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Attentive® is the AI marketing platform for 1:1 personalization redefining the way brands and people connect. We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships. By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and loyalty through real-time behavioral insights.
Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries. Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in revenue for our customers.
With a distributed global workforce and employee hubs in New York City, San Francisco, London, and Sydney, Attentive’s team has been consistently recognized for its performance and culture. We’re proud to be included in Deloitte’s Fast 500 (four years running!), LinkedIn’s Top Startups, Forbes’ Cloud 100 (five years running!), and Inc.’s Best Workplaces.
About the Role
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.
At Attentive, you will have the opportunity to drive impactful technical programs, work directly with high-performing engineering teams, and influence how we deliver value to our customers. If you are passionate about managing complex technical programs and enabling teams to succeed, we’d love to hear from you!
What You’ll Accomplish
- As a Technical Program Manager, you will:
- Drive Delivery of Complex Programs: Ensure successful planning, execution, and delivery of customer facing products and features that require alignment across Engineering, Product, Design (EPD), and Go-To-Market (GTM) teams. Develop and publish release plans based on product requirements, technical challenges, operational needs, and GTM constraints.
- 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 EPD & GTM initiative leads to proactively surface and resolve risks and issues within teams before escalating to leadership when necessary.
- Maintain Stakeholder Visibility: Maintain full visibility with leadership and other critical stakeholders throughout the planning, execution, and launch of new products and features, 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 engineering managers and teams 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: 5+ years of experience as an embedded, Technical Program Manager delivering customer-facing software products and features from planning through launch.
- Technical Expertise: Proven experience operating within the product development ecosystem—overseeing engineering programs that ship new features and products—rather than post-sales implementations or solely internal platform/infra initiatives.
- GTM Alignment: Demonstrated ability to align technical program execution with Go-To-Market strategies, ensuring smooth collaboration and synchronization between Engineering, Product, Design, and GTM teams (Finance, Marketing, Strategy & Operations, Legal, Sales, Customer Success) to meet business outcomes.
- Cross-Functional Leadership: Demonstrated ability to lead across Engineering, Product, Design, and other teams to align on priorities and drive execution.
- 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 $130,000 - $175,000 annually + equity + benefits
- Our salary ranges are determined by role, level and location
#LI-NR1
Attentive Company Values
Default to Action - Move swiftly and with purpose
Be One Unstoppable Team - Rally as each other’s champions
Champion the Customer - Our success is defined by our customers' success
Act Like an Owner - Take responsibility for Attentive’s success
Learn more about AWAKE, Attentive’s collective of employee resource groups.
If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.
At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
