Executive Director

Regard; New York, Northern (NY, KY); Hybrid; USD 150,000 - 340,000; Full time

Benefits offered by this job

Salary & equity

Medical coverage

PTO and holidays

Wellness budget

Team retreats

Office snacks

Relocation support

Remote weeks budget

Remote work weeks

Sabbatical program

Job summary

Regard is seeking an Executive Director to lead strategy and execution of sales into large health systems across the US. You will own the full sales cycle, build tailored business cases, and drive measurable ROI for Regard’s technology in clinical workflows.

You will engage C-suite stakeholders, quantify value, and navigate complex buying groups, with a compensation package including base salary plus uncapped commissions and equity. Remote work is available nationwide.

Qualifications

• 5+ years selling software to major health systems.
• Experience engaging C-suite executives.
• Proven ability to manage full sales cycle.
• Willingness to travel 30% and reside within 50 miles of a major airport.

Responsibilities

• Own full sales cycle from prospecting to contracting.
• Manage a strategic portfolio of enterprise accounts with targets.
• Develop tailored business cases showing ROI and value.
• Collaborate with executive stakeholders across health systems.
• Travel ~30% as needed to meet with clients.

Skills

Executive sales

Healthcare software

C-suite selling

Enterprise sales

Strategic storytelling

Job description

Join us on our mission to bring world-class healthcare to everyone. Join us on our mission to bring world-class healthcare to everyone.

We believe healthcare can be better. As a team, we hold a high bar, act with urgency, and grow together. We believe healthcare can be better. As a team, we hold a high bar, act with urgency, and grow together.

Culture

Our values

We ask hard questions, obsess over the details, practice constructive feedback, and never forget to say thank you. We ask hard questions, obsess over the details, practice constructive feedback, and never forget to say thank you.

Quality

We have high expectations for our product and for each other. We're building a platform that helps doctors diagnose and treat patients — ensuring the highest standard of quality is our top priority.

Action

We lean toward action over deliberation. We take action when we can learn from mistakes, prioritizing thoughtful analysis for more consequential decisions.

Improvement

We always strive to improve both the product and ourselves. We believe in a culture of radical transparency and consistent feedback.

Community

We believe our best work happens through inspiration from each other. We invest in meaningful time together to build relationships both internally and externally.

How we work

We're curious

We show attention to detail

We're resourceful

We give and receive constructive feedback

We proactively express gratitude

Total rewards

Perks and benefits

• Competitive salary
  and equity
• Medical, dental, and vision
  insurance
• 18 PTO days + 10 holidays +
  holiday break
• Monthly health &
  wellness budget
• Team retreats, social events,
  and celebrations
• Free lunches, beverages, and snacks in office
• Relocation support
• Semi-annual travel budget for team co-working weeks
• 6 annual remote work weeks
• Sabbatical program at 5 years

Open roles

Find your place on the team

Executive Director

Location

Employment Type

Location Type

Remote

Department

Compensation

At Regard, we carefully consider a wide range of factors when determining compensation, including your skills, qualifications, location, and experience. We expect the base salary range for this position to be $150,000 to $170,000 + uncapped commission (OTE $300,000 to $340,000). This is subject to change and may be modified in the future.

As an Executive Director at Regard, you will lead the strategy and execution of sales into large health systems across the US. This role requires a consultative mindset, a tactical sales approach, and a passion for workflow efficiency and ROI.

You will analyze your prospects' challenges, goals, and competitive landscape, developing tailored business cases that demonstrate how Regard's technology can address their most pressing needs.

Each sale is treated as a unique project, where you conduct deep discovery, multithread, and build consensus across clinical and financial buying groups, ultimately crafting a personalized story that shows how Regard’s technology will deliver measurable value and drive impactful results. This role requires travel 30% of the time.

About Regard

Regard's mission is to bring world-class healthcare to everyone. Our technology reasons through a patient's entire medical record to recommend diagnoses that would otherwise be missed, in real time at the point of care, during chart review, and in population-wide screening to identify patients who qualify for lifesaving treatment.

We work alongside some of the top health systems in the country to lead the change this industry needs. We're excited by challenges, mission-oriented work, and meaningful relationships. We want you to join us.

Responsibilities:

Full Sales Cycle Ownership: Own the entire sales cycle from prospecting, introductions, product demos, business case development, proposals, to contracting (with legal support)

Target Account Management: Oversee and manage a strategic portfolio of prospective enterprise accounts, driving sales activities to consistently achieve sales targets and cultivate long-term provider relationships

Revenue Generation: Acquire, develop, and grow a base of opportunities/accounts independently

Consultative Selling: Gain a deep understanding of prospect challenges, organizational structure, and long term vision, positioning Regard as a trusted strategic partner for addressing their key issues

Buyer Journey Advancement: Advancing deals by preparing for meetings with intention, engaging purposefully at every stage, and project managing the entire buyer journey

Business Case Mastery: Conducts deep discovery and creates compelling business cases

Consensus Building: Builds consensus across multiple stakeholders, including financial and clinical leadership, to align on solutions and drive deal progression

Sales Enablement: Collaborates with Marketing, Product, and Sales leadership to refine sales processes and collateral as the product evolves and the company scales

Executive Selling: Confidently leads strategic and critical conversations with decision makers who will carefully examine the investment, knowing how to navigate these discussions effectively

Qualifications:

5+ years of experience selling software to major health systems ($800M+ in net patient revenue) with a demonstrated ability to manage the full sales cycle and engage C-suite executives (CFO, CMIO, COO, CIO), as well as VP of Revenue Cycle and Director-level decision makers

Experience selling novel healthcare technology and products that improve clinical efficiency and patient safety

Ability to build tailored business cases and multithread, building consensus across multiple executive stakeholders (including financial and clinical leadership)

Located within 50 miles of a major airport and willing to travel, as needed (30% of time)

Preferred Qualifications:

Robust knowledge and background in revenue cycle and/or with AI-driven clinical co-pilot technologies in healthcare

Strong background in selling software solutions in areas such as documentation, patient safety, CDI, revenue cycle, and/or clinical workflows

Proven success in a high growth startup environment (early stage strongly preferred)

Existing relationships with C-suite executives within health systems

Location | Work Authorization

For this role, Regard is currently only considering candidates who are authorized to work in the US without visa sponsorship, and are within metropolitan areas

For those who enjoy working from our New York City or Los Angeles offices, we offer catered lunches and other fun perks

Generous commission plan

Eligible for equity

99% employer paid health benefits (Medical, Dental, and Vision) + One Medical subscription

18 PTO days/yr + 1 week holiday break

Annual $750 learning & development stipend

Company-sponsored team retreat + social events

A sabbatical program

Our goal at Regard is to provide and maintain a work environment that fosters mutual respect, professionalism and cooperation. Regard is proud to be an equal opportunity employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, national origin, ancestry, alienage or citizenship status, age, disability or handicap, sex, gender identity, marital status, familial status, veteran status, sexual orientation or any other characteristic protected by applicable federal, state or local laws. We celebrate diversity and are proud of our supportive, inclusive workplace.

All candidates must successfully complete a background check as part of the hiring process.