Chief of Staff

Provision

Provision is automating construction. We help contractors speed up their work, reduce risk, and eliminate errors that cost the industry more than $500B every year. Our mission is to make construction more profitable, so society can build more. We are building the most ambitious vision of what is possible with AI in construction. Provision is a YC-backed late Seed stage company with over 10M in recent funding from some of the world's best investors and operators in the construction technology space, including YCombinator, Sequoia Capital (via their scout program), DroneDeploy, PlanGrid (acquired by Autodesk), and Cercano (Microsoft Co-Founder Paul Allen’s fund), formerly known as Vulcan Capital (investors in Uber, Alibaba and Spotify). Come join our team and work alongside builders from Procore, Fidelity, and YC-backed startups who move fast and solve hard problems. Chief of Staff

We’re looking for a Chief of Staff to join Provision’s leadership team. In this role, you will act as a force multiplier for the CEO, driving critical finance, operations, and cross-functional priorities. This role is based in Toronto, Ontario. You’ll bring structure, accountability, and clarity to company-wide initiatives, ensuring Provision scales with discipline while freeing up the CEO to focus on product and growth. What you’ll do:

Act as a “force multiplier” for the CEO, working directly with leadership to handle operations and strategic initiatives.

Track runway and spend across initiatives, conduct monthly expense reviews, and support zero-based budgeting.

Lead preparation for board meetings and investor updates, including metrics, financials, and forward-looking analysis.

Partner with leadership on hiring models, capacity planning, and strategic initiative analysis.

Oversee contract compliance, vendor management, and operational risk monitoring.

Program manage cross-functional initiatives, bringing accountability to execution and surfacing risks early.

Maintain accurate monthly financials, reconciliations, and rolling forecasts to ensure cash visibility and GAAP compliance. Alternatively, work with our fractional CFO to help oversee their work and report to the CEO.

Work with the CEO on strategy and operations discussions, reducing CEO context-switching.

Improve internal processes wherever leverage is highest.

What we’re looking for:

4–6 years of experience in finance, consulting, or operations (high-growth startup, strategy, or FP&A preferred).

Proven track record of building systems that scale, finance, operations, or cross-functional processes.

Exceptional organization and program management skills; able to distill complexity into clear priorities.

Strong communicator with board- and investor-ready writing and presentation skills.

Comfort with financial modeling, forecasts, and budget analysis (Excel/Google Sheets expertise required).

High trust, high discretion, and ability to thrive in a fast-paced environment with shifting priorities.

Nice to have: experience in SaaS or construction technology.

High agency and ability to execute independently.

Willingness to tackle both strategic and tactical work.

Seen as a stepping stone role; ambitious to grow into senior leadership.

Strong operator who thrives in ambiguity and can bring order to chaos.

Trusted proxy for the CEO, with sound judgment and maturity beyond years.

Additional Information

Base Pay Range: 150,000 to 190,000 CAD with 0.15 to 0.30% in equity. Perks & Benefits

Flexible work from home (up to 2 days per week)

$4,000 health spending account (health + wellness)

4 weeks paid vacation + additional paid time around Christmas

Monthly educational book reimbursement

Office in downtown Toronto with complimentary gym access

About Us

We are at the leading edge of innovation in the construction technology space. We are using the latest practices in LLM, data engineering, and workflow automation to build transformational tools that promise to fundamentally change how construction companies operate. Provision was co-founded by Luigi La Corte, who worked as a civil engineer before investing in infrastructure assets at a private equity firm in Toronto, Plenary Americas, and Brendan Ardagh, a trained quantity surveyor and lifelong software engineer who was the CTO of two venture backed companies in South Africa. Only those applicants under consideration will be contacted. Please accept our utmost appreciation for your interest. We are committed to continuous improvement, and a diverse and inclusive workplace for all. Provision is an Equal Employment Opportunity employer and employment decisions are based on merit and business needs only. Reasonable accommodation is available for qualified individuals with disabilities, upon request.

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