InsurePay · 14 hours ago
Vice President Operations
United States
Full-time
Remote
Mid, Senior Level
7+ years expInsurePay is a venture-backed Insurtech company seeking a Vice President of Operations to drive the planning and execution of critical cross-functional operational needs. This role focuses on AI-native, automation-first operations, managing initiatives across Operations, Product, Engineering, Customer Experience, Finance, and Sales.
BillingInsuranceInsurTechPaymentsSaaS
Responsibilities
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
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
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
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
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
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 and implement operational excellence wherever required inside the organization, working directly with the CFO, CEO and other senior leaders
Qualification
Required
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
Company
InsurePay
InsurePay is an insuretech SaaS platform that provides pay-as-you-go, payables, reconciliation, premium refunds, and claims.
51-200 employees
H1B Sponsorship
InsurePay has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2024 (1)
Funding
Current Stage
Growth StageTotal Funding
$5MKey Investors
Aquiline Technology GrowthFINTOP Capital
2022-04-06Series B
2022-01-11Series B
2021-02-17Series A· $5M
Leadership Team
Adam Beck
President and CEO
Patrick Davis
Chief Executive Officer
Recent News
2025-09-02
2022-04-18
2022-04-18
Company data provided by crunchbase