Chief Technology Officer (CTO)

Chief Technology Officer (CTO)

Department: Technology

Employment Type: Full Time

Location: Pittsburgh, PA

Compensation: $300,000 / year

Description

Wolfe is a Pittsburgh-based FinTech company reshaping the gift card and gifting industry, and we are actively embedding AI across our products, our internal processes, and the way our teams work day-to-day. We are seeking a hands-on, technically deep Chief Technology Officer to lead that AI transformation and raise the engineering bar across a company where roughly half the staff are technologists. Reporting to the CEO, you will set and enforce the technical standards that our engineering teams build against, bring modern AI capabilities into production, and partner closely with the Business Units. This is a role for a builder who is energized by turning emerging AI tooling into reliable, shipped systems rather than slideware. This is a 5-day onsite role in Pittsburgh, PA.


Responsibilities

• Drive adoption of AI across Wolfe's products and engineering workflows, moving concrete use cases (AI-assisted development, customer-facing features, internal automation) from proof-of-concept to production.
• Define and enforce company-wide engineering standards (SDLC, code quality, observability, security in the code level, release practices) that the Business Unit engineering teams build against.
• Evaluate and select the technology, frameworks, and AI/ML platforms Wolfe standardizes on, and lead the migrations required to adopt them.
• Lead high-impact, cross-team technical initiatives that individual Business Units cannot solve alone, such as logging standardization, environment consistency, and application performance monitoring.
• Directly lead a focused group of senior technologists and platform/AI staff, and partner with Business Unit leaders on hiring, architecture reviews, and technical performance metrics across engineering.
• Ai governance and security.
• Oversight over developers, Quality assurance, dev-ops, architect and systems.
• Cost controls on cloud spending, tooling, external vendors and consultants
• Talent management and growth of engineers.
• Assess Wolfe architecture, and provide CEO with a SWOT report.

Impact Statement For more clarity on the role, below are the success metrics and measurements for this role in the first 90 to 120 days.:

• Ship at least one AI capability into production (developer tooling, a customer-facing feature, or an internal automation) with adoption or performance measured before and after.
• Publish a company-wide engineering standards baseline (covering SDLC, observability, and security) and get it adopted by every Business Unit engineering team, evidenced by teams building against it.
• Complete a documented architecture and tooling review across the three eCommerce sites and SaaS platform, and deliver a prioritized 12-month technical roadmap that the CEO and Business Unit leaders sign off on.
• Engineering productively improvement to 100% Claude Code up from 75% now.
• Reduction in deployment failures and incidents, improving code quality
• Roadmap for technical Debt and reduction Qtly.
• Improve engineering velocity.

Qualifications

• 15+ years in software engineering with progression into executive technology leadership, including prior time as a CTO or equivalent at a company of comparable scale.
• Demonstrated, recent, hands-on experience delivering AI/ML capabilities into production (LLM applications, AI-assisted engineering, or ML systems), not just sponsoring them.
• Track record of setting engineering standards and driving technical change across teams you do not fully own, in a matrixed or distributed org structure.
• Experience with eCommerce and/or SaaS platform environments, and fluency with a modern stack (e.g., cloud infrastructure, Kubernetes, React/Next.js, and observability tooling such as Datadog).
• Bachelor's degree in Computer Science or equivalent practical experience.

Compensation, Benefits, and Perks

The compensation shown includes Base Salary plus Target Incentives Bonus. In addition, you will receive RSUs. Wolfe is committed to providing a comprehensive benefits package to support your well-being, along with competitive compensation. Our benefits and perks include but not limited to:

• Restricted Stock Units (RSUs)
• Incentive Bonus
• Profit Share
• Medical, Prescription, Vision, and Dental insurance for employees and dependents (Wolfe pays 80% of premium)
• Short-Term Disability Insurance (Wolfe pays 100% of premium)
• Voluntary Long-Term Disability Insurance, Life Insurance, Critical Illness Insurance, Accident Insurance, and Hospital Indemnity coverage
• PTO (vacation and sick time)
• Corporate Holidays and Floating Holidays
• 401(k)
• Employee recognition program
• Charitable Donation to a charity of your choice yearly
• Employee Referral Bonus
• Tuition Reimbursement
• Internal Training and Information sessions
• Family Picnic, Holiday Party, and other outings
• Internal Culture Club