Remotehey

Location: Remote (US) / Hybrid (Buffalo, NY)

Reports to: CFO & COO

About the role:

InsurePay is seeking a VP of Operations who will be responsible for driving the planning and execution of InsurePay’s most critical cross-functional operational needs. This role is ideal for an operator who believes the future of operations is AI-native, automation-first, and built by leaders who are willing to get their hands dirty. This role owns the roadmap of initiatives that sit at the intersection of Operations, Product, Engineering, Customer Experience, Finance, and Sales, with a heavy focus on:

• Client onboarding and implementations
• Adoption initiatives
• Payroll integrations and connections
• Churn prevention and revenue preservation
• Operational scalability for InsurePay Pulse and InsurePay Flow
• AI-Driven Operations & Automation (Core to the Role)
• Own the strategy and execution of AI-enabled and automation-first operations across InsurePay, with a mandate to aggressively reduce manual work, improve cycle times, and increase operational leverage.
• Identify, prototype, and productionize AI-powered workflows across onboarding, implementations, support, finance ops, and internal reporting.
• Act as a bridge between business users and technical teams, translating operational problems into automation, agent, or workflow designs.

This is a high-visibility role and requires strong executive presence, exceptional program management discipline, and the ability to turn old work streams and cross-team problems into ownership of clear, executable plans. Independence in this role is key, with the ability to analyze, review, and make minor and mid-level decisions independently, while escalating critical issues with suggested resolutions as needed. The ability to analyze the organization and recommend additional changes and improvements to operations to drive your own roadmap is essential.

You’re excited about this opportunity because you will ....

Portfolio & Initiative Ownership:

• Own the cross-functional operational initiatives roadmap (onboarding, payroll integrations, billing accuracy, PMO support, churn prevention, and cross-sell/crossover efforts), ensuring clear alignment to company KPIs and priorities.
• Translate executive strategy into structured initiative charters with defined scope, success metrics, ROI, assumptions, and resourcing needs across Operations, Product, Engineering, Finance, and Sales.
• Partner with executive leadership to prioritize initiatives and manage trade-offs, ensuring the organization is focused on the highest-impact work and that dependencies are understood and managed.

Cross-Functional Planning & Execution:

• Build and maintain integrated project plans that stitch together cross-departmental workstreams (milestones, dependencies, owners, critical path, risks) and keep them current and transparent.
• Stand up and continuously refine a structured client request intake process so internal and client-facing teams have a consistent, reliable path for getting work prioritized and delivered.
• Run effective meetings and process (e.g., weekly initiative standups, cross-functional working sessions, and monthly steering with executives), including agendas, pre-reads, action items, and decision logs.
• Proactively manage risks, issues, and dependencies across departments and escalate with clear options and recommendations.
• Make decisions within your authority level and escalate where needed.

Process, Data, and Systems Integration:

• Map and regularly update end-to-end operational flows that matter most to carriers and policyholders identifying friction points and failure modes between teams and systems.
• Partner with Product, Engineering, Sales and Operations leaders to design and implement improved workflows, shifting repeatable work from manual/operational fixes into productized and automated solutions wherever possible.
• Collaborate with Finance to define and maintain trusted KPI views and dashboards (e.g., implementation cycle times, onboarding satisfaction, error/exception rates, contact/churn drivers, cross-sell/crossover adoption) and to track benefits realized vs. Planned.
• Develop reporting across the org on KPI, metrics via our Qlik reporting tool and data warehouse.
• Personally build and iterate on dashboards, views, and operational reporting (Qlik, SQL, BI tools) rather than delegating all analytics work.
• Define operational metrics that power automation triggers, alerts, and exception workflows, not just executive reporting.
• Partner with Data & Engineering to ensure AI and automation initiatives are grounded in trusted, well-modeled data.

AI, Automation & Internal Tooling

• Design and deploy low-code / no-code and AI-assisted workflows using tools such as n8n, Zapier, Make, Retool, internal admin tools, and LLM-based agents.
• Build and maintain internal “ops tooling” to automate repeatable workflows (client onboarding steps, payroll validation, exception handling, reconciliations, reporting, internal alerts).
• Partner with Engineering to determine what should live as:
• Lightweight automation
• Internal tooling
• Fully productized platform capabilities
• Prototype solutions quickly (“vibe coding”) to validate operational improvements before engineering investment.
• Establish guardrails for automation reliability, monitoring, auditability, and security in regulated environments.

Change Management & Frontline Readiness

• Own the operational change and rollout plan for major cross-functional initiatives (new flows, new capabilities, policy/process changes), ensuring all impacted teams are prepared ahead of go-live.
• Coordinate with Operations, PMO/Implementations, and Customer Support leaders to ensure SOPs, playbooks, knowledge base content, and training materials are updated and delivered on time.
• Monitor post-launch adoption and performance, identify gaps or unintended effects, and drive corrective actions with relevant leaders until the new way of working is stable and performing to target.

Standards, Playbooks & Continuous Improvement

• Define, maintain, and enforce standards for cross-departmental work to ensure simplicity, consistency and scalability.
• After each major initiative, run structured retrospectives and convert learnings into reusable playbooks, checklists, and templates
• Coach project and process owners across the organization on best practices in cross-functional planning, execution, and communication, raising the overall bar for how InsurePay runs initiatives.
• Help to maintain an implement operational excellence wherever required inside the organization, working directly with the CFO, CEO and other senior leaders.

We’re excited about you because you have ….

• 7+ years of experience in project/program management or operations leadership, with clear ownership of complex cross-functional initiatives in SaaS, fintech, insurtech, or adjacent B2B environments.
• Demonstrated success leading cross-departmental programs that touch Product, Engineering, Operations, Support, and Finance
• Strong, demonstrable skills in portfolio and project management:
• Building integrated plans across teams and systems
• Managing dependencies, risks, and issues
• Running effective governance and stakeholder forums
• Delivering initiatives on time and within agreed scope
• Proven ability to translate executive strategy into actionable roadmaps and charters, and to communicate trade-offs and options clearly at the executive level.
• Experience mapping and improving end-to-end processes (e.g., quote-to-cash, onboarding-to-billing, incident-to-resolution) using structured methods and tools.
• Strong analytical skills and comfort with operational and financial metrics; able to work closely with Finance and Product teams to frame business cases and track realized impact.
• Excellent stakeholder management and communication skills, including:
• Clear, concise status and executive summaries
• Strong meeting facilitation and conflict-resolution skills
• Ability to influence without direct authority across functions
• AI & Automation Experience (Required)
• Hands-on experience designing or building AI-assisted workflows, internal tools, or automations
• Practical experience with low-code / no-code automation platforms (e.g., n8n, Zapier, Make, Retool, internal admin tools).
• Comfort using modern LLMs (ChatGPT, Claude, etc.) to prototype workflows, generate scripts, and accelerate operational problem-solving.
• Ability to “vibe code” or rapidly prototype solutions to validate ideas before formal engineering build-out.
• Experience building internal agents, workflow orchestration, or AI-powered ops tooling in production environments.
• Familiarity with event-driven systems, APIs, webhooks, and data pipelines.

Preferred

• Experience in insurance, payments, or financial services environments.
• Prior experience working in a high-growth startup or scale-up environment with evolving processes and systems.
• Familiarity with dev practices (e.g., Scrum, Kanban) and tools such as Jira, Confluence, and modern collaboration platforms.
• Formal project/program management training or certifications.

Benefits

• Competitive base
• Generous vacation policy
• Full medical, dental, and vision packages
• LTD and STD coverage options
• 100% employer covered Basic life and AD&D
• 100% employer covered Employee Assistant Program
• Paid Parental Leave
• Paid Volunteer Time Off
• 401(k) with company match

About Us

InsurePay® is a SaaS billing and payments platform that ensures accuracy of insurance premiums and offers integrated payments and reconciliations for Agencies, Carriers, MGAs, and insurance technology providers. We are empowering carriers to allow policyholders to pay only for what they need through accurate, timely, and data-driven reconciliations with a feature-rich platform that offers carrier payables, vendor payables, and claims payments all integrated to back-office systems. We are a venture backed Insurtech company who is growing fast … like really fast! Come join us!