About LeadSimple LeadSimple builds modern operations and communication software for residential property management companies. We serve thousands of customers and are expanding rapidly into enterprise workflows, automation, and AI-powered operations management.
Role Overview LeadSimple is seeking a Technical Solutions Architect with deep Twilio expertise to guide the architecture and implementation of our communication platform. This role sits above a Senior Engineer level and will be responsible for designing scalable solutions using Twilio APIs, advising engineering teams on best practices, and ensuring our products meet enterprise-grade reliability and performance standards.
Responsibilities
Serve as the principal architect for Twilio-powered solutions, designing and implementing scalable, reliable communication systems.
Provide technical leadership and mentorship across engineering teams, elevating domain expertise in telephony, messaging, and workflow automation.
Collaborate with Product and Engineering leadership to translate customer requirements into robust technical designs.
Evaluate and integrate new Twilio features and related technologies to enhance our platform’s capabilities.
Troubleshoot and resolve complex technical issues across the stack, ensuring high availability and performance.
Requirements
10+ years of software engineering experience with a strong background in designing and building distributed systems.
Expert-level knowledge of Twilio’s API suite (voice, SMS, video, programmable messaging) and related communication protocols.
Proven experience architecting large-scale SaaS solutions with high reliability and security requirements.
Strong coding skills in languages such as Ruby, Python, or JavaScript, and familiarity with frameworks like Rails and React.
Ability to communicate complex technical concepts to both technical and non-technical stakeholders.
Nice to Have
Experience integrating Twilio with CRM or property management systems.
Background in telecommunications, real estate tech, or workflow automation platforms.
Knowledge of other communications platforms (e.g., SendGrid, Nexmo) and AI-driven messaging systems.
Why LeadSimple
Impactful role shaping the technical direction of a growing vertical SaaS company.
Collaborate directly with senior leadership and a high-performing engineering team.
Remote-first culture promoting autonomy, ownership, and professional growth.
Competitive compensation, equity opportunities, and a mission-driven product focused on modernizing property management operations.
Similar Jobs
What you need to know about the Chicago Tech Scene
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
