Head Of Software Development Jobs (NOW HIRING)

About Karmak

Karmak is a 100% employee-owned software company that has helped keep the commercial transportation industry moving for more than 40 years. Our flagship platform, Karmak Fusion, powers the parts, service, accounting, and business operations of heavy-duty truck dealerships and transportation companies across North America. Simply put, our customers keep America moving-and we build the technology that helps them do it.

We develop on the Microsoft technology stack, including .NET, SQL Server, and Microsoft Azure, creating modern, scalable solutions for a mission-critical industry. As employee-owners, we think beyond our individual roles and share responsibility for our company's success. We're looking for leaders who embrace that same ownership mindset and are excited to make a lasting impact.

Position Summary

Remote (US); limited travel (1–2 trips per year)

The Director of Software Development is responsible for the management and daily execution of Karmak's development organization in support of Karmak Fusion. Leading through four development managers spanning application development, QA, and database/reporting teams (a 30+ person engineering organization), this position owns the flow of work between Support, Implementation, Product, DBA, and the development teams; serves as the development-side approval authority on customer patches; and makes go/no-go decisions across a multi-version release train.

The Director is the primary point of escalation into development for the rest of the organization and the VP of Development's operational right hand - a role requiring the technical credibility to challenge a root-cause analysis, the judgment to weigh customer risk on every patch and release decision, and the leadership to run cross-team incident response when a customer-impacting issue crosses team boundaries.

How You'll Operate

This role is built for a high-agency leader. Here is the working relationship you should expect:

• You'll get context and priorities from the VP of Development - not task lists. We expect you to identify what will move the needle, commit to outcomes, and run with them. You bring the VP problems with proposed answers, not open questions.
• This is not a hands-on coding role, but you haven't stopped being an engineer. You can read C# and SQL, sit in architecture and root-cause reviews and challenge them, and tell a real fix from a symptom patch. Senior engineers respect you because of it.
• You own escalations end to end: you move them, you don't track them. When plans change, you re-plan in hours, not weeks, and keep the train moving.
• You communicate proactively upward so leadership is never blindsided. Exceptions come with verified data, options, and a recommendation.

What You'll Own in Year One

Success in this role is measured in outcomes, not activity. In your first year, a home run looks like:

• Release predictability - Releases and patches across the multi-version release train ship on schedule with fewer defect escapes, and go/no-go discipline holds at every checkpoint - without the VP in the room.
• Escalations owned and closed - Escalations from Support, Implementation, and Product get a single accountable owner, are driven to root cause rather than symptom fixes, and are closed with clear communication - they stop bouncing upward.
• AI-assisted development adoption - The organization measurably advances on AI-assisted engineering - code analysis, automated review, test automation, and agentic tooling - with honest evaluation of where it multiplies velocity and where it doesn't.
• Manager bench strength - The four development managers grow into leaders who plan, prioritize, and make sound calls with less direction - the organization runs well when you step away from it.

Essential Job Functions

• Provide technical leadership and direction to the development managers and their teams, assisting with planning, prioritization, technology assessment, professional development, and cross-team coordination
• Serve as the development-side approval authority on customer patches, weighing patch-versus-upgrade paths, deployment risk windows, and multi-version complexity; ensure patch decisions protect both the customer and the maintainability of the release line
• Own go/no-go decisions at each release checkpoint - integration close, QA greenlight, smoke test, packaging, and staged customer rollout - including the authority to hold or pause a release when quality or customer risk demands it
• Serve as the primary point of escalation to development for Support, Implementation, and Product; route issues to the correct team or subject-matter expert, chase them to closure, and keep requestors informed with clear status and next steps
• Lead incident response for customer-impacting issues that cross team boundaries; drive to root cause rather than symptom fixes, convene the right people quickly, and communicate resolution paths to stakeholders
• Direct the daily product delivery rhythm in partnership with Support, DBA, Installations, and Product, and chair recurring quality reviews with the support organization, converting findings into tracked work items
• Keep the VP of Development ahead of surprises: escalate exceptions with verified data, options, and a recommendation; draft customer-facing technical communications for executive review
• Manage relationships with external technical consultants and vendors in support of development initiatives
• Champion continuous improvement of engineering practice, including branch and merge policy, automated code review, test automation, and AI-assisted development tooling
• Manage the personnel activities of the team to include hiring, training, and evaluating employees; lead merit and salary planning through the development managers
• Lead the team in change management and effectively apply new process improvements
• Embrace self-development, professional growth, and desire for feedback for individual growth
• Maintain confidentiality
• Be a champion for Karmak and the team

Essential Knowledge, Skills and Abilities

• Bachelor's degree (B.A./B.S.) in Computer Science or a related field and a minimum of 10 years of software development experience, including 5+ years leading developers and experience managing managers or an organization of 30+ engineers; or equivalent combination of education and experience
• Required: current technical depth on the Microsoft development stack - able to read and reason about .NET code (C#/VB.NET) and Microsoft SQL Server (T-SQL, database design, query performance) well enough to be credible with senior engineers, interrogate a root-cause analysis, and distinguish a real fix from a symptom patch
• Strongly preferred: experience running teams that build and operate on Microsoft Azure (PaaS services, cloud architecture) and Azure DevOps for work tracking, pipelines, and release management
• Direct experience owning production release and patch decisions for commercial, customer-installed or hosted software, including versioned release trains and customer-impact risk assessment; ERP or other business-critical domain experience strongly preferred
• A demonstrated pattern of high-agency ownership: identifying what matters, driving it to done without waiting for direction, and being accountable for outcomes, not just process
• Demonstrated pattern of calm incident leadership and cross-functional coordination across support, QA, DBA, and product organizations
• Exceptional team leadership skills, including the ability to effectively coach, motivate, and empower team members and develop the judgment of front-line managers
• Ability to build and sustain trusted relationships internally and externally, sound judgment in dealing with business issues, and the instinct to communicate proactively upward so leadership is never blindsided
• Strong initiative, teamwork, and interpersonal skills; strong written and verbal communication skills, including drafting customer-facing technical communications
• Capable of working in a growth-oriented environment, with ability to manage and prioritize multiple concurrent requests, projects, and responsibilities
• Hands-on experience adopting AI-assisted development practices (code analysis, automated review, agentic tooling) preferred
• Knowledge of the heavy-duty or commercial transportation industry a plus

The above statements describe the general nature and level of work being performed in this job. They are not intended to be an exhaustive list of all duties. Additional responsibilities may be assigned by Karmak.