Dragan M.-Fractional CTO · Engineering Leader · AI-First SaaS at Scale
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Experience
Fractional CTO
Calibra — Synaptik GmbH
Fractional, project-based technical leadership for an early-stage health-tech platform.
- Own technical architecture and the development operating model: engineering standards, code review and repository governance.
- Lead security posture, access-control design and GDPR-related technical decisions alongside the company’s data-protection process.
- Evaluate and recommend external development partners, vendors and tooling; provide technical representation in accelerator and partnership conversations.
Director of Engineering
Smartcat
Engineering roadmap, talent management and customer-facing delivery across a 50+ engineer organization, with three concurrent mandates: OKR product delivery, Customer Improvements and Customer Care.
- Transformed the organization from static, fixed teams into a flexible pod-based structure, allocating engineers by business priority rather than legacy team boundaries.
- Designed and rolled out a three-track operating model (Customer Care / Customer Improvements / OKRs) with structured rotation, making customer retention a first-class engineering priority.
- Stood up Customer Improvements as a properly funded track, resourced to clear a backlog of churn-risk items tied to revenue at risk.
- Drove engineering across four product OKRs: Smart AI, PDF pipeline, SmartWords/Marketplace and Website Translation.
- Introduced semi-annual performance reviews based on peer feedback and calibration circles, giving engineers a structured, transparent career path.
- Led hiring and restructuring to build an AI-first engineering team, and integrated outsourced contractors into pods with clear delivery accountability.
Program Manager
Quipu GmbH
- Led efforts to attract and retain talent for strategic roles, supporting organizational growth.
- Identified business-process improvements and implemented strategies that raised operational efficiency.
- Worked with senior management and external consultants to establish a company-wide agile culture.
Software Engineering Manager
SOCi, Inc.
- Helped launch the first AI-powered solution in MarTech (April 2023), establishing SOCi as an early mover in the market.
- Led engineering teams designing, building and deploying solutions across five products; brought two new products to market.
- Tripled the size of the engineering organization while improving employee retention through mentoring and career development.
- Implemented agile development practices and streamlined cross-team communication during SOCi’s growth to Centaur status.
Success Engineering Manager
H4
H4 is a digital platform for creating and analysing documents.
- Led 20 engineers across several teams customizing the platform per client use case, reporting to an ex-Google VP of Engineering.
- Ran business analysis on client use cases and coordinated the release process.
Development Team Lead
H4
- Delivered a web-based, microservices CLSM platform; managed the OKR process and authored technical specifications for platform modules.
Technical Lead / Engineering Manager
Quipu GmbH
Nearly 12 years building banking software for the ProCredit group, progressing from Senior Software Engineer to Technical Lead (Apr 2014 – Jul 2019), with Project Manager assignments in 2014 and 2018.
- Defined the architecture for, and led the team delivering, an N-tier accounting system covering IFRS for ProCredit banks.
- Architected and developed an N-tier core banking system, implemented in ProCredit banks in Germany, Ghana, Bosnia, Kosovo, Albania and North Macedonia.
- Integrated core banking with payment systems and e-banking; owned database design and optimization (C#, .NET, Microsoft SQL Server).
- Project-managed e-banking upgrades for ProCredit Bank Macedonia, Kosovo and Albania, and the accounting system rollout in Macedonia.
Chief Software Architect / Software Developer
Semos
- Developed an accounting and warehousing application on .NET and SQL Server.
- Implemented SharePoint solutions for document-lifecycle management for the Government of the Republic of Macedonia.
Industry experience
See where this freelancer has spent most of their professional time.
Experienced in Information Technology, Banking and Finance, Government and Administration, Advertising, and Healthcare.
Business area experience
See which departments and functions this freelancer has contributed to most.
Experienced in Information Technology, Product Development, Project Management, Human Resources, and Customer Service.
Summary
Fractional CTO, Calibra: fractional, project-based technical leadership for an early-stage health-tech platform, owning technical architecture, the development operating model, security posture and GDPR-related technical decisions. 24 years in software, from developer and chief software architect to Director of Engineering, most recently leading a 50+ engineer organization at an AI-first SaaS company. Helped launch the first AI-powered solution in MarTech, tripled an engineering organization, and spent nearly 12 years on ProCredit banking software, including a core banking system implemented in six countries.
Skills
- Strategy & Execution: Engineering Roadmaps And Okr-Driven Delivery, Seen Through From Strategy To Release.
- Organizational Design: Pod-Based Operating Models That Move Engineers To Where The Business Needs Them.
- People & Talent: Hiring, Performance Calibration And Career Development For Ai-Native Engineering Teams.
- Architecture & Cloud: Resilient Systems On Azure, Aws Or On-Premises, With Gdpr-Native, Security-First Design.
- Regulated Domains: Banking, Accounting (Ifrs) And Government Document-Lifecycle Systems.
Languages
Education
Faculty of Electrical Engineering (Elektrotehnički fakultet)
BS · Software Development · Skopje, North Macedonia
Certifications & licenses
AZ-300 Microsoft Azure Architect Technologies
Agile Scrum Master
Statistics
Experience
Global experience
Expertise
Qualifications
Frequently asked questions
Have questions? Find more information here.
Dragan is based in Skopje, North Macedonia and prefers 100% remote projects.
Dragan speaks the following languages: Macedonian (Native), English (Advanced).
Dragan has at least 24 years of experience. During this time, Dragan has worked in at least 8 different roles and for 6 different companies. The average length of individual experience is 3 years. Note that Dragan may not have shared all experience and actually has more experience.
Based on recent experience, Dragan would be well-suited for roles such as: Fractional CTO, Director of Engineering, Program Manager.
Dragan's most recent position is Fractional CTO at Calibra — Synaptik GmbH.
In recent years, Dragan has worked for Calibra — Synaptik GmbH, Smartcat, Quipu GmbH, SOCi, Inc., and H4.
Dragan is most experienced in industries like Information Technology, Banking and Finance, and Government and Administration. Dragan also has some experience in Advertising and Healthcare.
Dragan is most experienced in business areas like Information Technology, Product Development, and Project Management. Dragan also has some experience in Human Resources and Customer Service.
Dragan has recently worked in industries like Information Technology, Advertising, and Banking and Finance.
Dragan has recently worked in business areas like Information Technology, Product Development, and Project Management.
Dragan holds a Bachelor in Software Development from Faculty of Electrical Engineering (Elektrotehnički fakultet).
Dragan has 5 certificates. Among them, these include: AWS Certified Cloud Practitioner, AWS Cloud Quest: Cloud Practitioner, and AZ-300 Microsoft Azure Architect Technologies.
Dragan is immediately available part-time for suitable projects.
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Calculated based on our freelancers’ daily rates as of 13 Nov 2026. Actual rates may vary depending on seniority level, experience, skill specialization, project complexity, and engagement length.
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