Principal Recruiter

You could be a recruiter anywhere. Why us?

• Join a pre-IPO startup with capital, traction and runway ($240M funded, $2T market size, and we are profitable💰)
• Report directly to a cofounder and work closely with brilliant leaders from companies like McKinsey, BCG, Bain, Andreessen Horowitz, Nvidia, Nerdwallet, Amazon, GEICO, etc.
• Opportunity to take us to a $10B market cap business and a household name in the next few years
• Be immersed in a talent-dense environment, greatly accelerate your learning and career growth

About the opportunity: We are looking for a Principal Recruiter to join our growing team! We hit a huge milestone in early 2024 by achieving profitability and have ambitious goals for the next few years — scale from 5M to 50M customers and become a $10B business. We hold an exceedingly high bar for talent, and continuing to hire intentionally and thoughtfully is the single most important lever in getting there. Our goal is not to hire quickly, but to ensure that we are building a small and mighty team of the highest caliber people which will allow us to stay lean, agile, learn from brilliant colleagues, and accomplish big things together. At Jerry, recruiters play a much bigger role than at most other organizations, we are responsible for, and take ownership over, elevating our organizational talent density with each hire and ensuring that every team at Jerry operates at an extremely high level. Reporting directly to one of our cofounders, you will partner closely with senior leaders and lead our most impactful and complex searches across R&D, GTM, and G&A, including leadership hiring. We are deeply connected to the work we do and the impact we make. We are continuously raising the bar for ourselves and working on perfecting our craft. If you're looking for an opportunity to master the craft of interviewing and assessing talent at the level of highly skilled hiring managers, make a massive impact, and learn from exceptional team members, we'd love to hear from you! How you will make an impact:

• You will act as the project leader on the roles you are running, driving the search forward, identifying blockers and bottlenecks along the interview process, search parameters and/or candidate funnel, and ensuring we are constantly learning and making progress.
• Recruiters at Jerry conduct very thorough initial screens that include carefully crafted interview questions that mimic later stage hiring manager interviews at other organizations and often take 45-60 minutes to complete. You will analyze the key requirements for the roles you are leading to craft, conduct, and iterate on the questions you are asking during the initial recruiter screen stage to surface the most valuable insights including evidence for candidates' track record of high performance, whether candidates are exceeding our bar on the skills, traits and any other dimensions that are critical to success at Jerry.
• As a senior member of our recruiting team, you will primarily own senior-level searches in the U.S. and Canada across a variety of business areas including product management, business operations & analytics, product design/research, growth marketing, communications, legal, content, human resources, finance and administration.
• As a senior member of our recruiting team, you will also mentor and support the development of our junior team members through coaching and contributing to our training resources.

Who you are:

• You are deeply curious. You seek to really understand the business and the teams you are supporting, the people you are trying to recruit, and you're constantly striving for greater depth in your understanding as opposed to being okay with drawing surface level conclusions.
• You are a driver. You are impatient and dissatisfied when progress is stalled, and you relentlessly push yourself and your team members to produce results.
• You are as comfortable operating within defined parameters as you are with a high degree of ambiguity.
• You appreciate the complexity and nuance involved in delivering a truly stellar recruiting experience, and you are passionate about perfecting your craft.

Ideal profile:

• 9+ years of recruiting experience with progressively increasing complexity in the types of searches you are running.
• Prior experience recruiting senior IC to leadership roles across a wide variety of functions such as product, business operations, software engineering, data science, finance or business analytics (bonus points if you have weathered a competitive contingency agency).
• Prior experience managing and driving progress across multiple searches.
• Track record of being successful in a high velocity, output-driven and demanding environment.
• Bachelor's degree in an intellectually rigorous discipline.

Created at 2025-04-10 22:55:29 Updated at 2025-05-14 00:00:34 Location: Remote (United States, Ontario, Canada); In-office (Toronto, Canada, Palo Alto, CA); About Jerry: At Jerry, we refuse to settle for the status quo. If it’s frustrating, we fix it. If there’s a problem, we solve it. If it’s hard, we make it easy. We don’t wait for change; we make it happen. And we welcome the discomfort of growing and trying new ways of doing things. We’re deeply committed to the work we do and the impact we make every day. We embrace hard work, and we’re constantly learning and perfecting our craft. At Jerry, you’ll have full ownership over what you do—but no one will ever tell you to stay in your lane. Here, you’re empowered to question the norm, generate new ideas, and test new approaches. And you know your team will always catch you if you stumble. Working at Jerry isn’t just a job—it’s a chance to build something, solve real problems, and make a tangible impact on the lives of millions. All with an exceptional team by your side. Open positions:

• Jerry - Principal Recruiter
• Jerry - Manager, Strategic Partnerships (Emerging Products)
• Getjerry - Sample Job

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