final candidates may complete a hiring exercise involving territory strategy, workflow discovery, and a live platform demonstration simulation designed to assess communication style, operational thinking, learning agility, and customer engagement approach.

Due to high interest, we will only respond to candidates who meet all the required qualifications.

Clinically AI provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, or genetics.