Senior Manager, People Operations

About The Role We're hiring a Senior Manager, People Operations to own HR end to end: payroll, benefits, employment tax, compliance, employee relations and our HRIS. You'll be our senior-most HR leader, reporting to the Chief of Staff and partnering closely with our hands-on CEO. Much of our workforce is global contractors, so you'll support both U.S. employees and an international contractor population. This is a hands-on role. Much of our People foundation was built quickly, and we've inherited processes that work but need attention. Your job is to keep day-to-day operations accurate and reliable while steadily improving how we work, so the function matures with the business. Best fit: an experienced HR or People Ops manager who has done the hands-on work and is ready to own the whole function. There's room to grow toward “Director” level as the function and scope grows. What you'll own Payroll, Benefits And Tax Run multi-state payroll, audits and reconciliations, and resolve issues quicklyOwn benefits administration, annual renewal, open enrollment and broker relationships, with clear employee communicationKeep employment tax filings and registrations accurate and on time, including Q4 filings and W-2sManage compliance for our global contractor population HRIS and systems Lead our in-flight migration to BambooHR: data cleanup, testing, parallel payroll runs, cutover and adoptionOwn PeopleOps systems, vendors and budgetKeep employee data clean and audit-ready Employee relations and compliance Handle HR cases: investigations, corrective action, performance issues, accommodations and terminationsCoach managers through sensitive situations, and bring in outside counsel when neededOwn the handbook, policies and compliance calendar (I-9, EEO-1, ACA, leave laws, postings) Employee lifecycle Own onboarding through offboarding, including new-hire orientationTurn manual, inconsistent processes into documented, repeatable onesPartner with leaders on performance management, role clarity and org design Leadership and partnership Lead and develop 2 PeopleOps Generalists (global contractors): Payroll & Benefits, and HR OperationsWork daily with IT Support, Facilities and Recruiting on onboarding, offboarding, access and hiringAct as HR Business Partner to department leaders, especially Sales and Customer SuccessPartner directly with the CEO and leadership team, bringing data, risks and clear recommendations What success looks like First 90 days Year-end payroll and tax work (Q4 filings, W-2s) is completed accurately and on timeBenefits renewal and open enrollment run smoothly, and employees understand any changes before they enrollEvery open HR case is triaged and documented, with outside counsel in place for complex mattersThe BambooHR migration has a clear plan with owners, dates and risksLearn the entire payroll processRegular 1:1s are in place with your team, and you've built working relationships with leadership and partner teams By 6 months BambooHR is live, data is clean and payroll runs without errorsOne onboarding and offboarding process runs across PeopleOps, IT, Facilities and RecruitingHR cases follow a consistent process, and managers come to People Ops earlyPerformance management and other lifecycle processes are documented and in useYour team is stable, engaged and spending less time firefighting What you bring Must-haves Minimum of 6 years of progressive HR / People Operations experience, including 2+ years at a startup or high-growth company with 100+ employeesLed at least one full HRIS or payroll system migration from kickoff through go-liveHands-on ownership of payroll, benefits and employment tax complianceDeep employee relations experience, including investigations and terminationsExperience in B2B SaaS or another fast-growing, sales-led tech companyExperience managing people, contractors and vendors, including global contractorsA track record of building buy-in at the executive level and turning manual processes into scalable ones with limited toolsA go-getter who advocates at the right time: when you hear "no" or "not yet," you come back with a clear Phase I, II, III plan that matures People Ops step by stepGrowth mindset: curious, coachable and quick to adapt Nice-to-haves Experience with Gusto and/or BambooHRHRBP experience with high-volume Sales or Customer Success teamsMulti-state and international workforce experienceSHRM-SCP, SPHR or similar certification What we offer Full transparency: the base salary range for this role is $115,000 to $140,000, based on experience, with room to grow over time into Director level roleMedical, dental and vision coverage through SANA, Beam and VSP15 days of PTO for vacation, mental wellness and sick time that grows with tenure, plus 10 paid holidays8 weeks of paid parental leave, plus 4 additional weeks through FMLA401(k) with a company match of up to 3%Real ownership: you'll be our senior-most HR leader, with a seat at the table and room to grow toward DirectorFull-scope experience you won't get at a bigger company: payroll, benefits, ER, systems and team leadership in one roleVisible impact: the processes you build become how the company runs, and leadership will see itYour choice of our Austin or Charlotte office Is this role right for you? We want to be upfront about what this job is really like. What To Expect A busy, fast-paced, fully in-office role in Austin or Charlotte. This is not a 9-to-5 job. No polished onboarding program. You'll jump in, learn our history and existing processes quickly, and apply your expertise early. A limited budget and lean tech stack. You'll find scrappy ways to get things done, build the case for better systems, and know when an investment needs to wait. You'll hear "not yet." The people who do well here come back with a phased plan (what we can do now, what comes next, what waits until the business is ready) and keep moving. Constant multitasking, and this is one of the biggest parts of the job. You'll move quickly between live conversations, Slack notifications and a full inbox of questions, often at the same time, and go from fixing a payroll issue to guiding a leader through a hard termination within hours. You'll thrive here if you: Would rather fix a broken process yourself than wait for a tool or a teamMake sound calls with incomplete information and adjust as you learnEnjoy working directly with a hands-on CEO: you bring clear recommendations, push back respectfully and follow throughSee messy systems as a chance to buildLearn the history before you change it, respecting what works while improving what doesn't This role may not be the right fit if you: Do your best work in an established HR function with mature systems and a larger teamWant a primarily strategic or advisory role with less hands-on workPrefer to execute a strategy someone else has set, rather than shape and advocate for oneAre looking for a predictable 9-to-5 schedule, or eventually a remote or hybrid setupPrefer to focus on one thing at a time, rather than juggling constant requests and frequent changeNeed direction from a single leader. You'll report to the Chief of Staff but work closely with our hands-on CEO, so priorities will sometimes come from both These are all reasonable things to want. In the spirit of transparency, one of our core values, we share them so you can decide whether this role fits what you're looking for. Must be authorized to work in the United States. We are unable to provide visa sponsorship at this time. Olly Olly is an equal opportunity employer. We welcome applicants of all backgrounds and do not discriminate on the basis of any protected characteristic.