Enterprise Sales Representative

Insight Global; United States; Remote; USD 160,000 - 180,000; Full time

Job summary

Insight Global is seeking a Sales Director, Enterprise Software to lead new-logo acquisitions within the Insurance & Benefits sector. This remote role in the United States requires travel for client face time and a track record of closing multi-million-dollar enterprise deals.

You will own the full sales cycle from discovery to close, build executive relationships, and collaborate with product, marketing, and engineering teams to translate business challenges into technology outcomes for

Qualifications

• 6+ years of enterprise software, SaaS, or technology sales experience.
• Experience winning net-new enterprise business and generating your own pipeline.
• Proven ability to navigate complex sales cycles with multiple decision-makers.

Responsibilities

• Develop and execute a strategy to identify and win new enterprise customers.
• Independently generate pipeline through prospecting, networking, relationship building, and account development.
• Lead complex, consultative sales cycles from initial discovery through negotiation and close.
• Build relationships with senior business, technology, and operational leaders.
• Uncover customer challenges and develop solution-oriented business cases rather than leading with a product catalog.
• Navigate large, multi-stakeholder opportunities that may involve lengthy buying cycles and significant technology implementations.
• Partner with internal product, technical, marketing, and leadership teams throughout the sales process.
• Identify opportunities to expand relationships and introduce additional solutions within strategic accounts.

Skills

Enterprise software sales

New logo sales

Consultative selling

Executive relationship building

Multi-stakeholder selling

MEDDPICC

Job description

Sales Director, Enterprise Software | Insurance & Benefits

Location: Remote | United States – travel for client face time

Employment Type: Full Time W2 Employee of Client

Compensation: $160K-$180K base + $350K-$380K OTE, accelerators possible

We are seeking an experienced enterprise sales professional to drive new business growth within the insurance and benefits market. This is a true new-logo role for a seller who can create opportunities, build senior-level relationships, and navigate complex enterprise sales from initial outreach through close.

The ideal candidate combines strong enterprise software sales experience with familiarity across insurance, InsurTech, Life, Annuity & Health, P&C, benefits, or related markets. Deep insurance expertise is helpful but not required. More important is the ability to understand a customer’s challenges, ask the right questions, and connect technology solutions to meaningful business outcomes.

What You'll Do

• Develop and execute a strategy to identify and win new enterprise customers.
• Independently generate pipeline through prospecting, networking, relationship building, and account development.
• Lead complex, consultative sales cycles from initial discovery through negotiation and close.
• Build relationships with senior business, technology, and operational leaders.
• Uncover customer challenges and develop solution-oriented business cases rather than leading with a product catalog.
• Navigate large, multi-stakeholder opportunities that may involve lengthy buying cycles and significant technology implementations.
• Partner with internal product, technical, marketing, and leadership teams throughout the sales process.
• Identify opportunities to expand relationships and introduce additional solutions within strategic accounts.

What We're Looking For

• 6+ years of successful enterprise software, SaaS, or technology sales experience.
• Demonstrated success winning net-new enterprise business and generating your own pipeline.
• Experience selling complex, high-value solutions with multiple decision-makers and extended sales cycles.
• Familiarity with insurance, InsurTech, employee benefits, or technology supporting highly regulated industries.
• Strong discovery and consultative selling skills with the ability to translate business problems into technology solutions.
• Proven ability to build credibility with senior and executive-level stakeholders.
• Experience with structured enterprise sales methodologies such as MEDDPICC, Challenger, Gap Selling, or similar approaches is a plus.

Ideal Background

Candidates may come from insurance technology or from broader enterprise software organizations where they have sold complex solutions into large insurance carriers, benefits organizations, or multinational employers.

We're particularly interested in hunters who are comfortable creating opportunities from the ground up, rather than relying primarily on inbound leads or established accounts.