Director of IT Engineering

Team: IT

Location: Remote

Commitment: Full-time

Workplace Type: remote

Salary:

As our Director of IT Engineering, you will:

Lead and grow the IT Engineering team as a hands-on player-coach — pairing, reviewing work, and unblocking the team, not just directing from above
Mentor and level up the team as they move from a traditional IT/sysadmin skill set toward an engineering-first operating model, coaching on infrastructure-as-code, automation, and CI/CD practices
Own the strategy and roadmap for Proofs corporate technology: identity and access management, productivity tools, endpoint management, SaaS/vendor management, and IT procurement and budgeting
Champion the adoption of AI and agentic tooling to further reduce manual toil and ticket volume
Partner closely with InfoSec leadership on identity, access, and compliance
Bring a root-cause, data-driven approach to support — tracking ticket trends and metrics to prioritize the highest-leverage fixes rather than just closing tickets faster

As our Director of IT Engineering, you should have:

10–15 years of experience across IT, systems administration, DevOps, or corporate/business technology engineering
Deep, hands-on experience with Okta (required), across all aspects of its configuration
Google Workspace experience strongly preferred
Experience building IT as code practices: Terraform or similar IaC, CI/CD, and GitOps workflows applied to corporate SaaS systems
A track record of reducing ticket volume and manual toil through automation and root-cause fixes, not just faster triage
Experience mentoring or providing technical leadership to mid-level IT analysts
Comfort operating as a hands-on IC on a small team while also setting strategy — this is a working leadership role, not a purely managerial one
Familiarity with security and compliance fundamentals, and genuine enthusiasm for close partnership with InfoSec
Curiosity about and early adoption of AI/agentic tools for operational efficiency
A strong communicator who can translate between technical execution and the needs of stakeholders across the business

Our Proof Pillars:

Pave the Way: When obstacles arise, we break through barriers with passion and perseverance. We lead with creativity and forward-thinking. We aim to set new standards and shape the future in a repeatable, scalable way so the path to success is easier for our team to follow.
Own It: We embrace the responsibility that comes with supporting lifes most important transactions. When a problem arises we relentlessly pursue the solution with a Yes before no attitude. Because every problem and every transaction is treated like its our own.
Act with Integrity: We are in the business of building trust and it is at the core of everything we do. We are honest and transparent with our customers, each other and ourselves. If we make a mistake, we own up to it right away and do what it takes to make it right. Our dedication to security and compliance is key to earning trust, fighting fraud and ultimately, our success.
Play to Win: We believe excellence is about always striving to be better so when we get it wrong, we iterate, we learn and we grow. We know we can only go so far alone, were better together and collectively, we win!

Here are some of our great benefits:

Medical, dental, and vision benefits
Life insurance, long and short-term disability coverage
401k Plan with a 4% match, beginning on your hire date
Unlimited Sick and Vacation time
14 paid company holidays
12 weeks of paid parental leave
4 week sabbatical after 5 years of continuous full time employment
Health Reimbursement Arrangements for fertility and gender affirmation
Lunch on Proof through Grubhub credit
Monthly work from home stipend
Professional development credit
Monthly reimbursement for Wellness
And more!