Senior Director of Engineering

About Us: Our mission at Wrapbook is to increase the prosperity of the project economy. A significant shift has occurred within the workforce recently and 50M Americans are now engaged in freelance or project-based work. The popularity of project based employment has introduced flexibility for both employers and employees but also added complexities from a compensation and administrative standpoint. Our vertical fintech platform enables companies to seamlessly onboard, pay and insure their workforces. We’re building the best product for the entertainment industry but operate in a 50B market and have big goals we want to achieve. With legacy competition slow to react and over 30M raised from Andreessen Horowitz, Equal Ventures, Uncork Capital, Jeffrey Katzenberg and CAA co-founder Michael Ovitz, we are at an exciting stage of growth and there isn’t a better time to join! The Opportunity - Senior Director, Engineering - Agentic Business Systems (Remote - USA / Canada) Wrapbook is the system of action for the entertainment industry — where every decision, dollar, and day is planned, executed, and understood in one place. Wrapbook processes payroll, accounts payable, and accounting for film, TV, and commercial productions. We provide a system that connects production companies with cast, crew, and talent agents to keep productions on time and on budget. We're not building toward incremental improvement. We're building toward a company that operates at the output of one 5x our size — by putting AI at the center of how we work, not as a feature, but as infrastructure. This is a deeply technical leadership role. You are someone who is already building managed agents and you're excited by the hard, unsolved problems: how to give agents persistent context across an entire company, how to wire identity and memory so an agent knows what it should and shouldn't, how to make all of this safe and scalable. You'll own how Wrapbook deploys AI internally within business units. You'll lead a mixed team of engineers, product managers, and embedded business users responsible for two things at once: building the platform capabilities that make AI usable across the company, and directly shipping the workflows that run on top of it. Those workflows span Marketing, Sales, Customer Success, Support, Finance, and Operations. Your team won't just hand business users tools — you'll sit with them, understand their work, and build agentic workflows that take real tasks off their plates. You'll report to the CEO and work cross-functionally. You'll have the mandate, the visibility, and the air cover to move fast — and the expectation to build software with meaningful business impact. What You'll Do Build the platform. Own the internal AI deployment infrastructure — make it possible for non-engineers to safely build and run AI workflows at scale. Ship the workflows. Directly build high-leverage agentic workflows across Marketing, Sales, Success, Support, Finance, and Operations. Find the highest-friction, highest-volume work in each function and automate it. Enable business users. Turn business stakeholders into builders. Create the patterns, guardrails, skills, and training that let people across the company build their own AI workflows on your platform. Lead a mixed team. Manage a cross-functional group of engineers, PMs, and embedded business users. Set direction, hold a high bar, and build a culture where shipping and learning happen fast. Partner across the org. Work directly with functional leaders to understand their goals, prioritize ruthlessly, and measure the business impact of every deployment. Own the outcomes. Define what success looks like — adoption, time saved, throughput gained, cost avoided — and report on it credibly to the SVP of Engineering and CEO. Champion responsible adoption. Ensure everything you ship is secure, compliant, and aligned with how Wrapbook handles sensitive financial and personal data. What You'll Have You're genuinely excited by understanding and solving problems. You dig into challenges that span functions, embrace their nuance, and iteratively build workflows that address them one by one. Experience leading cross-functional teams — ideally a mix of engineering, product, and non-technical contributors. Strong product instincts. You can sit with a salesperson or an accountant, understand their work, and find the leverage point. You're technical and hands-on. A track record of building and shipping software, plus the leadership chops to run a team. You've been hands-on enough to earn an engineering team's respect and strategic enough to lead one. You're already building agents. This isn't aspirational for you. You've built and deployed agentic systems, and you have strong, earned opinions about what works. A bias toward action. You'd rather ship a rough workflow this week and improve it than spec the perfect one for a quarter. Excellent communication. You can translate between business stakeholders and engineers. Why Join Us: At Wrapbook, creativity meets technology — and not just in the product. In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts Benefits include: Unlimited Paid Time Off Work from anywhere in Canada and USA Health and Dental benefits Up to $1,500 USD/ $2,025 CAD towards IT set up for your home Up to 2% matching RRSP / 401K Learning and Development opportunities Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service Our Pledge to Fostering an Inclusive and Safe Workplace: Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation. Apply Now Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly! #LI-Remote