Our Company

Medicine is evolving faster than ever, and so is the way clinicians learn. At Sketchy, we partner with institutions, health systems, and learners to expand access to high-quality clinical education that prepares clinicians for what’s next.

Our mission is to help clinicians build the readiness and agility needed to deliver better decisions, stronger patient connections, and higher-quality care in a world shaped by AI and precision medicine.

We’re reimagining how clinical reasoning, communication, and other core competencies are developed, empowering every learner to adapt, grow, and lead in the future of healthcare.

Position Summary

The Vice President of Finance will serve as the company’s senior-most financial leader, responsible for driving excellence in financial planning, reporting, and strategic analysis. This role will partner closely with the CEO and leadership team to ensure financial discipline, transparency, and scalability as the company continues to grow.

Sketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington!  

Responsibilities:

Financial Planning & Analysis (FP&A)

• Lead and manage all budgeting, forecasting, and financial modeling processes to support strategic and operational decision-making.
• Develop dashboards and performance metrics to monitor key business drivers and company performance.
• Partner with department leaders to align financial plans with strategic goals and resource needs.
• Conduct scenario analysis and sensitivity modeling to guide investment and growth decisions.
• Develop and maintain compensation plans for the sales team, ensuring alignment with revenue goals and profitability targets.
• Support pricing strategy across both consumer and institutional channels, providing analysis and insights to optimize growth and margin.
• Partner with the Consumer and Sales teams to develop marketing spend plans, measuring ROI, applying SaaS benchmarks and ensuring strategic capital deployment.

Accounting & Financial Operations

• Oversee all accounting functions, including general ledger, accounts payable, and payroll, leveraging internal and external partners as needed.
• Ensure timely and accurate monthly, quarterly, and annual financial closings and reports.
• Establish and maintain strong internal controls, policies, and compliance processes to safeguard company assets and ensure regulatory compliance, including sales tax filings where applicable.
• Manage audits end-to-end, including vendor selection and coordination with auditors, tax advisors, and professional service providers.

Reporting & Investor Relations

• Prepare and present financial results, analyses, and commentary to the CEO, Board, and investors.
• Support fundraising activities by developing financial models, due diligence materials, and data-driven narratives.
• Establish and maintain consistent, high-quality reporting to ensure visibility into financial performance and forecasts.
• Build and maintain strong relationships with investors, financial institutions, and key stakeholders.

Cash, Capital, and Equity Management

• Oversee cash flow forecasting, working capital optimization, and capital allocation decisions.
• Manage capitalization table and employee stock option plans using tools such as Carta.
• Evaluate financing options, capital structure, and return on investment to support company growth.
• Identify and mitigate financial risks across the business.

Leadership & Collaboration

• Build and lead a high-performing finance team capable of scaling with the business.
• Serve as a strategic thought partner to the CEO and executive team, helping to shape data-driven decisions.
• Partner with HR and external providers to maintain a collaborative, engaging, and high-performance workplace.
• Drive a culture of accountability, analytical rigor, and continuous improvement.

What We’re Looking For:

• Bachelor’s degree in Finance, Accounting, Economics, or related field (MBA, CPA, or CFA preferred).
• 12+ years of finance experience, with at least 3 years in a senior leadership role 
• Experience in SaaS or subscription-based business models required.
• Proven success leading FP&A, accounting, and reporting functions in a high-growth or PE/VC-backed environment.
• Strong command of SaaS metrics (ARR, LTV/CAC, churn, gross margin, etc.).
• Hands-on leader with excellent communication and presentation skills; able to translate financial data into actionable insights for executives and investors.

Preferred Attributes

• Experience managing equity programs and capitalization tables (Carta preferred).
• Deep familiarity with fundraising processes, investor communications, and board reporting.
• Strategic thinker with operational excellence and a bias for execution.
• Collaborative, proactive, and highly analytical approach.

If you don’t have 100% of the bullets listed above, that’s okay! We know there are no perfect applicants. If you are passionate about making a meaningful difference, we want to hear from you! Learn more about Sketchy’s culture at sketchy.com/careers. 

Salary Range

$230,000 to $275,000 annual salary plus a performance-based annual bonus and stock options

Our Perks 

• 100% Individual Health Coverage - We got you covered!
• Equity - From day one, you’ll have a stake in our future growth. 
• 401(k) - We support your financial future with up to 5% matching. 
• Annual Company Retreat in Cool Places
• Flexible Time Off 
• Annual Work Anniversary Stipend 
• Monthly Wifi & Phone Reimbursement 
• Short Term & Long Term Disability 

Sketchy Group LLC is an Equal Opportunity Employer. All applicants will receive consideration without discrimination on the basis of race, religion, color, sex, age, sexual orientation, marital status, national origin, disability or any other basis prohibited by applicable law.