Winston Flowers
Human Resources Generalist

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Description
For over 80 years, the dedicated team at Winston Flowers has been committed to fostering excellence in everything we do. Today, our family-owned company has a worldwide online presence, two state-of-the-art design studios—60,000 square feet in Boston and 12,000 square feet in New York City—and retail shops throughout the Greater Boston area and in Greenwich, Connecticut. Each and every person on our team works in pursuit of a singular goal: to take care of our clients’ precious moments as if they were our own.
We are seeking a full-time Human Resources Generalist to provide exemplary internal customer service and execution of Human Resources functions and processes in accordance with applicable laws, plan provisions, and company guidelines. The ideal candidate is energetic, proactive, and self-motivated, with the ability to work independently and collaboratively in a fast-paced, diverse, and creative environment.
Job Responsibilities
- Primary employee benefits administrator for medical, dental, COBRA, workers’ compensation, disability & life insurance, and 401(k) plans; maintains a strong knowledge of all plans and responsible for performing all compliance-related recordkeeping functions and reconciliation of monthly invoices
- Administers and maintains HRIS (Paylocity) data and employee records, including ensuring accurate and timely processing of updates, including new hires, transfers and promotions, pay rate changes, wage garnishments in compliance with federal, state, and local payroll, wage, and hour laws and best practices
- Consults on employee questions and issues, ensuring confidentiality and consistency with company policy and practices, escalating to Director of Human Resources as appropriate
- Leads new hire orientations, processes pre-hire information and applicable benefits plans, coordinates setup of IT needs, and partners with hiring manager to coordinate onboarding events for all new hires, ensuring an exemplary new employee experience
- Performs exit interviews and reports feedback as appropriate; primary point of contact for post-employment activities - COBRA, employment verifications, etc.
- Administers annual benefits open enrollment, benefits fair, and annual 401(k) testing and audit, as well as planning of select employee events
- Consistently evaluates policies, processes, and best practices within the department and company and partners with Director of Human Resources to evolve and update as needed
- Partners with Director of Human Resources and/or managers on other special projects as needed
Reasons to use Rodeo
I’m in my final year doing Economics and I don’t know whether to apply for grad schemes now or do a masters first. What do you think?
Honest answer — it depends on where you want to end up. A lot of top grad schemes (Big 4, civil service, banking) don’t need a masters. Let’s look at the ones you’d be competitive for now, and we can decide if a masters actually adds anything.
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Graduate Consultant — 2026 Scheme
Why you're a good match
StrongYour economics background and your summer at a regional bank line up with what PwC looks for on the consulting scheme. Applications close in four weeks.
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Why you're a good match
You’ve got the grades and the economics background, and your bank internship is exactly the experience this scheme looks for. Apply soon — deadlines close within the month.
Experience fit
Your summer at the bank plus your econometrics coursework map directly to the day-one responsibilities on this scheme — client modelling, market briefings, and deal support.
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Requirements
- Three years of progressive experience in Human Resources and benefits administration, with a strong working knowledge of employment laws, benefits compliance, and HR best practices. Experience in a creative, retail, or fast-paced environment is preferred
- Bilingual in English and Spanish, with strong written and verbal communication skills in both languages, required.
- Proactive, analytical, and service-oriented, with the ability to build collaborative relationships and communicate effectively with a diverse employee population.
- Exemplary written, verbal, and interpersonal communication skills; bilingual in spoken and written Spanish is a plus
- Proactive and analytical with a customer service orientation, with the ability to communicate collaboratively and effectively with a diverse employee population
- Highly organized and detail-oriented, with the ability to prioritize and manage multiple projects and initiatives
- Ability to resolve highly confidential, time-sensitive, and complex issues independently and with sound judgment
- Must be proficient with standard Microsoft Office programs, primarily Word and Excel; previous experience with Paylocity or other HRIS systems


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Other
- Full-time position; core schedule will be Monday – Friday, with occasional weekend availability as business needs require
- On-site; Four days/week
- Flexible to perform other business support responsibilities and projects during peak business periods
- Occasional local and/or regional travel may be required
Winston Flowers’ benefits are comprehensive and include competitive compensation, free on-site parking, paid time off, medical, dental, and vision insurance, company-paid life and long-term disability insurance, short-term disability, pre-tax commuter and dependent care accounts; 401(k) and health savings account, both with company match, and a generous employee discount.
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