Head of People
$160k - $230kCorgi Insurance Services, Inc
Corgi
Corgi is vertically integrating the entire insurance industry. We design, underwrite, price, and issue insurance directly. Insurance is the largest unautomated industry in financial services, and we're rebuilding it from the ground up using AI. We've raised $374M from Kindred, TCV, and others to do so.
Building something great requires working hard. We are in the office 6-7 days a week. We are meritocratic with very high standards. If you don't meet them, you'll get cut. But if you deliver, you have unlimited scope to grow.
We move quickly, care deeply about talent density, and hire people who want to solve difficult problems with unusually high ownership.
About the Role
We've raised over $108M to build insurance from the ground up. Now we're building the team that builds the team.
This is our first dedicated People hire. You'll own everything from how we find talent to how we retain it. Think recruiting, people ops, culture, comp, and everything in between. This isn't a "post jobs and review inbound" seat. We need someone who moves fast, builds from scratch, and has a hunter mentality.
What You'll Do
- Own full-cycle recruiting across all functions: sourcing, closing, and everything in between
- Stand up repeatable hiring playbooks by role and team
- Build and run core people ops: HRIS, payroll, onboarding, compliance
- Design comp frameworks, leveling, and performance processes as we scale
- Shape culture intentionally… not with perks, but with systems and standards
- Partner directly with leadership on headcount planning and org design
What We're Looking For
- 3+ years of experience building a people function from scratch at a high-growth startup
- Strong sourcing chops, going beyond LinkedIn and close competitive candidates creatively
- Hands-on with modern recruiting tools and ATS platforms (we currently use Ashby)
- Equally comfortable in the weeds of people ops and thinking strategically about org health
- High ownership and scrappy – you build the plane while flying it!
Bonus
- Experience hiring enterprise or technical talent
- Background in tech or SaaS sales
- Familiarity with insurance or financial services
Why Join
- Get in early at a company that's already won with $108M raise
- Direct line to leadership and real influence over how we grow
- You're not inheriting someone else's playbook — you're writing it
Compensation
- Base: $160,000-$230,000
- Equity: included
Interview Process
- Screening Call
- Work Trial
- Decision
Vacancy posted 3 days ago
Similar jobs that could be interesting for youBased on the Head of People in Chicago, IL vacancy
- ...Pylon People Leader Notice: This is an on-site role based in San Francisco, California. Relocation is required, and we're happy to... ...Marathon, Happy Grinder, Product Fluency, and Win as a Team. Act as Head of Recruiting. Maintain the headcount plan and close the gap...SuggestedWork at officeRelocation
Pylon
Chicago, IL1 day ago - ...Head of People Operations About the Company High-growth, private equity-backed software acquirer with a global portfolio of 115+ operating companies. Industry Computer Software Type Privately Held, Private Equity-backed About the Role The Company...SuggestedContract work
- Coury Hospitality is seeking an experienced HR Director for Hotel 55 Chicago. This role oversees all HR functions, including recruitment, employee relations, and compliance with employment laws. The ideal candidate has a minimum of five years of HR leadership experience...Suggested
- ...Head of Human Resources About the Company Global alternative investment manager with $30 billion in assets under management.... ...strategic counsel on talent, leadership effectiveness, succession, and people-related risk. This role is pivotal in exercising oversight of...Suggested
- tastylive, Inc. is seeking a highly organized Executive Assistant to support the Head of People & HR in Chicago, IL. This position involves managing executive calendars, preparing materials for meetings, and ensuring effective communication. Candidates should have 3-5...SuggestedWork at office3 days per week
- tastylive is looking for an Executive Assistant to provide high-level support to the Head of People & HR in Chicago. The role requires 3-5 years of experience supporting executive-level leaders and exceptional organizational skills. Key responsibilities include managing...
$50k - $70k
...evolving organization and take pride in a culture of trust, where we celebrate diversity, equality and inclusion. We always put our people first, drive a growth mindset and foster a collective spirit. We understand that talent and potential come from every section of...Permanent employmentFull timeTemporary workWork experience placementLive inLocal areaRemote workWork from homeThe Adecco Group
Chicago, IL1 day ago$260k - $280k
Head of Employment Law, North America The Head of Employment Law, North America ("NA") is a Law and Compliance position responsible for partnering with the People Organization, setting and executing Aon's NA employment law strategy in line with Aon's people risk management...Full timeTemporary workPart timeWork at officeLocal areaWorldwide3 days per week- ...About the Role We are seeking a Recruiter / HR Specialist to support hiring and people operations across several growing businesses in accounting, marketing, print/production, and technology services. This role will begin with a strong focus on recruiting and talent...Work at officeFlexible hoursShift work
iDelta
Chicago, IL13 hours ago $18 - $25 per hour
Comprehensive Management, Inc. (CMI) is a small private for-profit management and consulting firm focused on improving performance and productivity while maintaining high quality standards for our not-for-profit client. Essential Duties: Administer various employee...Hourly payImmediate startMonday to FridayFlexible hoursFamily Guidance Centers, Inc.
Chicago, IL1 day ago$50k - $70k
...evolving organization and take pride in a culture of trust, where we celebrate diversity, equality and inclusion. We always put our people first, drive a growth mindset and foster a collective spirit. We understand that talent and potential come from every section of...Permanent employmentFull timeTemporary workWork experience placementLive inLocal areaRemote work- A leading grocery retailer in Chicago is seeking a Benefits Administrator to execute processes related to medical and pension payments. The role involves analyzing transactions for compliance, utilizing HR systems to support operations, and maintaining relationships with...
$18 - $25 per hour
Family Guidance Centers, Inc. is seeking a Benefits Administrator to manage employee benefits programs in Chicago, IL. This position involves administering health, dental, and life insurance benefits while ensuring compliance with FMLA and COBRA. The ideal candidate has...Hourly payFlexible hours- ...Head of Total Rewards About the Company Acclaimed organization in the consumer products & manufacturing industry Industry Consumer Services Type Privately Held About the Role The Company is in search of a Head of Total Rewards to spearhead the...
- ...when relevant to our clients, can generate value and drive positive change. Job Description The Head of Human Resources is responsible for leading the people strategy for L&G – Asset Manager, America (LGIMA), partnering closely with the CEO, Executive Committee,...Full timeTemporary workLocal areaWorldwideFlexible hours
LegalAndGeneral
Chicago, IL20 days ago $40.28k - $53.45k
Infinite Roar seeks a Human Resources Coordinator in Chicago, IL. This role is integral in supporting employees by overseeing the onboarding process, addressing payroll and benefits inquiries, and administering HR systems. Successful candidates will possess experience in...- A distinguished higher education institution in Chicago seeks a Human Resources Recruiting Coordinator to support full-cycle recruiting and onboarding for staff and adjunct faculty. Key responsibilities include managing recruiting processes, ensuring compliance, and providing...
- A packaging services company located in Chicago is seeking a Human Resource Coordinator to assist with the HR process. This full-time, onsite position involves duties such as recruiting candidates, conducting interviews, and managing employment records. Applicants should...Full time
- ...closing—while delivering an exceptional candidate experience through their first week on the team. If you thrive in a fast-paced, people-centered environment, this role is for you. What You'll Do Assist with interview coordination, candidate communication, and offer...Local area
$20 per hour
Samaritan's Purse is seeking a Seasonal HR Associate in Chicago, IL, to recruit and support staff for the Operation Christmas Child project. This full-time role runs from mid-August through mid-December and involves recruitment, onboarding, administrative support, and ensuring...Hourly payFull timeSeasonal workWork at office- TransLoop Logistics is seeking a motivated Recruiting & HR Coordinator to enhance the recruitment of top talent in Chicago. This role supports the entire recruitment cycle while ensuring exceptional experiences for candidates. You will coordinate interviews, source candidates...
$21.88 - $30.64 per hour
Human Resources Recruiting Coordinator Job ID: 2026-1765 Location: US-IL-Chicago Category: Human Resources Position Type: Staff (Full-Time) Overview Who We Are: National Louis is a 135+ year old university that has been grounded in the values of innovation, access, ...Hourly payFull timeWork at officeShift work- Take a look at our current career opportunities across Europe, North America and the UAE. About Corston Architectural Detail Corston Architectural Detail is a British design brand creating beautifully engineered switches, sockets, lighting, and architectural hardware. ...Part time
$50 - $55 per hour
...organization is known for delivering innovative solutions within the healthcare and professional services space, with a strong emphasis on people, collaboration, and impactful work. Job Description: The Executive Recruiter will play a key role in driving executive-...Local areaAddison Group
Chicago, IL13 hours ago$160k - $190k
Description As a member of Fox Rothschild’s Legal Talent team, the Senior Manager of Entry‑Level Recruitment is responsible for the end‑to‑end strategy, execution, and continuous improvement of the firm’s law student and entry‑level hiring programs across all offices...Full timeContract workSummer workWork at officeNight shiftFox Rothschild
Chicago, IL5 days ago- Sims Metal Management is a global leader in metal and electronics recycling, dedicated to sustainability and responsible resource management. With over a century of experience, we play a crucial role in the circular economy, ensuring resources are available for future ...Local area
Sims Metal
Chicago, IL1 day ago $90k - $125k
...strong generalist foundation, deep benefits expertise, and the confidence to advise executives on employment law, compliance, and people strategy. The Human Resources Manager will lead and elevate HR operations across corporate, retail, and distribution center environments...Hourly payPermanent employmentWork at officeLocal areaLHH
Chicago, IL13 hours ago- Volunteer/Intern: Board Recruitment Director Hasana, Inc. is an accessible luxury brand. The collection features high-end men's and women's clothing and accessories for timeless style. We provide custom, hand-made items ranging from contemporary to classic. Each item...Internship
The Aparecio Foundation, NFP
Chicago, IL3 days ago $48k
...understand consultative selling, relationship management, and working toward measurable goals. Recruiting at CPS is fast-paced, people-driven, and results-oriented. You’ll learn how to identify talent, build professional relationships, and contribute directly to...Flexible hoursCPS
Westchester, IL1 day ago$81.7k - $165.1k
...communities through volunteering and charitable giving. We continually seek highly motivated and talented individuals as our people are critical to our success. In return, we offer competitive compensation with our salary and incentive program, in addition to medical...Full timeLocal areaImmediate startOld National Bank
Chicago, IL1 day ago
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Head of People. Be the first to apply!
