VP of Software Development & IT

As VP of Software Development & IT, you own the entire technology function of one of our clients. Software development, product delivery, IT infrastructure, security, compliance, and enterprise AI strategy all roll up to this seat. You are the technology owner the CEO trusts to execute her vision and deliver on the product through the software and IT infrastructure that powers it. You lead with urgency and accountability, building the velocity of a modern software organization while protecting the reliability, security, and compliance posture the business depends on.

This role needs to be at the office in Menands, NY, at least Tuesday through Thursday each week   Duties: LMA - Lead, Manage, & Hold Accountable ● Lead, mentor, and hold the Director of Engineering, Director of Product, and Director of IT & Security accountable to company standards, sprint commitments, delivery targets, and infrastructure health metrics. ● Set the tone of the Software Development department: high-velocity, AI-forward, quality-driven, and cross-functionally collaborative. ● Model company culture and core values (FLASH'D) through example, hiring, and performance management. ● Provide coaching and mentoring to direct reports and downline as necessary. ● Log performance of direct reports via the HR logging system. ● Ensure adherence to development SOPs, IT operating procedures, sprint methodology, release protocols, and security policies as documented in the company's GitBook knowledge base. ● Assess workload and resources available to determine department needs. ● Host the weekly Technology L10 Meeting. ● Host the bi-weekly Sprint Planning Meeting. ● Attend the weekly, quarterly, and annual Leadership L10 Meetings. ● Own department rocks and drive to completion.

ENTERPRISE AI STRATEGY ● Own the company's enterprise AI strategy across software development, internal operations, sales, marketing, and client services. ● Lead the development team — including the Director of Engineering — into an AI-forward operating model. Modernize the software development lifecycle through AI: AI-assisted coding, automated testing, AI-driven code review, and agentic workflows so the team ships faster, with higher quality, and with leverage no traditional dev org has. This is not optional; it is the future of how this department operates and the central reason this seat exists. ● Partner with the CEO and CSO to define the long-term role of AI in The Mailworks' competitive positioning and product strategy. ● Drive a culture of experimentation and continuous learning across the technology organization and the broader company, normalizing AI tooling as a standard part of how work gets done. ● Evaluate emerging AI technologies for inclusion in future product and platform strategy. ● Own AI governance, security review, and documentation standards across all AI tools, workflows, and integrations adopted by the company. All documentation is maintained in the company's GitBook knowledge base. ● Ensure AI adoption translates to measurable business outcomes: development velocity, operational efficiency, product capability, or revenue impact.

CROSS-FUNCTIONAL LEADERSHIP & STRATEGIC PLANNING ● Collaborate with the leadership team to offer advice on what is possible within realistic timelines and oversee execution of corresponding tickets and rocks. ● Collaborate with the team to determine best methods and allocation of department resources to determine how to proceed with company initiatives. ● Provide guidance for long-term and short-term projects across all software platforms and IT infrastructure. ● Serve as the primary technology partner to Operations, Sales, Client Services, and Marketing for any software-driven, infrastructure-driven, or AI-driven initiative. ● Translate business needs into clear technical requirements and ensure the technology organization delivers against them. ● Maintain working knowledge of regulations and laws involving software development, IT, security, HIPAA, USPS regulations, and industry trends. ● Maintain a rolling 5-year technology plan covering software, infrastructure, security, and AI. ● Review, approve, and monitor third-party integrations and vendor relationships to ensure security and compliance standards are met. ● Ensure that all human resources on the team are maximized to capacity to maintain a highly functional, cost effective technology organization.

SOFTWARE DEVELOPMENT, SPRINT EXECUTION, & SYSTEMS ARCHITECTURE ● Own the Roadmap documents for all software applications ensuring future features are scoped and considered in daily execution. ● Own sprint planning, execution, and retrospective processes across all development teams. ● Drive accountability for ticket completion, story point velocity, and release commitments. ● Ensure development resources are allocated effectively across Portal (P1, P2), JOII, and internal initiatives. ● Collaborate with the Director of Product to prioritize backlog, align roadmap to business goals, and manage scope. ● Maintain consistent development standards, code review practices, and QA integration across all sprints and developers. ● Own the creation, maintenance, and continuous improvement of department documentation in the company's GitBook knowledge base, transitioning existing Wiki content into formal, auditable procedures. ● Research emerging trends for possible inclusion in future projects. ● Oversee the overall conception, mockups, and implementation of new system features and inter-workings. ● Consult with developers to ensure the best possible methods are applied in bug fixes and feature enhancements. ● Ensure bugs submitted are triaged with in-depth discovery and corrected in a timely manner to support company workload.

IT INFASTRUCTURE, SECURITY, & COMPLIANCE ● Own the company's IT infrastructure, security posture, and regulatory compliance programs end-to-end. ● Directly manage the Director of IT & Security, ensuring infrastructure health, network reliability, hardware lifecycle management, and helpdesk responsiveness meet company standards. ● Own the company's SOC 2 and HIPAA compliance programs, including audit readiness, evidence collection, policy maintenance, and remediation of findings. ● Own all IT, security, and compliance documentation in the company's GitBook knowledge base and ensure it remains current, auditable, and aligned with industry best practices. ● Embed security and compliance review into the sprint and release process. No deployment proceeds to production without documented compliance review. ● Train and hold engineering, product, and broader company staff accountable to secure coding standards, data-handling policies, and acceptable use policies. ● Own incident response, breach protocols, and disaster recovery planning. ● Manage vendor relationships for infrastructure, security tooling, and IT services. Negotiate contracts and ensure value delivered against cost. ● Ensure the technology organization operates within budget across software, infrastructure, security tooling, and AI investments.

Required Skills/Abilities: ● Proven ability to lead a combined software development and IT organization at the VP or CTO level. ● Demonstrated experience modernizing a software development lifecycle through AI: AI-assisted coding, automated testing, AI code review, and agentic workflows. Fluent in where the industry is going and how to bring a team there. ● Demonstrated experience owning enterprise AI strategy, including evaluation, adoption, governance, and measurable business impact. ● Deep experience with modern software development methodologies: Agile, Scrum, sprint-based delivery. ● Strong technical foundation in software architecture, APIs, platform development, cloud infrastructure, and network security. ● Experience owning SOC 2 and HIPAA compliance programs, including audit cycles and remediation. ● Demonstrated track record of leading both software engineers and IT operations professionals — distinct disciplines with distinct needs. ● Experience managing cross-functional product delivery across multiple platforms simultaneously. ● Excellent communication and leadership skills with the ability to drive urgency and alignment across departments without losing the team. ● Proficiency with project management, development tooling, IT service management, and security tooling. ● High accountability orientation: comfortable setting and holding aggressive commitments. ● Vendor management experience including contract negotiation and infrastructure budgeting.