Head of Engineering

About Upper Hand Upper Hand is a vertical SaaS platform serving youth sports facilities and clubs across North America. We provide sports management software that helps facilities run their operations, from scheduling and registration to payments and member management. We’re at an exciting inflection point – scaling our customer base while modernizing our technical infrastructure to support sustainable growth.

The Role We’re looking for a Head of Engineering to lead our distributed engineering team through a period of strategic technical evolution. Reporting to our executive team, you’ll be responsible for scaling our Ruby-based SaaS application and business intelligence suite, managing ongoing cloud infrastructure modernization, and balancing the constant tension between delivering customer value and paying down technical debt.

This is a hands‑on technical leadership role that requires strong technical skills at the senior manager level, combined with the ability to lead, mentor, and coordinate an international team split between Ukraine and Indianapolis.

Critically, you’ll serve as a bridge between engineering and the executive team – translating business objectives into technical roadmaps, and explaining technical decisions in terms of business impact. You should be comfortable using data and KPIs to drive decisions and demonstrate engineering’s contribution to company goals.

• Lead the engineering execution strategy, balancing feature development with critical infrastructure improvements
• Guide the ongoing migration from Heroku to Google Cloud Platform (GCP)
• Develop and implement approaches to systematically address technical debt while maintaining delivery velocity
• Make pragmatic architectural decisions that support business growth without over-engineering solutions
• Translate non-technical business needs from stakeholders into effective technical solutions and realistic delivery plans

• Establish and improve engineering KPIs, with particular focus on DORA metrics (deployment frequency, lead time, change failure rate, time to restore)
• Build observability and monitoring practices that enable proactive issue detection and rapid response
• Drive continuous improvement in development processes, CI/CD pipelines, and release management
• Use data to identify bottlenecks, inefficiencies, and opportunities for engineering productivity gains

• Manage and mentor a distributed engineering team across Ukraine and Indianapolis, fostering collaboration and effective communication across time zones and cultures
• Build team capabilities through coaching, code reviews, and knowledge sharing
• Create structure and processes that enable a hybrid, distributed engineering team (with team members in Indianapolis and Ukraine) to execute effectively.

• Drive consistent, reliable delivery of features that grow our customer base
• Work closely with product and company leadership to prioritize engineering efforts
• Establish engineering best practices that improve quality and reduce operational overhead

• 7+ years of software engineering experience with significant time in Ruby/Rails environments
• 3+ years leading engineering teams, preferably in SaaS or product companies
• Demonstrated experience using DORA metrics or similar KPIs to drive engineering improvements
• Strong track record partnering with executive leadership and translating between technical and business domains
• Proven ability to manage and pay down technical debt at scale
• Experience managing distributed/remote teams across different cultures and time zones
• Experience with cloud infrastructure modernization (ideally GCP, but AWS/Azure experience translates)
• Excellent written and verbal communication skills, with ability to explain complex technical decisions to non-technical stakeholders
• Comfortable with the ambiguity and pace of a startup environment

• Direct GCP experience (Compute Engine, Cloud SQL, networking, IAM)
• Experience with data warehousing, star schemas, and business analytics infrastructure
• Background working with or alongside data science teams
• Fam…