Director of Technology

We’re growing and looking for a Director of Technology to join our team! Do you share our passion for accountability, love our
core values, and enjoy building dependable technology? Read on!

What’s the starting salary range?

Depending on your experience, this full-time salaried role starts between $140,000 and $185,000 annually.

Job Overview

At Accountable2You, our technology helps people pursue accountability and integrity in their daily lives. Our customers depend on us, and we take our responsibility to provide reliable software seriously.

We’re looking for a Director of Technology to lead our technology team, establish technical direction, and improve the quality and predictability of our software delivery. You’ll lead a small team of software engineers, quality assurance engineers, and technology contractors within the department.

Reporting directly to the CEO, you’ll develop clear plans for technical initiatives, explain the expected benefits and tradeoffs, and recommend the people and resources needed to succeed. Once a plan is approved, you’ll lead execution, communicate progress, and bring significant changes back for review.

Your primary focus will be leading the team, setting technical direction, and driving execution, while staying involved in architecture discussions, code reviews, complex troubleshooting, and occasional hands-on development.

You’ll work closely with our Product team, who owns customer requirements, design, and the product roadmap. Together, you’ll turn customer needs and company priorities into practical plans and dependable releases. You’ll also participate in company leadership meetings, quarterly planning, and setting company priorities.

About you

• You’re an outstanding human. We get it, no one is perfect, yet you possess a strong moral character that loves our core values and affirms Accountable2You's mission and purpose.
• You believe the struggle is real. You believe purity is important and that bondage to pornography is a serious matter.
• You’re a team player. You are humble, hungry, smart, and genuinely enjoy collaborating with others. You actively seek out accountability from others and eagerly receive constructive criticism.
• You’re a natural leader with a heart to serve. You don’t seek out the limelight, but you’re not afraid of it either. When you see a need, you rise (or bend) to fill it, even when the results are not glorious. As a result, others naturally look to you for leadership. You don’t shrink from responsibility, but you do look for opportunities to “elevate and delegate” depending on the skills of your team.
• You’re a motivated self-starter. You can work independently, have a knack for solving problems, and don’t need hand-holding to make plans and get results.

Responsibilities

• Develop and maintain a technology plan aligned with company priorities and the product roadmap, presenting major initiatives, staffing recommendations, and investment needs to the CEO for approval.
• Lead approved plans through execution, establishing clear responsibilities, realistic commitments, and visibility into progress, dependencies, and risks.
• Lead, coach, and develop engineers and quality assurance staff, providing regular feedback and addressing performance concerns with humility and clarity.
• Partner with the CEO on hiring, staffing, department budgets, and significant vendor or contractor commitments.
• Own the technical development, maintenance, and reliability of our monitoring agents across supported platforms.
• Lead the evaluation and implementation of AI capabilities within the team, considering effectiveness, privacy, reliability, and operating costs.
• Guide software architecture and technical decisions, balancing customer needs, maintainability, scalability, delivery speed, and long-term product health.
• Establish practical engineering standards for code review, testing, documentation, and releases.
• Manage technical debt and prepare for operating-system changes, platform restrictions, and distribution requirements that affect our software.
• Collaborate with IT on backend services, APIs, databases, production infrastructure, and cloud operations, establishing clear responsibilities for shared work.
• Partner with IT and other relevant teams to strengthen security practices and protect customer data.
• Coordinate technical contributions to the marketing website and related integrations as needed.
• Establish meaningful measures of product reliability, release quality, and delivery performance, using the results to guide improvements.
• Ensure appropriate monitoring and incident-response coverage for systems within the department’s scope, helping coordinate resolution and follow-up improvements.
• Work with Product and Customer Experience to understand customer problems and address their underlying technical causes.
• Communicate technical decisions, recommendations, and tradeoffs clearly to nontechnical leaders.
• Other tasks and duties as assigned

Requirements

• Demonstrated success leading software engineering teams and delivering customer-facing software.
• A substantial software development background and the technical judgment to guide specialists across different technologies.
• Strong project management skills, with experience turning priorities into actionable plans, coordinating resources and dependencies, and keeping delivery on track.
• Experience with mobile or desktop applications and an understanding of the challenges of supporting software across multiple operating systems.
• Familiarity with cloud services, APIs, databases, and secure software development practices.
• Ability to evaluate AI capabilities and guide their implementation with attention to quality, privacy, and cost.
• Ability to turn ambiguous problems into clear recommendations and practical execution plans.
• Sound business judgment when evaluating priorities, budgets, vendors, and technical investments.
• Clear communication and strong collaboration skills
• Willingness to participate in architecture reviews, code reviews, troubleshooting, and occasional hands-on development.
• A team player who’s humble, hungry, and smart
• A growth mindset toward self and others (Tip: 1.25x playback speed 😉)

You don’t need to be an expert in every part of our technology stack. You do need the judgment to ask good questions, recognize risks, and help the team make sound decisions.

What kind of leader thrives here?

Humility matters at Accountable2You. We’re looking for someone who listens carefully, welcomes feedback, respects the expertise of others, and changes direction when presented with better information.

You should be comfortable taking responsibility when things go wrong, sharing credit when things go well, and having honest conversations that help people improve. We value leaders who bring thoughtful recommendations, communicate disagreements respectfully, and follow through on agreed decisions.

A genuine passion for our mission and the people we serve is essential.

When and where do you work?

This role works standard business hours, Monday through Friday, 8 AM–5 PM Eastern Time. Our team collaborates throughout these hours, so working this schedule is essential, whether you’re in the office or working remotely.

It is a hybrid position based in Williamstown, Kentucky, with one to two days per week in the office for collaboration, planning, and team interaction. The remainder of your work can be performed remotely.

The role includes responsibility for ensuring appropriate monitoring and response coverage for technology systems within the department’s scope. Availability outside normal business hours is occasionally required to coordinate or assist with significant incidents and critical releases.

We recognize that the right person may not currently live within commuting distance. We offer relocation assistance to help our selected candidate move to the area.

As part of our commitment to accountability, all devices used for company work must have Accountable2You software installed and active. Activity reports from these devices are shared with designated company personnel.

What benefits do we offer?

We offer health, dental, and vision insurance, along with eligibility to participate in our 401(k) plan after one year of employment.

Does this sound like a good fit?

We hire for more than a list of technical qualifications. If you love our
mission and values and model the humble, hungry, smart ethos we aim for at Accountable2You, we encourage you to apply.

PS - We love cover letters! Be sure to include one with your application to let us know why you'd like to work for Accountable2You!

We respond to all applicants, so you’ll hear back from us.

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