Director / VP Engineering · CTO | Building AI-First, Agentic Engineering | Scaled teams 0→1 and 1→100 | ex-Microsoft

Bengaluru, Karnataka, India

Bengaluru, Karnataka, India

Bengaluru, Karnataka, India

Bengaluru, Karnataka, India

Bengaluru, Karnataka, India

Bachelor of Engineering, Information Technology
National Institute of Technology Karnataka
LFS, Hospet
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Download Tal BossDirector / VP Engineering · CTO | Building AI-First, Agentic Engineering | Scaled teams 0→1 and 1→100 | ex-Microsoft
I am a technology leader with 20 years of experience spanning two startup co-founding roles, senior leadership at Microsoft, and scaling engineering organizations from zero to 100. I specialize in building high-ownership, psychological-safety-driven teams that prioritize customer outcomes over vanity metrics. My current focus is on AI-first engineering and developing open-source infrastructure for hybrid human-AI agent collaboration. Whether architecting platforms or designing organizational frameworks, I am passionate about driving technical vision and operational excellence for ambitious, high-growth organizations.
Bengaluru, Karnataka
Director of Engineering at Affinidi, May 2023 - Nov 2025 · 2 yrs 7 mos, Bengaluru, Karnataka, India, Affinidi (part of Lemmatree group) is revolutionizing data ownership champinoing the concept of "Holistic Identity" that encompasses the complete spectrum of discovering, collecting, sharing, storing, and even monetising one’s own personal data in the digital world. At Affinidi, I played a key role in integrating a Bengaluru-based engineering team into a globally distributed organization spanning Berlin, Ukraine, Singapore, and India. My primary responsibility was leading the Data Engineering team based in Berlin, where I drove the development of foundational data infrastructure and analytics tools to support both internal stakeholders and external customers. In addition to my data engineering leadership, I actively contributed to the open-source ecosystem by leading the development of core Web3 capabilities through our Dart libraries implementing several specifications around Verifiable Credentials, Selective Disclosures and DIDs. More recently, I took on the leadership of the Developer Experience team, focusing on building intuitive and impactful tools that simplify Web3 adoption for our customers. Beyond engineering, I worked closely with the India Business team to drive strategic initiatives, including testing various Web3 hypotheses in the Indian e-commerce market — helping shape product direction and assess product market fit.
Director Of Engineering at GoodWorker, Aug 2021 - May 2023 · 1 yr 10 mos, Bengaluru, Karnataka, India, Goodworker (part of Lemmatree group) is focused on becoming India’s largest full-stack, blue-and-grey collar recruitment and learning platform. It is a unique combination of a hungry tech startup with a genuine social impact agenda. I joined Goodworker at its inception, contributing from the earliest stages when company values and strategy were still being defined. I played a pivotal role in scaling the engineering organization to over 80 members, establishing mature processes and driving operational excellence. As the head of the Platform organization, I championed a platform-first mindset across the company, laying a strong architectural foundation and building core capabilities that enabled business teams to deliver advanced offerings with greater reliability and consistency. This included leading initiatives in Data Engineering, DevOps, Core frameworks, and Standardized Product Capabilities. As a member of the core leadership team, I was deeply involved in shaping the company’s business strategy, organizational goals and structure, hiring practices, people policies, product direction, technology vision, and budget planning. Our mission was to transform the blue-collar job market through innovative solutions such as live virtual hiring days, automated assessments, personalized skilling recommendations, and Web3-compliant certifications. Following Goodworker’s shutdown, a select few of us were absorbed into Affinidi (a sister company within the Lemmatree group) in May 2023.
Principal Engineering Manager at Microsoft, Jan 2019 - Jun 2021 · 2 yrs 6 mos, Bengaluru, Karnataka, India, At Microsoft, I joined a newly formed team tasked with rebuilding Outlook for mobile web from the ground up—starting from first principles and core user jobs for this endpoint. This initiative involved rethinking data analysis, application architecture, performance optimization, reusability across M365 products, reliability metrics, and monitoring infrastructure. We were among the first teams in the Outlook ecosystem to adopt a bottom-up, data-driven culture and one of the earliest mobile web teams across M365 to prioritize accessibility as a core part of feature development. The team was initially facing widespread discontent, and I played a key role in turning it around—mentoring engineers, fostering psychological safety, and cultivating a culture of learning, experimentation, and collaboration. We evolved into an aspirational team that now leads mobile web efforts within Microsoft IDC and beyond. The refactored Outlook launched to strong user reception, with a 15% increase in monthly active users (MAU) and a 30% year-over-year MAU growth. In addition to engineering leadership, I contributed to strategic initiatives aimed at introducing a new generation of internet users in emerging markets to productivity tools like Outlook. I also helped build a vibrant community of web developers across Microsoft IDC by being a key community builder, organizing and planning it's activities.
VP, Head of Platform & Infra at NestAway Technologies Pvt Ltd, May 2016 - Oct 2018 · 2 yrs 6 mos, Bengaluru, Karnataka, India, Headed the Platform & Infra division with the following teams: Payments & Accounting Infra, Microservices Infra, Communications Infra, E-Commerce Platform, Security, DevOps and Data Infra. Helping with decisions on all major technology and architectural choices in the company. Architected and implemented systems that handled tens of millions of events on a daily basis. Involved in setting up Eng Org Structure, Hiring processes and Diversity Initiatives. Scaled the Platform & Infrastructure team from 3 to 35 top notch engineers managers and architects.
CoFounder, CTO at Kyash, Sep 2012 - Apr 2016 · 3 yrs 8 mos, Bengaluru, Karnataka, India, Simplest way to collect physical cash for online transactions Country wide network of 30,000+ shops in 5000+ pincodes. Part of Village Capital accelerator program 1.5Lakh+ total transactions done. Order2cash flows for companies focused on BPL & rural service delivery Mentored several interns from top tier institutes.
Bachelor of Engineering, Information Technology, National Institute of Technology Karnataka
LFS, Hospet