Strategic Enterprise Account Executive - Regulated Industries

Cloud Software Group, LLC; Illinois; Remote; USD 147,000 - 221,000; Full time

Benefits offered by this job

Healthcare benefits

401(k) with company match

Disability insurance

Job summary

Cloud Software Group is seeking a Principal Account Executive to drive net-new logo acquisition and revenue expansion across highly regulated industries. You will own the end-to-end sales lifecycle, from strategic targeting to final contract negotiations, engaging C-suite buyers and leading complex, multi-stakeholder deals.

You will partner with Solutions Engineers, Product, and Marketing to run targeted campaigns into Fortune 500 prospects, delivering ROI and compliance-focused business cases.

Qualifications

• 10+ years of quota-carrying enterprise SaaS sales experience.
• 5+ years selling enterprise archiving or communications surveillance solutions.
• Proven track record closing $1M+ ARR quotas.
• Experience selling into regulated industries (Finance, Healthcare, Legal).
• Excellent communication with executive stakeholders.
• Ability to work autonomously in a fully remote environment.

Responsibilities

• Full-Cycle Revenue Ownership: Own, manage, and close a strategic enterprise pipeline to meet ARR targets.
• C-Suite Engagement: Engage executive stakeholders including C-suite peers.
• Complex Deal Orchestration: Lead multi-stakeholder, long-cycle enterprise sales ($500K-$1M+ ARR).
• Strategic Account Planning: Collaborate with Solutions Engineers, Product, Marketing for Fortune 500 campaigns.
• Value-Based Selling: Deliver ROI, risk mitigation, and regulatory compliance stories.
• Accurate Forecasting: Maintain a clean Salesforce pipeline with weekly/monthly forecasts.

Skills

Quota-carrying sales

Enterprise SaaS sales

C-suite engagement

Strategic account planning

Forecasting

Remote work

Tools

Salesforce

Oracle CRM

HubSpot

Gong

LinkedIn Sales Navigator

ZoomInfo

Outreach

Salesloft

Job description

Cloud Software Group is seeking a Principal Account Executive to drive net-new logo acquisition and revenue expansion across highly regulated industries. You will own the end-to-end sales lifecycle, from strategic targeting to final contract negotiations, engaging C-suite buyers and leading complex, multi-stakeholder deals.

You will partner with Solutions Engineers, Product, and Marketing to run targeted campaigns into Fortune 500 prospects, delivering ROI and compliance-focused business cases.