Senior IT Engineer

About Attentive

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

Attentive is seeking a Senior IT Engineer to design and build systems that eliminate manual work, increase operational throughput, and scale internal teams efficiently.

You will build production-grade automation to directly impact how efficiently Attentive operates as we scale. Additionally, this role will co-own and help shape the automation infrastructure, ensuring it scales for users across the organization.

What You’ll Accomplish

• Build Automation That Replaces Work
  • Design and implement end-to-end automation that eliminates manual operational workflows across IT, Security, Revenue, Support, and other teams.
  • Build durable, observable systems.
  • Default to automation and agents over manual action and training.
• Operate AI-First
  • Use AI agents and workflows to replace manual decision-making and execution.
  • Treat AI as a production tool with clear guardrails and measurable outcomes.
  • Continuously identify opportunities to apply AI to reduce effort and cost.
• Build the Automation Platform
  • Help design the automation infrastructure so it scales beyond yourself and individual engineers.
  • Create reusable patterns, templates, and guardrails that enable others to build safely.
  • Prevent automation from becoming a bottleneck through thoughtful architecture, observability, and documentation.
• Drive Measurable Efficiency
  • Partner with stakeholders to identify high-cost workflows and quantify opportunity.
  • Measure success in hours eliminated, cycle time reduced, and cost avoided.
  • Scale what works; deprecate what doesn’t.

Your Expertise

You May Be a Strong Fit If You’ve

• Built automation or systems that materially reduced operational cost or effort
• Owned workflows end-to-end, including data ingestion, logic, execution, and monitoring
• Worked in IT, Business Systems, Data, Platform, or Automation Engineering
• Designed systems where correctness and reliability had real consequences

You Likely

• Think in systems, workflows, and failure modes
• Bias toward simplification and elimination of work
• Are comfortable operating autonomously with outcome-based goals

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

Key skills/competency

• IT operations
• Automation engineering
• System design
• AI agents
• Workflow optimization
• Scalability
• Reliability engineering
• Data ingestion
• Monitoring systems
• Security automation