Head of Technical Sales

Company description:

About Digicel

Digicel is a leading digital connectivity and communications provider, delivering modern wireless and fibre networks across 25 markets in the Caribbean, Central and South America. Serving nine million customers through mobile, home, and business solutions, we play a critical role in enabling economic participation and digital inclusion in the region. Our commitment to strong governance, inclusive access, and long-term value creation is embedded in how we operate every day. Backed by our DIGI values - Diversity, Integrity, Growth, and Innovation - our 5,000 employees are focused on driving impact for the customers, communities, and countries we serve.

Visit www.digicelgroup.com for more.

Job description:

Job Title: Head of Technical Sales  

Primary objective of the job:

The Head of Technical Sales will be fully embedded in the sales cycle — owning upsell, cross-sell, and product-led client acquisition strategies that position the business for sustained commercial success.

He/she will be responsible for leading the strategic commercialization of the product portfolio by deepening penetration within the existing client base and driving new revenue growth through market-relevant, innovative solutions.

Main Duties and Responsibilities:

Commercial & Deal Ownership

• Owns end-to-end sales cycles for complex B2B technology solutions, from discovery through contract closure.
• Demonstrate strong commercial discipline, including pricing, margin management, and deal structuring.
• Consistently deliver value-based outcomes rather than price-led transactions.

Technical & Solution Expertise

• Apply strong technical knowledge across cloud, connectivity, security, managed services, and enterprise ICT solutions.
• Translate complex technical architecture into clear, business-relevant value propositions for senior stakeholders.
• Ensure solutions sold are scalable, deployable, and aligned with service delivery capabilities.

Consultative & Strategic Selling

• Adopt a consultative selling approach, diagnosing customer needs and designing tailored solutions.
• Act as a trusted advisor to Enterprise, Government, and high-value SMB customers.
• Confidently challenge customer assumptions to drive optimal solution design and outcomes.

Stakeholder & Collaboration Management

• Engage effectively with CIO, CTO, IT leadership, and executive decision-makers.
• Work cross-functionally with product, technical, cloud, and service delivery teams to shape viable solutions.
• Influence internal stakeholders to align solution design with customer and business objectives.

Market & Customer Insight

• Maintain strong awareness of market trends, customer challenges, and emerging technologies.
• Provide structured customer and market insights to support go-to-market and solution development initiatives.

Sales Leadership & Capability Building

• Act as a technical mentor to sales teams, supporting capability uplift in solution selling.
• Contribute to improving overall sales effectiveness and win-rate on complex opportunities.

Execution & Governance

• Maintain accurate pipeline, forecasting, and reporting through Salesforce tools.
• Operate with high standards of professionalism, accountability, and execution discipline.

Academic Qualifications and Experience Required:

• Bachelor’s degree in Business, Marketing, or Technology; MBA preferred.
• Minimum of 7 years in product management, sales enablement, or commercial strategy roles.
• Telecom, IT, SaaS, or managed services background strongly preferred.

Functional Skills:

• Strong understanding of Digicel Business product lifecycle and customer needs.
• Proven ability to translate technical concepts into business value for both technical and non-technical audiences
• Commercial acumen in pricing, margin, and value proposition development.
• Proficiency in competitive benchmarking, GTM planning, and vertical segmentation.
• Experience managing performance and driving accountability

Working conditions:

• Predominantly 8am – 5pm; may be required to work outside the set work hours
• Office-based with cross-functional collaboration and client/sales engagement
• Requires interaction with regional group teams and front-line sales leadership