Principal Technical Program Manager

About the Role

As a Principal Technical Program Manager at Attentive, you’ll lead complex, cross-functional initiatives across Security, Business Systems, and IT, including our enterprise AI transformation efforts. You’ll play a key role in bringing internal tools and systems to life end to end, from planning and execution through adoption and impact. This role is ideal for someone who thrives in ambiguity, drives alignment across teams, and is deeply focused on delivering meaningful business outcomes, ensuring the work not only ships on time but truly moves the company forward.

Who we are

The PMO at Attentive is responsible for managing the delivery of top company initiatives and helping guide them from planning all the way through execution and ultimately tracking the results / KPIs and reporting them. We drive delivery excellence across the enterprise to ensure business outcomes are achieved.

What You'll Accomplish

As a Principal Technical Program Manager, you will:

• Drive Delivery of Complex Programs: Ensure successful planning, execution, and delivery of Security, IT & Business Systems projects that require alignment both internally and across Engineering, Finance, and Go-To-Market (GTM) teams. 
• Own Projects End-to-End Within Your Domain: For programs that fall squarely in your area of expertise — whether AI transformation, security tooling, or improving a business systems workflow — step in as the project owner, not just the program coordinator. Drive the work alongside your engineering partner to ensure scope is defined, own accountability for the outcome, ensure day-to-day decisions are made, and remove blockers without waiting for someone else to take the lead. This is about operating as a practitioner, not just an orchestrator, when the work calls for it.
• Ensure Accountability Across Teams: Ensure all parties are aware of the work for which they are responsible, and partner with leads to map dependencies and sequence work effectively.
• Identify & Mitigate Risks: Work with your initiative leads to proactively surface and resolve risks and issues within teams, and escalate to leadership when necessary.
• Maintain Stakeholder Visibility: Maintain full visibility with leadership and other critical stakeholders throughout the planning, execution, and launch of projects, including raising escalations when needed.
• Track Results & KPIs: Ensure results and KPIs are defined, tracked, and consistently reported to measure program success.
• Conduct Post-Mortems: Lead post-mortems to assess lessons learned and implement improvements for future initiatives.

Team Level Execution Responsibilities

Support team level project execution and operations to ensure teams are positioned to successfully ship & maximize their velocity –adjusting depth and frequency based on project priority, complexity, timelines, and risks.

• Support Team-Level Objectives: Collaborate closely with Security, IT and Business Systems team leads to ensure alignment with team goals, milestones, and deliverables. Partner with Product and Design to ensure requirements are clear, prioritized, and achievable.
• Enable Technical Decision-Making: Partner with engineers to understand technical challenges, facilitate discussions, and help balance trade-offs between scope, quality, and speed.
• Coordinate Cross-Team Dependencies: Act as a bridge between engineering teams and other stakeholders, ensuring dependencies are well-documented and timelines are met.
• Optimize Agile Practices: Facilitate sprint planning, stand-ups, retrospectives, and other Agile ceremonies, ensuring the teams operate effectively and efficiently to plan and execute..
• Drive Process Improvements: Identify and address bottlenecks, inefficiencies, or gaps in engineering workflows. Implement solutions that enhance team productivity.
• Ensure Delivery Transparency: Maintain clear documentation and reporting for team progress, risks, and decisions, ensuring alignment across all stakeholders.

Your Expertise

• Experience: 10+ years of experience as an embedded, Technical Program Manager delivering impactful initiatives from planning through launch.
• Technical Expertise: Proven experience operating within the Security, IT, and/or Business Systems ecosystem—overseeing technical programs that ship new tooling, features and products to internal customers..
• Business Stakeholder Alignment: Demonstrated ability to align technical program execution with business objectives, ensuring smooth collaboration and synchronization between Finance, Revenue, Engineering, and other key partners.
• Exceptional Communication: Strong verbal and written communication skills, with experience tailoring messages for technical and non-technical audiences at all levels.
• Problem Solving & Execution: Analytical mindset with a focus on identifying solutions to challenges and delivering outcomes. Experience managing ambiguity and competing priorities.
• Agile Practices: Hands-on experience with Agile frameworks and methodologies, including Scrum, Kanban, or SAFe, and a track record of improving team workflows.
• Self-Starter: Thrives in a dynamic, fast-paced environment where autonomy, ownership, and proactive decision-making are key.
• Continuous Improvement: Committed to driving process improvements and leveraging feedback to enhance future program delivery.

You'll get competitive perks and benefits, from health & wellness to equity, to help you bring your best self to work.

For US based applicants:

• The US base salary range for this full-time position is $152,000 - $210,000 annually + equity + benefits
• Our salary ranges are determined by role, level and location

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