Head of Product & Technology

About CalCom Software:

CalCom Software is a global leader in security hardening automation, dedicated to helping enterprises deploy security hardening and achieve compliance. We provide cutting-edge solutions that enhance the security posture of organizations worldwide. Our team is composed of highly skilled, system engineers and developers with deep expertise in server administration and security. If you're looking for a dynamic environment to grow your technical expertise and take on new challenges, CalCom is the place for you. CalCom is a stable and profitable, fully owned by Private Equity.

Job Summary:

We are seeking an experienced Head of Product & Technology to lead CalCom’s overall product strategy, technical architecture, and software delivery.

This is a hands-on, dual-function leadership role reporting to the CEO

In this role, you will bridge the gap between business vision and engineering execution, own the formal product roadmap, oversee offshore software development partners, and drive the modern evolution of our tech stack and agile project management frameworks.

The ideal candidate has a proven track record in Product management for enterprise-grade platforms. Strong hands-on architecture experience in enterprise software, a deep understanding of IT security baselines, and a proven track record of managing technical teams and delivery workflows.

Key Responsibilities:

Product Vision & Strategic Road mapping:

• Establish a formal, documented product roadmap process with clear milestones, timelines, and business priorities.
• Translate enterprise customer feedback, market trends, and security compliance updates (e.g., CIS benchmarks) into actionable product backlog items.
• Define governance and strategic frameworks to ensure alignment across leadership, engineering, and customer success teams.

Technical Leadership & Delivery Management:

• Oversee the architectural design and maintainability of CalCom’s software suite.
• Manage and hold external/offshore development resources accountable to timelines, technical quality standards, and secure coding practices.
• Lead major technology modernization initiatives, such as the replacement of our current end-point architecture

Agile Process & Governance:

• Adopt, roll out, and standardize centralized project management tooling (e.g., Jira, Azure DevOps, or GitHub Projects) across internal and external teams.
• Formalize technical, deployment, and architectural documentation to remove knowledge silos and streamline future team transitions.

Cross-Functional & Customer Alignment:

• Partner with Customer Engineering and Professional Services to ensure seamless product implementation in enterprise, non-internet-connected environments.
• Serve as the executive technical liaison for high-tier enterprise customer escalations and security architecture discussions.

Required Managerial Skills:

Product Lifecycle Management:

• Proven experience in managing the end-to-end product lifecycle, from ideation and discovery to launch and post-launch optimization.
• 4 years of experience in enterprise software companies
• Experience as a PM in Cyber/Compliance/IT products companies - advantage

Backlog Prioritization:

• Proficiency in maintaining a prioritized product backlog, balancing customer needs, technical debt, and business objectives.

Vendor and Resource Management:

• Proven experience in managing external service providers, including contract negotiation, performance oversight, and relationship management.

Performance Leadership:

• Expertise in setting clear KPIs, providing constructive feedback, and mentoring engineering leads to drive team productivity and professional growth.

Market & Competitive Analysis:

• Ability to conduct market research and competitive analysis to inform product strategy and differentiation.

Required Technical Skills:

Software Architecture & Frameworks:

• Deep background in enterprise architecture utilizing C# / .NET (.NET Framework 4.8 and .NET Core/.NET 7+), REST APIs, and gRPC microservices communication.
• Experience with modern web front-end applications

Security & Enterprise Infrastructure:

• Strong knowledge of Windows Server administration, Active Directory (AD), Group Policy Objects (GPO), and Linux environments.
• Solid understanding of cybersecurity hardening guidelines (e.g., CIS Benchmarks, NIST, PCI DSS, HIPAA).
• Familiarity with enterprise, air-gapped, or highly restricted on-premises deployment environments.

Required Soft Skills:

Executive & Remote Leadership:

• Proven ability to lead, mentor, and govern remote or third-party/offshore engineering organizations.
• Strong strategic planning capability with the ability to balance technical debt reduction against new business feature delivery.

Communication & Stakeholder Management:

• Fluent in English (both written and spoken).
• Exceptional capacity to articulate complex technical decisions to C-level stakeholders, external developers, and enterprise clients.

Problem-Solving & Analytical Thinking:

• Strong analytical skills with a proactive approach to issue resolution, system reliability, and process improvement.

Stakeholder Communication:

• Expertise in presenting product roadmaps and status updates to diverse stakeholders, ensuring transparency and alignment across the organization.

Advantage:

• Background working for an enterprise cybersecurity software vendor, system integrator, or B2B SaaS company.