Bojan Rajkovic

Hi, I’m Bojan. I’m a technology generalist, with interest areas in engineering systems & culture, API design, and performance engineering.

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About Me

I build engineering organizations that move the numbers the business actually tracks — not by accident, but by design. I believe in value-stream aligned teams where engineers own their products and understand the business they operate in, rather than working as passive order-takers. My teams are consistently highly engaged, care deeply about their customers, and it shows in their results.

I’m T-shaped: comfortable leading organizations of 60+ engineers, diving deep into architecture and code, building platforms, designing systems, and working cross-functionally with product, operations, and executives. I’ve been employee 30 at a pre-Series A startup that was acquired by Microsoft, built the business intelligence that powered fundraising, and scaled engineering organizations that underpin ~$700M in annual recurring revenue.

I’m also an active builder — I stay technical through experimentation, open-source contributions, and voracious reading. I co-authored SimpliSafe’s AI strategy: I believe agentic AI will be transformative for how we build software, and that strong engineering platforms become more important, not less, in the AI age.

Skills

Organizational design · Engineering strategy · AI strategy · LLM & agentic systems · AI-augmented SDLC · Platform engineering · Cloud architecture (AWS, Kubernetes) · Event-driven systems (Kafka, DynamoDB) · APIs and API design · M&A integration

Experience

VP, Engineering — Customer Lifetime Value at SimpliSafe

From March 2026 to Present

  • Promoted to VP to own customer lifetime value: a ~60-engineer organization covering activation and adoption, engagement and retention, professional monitoring service delivery, and the iOS, Android, and web apps, paired with a product organization that owns the same customer-lifetime-value domain
  • Restructured the organization into value-stream teams aligned to customer lifecycle stages, scaling what worked in monitoring (employee engagement 15–30 points above company average) across the rest of the portfolio
  • Co-authored the company's AI strategy covering customer-facing AI and AI-augmented engineering, and began rolling out agentic development tooling across the organization

Technologies: JavaScript/TypeScript, Swift/Kotlin, AWS (ECS/EKS, DocumentDB, DynamoDB, etc.), Kafka, OpenTelemetry, LLM & agentic tooling

Sr. Director, Software Engineering at SimpliSafe

From May 2021 to March 2026

  • Built the engineering organization behind SimpliSafe's professional alarm monitoring line of business, growing it from 5 engineers to 27 and partnering with product management, UX, and a 165-person operations organization on everything from site standup to hiring. Surveyed engagement scores have consistently run 15+ points above the company average, and 30+ above in key areas of leadership and management. Promoted from Principal Software Engineer to Director to Sr. Director along the way.
  • Improved unit economics for the Active Guard Protection outdoor monitoring business through a next-generation specialist UX: a 14-percentage-point gain in gross margin, 28% faster handle time, and 22% lower cost to serve
  • Led the design and delivery of a new alarm platform that drove a 39% reduction in handle time, 27% reduction in dispatch rate, 33% reduction in inbound calls, and NPS improvements for the core intrusion monitoring business
  • Launched SimpliSafe's Live Guard Protection (now Intruder Intervention) live video monitoring capability from scratch, designing the privacy and trust & safety framework: event-driven access controls tied to alarm lifecycle, specialist identity and authentication, and on-camera recording of specialist sessions for customer auditability
  • Established value-stream aligned teams with strong product partnerships, turning a previously fractious engineering-product relationship into one ICs praise unprompted; each team delivers toward clear customer value goals with a dedicated product partner
  • Built a common microservice platform that reduced new service standup time from weeks to hours, enabling a single unified on-call rotation across the entire organization because every team runs the same stack
  • Developed a talent pipeline that produced a Distinguished SWE (now advising Sr. Directors and the CTO), 2 Sr. Engineering Managers, and multiple Staff SWEs
  • Partnered with product, business, operations, and executives to define strategy and roadmap for the professional monitoring business, and drove systems design improvements across the broader engineering organization
  • Internal leader in applied AI: developed agentic workflows for engineering productivity, delivered company-wide training on AI-augmented development, and helped select the enterprise tooling

Technologies: JavaScript/TypeScript, AWS (ECS/EKS, DocumentDB, DynamoDB, etc.), Kafka, OpenTelemetry

Director, Systems Architecture at First Republic Bank

From February 2019 to April 2021

  • Served as chief architect for all API work on a strategic core banking replacement program spanning 10+ major workstreams and 50+ projects; led a team of 4 that provided horizontal solution architecture and API expertise to hundreds of engineers
  • Led greenfield enterprise implementations of API gateway (Apigee) and real-time event streaming (Kafka) infrastructure, owning the architecture for both platforms
  • Worked with VP- and SVP-level business technology leaders across lines of business to drive technology roadmaps and identify opportunities for reuse
  • Led enterprise efforts on software quality and SDLC compliance, and built developer guidance on application architecture, non-functional requirements, software patterns, and API design
  • Drove knowledge management improvements across the engineering organization, including transitioning from SharePoint to Confluence and establishing workflow guidelines for Jira

Technologies: Kafka, Apigee, .NET Core, JavaScript/TypeScript, OpenShift/Kubernetes, AWS

Principal Software Engineering Manager at CareStack

From October 2018 to December 2018

  • Led a tribe of 17 engineers working on the front office portions of CareStack's dental practice management system, organizing the team into multiple squads with product focus areas
  • Implemented engineering systems and culture changes that improved throughput, code quality, and developer quality-of-life
  • Led a release that fixed dozens of bugs, stabilized the product, and delivered a 1000x performance improvement in a critical billing component
  • Short tenure resulted from a disagreement between the CEO and the entire senior engineering staff about best practices

Technologies: Azure, SQL Server, .NET, TypeScript/JavaScript

Sr. Software Engineering Manager at Microsoft

From July 2016 to September 2018

  • Planned and executed the post-acquisition transition of Xamarin services and teams into Microsoft, migrating half a dozen critical services (sales pipeline, activation/DRM, SSO) and finding landing spots for team members across the new organization
  • Joined the Xamarin Workbooks team as a senior contributor after winding down Xamarin commerce operations; drove an early bet on WebAssembly-based evaluation that anticipated the browser-based development environments StackBlitz and CodeSandbox later made mainstream
  • Developed engineers who went on to significant roles: TypeScript compiler team, Sr/Staff SWEs at GitHub, a startup co-founder, and a Principal SWE Manager at Microsoft
  • Worked with release engineering to maintain and improve the build systems behind day-to-day development and releases

Technologies: Xamarin, .NET, Cocoa/AppKit, Android, TypeScript, WASM, Azure DevOps

Engineering Manager/Operations Lead at Xamarin

From February 2012 to July 2016

  • Joined as employee ~30 (pre-Series A) and grew with the company to a few hundred employees through Microsoft acquisition. Led the team responsible for most of Xamarin's customer-facing infrastructure: Store, Component Store, Single Sign-On, and Licensing. Reported directly to the CEO.
  • Scaled and optimized critical licensing and billing infrastructure to serve billions of API calls per month on 2-3 EC2 instances, stabilizing a platform whose reliability had become a running joke at developer conferences
  • Built a business intelligence platform that powered Series C fundraising, enabling cohort-based analysis of ARR, LTV/CAC, and customer behavior
  • Transformed the sales quote process from a painful manual workflow to a one-click Salesforce integration, reducing customer quote fulfillment time to under 30 seconds
  • Redesigned licensing on both the server and client side: more robust client licensing, better performance, and far easier debugging
  • Participated in Microsoft acquisition due diligence, providing detailed knowledge of sales infrastructure and customer-facing systems

Technologies: .NET, AWS, Azure, Salesforce, GTK+, JavaScript, Redis, SQL Server, MySQL

Software Developer/Consultant at Cane Systems

From August 2010 to February 2012

  • Worked as an on- and off-site consultant in the telecommunications industry, focusing on operations support systems (OSS) and other network/physical plant management projects
  • Developed a new system for tracking fixed assets and points of presence, including rich mapping and navigation capabilities built in
  • Built solutions to collect and manage hardware inventory and hardware status from native systems that did not integrate into centralized OSS

Technologies: Java, PostgreSQL, Oracle DB, Cisco/Juniper

Software Developer at Air Power Analytics

From February 2009 to February 2012

  • Rewrote a sensor metrics collection platform from the ground up, delivering multiple order of magnitude improvements in polling and memory efficiency
  • Built infrastructure to securely deliver collected data back to central server from each on-site location, and pre-process it for ETL
  • Built two front-ends, a "live" frontend that could run on any computer on the same network as the collection platform and view live data, and a reporting frontend that worked off ETLed data
  • Evaluated and selected hardware rugged enough to run the metrics collection platform in industrial plants

Technologies: Java, C#, ActionScript/Flash, PHP, Oracle, Serial Protocols

Awards and Publications

  • SimpliSafe Inventor of the Year, 2023

  • US Patent 12,073,706: “Consolidated alarm screen” (August 2024)

  • US Patent 12,250,496: “Communication sessions with autonomous security device preparation” (March 2025)

  • US Patent 12,444,293: “Alarm platform with aggregated alarm events” (October 2025)

  • US Design Patent D1,087,116: “Display screen or portion thereof with a graphical user interface” (August 2025)

  • US Design Patent D1,087,115: “Display screen or portion thereof with a graphical user interface” (August 2025)

  • Canadian Patent 3,253,554: “Managing remote access to image capture devices” (December 2025)

  • Multiple additional pending patent applications from my work at SimpliSafe

Contacting Me

The best way to reach me re: hiring is via email. You can also message me on LinkedIn, or find my Twitter, etc.