Chief of Staff / BizOps Lead

About the role

You orchestrate the execution of the product and engineering roadmap alongside the founders, ensuring that strategic intent converts into shipped outcomes. You synthesize complex cross-functional inputs into a single, coherent plan that the entire team can execute without you. You run the end to end OKR lifecycle, translating high level goals into measurable results that the company can track in real time. You design lightweight systems that replace hours of manual work with automated reporting and clear decision triggers. You act as the primary thought partner to the leadership team, compressing long analyses into sharp, actionable recommendations. You own the messy in between work that keeps the business running but never shows up on a roadmap. You build the playbook and the machinery so that the company can operate at speed even when you are not in the room.

Key facts

What you'll do

Run the end to end OKR cadence, from goal setting through weekly tracking and quarterly business reviews, ensuring every team member understands their contribution to the most important number.

Own the weekly business review, turning raw performance data into a clear narrative for the leadership team, highlighting risks, wins, and the next actions required.

Design and automate recurring reports that currently take hours to build, creating systems that run reliably without manual intervention.

Translate ambiguous strategic questions into clear analytical plans, using data and first principles to narrow scope and accelerate decisions.

Act as the primary bridge between engineering, growth, and operations, aligning priorities and unblocking dependencies before they become fires.

Own special projects from initial analysis through execution, including vendor conversations, ad hoc modeling, and post mortems that would otherwise be ignored.

Step in as a pragmatic product partner to ship features when urgency demands, writing briefs, defining success metrics, and coordinating the work.

Write concise one page briefings that distill complex, multi variable problems into a few sentences an executive can act on within three minutes.

Use SQL as a core tool of the role, writing queries independently to reach for data before reaching for an opinion.

Be genuinely AI native, leveraging LLMs and agents to replace manual workflows and augment personal productivity across the team.

Requirements

You have 4+ years of relevant experience in consulting, investment banking, high growth startup BizOps or strategy, or strategic finance.

You are a first principles problem solver who starts with why a process exists, what the true constraints are, and what the simplest thing is that could work before jumping to how.

You are obsessed with data, refusing to make claims you cannot quantify, and you are suspicious of any decision that can be measured but is not.

You have extreme attention to detail and are highly organized, constantly re-prioritizing work and context switching without dropping critical items.

You are technically literate, reading SQL fluently and able to hold your own in engineering conversations about tradeoffs and constraints.

You are comfortable with ambiguity and speed, making decisions clearly even when scope is unclear and priorities shift on incomplete information.

You operate with very high agency, choosing not to be told twice, and fixing obvious problems as soon as you spot them by turning them into a plan by the next day.

You genuinely want to be challenged, maintaining a growth mindset, taking feedback seriously, and showing zero tolerance for your own complacency.

You communicate with concise clarity, using the minimum number of words required to convey your point accurately and effectively.

You have low ego, happily writing a product spec in the morning, fixing a broken Slack workflow at lunch, and joining a vendor call in the afternoon without seeing any of that work as beneath you.

Practical notes

Work model: hybrid, 3 days per week in the Yorkville office in Toronto.

Office hours: 10:00 to 16:00 for synchronous collaboration.

Annual learning and home office stipend: $1,500.

Annual wellness stipend: $1,000.

Monthly lunch stipend.

Commuter benefits.

Paid parental leave.

20 days of PTO plus unlimited sick days.

Quarterly team gatherings.

In office amenities.