Enterprise Sales Executive

My client is a growth-focused operating and investment company dedicated to building, acquiring, and scaling businesses across financial services, business process outsourcing (BPO), customer experience, collections, technology, and business services. Their portfolio includes innovative companies delivering outsourced sales, customer experience, collections, debt resolution, AI-enabled business solutions, technology services, and operational support to organizations across North America. As they continue their aggressive growth strategy, they are seeking an exceptional Enterprise Sales Executive to help lead their next phase of expansion.

About the Role

Reporting directly to executive leadership, the Enterprise Sales Executive will develop and execute enterprise sales strategy while personally generating new business opportunities across a portfolio of companies. This executive will build relationships with CEOs, founders, private equity firms, financial institutions, enterprise organizations, and strategic partners to deliver customized business solutions that solve complex operational challenges. The ideal candidate is a consultative, hands-on sales leader with a proven history of creating pipeline, building executive relationships, closing complex enterprise opportunities, and driving sustainable revenue growth.

Key Responsibilities

Enterprise Business Development

• Develop and execute Grass Island Capital’s enterprise sales strategy.
• Personally build and maintain a high-value pipeline of enterprise opportunities.
• Identify, qualify, negotiate, and close strategic partnerships.
• Build trusted relationships with C-suite executives and senior decision-makers across North America.
• Represent Grass Island Capital at industry conferences, networking events, and executive meetings.

Strategic Sales Leadership

• Develop customized solutions utilizing the full capabilities of the Grass Island Capital portfolio.
• Collaborate with executive leadership to identify new markets, industries, and growth opportunities.
• Lead complex sales cycles from initial engagement through contract execution.
• Assist with pricing strategies, proposals, contract negotiations, and long-term partnership development.

Cross-Portfolio Sales

Represent solutions across multiple business lines, including:

• Business Process Outsourcing (BPO)
• Customer Experience (CX) and Contact Center Solutions
• Sales Outsourcing
• Financial Services Support
• Collections and Recovery Services
• Debt Resolution
• AI-Enabled Business Solutions
• Technology and Operational Services

Executive Collaboration

• Partner directly with founders and executive leadership.
• Work closely with operational leaders to ensure successful client onboarding and long-term client success.
• Provide executive-level sales forecasting, reporting, and market intelligence.
• Help shape the long-term growth strategy of Grass Island Capital.

Qualifications

We are looking for an entrepreneurial business development executive who has personally built lasting client relationships—not simply managed a sales pipeline or coached a sales team. This is a hunter role, and the successful candidate will be responsible for new logo generation.

Required Qualifications

• 10+ years of enterprise B2B sales experience.
• Proven success personally closing six- and seven-figure enterprise opportunities.
• Experience selling outsourcing, financial services, technology, SaaS, consulting, customer experience, BPO, or business services.
• Demonstrated ability to independently create pipeline and build executive-level relationships with C-suite decision-makers.
• Exceptional communication, presentation, and negotiation skills.
• Entrepreneurial mindset with a passion for growth and performance-based compensation.
• Willingness to travel throughout North America.

Preferred Industry Experience

• Business Process Outsourcing (BPO)
• Contact Centers and Customer Experience (CX)
• Financial Services, Banking, and Lending
• Debt Resolution and Collections
• FinTech, SaaS, and Artificial Intelligence
• Professional Services and Private Equity

Aleron companies (Acara Solutions, Aleron Shared Resources, Broadleaf Results, Lume Strategies, TalentRise, Viaduct) are an Equal Opportunity Employer. Race/Color/Gender/Religion/National Origin/Disability/Veteran.

Applicants for this position must be legally authorized to work in the United States. This position does not meet the employment requirements for individuals with F-1 OPT STEM work authorization status.