Benny O.

Tech Leadership is a community of longtime, new and aspiring technology leaders. Our mission is to help each other learn through conversations and sharing ideas. -Co-organise a technology leadership community (~4,400 members), facilitating learning and leadership development through shared experience.

Matchbox Solutions is a distributed consultancy that partners with scale-ups to build software, scale engineering teams, and mature delivery practices. As Director and Principal Consultant, I was responsible for day-to-day business operations, business development, and acting as an embedded engineering and delivery leader across client engagements. Selected Engagements & Responsibilities: -Interim Head of Engineering — African Healthtech: -Appointed as Interim Head of Engineering during a period of rapid growth and delivery pressure. -Led and grew a multidisciplinary engineering team (~20 direct reports). -Mentored engineers and leaders on engineering standards and best practices, including testing strategy, branching strategy, and solution design. -Worked closely with Product Management and regularly stepped in to coordinate and unblock production releases. -Stabilised delivery and enabled sustained progress within the first 6–9 months. -Delivery Manager — Fintech (Credit Scoring for the Informal Sector): -Served as Delivery Manager for a credit scoring module aimed at the informal market. -Maintained steady delivery momentum by clarifying requirements between the client and consulting engineering teams. -Balanced delivery expectations with technical constraints, ensuring realistic timelines and predictable outcomes. -Talent & Hiring Partner (Multiple Clients): -Supported clients as a talent partner, helping shape hiring strategies for technical roles. -Advised leadership teams on role design, team composition, and hiring quality. -In some cases, assisted directly with identifying and assessing senior technical talent. This role required operating comfortably across engineering leadership, delivery execution, and organisational design, often in ambiguous and fast-moving environments.

Over was a high-growth mobile design startup, at one point a top-ranked and highlighted app on the Apple App Store, and later acquired by GoDaddy. -Contributed to scaling the organisation from approximately 20 to 70 employees, supporting rapid growth while maintaining delivery capability. -Built and owned the company’s hiring infrastructure, including selecting and implementing Greenhouse as the applicant tracking system, and regularly evaluating additional tools to improve sourcing and reach. -Designed and structured the employee referral programme, helping the organisation better leverage internal networks for high-quality hires. -Created the end-to-end interview and decision-making process, defining clear roles for interviewers and assessors, with hiring managers owning final decisions and CEO-level veto where appropriate. -Partnered closely with leadership and line managers to align hiring priorities with delivery needs and organisational readiness. -Remained hands-on throughout the process, actively sourcing, interviewing, and helping identify top technical and non-technical talent.

This role was created in response to increasing technology demand and a growing challenge in attracting engineering talent in a competitive market. As a traditional asset manager, Allan Gray was competing with global technology companies for a relatively small pool of skilled engineers. -Owned technology talent attraction and developer relations initiatives, working closely with marketing to shape Allan Gray’s employer brand for engineering. -Took a highly hands-on approach to sourcing and assessment, personally conducting ~500 first-round interviews within the first six months of the role. -Initiated and established technology hiring in Johannesburg, expanding Allan Gray’s hiring footprint beyond its existing locations. -Actively represented Allan Gray within the local tech ecosystem by speaking at meetups, engaging with universities, and advocating for how software was built internally. -Designed and ran internship programmes and collaborated with well-known coding bootcamps to create accessible entry points into the organisation. -Defined and implemented an internal employee referral programme, creating new, scalable sourcing channels beyond traditional recruitment methods. -Built and sustained a long-term technical talent pipeline through ongoing engagement with universities and early-career programmes.

-Worked as a backend software developer on the Business Process Management (BPM) team, responsible for core processing within Allan Gray’s retail systems. -Built and maintained mission-critical backend services using Scala, working in a functional programming paradigm. -Implemented and evolved business process flows, transaction handling, and integrations with downstream systems. -Collaborated closely with a cross-functional team consisting of a Product Owner, analysts, and a development team of ~6–7 engineers. -Operated in a production-critical environment where correctness, reliability, and system stability were essential. Growth & Development: -Intentionally stepped back into a pure IC role after prior leadership experience, using the opportunity to deepen technical focus. -Learned to lead without authority, allowing space for the designated team lead to operate while continuing to contribute meaningfully as a senior engineer. Technology: - Scala

This role was introduced to improve delivery predictability, strengthen collaboration between technology and business, and build stronger team cohesion as engineering practices matured. -Worked as an Agile Coach across two teams: the Continuous Delivery team and the Business Intelligence (BI) team. -Coached teams and leaders on applying agile practices in a way that supported predictable delivery and healthier team dynamics, rather than rigid process adherence. -Helped teams adopt and refine best practices appropriate to their context, improving flow, ownership, and collaboration with business stakeholders. -Supported teams through different stages of maturity, adjusting focus based on team needs and dynamics. Approach & Philosophy: -Evolved from a traditionally Scrum-centric approach toward a context-driven model, balancing pragmatism with established practices. -Placed greater emphasis on people and team cohesion for teams in forming or storming phases, recognising that delivery follows stability. -Shifted focus toward delivery outcomes and execution as teams moved into norming and performing stages, tailoring practices accordingly.

Led engineering delivery for Allan Gray’s Retail E-Commerce platform, supporting ongoing delivery in a highly regulated financial environment. -Acted as Lead Developer for a multidisciplinary team of ~20 people, including product, QA, analysts, and three engineering squads. -Held direct responsibility for nine developers, combining performance management, mentoring, and technical leadership. -Balanced people leadership with hands-on technical contribution, including design, code reviews, and production support. -Worked closely with Product Owners, analysts, and business stakeholders to coordinate delivery. Technical & Delivery Leadership: -Helped lift engineering standards across the team by introducing and reinforcing stronger design patterns, Domain-Driven Design (DDD) principles, and more disciplined coding practices (e.g. improved use of GoF patterns). -Contributed to the team being recognised internally as one of the top-performing engineering teams, combining delivery reliability with code quality. Technology: -Microsoft stack: C#, SQL Server, LINQ, NHibernate -Early adoption of functional programming concepts in C#, including heavy use of lambdas and expressive querying

-Worked as a software developer on the Retail E-Commerce team, contributing to core customer-facing systems. -Built and maintained backend and frontend functionality supporting transactional workflows and production operations. -Gained early exposure to regulated financial systems and production-critical environments. -Established a strong technical foundation that later supported progression into technical leadership roles Technology: -Microsoft stack: ASP.NET, C#, SQL Server, LINQ, NHibernate -Early adoption of functional programming concepts in C#, including heavy use of lambdas and expressive querying

https://www.imdb.com/name/nm2635395/

Global Vision built channel marketing software used by large organisations, including global brands such as Diageo. I worked on Adora, the company’s next-generation channel marketing platform. -Served as Lead Developer within a squad of five, providing technical leadership through influence rather than formal line management. -Contributed as one of several lead developers within a larger Adora engineering group (~20 people), reporting to the Head of Engineering and collaborating closely with Product. -Played a key role in establishing and reinforcing strong engineering practices across the team, including Domain-Driven Design (DDD), Test-Driven Development (TDD), Continuous Integration, and disciplined use of design patterns. Adora Query Language (AQL): -Designed and implemented the Adora Query Language (AQL), a domain-specific query language created to abstract data access across multiple heterogeneous data sources. -Enabled a single query model to retrieve and combine data from: -relational databases -a data warehouse structured as a star schema -Microsoft CRM -Took inspiration from ORM query languages such as Hibernate Query Language (HQL) and LINQ, applying similar principles to a broader, multi-source integration problem. -Reduced coupling between the application and underlying data representations, allowing data sources to evolve independently without breaking consuming systems. Approach & Impact: -Known within the team for strong systems thinking and for introducing novel technical ideas in a pragmatic, understandable way. -Frequently explained complex concepts—such as language parsing and Abstract Syntax Trees (ASTs)—using simple analogies, helping teams rally around and adopt new approaches. -This work reinforced a long-term focus on designing for change, maintainability, and clarity of intent.

DVT is a software development consultancy delivering solutions across multiple industries and client environments. -Worked as a software developer across a range of client projects, including engagements with a large international bank, major South African retailers, and an asset management firm. -Contributed primarily to backend development, with occasional frontend work depending on project needs and client context. -Built and maintained production systems using the Microsoft .NET stack, including C#, VB.NET, and SQL Server. -Operated largely within waterfall delivery environments, gaining exposure to structured, plan-driven development approaches. -Attempted early adoption of Scrum practices within one team, introducing agile concepts in an otherwise traditional delivery setting. -Worked predominantly from consultancy offices, collaborating with teams across multiple client engagements. Key Takeaway: -Gained broad exposure to different business domains and problem spaces, helping build adaptability and the ability to ramp up quickly in unfamiliar contexts.

Co-founded a sports nutrition and nutraceuticals distribution business supplying products to a major retail chain. -The business secured the distribution rights for Reflex, a well-known international sports nutrition brand (rights secured by a co-founder). -Helped establish the company operationally, supporting marketing, distribution, and retail engagement. -Set up and managed the company website, contributing to early brand presence and product awareness. -Led marketing and in-store initiatives, including calling on retail outlets and educating sales staff on product positioning and benefits. -Represented the company at exhibitions and public events (e.g. major sporting and lifestyle expos), engaging directly with customers and partners. Key Takeaway: -Gained early experience in building and operating a small business, understanding retail dynamics, and translating product value to non-technical audiences.

Worked on enterprise legal and conveyancing software in a structured delivery environment, taking on multiple roles as the organisation evolved its approach to software delivery. -Contributed as a software developer on a product built using Rational Unified Process (RUP), operating in a heavily structured, plan-driven delivery model. -Supported quality and delivery through test analysis and project coordination responsibilities. Following the termination of a major product initiative due to delivery challenges, participated in a shift toward alternative delivery approaches. -Trained as a Scrum Master as Korbitec became an early adopter of Scrum within South Africa. -Facilitated early Scrum practices and supported teams during the transition from heavyweight process toward more lightweight, iterative delivery. -Gained first-hand exposure to both traditional waterfall-style methodologies and early agile practices. Key Takeaway: -Developed a grounded understanding of why delivery approaches succeed or fail, shaped by direct experience with both heavyweight and lightweight methods early in my career.