10+ years of progressive leadership experience, including 3-5 years in a senior operational role
Deep understanding of insurance workflows and market dynamics
Experience with insurtech platforms or insurance data analytics
Strong financial acumen, including P&L management
Exceptional leadership presence and accountability skills
Proven ability in scaling cross-functional teams in growth environments
Responsibilities
Partner with CEO to execute growth strategy and operational roadmap
Translate company goals into measurable outcomes across departments
Lead annual planning cycles, budgeting, and business reviews
Design and improve operational processes for sustainable growth
Establish KPIs and drive decisions through data analysis
Ensure high-quality delivery of products and services to clients
Own and enhance the end-to-end client experience
Benefits
A seat at the table in a growing, mission-driven software company
Competitive executive compensation package
Comprehensive health, dental, vision, and retirement benefits
A collaborative culture valuing transparency, ownership, and innovation
The chance to shape Insuresoft's future and its market position
Full Job Description
Job Summary: The Chief Operating Officer will serve as a key strategic partner to the CEO, responsible for translating vision into execution across all areas of the business. This is a highly cross-functional leadership role that spans operations, product and technology delivery, sales and marketing, revenue growth, and people, designed for a seasoned operator who can think both strategically and roll up their sleeves to get things done.
The ideal candidate brings a rare combination of deep knowledge of the insurance industry and the operational discipline of a high-performing SaaS company. They are energized by building systems, developing talent, and driving results in an environment where the stakes are high and the opportunities are significant.
Job Description:
Strategic Leadership & Execution
Partner closely with the CEO to develop and execute Insuresoft's growth strategy and operational roadmap
Translate company goals into clear priorities, plans, and measurable outcomes across all departments
Lead cross-functional planning cycles including annual operating plans, budgeting, and quarterly business reviews
Identify and act on opportunities to improve efficiency, scalability, and competitive positioning
Operations & Scaling
Own the design and continuous improvement of operational processes, workflows, and infrastructure that support sustainable growth
Establish and monitor key performance indicators (KPIs) across the business, using data to drive decisions
Ensure consistent, high-quality delivery of products and services to clients at scale
Lead vendor relationships, contract negotiations, and operational partnerships
Client Experience & Relationships
Own the end-to-end client experience, ensuring consistency, quality, and accountability across all client touchpoints
Build and maintain strong executive relationships with key clients, acting as a strategic partner and escalation point when needed
Drive a culture of client-centricity across the organization, aligning teams around client outcomes and long-term value
Implement systems to gather client feedback and translate insights into product, service, and operational improvements
Partner with Sales and Delivery teams to support retention, expansion, and overall client success
Product & Technology Oversight
Collaborate with product and engineering leadership to align the technology roadmap with business priorities and client needs
Champion a culture of innovation, quality, and continuous improvement in product delivery
Maintain accountability for product delivery timelines, technical quality, and client satisfaction
Stay current on AI, automation, and emerging technologies relevant to the insurance software space
Sales & Revenue Growth
Partner with sales and marketing leadership to support pipeline development, client retention, and revenue growth initiatives
Support the expansion of existing client relationships and the onboarding of new enterprise accounts
Develop and refine go-to-market strategies in alignment with insurance industry trends and buyer needs
Represent Insuresoft at industry events, conferences, and client-facing engagements as appropriate
People & Culture
Build, mentor, and retain a high-performing leadership team and broader organizational culture aligned with Insuresoft's values
Champion employee development, engagement, and well-being across the organization
Foster an inclusive, collaborative, and accountable workplace culture
Partner with HR on talent acquisition, succession planning, and organizational design as the company scales
Qualifications
Required
10+ years of progressive leadership experience, with at least 3-5 years in a senior operational or executive role
Demonstrated experience in the insurance industry, deep understanding of insurance workflows, carrier/agency relationships, and market dynamics
Experience with insurtech platforms, policy administration systems, or insurance data/analytics solutions
Strong financial acumen, including experience owning P&L, budgets, and operating plans
Exceptional leadership presence with the ability to inspire, align, and hold teams accountable
Track record of building and scaling cross-functional teams in a fast-paced, growth-oriented environment
Preferred
Background working with mid-market or enterprise insurance carriers and MGAs
MBA or advanced degree in business, technology, or a related field
Experience leading organizations through periods of significant growth or transformation
What We Offer
A seat at the table in a growing, mission-driven software company with real impact on the insurance industry
Competitive executive compensation package including salary, performance incentives, and equity participation
Comprehensive benefits including health, dental, vision, and retirement
A collaborative leadership team and culture that values transparency, ownership, client relationship and innovation
The opportunity to help shape the future of Insuresoft, its people, its products, and its place in the market
Worker Type:
Number of Openings: 0
About Volaris Group Inc.
Volaris Group Inc. is a Canadian software company that acquires and manages vertical market software businesses. The company was founded in 1999 and is headquartered in Toronto, Ontario. Volaris Group operates through a number of subsidiary companies that provide software solutions to various industries including healthcare, education, and transportation. The company's strategy is to acquire and grow software businesses that have a strong market position and a loyal customer base. Volaris Group is committed to providing its customers with high-quality software solutions and excellent customer service.
