Who We Are

At Clearstep, we believe healthcare should be easy. We build technology that enables patients to find the exact right care while also allowing healthcare systems to tackle the most pressing capacity issues in their organization. As the most prevalently adopted self-service, AI triage platform (both in the federal and commercial spaces), Clearstep is on a mission to improve outcomes for patients and providers alike. Clearstep reaches patients in all 50 states, having directed millions of patients to the best care at the right time.

Why Work With Us

You should consider joining us if you are looking for mission-oriented work, are driven to improve the healthcare experience, are excited to catalyze change in a complex industry, and want to build a solution that can help your friends/family easily navigate healthcare. Clearstep provides abundant opportunities for individual career growth in addition to giving you the chance to directly impact the success of an innovative market leader in the AI healthcare industry.

Core Responsibilities

Financial and Accounting Oversight:

• Manage the finance and accounting team, including the controller, to ensure timely monthly closes and accurate financial reporting.
• Oversee invoicing, collections, and external contractor payments.
• Maintain and update the company’s financial model, assist with forecasting, and help create and manage budgets.

Board and Investor Support:

• Help prepare for board meetings by gathering materials, setting up templates, and coordinating with various team members to compile presentations and reports.
• Assist in scheduling board and leadership meetings.
• Complete investor questionnaires and requests for company updates, including drafting quarterly investor update letters.

Operations Management:

• Assist with contract creation and review, working with company legal counsel.
• Manage company mail, particularly state and federal correspondence, including tax-related communications.

HR, Team, and People Operations:

• Plan and execute quarterly team activities, including coordinating travel, reservations, and event planning.
• Serve as the main point of contact for all HR-related questions and tasks.
• Manage payroll, benefits, and the HR platform.
• Support onboarding and offboarding processes for employees and contractors.

Generalist and Operational Support:

• Be the “right hand” to the CEO in all administrative functions.
• Act as the primary full-time point of contact for all operations, finance, accounting, HR, and miscellaneous administrative tasks.
• Identify and implement process improvements to streamline workflows and support company growth.

Requirements

Education:

• Preferred background in Accounting to ensure proficiency in managing the company’s financial model and related tasks.

Experience:

• 5+ years of relevant experience, ideally in operations, finance, or HR, preferably in a startup or fast-paced environment.

Skills:

• Strong organizational and project management skills.
• Excellent communication and interpersonal skills.
• Excellent excel skills.
• Proficiency with financial modeling, forecasting, and budgeting.
• Ability to handle multiple priorities and thrive in a dynamic, collaborative environment.
• Proactive, detail-oriented, and able to take ownership of core responsibilities.

Personal Attributes:

• Passionate about building and improving operational systems.
• Comfortable translating ambiguous requirements into actionable plans.
• Ability to learn quickly and adapt to evolving business needs.

Nice-to-Haves

• Experience managing payroll, benefits, and HR platforms.
• Familiarity with healthcare and technology industries.
• Experience supporting leadership teams in a startup environment.

Compensation & Benefits

• Competitive salary, commensurate with experience
• Stock compensation plan – you’ll be a Clearstep co-owner
• Health insurance
• 401k with 4% match
• Flexible work schedule and unlimited PTO
• Monthly WFH and Health stipends
• Fully remote with one day a week of in-person time recommended (preferred location: Chicago or New York)
• Strong emphasis on collaborative learning and career development