Upper Hand · 17 hours ago
Head of Engineering
Indianapolis, IN
Full-time
Hybrid
Director/Executive
7+ years expUpper Hand is a vertical SaaS platform serving youth sports facilities and clubs across North America. They are seeking a Head of Engineering to lead their distributed engineering team through a strategic technical evolution, focusing on scaling their Ruby-based SaaS application and managing cloud infrastructure modernization.
FitnessInformation TechnologySchedulingSoftwareSportsTraining
Responsibilities
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
Qualification
Required
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
Preferred
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
Familiarity with payment systems or financial transaction processing
Experience implementing or improving CI/CD pipelines and development automation
Proven leadership navigating competing needs of product development and technical debt management
Benefits
Company-subsidized medical/dental coverage
401(k) plan
Unlimited paid time off
Company
Upper Hand
Upper Hand provides sports scheduling software for the sports and fitness industries.
11-50 employees
H1B Sponsorship
Upper Hand has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (2)
2024 (1)
Funding
Current Stage
Early StageTotal Funding
$11.59MKey Investors
Park Ten CapitalElevate VenturesDon Courtney,Larry Sablosky,Steve Schneider
2025-12-11Acquired
2024-07-10Series Unknown· $0.56M
2022-09-09Series Unknown· $6.59M
Leadership Team
Kevin MacCauley
Founder, CEO
Recent News
Indianapolis Business Journal
2024-10-24
Company data provided by crunchbase