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JOB DETAILS

Human Resources Generalist

CompanyWinston Flowers
LocationBoston
Work ModeOn Site
PostedAugust 28, 2026
About The Company
Here at Winston Flowers, our team shares a singular goal: to take care of your precious moments as if they were our own. For over 75 years, we've been committed to fostering excellence in everything we offer, from world-class floral design and unique home décor to corporate services, weddings, and special events. Today, our family-owned company has two state-of-the-art floral design studios in Boston and New York City, as well as seven retail shops in Massachusetts and Greenwich, CT. We offer same-day flower delivery throughout Greater Boston, New York City, Fairfield County, and Westchester County, as well as nationwide flower delivery through our extensive network of partner florists. Following the example of Robert and Maynard Winston, the father-son duo that founded Winston Flowers in 1944, we pride ourselves on 5-star service and place incredible value on our relationships with clients. We strive to make every person feel special, and pour our hearts and souls into creating floral designs that allow people to communicate what words cannot.
About the Role

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 to perform all compliance-related recordkeeping functions and reconciliation of monthly invoices 
  • Administers and maintain 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, process pre-hire information and applicable benefits plans, coordinate setup of IT needs and partner with hiring manager to coordinate onboarding events for all new hires, ensuring an exemplary new employee experience 
  • Performs exit interviews and report 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 partner 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 

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 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  

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. 

Key Skills
Benefits administrationHRIS managementPaylocityEmployee relationsOnboardingCompliancePayroll processingConflict resolutionMicrosoft OfficeBilingualSpanishCommunication skillsTime managementAnalytical skillsCustomer service
Categories
Human ResourcesAdministrativeRetail
Benefits
Medical insuranceDental insuranceVision insuranceLife insuranceLong term disability insuranceShort term disability insurance401(k)Health savings accountPaid time offCommuter benefitsDependent care accountsEmployee discountFree on-site parking
Job Information
📋Core Responsibilities
The Human Resources Generalist will manage employee benefits administration, HRIS data maintenance, and payroll compliance. They will also lead new hire orientations, conduct exit interviews, and support the Director of Human Resources with special projects.
📋Job Type
full time
💰Salary Range
$75,000 - $85,000
📊Experience Level
2-5
💼Company Size
143
📊Visa Sponsorship
No
💼Language
English
🏢Working Hours
40 hours
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