Head Of Operations Jobs in Vermont (NOW HIRING)

Reports to: Chief Executive Officer

Location: Burlington, VT (hybrid) or remote

Compensation: Base, plus equity

OhMD is an AI patient communication platform used by thousands of healthcare organizations. Our product suite includes two-way patient texting, an AI voice and text assistant that handles inbound patient calls with a human always in the loop, and integrations with 85+ EHRs. Practices using OhMD reduce inbound call volume by 50% or more which is the difference between a front desk that is drowning and one that can actually take care of patients.

We are at the stage where the financial infrastructure needs to get ahead of the growth - and where the person building it gets to shape how the company operates.

The Head of Finance & Operations owns OhMD's financial planning, reporting, and operations - giving the company the visibility and infrastructure it needs to make sound decisions as it scales.

This is a builder's role. You will be the primary finance resource in a lean organization, which means you will do the modeling, set the strategy and reconcile the AR. You will own the numbers, build the systems that make them trustworthy, and act as a real thought partner to the CEO and leadership team on where the business goes next.

The operational half of the role is secondary in title only. You will work on pricing and packaging, tighten cross-functional processes, and bring order to systems that grew faster than the company's ability to formalize them. We also expect you to use AI aggressively - to model faster, close faster, and automate work that a finance team of one should not be doing by hand.

Success looks like clean financials, forecasts leadership and the board trusts, and a finance function that stays a step ahead of the company instead of catching up to it.

In the first 90 days: You know the numbers cold and you have identified the three biggest gaps in our financial reporting and infrastructure.

By month six: Leadership is working from a financial model you built and own. ARR and SaaS metrics are reported consistently and reconcile to the billing system. You have delivered an updated pricing and margin analysis with recommendations.

By the end of year one: Board and investor reporting runs on rails. Forecast accuracy is good enough that we plan against it. You have automated or eliminated a meaningful share of manual finance work, and you have become the person other leaders come to before making a spend or resourcing decision.

• Build and own financial models, forecasts, and budgets from scratch — including three-statement models, scenario planning, cash and runway forecasting, and unit economics.
• Partner with the CEO and leadership team on strategic financial decisions, scenario planning, and resource allocation.
• Translate financial data into clear, actionable recommendations for non-finance stakeholders across the company.

• Own ARR tracking and AI/SaaS revenue metrics — MRR, churn, expansion, NRR, LTV, CAC, payback — in partnership with Sales and Customer Success and ensure reported metrics reconcile to the billing system.
• Work with the product team on pricing and packaging design: model tier structures, unit economics, discounting, and margin impact, and translate that analysis into go-to-market recommendations.
• Oversee billing operations and subscription management in Chargebee, ensuring accuracy and timely AR resolution.

• Own all financial operations and support/refine our existing bookkeeping process.
• Produce accurate, timely financial reporting for internal leadership and external stakeholders, including board and investor updates.
• Manage relationships with external accountants, auditors, legal counsel, and financial vendors.
• Ensure compliance with applicable tax, regulatory, and reporting requirements.

• Manage the capital raise process alongside the CEO, including data room maintenance, investor reporting, diligence support, and document coordination.

• Identify operational inefficiencies and implement scalable systems and processes across the company as headcount and complexity grow.
• Own the finance and operations tech stack — selecting, implementing, and integrating tools that reduce manual work rather than adding to it.
• Evaluate and manage vendor contracts, software spend, and operational costs to support efficient growth.
• Apply AI tooling to finance and operations work: accelerating analysis and modeling, automating reporting and reconciliation, drafting board materials, and building lightweight internal tooling. We expect this role to be a visible example of how AI changes what a small team can do.

• Support people operations processes including offer letter coordination, compensation benchmarking, and headcount planning.
• Other duties as assigned.

• 7+ years of finance experience, including meaningful time in a B2B software or SaaS business with recurring revenue.
• Demonstrated ability to build financial models from a blank spreadsheet — three-statement models, forecasts, budgets, and scenario analysis — and own them end to end without analyst support.
• Strong command of SaaS financial metrics including ARR, MRR, churn, NRR, LTV, and CAC, and a clear understanding of what drives each.
• Experience in a growing or scaling company where finance and operations responsibilities overlap and process has to be built rather than inherited.
• Fluency with AI tools in daily work — you already use them for analysis, modeling, research, writing, or automation, and you have opinions about where they help and where they do not. This is not a "willing to learn" requirement.
• Experience producing board-ready financial reporting and working directly with senior leadership or investors.
• High degree of ownership and attention to detail — comfortable being the primary finance resource in a lean organization and moving between strategic work and hands-on execution in the same day.
• Strong written and verbal communication skills, with the ability to make financial reality legible to people who do not work in spreadsheets.

• Experiences of implementing or upgrading finance and operations systems — ERP, billing, procurement, reporting, or automation tooling.
• Experience owning pricing and packaging decisions in a software business.
• Background in healthcare technology, health IT, or HIPAA-regulated environments.
• CPA, MBA, or equivalent financial credential.
• Supporting or managing a venture capital raise, including data room preparation and investor reporting.
• Familiarity with subscription billing platforms (Chargebee, Stripe, or similar).