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Insurance Sales Director

Aspire Systems Digital Transformation IncOak Brook, IL🇺🇸United StatesPosted 8 Sept 2026

Why This Role Stands Out

This Director of Sales role offers a fantastic opportunity to drive growth within the insurance sector for a reputable company, leveraging your hunter mentality to generate new business. You'll thrive here if you're an experienced sales professional with deep insurance industry knowledge, ready to make a significant impact and advance your career. Apply today to join a dynamic team and contribute to exciting digital transformation initiatives.

Quick Overview

Seniority
Leader
Work mode
On Site
Location
Oak Brook, IL, United States
Posted
Yesterday
Contract NegotiationLead GenerationProspectingSolution Selling

Job Description

Job Title: Director 

Location: Chicago IL

Employment Type: Full time

Working Model: Hybrid

 

We are seeking a highly motivated and experienced hunter sales with experience on Insurance industry to join our team. The successful candidate will be responsible for generating new business in the insurance vertical for our North America Geo. The primary goal of the of the Salesperson will be to generate new business .

 

Employment Type: Full time position with Aspire Systems

 

Job Description

 

                     Develop and execute a strategic sales plan to achieve the company's sales targets in the insurance vertical.

                     Expert knowledge and understanding of P&C, Life and Auto insurance Carriers

                     Identify and develop new business opportunities through targeted prospecting and lead generation activities.

                     Cultivate and maintain strong relationships with key decision makers at client organizations to drive revenue growth and ensure customer satisfaction.

                     Collaborate with internal teams on effectively communicating the needs of the client

                     Manage the entire sales process from lead generation to contract negotiation and close

                     Prepare and deliver compelling presentations to clients and stakeholders

                     Stay up-to-date on industry trends and changes, and adjust sales strategies as needed to remain competitive

                     Achieve and exceed quarterly and annual sales targets

                     Exposure towards the Guidewire Cloud and Digital strategy and would be an advantage

 

Qualifications:

                     15+ years of successful sales experience in the insurance industry.

Demonstrated consecutive quarterly and yearly quota achievement in complex selling environments utilizing a   solution selling model and good understanding of customers’ business initiatives and its implication on the process and technology landscape

                     Strong understanding of the insurance industry and its unique challenges and opportunities

                     Experience on Selling one or more insurance product to the carriers.

                     Excellent communication and interpersonal skills with the ability to build and maintain relationships with senior-level executives

                     Demonstrated ability to develop and execute strategic sales plans

                     Understanding and selling of Onsite/Offshore/Nearshore IT services is a must

                     Strong negotiating and closing skills

If you are interested with this position, please revert me with your updated resume along with your available time slot to discuss.

 

About Aspire Systems

Aspire Systems is a $180+ million global technology services firm with over 4,900 employees worldwide, partnering with 275+ active customers. Founded in 1996, Aspire has grown steadily at a 19% CAGR since 2020.

Headquartered in Singapore, we operate across the US, UK, LATAM, Europe, the Middle East, India, and Asia Pacific regions, with strong nearshore delivery centers in Poland and Mexico. Aspire has been consistently recognized among India’s 100 Best Companies to Work For for 12 consecutive years by the Great Place to Work Institute.

Who We Are

Aspire is built on deep expertise in Software Engineering, Digital Services, Testing, and Infrastructure & Application Support. We serve diverse industries including Independent Software Vendors, Retail, Banking & Financial Services, and Insurance.

Our proven frameworks and accelerators enable us to create future-ready, scalable, and business-focused systems, helping customers across the globe embrace digital transformation at speed and scale.

What We Believe

At the heart of Aspire is our philosophy of “Attention. Always.”—a commitment to investing care and focus on our customers, employees, and society

Our Commitment to Diversity & Inclusion

At Aspire Systems, we foster a work culture that appreciates diversity and inclusiveness. We understand that our multigenerational workforce represents different regions, cultures, economic backgrounds, races, genders, ethnicities, education levels, personalities, and religions. We believe these differences make us stronger and are committed to building an inclusive workplace where everyone feels respected and valued.

Privacy Notice

Aspire Systems values your privacy. Candidate information collected through this recruitment process will be used solely for hiring purposes, handled securely, and retained only as long as necessary in compliance with applicable privacy laws.

Disclaimer

The above statements are not intended to be a complete statement of job content, but rather to serve as a guide to the essential functions performed by the employee in this role. Management retains the discretion to add or change the duties of the position at any time.

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