Senior People & Operations Manager

About Cohesion

Cohesion builds the software, AI, and advisory services that connect people, systems, and spaces in commercial real estate: access control, smart maintenance, tenant experience, and energy management, all from one platform.

About the position

Cohesion is hiring a Senior People & Operations Manager to own the practical infrastructure that keeps a growing startup running. You report directly to the CEO. This is a hands-on role for an experienced operator who pairs sound People judgment with relentless operational follow-through, solves unfamiliar problems, and brings recommendations rather than raw questions.

The scope spans People Operations, recruiting, employee administration, policies, Brex and expenses, vendor management, office operations, training, insurance administration, and recurring compliance. This is not a narrow corporate HR role, and it is not an executive-assistant role. You move between sensitive employee matters, vendor negotiations, compliance deadlines, and the unglamorous details that keep the company functioning. You partner closely with Accounting, external HR resources, and employment counsel: you recognize the issue, gather the facts, form a point of view, and bring in the right expert when accounting entries, payroll accounting, legal interpretation, or high-risk employee investigations are involved.

What you will do

People operations and HR

• Own day-to-day People Operations across the employee lifecycle: onboarding, offboarding, employee records, HRIS workflows, benefits administration, and PTO and leave administration.
• Run recruiting operations from job descriptions and postings through candidate tracking, interview coordination, references, offers, and onboarding.
• Administer the performance-review process, including calendars, forms, reminders, completion tracking, and follow-through with managers.
• Maintain and improve the employee handbook and company policies. Research changes, draft updates, coordinate review with external HR or employment counsel, and drive rollout and acknowledgement.
• Serve as the first operational point of contact for routine employee questions and manager support, and escalate sensitive employee-relations, leave, accommodation, wage-and-hour, or employment-law issues appropriately.
• Keep People records clean and confidential, and make sure recurring employee obligations are completed on time.

Brex, expenses, and organizational spend

• Own day-to-day Brex administration: cards, limits, receipts, coding workflows, policy compliance, employee follow-up, and account hygiene.
• Review organizational spend for accuracy, business purpose, policy compliance, duplicate or erroneous charges, missing documentation, and unusual trends.
• Own the travel and expense policy and its administration.
• Validate vendor charges against contracts, approved pricing, usage, seat counts, and renewal terms, and pursue corrections, credits, refunds, and disputes to resolution.
• Find unused software, duplicate tools, and unnecessary renewals, and present clear recommendations before commitments renew.

Vendors, office, and company administration

• Own the vendor list, contract repository, renewal calendar, notice dates, pricing history, business owners, and vendor follow-up.
• Negotiate and challenge vendors when pricing, service levels, charges, renewal terms, or deliverables do not match expectations.
• Own company mail, shipping, office supplies, snacks and beverages, workplace readiness, building access coordination, and office vendors.
• Coordinate SaaS access, licenses, hardware, provisioning, and offboarding with system owners.
• Build and maintain SOPs, checklists, operating calendars, trackers, and clean document repositories, and fix operational gaps without waiting to be assigned.

Compliance, policies, and training

• Maintain the company compliance calendar and drive recurring obligations to completion: corporate registrations, insurance renewals, licenses, required filings, and evidence collection.
• Lead security-awareness training through KnowBe4, including assignments, completion tracking, reminders, reporting, and follow-up.
• Coordinate evidence and administrative work for SOC 2, customer security reviews, insurance, and audits.
• Own policy administration, version control, acknowledgement tracking, periodic review, and employee communication.
• Work with outside counsel, insurance brokers, registered agents, accountants, benefits partners, and IT providers when expert judgment is required.

AI-enabled research and execution

• Use AI tools as a normal part of the workflow to research unfamiliar HR and operational questions, analyze spend, compare vendor terms, draft SOPs and policies, and accelerate first-pass work.
• Validate AI-generated information against authoritative primary or expert sources before acting on legal, HR, compliance, financial, contractual, or security matters.
• When bringing an issue to the CEO, summarize the facts, research, sources, assumptions, options, risks, your recommendation, and the decision required.
• Use AI to increase leverage, not to replace judgment. You remain accountable for the quality and accuracy of the work.

Required qualifications

• 7-10 years of progressively responsible experience across People Operations, HR operations, company operations, or a similarly broad function. Strong candidates with 6+ years and unusually strong startup ownership will be considered.
• At least 3 years in a startup, scale-up, or small company where you personally owned the work rather than routing it to specialized departments.
• Prior experience as a People Operations Manager, Senior HR Generalist, HR & Operations Manager, People Operations Lead, HR Operations Manager, or a comparable hands-on role.
• Demonstrated judgment handling employee questions, policies, benefits, recruiting, vendors, compliance, expenses, and sensitive information.
• Strong research and problem-solving ability, with the sense to build a path forward on unfamiliar work and to know when expert help is warranted.
• Experience with HRIS and benefits administration, recruiting operations, employee lifecycle processes, corporate cards or expense platforms, vendor management, and recurring compliance.
• Comfort using modern AI tools extensively, paired with the discipline to verify high-stakes information and cite reliable sources.
• Strong written communication, follow-through, discretion, and attention to detail, plus comfort working directly with a CEO.
• Comfort working primarily in Cohesion's Chicago office, in a startup where priorities and hours sometimes shift with business needs.

Desired qualifications

• You have worked somewhere without perfect infrastructure and built what was missing.
• You get satisfaction from fixing messy systems, reducing waste, and closing open loops.
• You can be persistent without being abrasive, and direct without creating drama.
• You have enough HR experience to recognize risk, but you are not looking for a narrow corporate HR position.
• You want broad ownership, direct exposure to leadership, and the chance to grow into a Director-level People and Operations role as the company scales.

What you can expect from Cohesion

Cohesion is proud to offer a comprehensive benefits package to eligible, full-time employees in the United States. Our benefits are designed to invest in our employees and their families, supporting their health, happiness, and overall quality of life.

Health and wellness

United Healthcare PPO medical coverage, dental and vision through MetLife, short and long-term disability, a $40 monthly wellness reimbursement, and pet insurance.

Retirement

401(k) with a 100% match on the first 1% of compensation, plus a 50% match on the next 5%.

Work-life balance

Paid time off (PTO): enjoy a responsible unlimited PTO program after 3 months of employment.

Remote work: up to 4 weeks annually of fully remote work.

Hybrid work environment: Chicago-based employees work out of our bright and sunny HQ office Tuesday through Thursday, with snacks, drinks, collaboration space, and an outdoor patio overlooking the Chicago River.

Professional development and culture

Collaborative environment: work in an open environment with optional creative brainstorming sessions for all employees.

Annual all-staff gathering: participate in a two-day mix of professional development and fun.

Monthly events: enjoy an all-employee lunch per month, an all-employee breakfast per month, and monthly social events.

Additional perks: $50 monthly cell phone reimbursement and tax-free transit benefits.

At Cohesion, we see diversity and inclusion as a source of strength. We believe building trust and innovation are best achieved through diverse thought and practice. Individuals seeking employment at Cohesion are considered without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.