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AI Summary
Design and implement an AI-powered customer engagement system to deliver personalized, data-driven outreach at scale. Partner with cross-functional teams to leverage product telemetry and predictive models to drive retention, expansion, and business value realization.
WHY WE'RE LOOKING FOR YOU
Retool has had immense growth in the last few years including landing a third of the Fortune 100. With 10,000+ customers and a shift toward scaled engagement, we need to build intelligent systems that engage every customer with personalized, data-driven outreach — at the quality of a 1:1 conversation but at the scale of our entire base.
We're looking for a Scaled Customer Programs Engineer who can design, build, and operate an AI-powered customer engagement system that uses product telemetry, business value data, and maturity signals to deliver customized messages, surface expansion opportunities, and drive retention and growth across every account — automatically.
WHO YOU'LL WORK WITH
This role will report into the GTM Programs organization and closely partner with Data Engineering, Product, Revenue Operations, and Sales leadership.
You'll be joining a broader team of Retools who are passionate about serving our customers, enjoy collaborating to build an incredibly innovative product, and partake in some occasional but well-intentioned sarcasm. If this sounds like you, we'd love to hear from you!
WHAT YOU'LL DO
- Build an AI-Powered Customer Engagement System: Design and implement an automated platform that delivers personalized, 1:1-quality engagement to every Retool customer using AI, generating customer-specific messages based on their product usage, business value realization, and maturity stage
- Develop Telemetry-Driven Customer Intelligence: Partner with Data Engineering to leverage product telemetry, usage patterns, and support signals to build a real-time view of customer health and expansion readiness. Perform daily deep-dive analysis on customer usage data to surface actionable signals for the GTM Programs team.
- Create & Operationalize Customer Momentum Scoring: Maintain and iterate on predictive models (e.g., churn prediction) in partnership with Data Engineering, regularly backtesting results, sharing findings with leadership, and identifying opportunities to increase model sophistication over time
- Deliver Personalized Business Value Communications: Build AI-driven workflows that generate and deliver tailored messages to Economic Buyers communicating the realized value from their Retool investment, benchmarking their outcomes against peers, and engaging them around next steps to drive additional ROI
- Identify & Engage Customer Cohorts at Scale: Use data science, AI-assisted tooling and segmentation to identify customer cohorts with shared characteristics (risk signals, growth opportunities, migration readiness) and design automated, targeted programs that address each cohort's specific needs
- Surface Expansion Offers & Retention Interventions: Build trigger-based systems that automatically surface contextually relevant offers — upsell packages, services engagements, migration assistance, premium support — to the right customer at the right moment based on behavioral and telemetry signals
- Integrate Across the GTM Tech Stack: Connect the engagement system with CRM, marketing automation, product analytics, and support platforms to ensure seamless data flow and coordinated customer touchpoints across all channels
- Measure, Iterate & Optimize: Measure the effectiveness of apps, automations, and engagement programs through usage tracking and outcome analysis. Iterate on tools and workflows based on feedback from GTM stakeholders and observed results.
- Leverage AI-assisted development tools including Retool's AI app generation capabilities to rapidly prototype and ship internal applications, automate workflows, and perform data analysis. Serve as a force multiplier for the GTM Programs team by translating business needs into working tools quickly
THE SKILLSET YOU'LL BRING
- Bachelor's degree in a quantitative or technical field (computer science, data science, economics, engineering, or similar) or equivalent professional experience in a technical GTM or operations engineering role.
- 3-5 years of experience in GTM engineering, marketing operations/technology, data engineering, or a similar role building data-driven customer engagement systems in a B2B SaaS environment
- Proficiency with AI-assisted development workflows including prompt engineering, AI code generation tools, and LLM-based automation. Ability to evaluate, iterate on, and maintain AI-generated outputs as well as build models from scratch.
- Working proficiency in Python, SQL, and JavaScript. Familiarity with data platforms (e.g., Snowflake, BigQuery) as a consumer/analyst rather than infrastructure owner. Experience with AI-assisted app development platforms is a strong plus
- Experience with CRM platforms (Salesforce), marketing automation tools (e.g., Marketo, Iterable, Outreach.io, Hubspot), and product analytics platforms (e.g., Amplitude, Mixpanel, Heap) with hands on experience designing multi-touch nurture sequences, dynamic content logic, and deliverability management.
- Familiarity with experimentation and applied statistics, comfortable designing A/B tests, understanding statistical significance, and structuring controlled experiments to measure program effectiveness.
- Demonstrated ability to build customer scoring models (health scores, propensity models, momentum scores) and translate them into automated engagement workflows
- Strong understanding of SaaS business metrics, net revenue retention, expansion rates, churn indicators and how customer engagement drives them
- Familiarity with B2B selling frameworks like Command of the Message and MEDDIC/MEDDPIC
- Comfortable operating at the intersection of data engineering, AI, and go-to-market strategy. You think in systems, not just scripts
- Excellent communication skills with the ability to explain technical systems and their business impact to non-technical stakeholders
- Self-directed builder who thrives in ambiguity, moves fast, and is energized by creating something new from scratch
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