Gusto

Experiential Retail Director

Gusto$120K — $150K *
Retail & Consumer Goods
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years of experience in experiential retail or related field.
  • Proven track record in negotiating short-term leases and venue agreements.
  • Strong visual merchandising and retail design skills.
  • Hands-on experience managing construction and build-out vendors.
  • Excellent budget management and P&L reporting skills.
  • Flexible, can-do attitude in various working environments.
  • Willingness to travel frequently to activation sites.

Responsibilities

  • Identify and cultivate relationships with landlords and partners for activations.
  • Lead negotiations on leases and pop-in agreements.
  • Evaluate and build business cases for potential activation locations.
  • Collaborate with teams to design and concept activations tailored to each venue.
  • Manage logistics for installation and execution of each activation.
  • Develop operational playbooks for scalable activations.
  • Support new store buildouts and renovations as needed.

Benefits

  • Hybrid work schedule (3 days in-office, 2 days remote).
  • Opportunities for travel to activation sites.
  • Collaboration with leadership across various departments.
  • Access to a network of retail partners and landlords in unique venues.
  • Potential for a performance bonus based on success metrics.
Full Job Description
Roller Rabbit is seeking an Experiential Retail Director to own the end-to-end lifecycle of our pop-up shops, campus tours, pop-ins, and brand activations - the perennial experiences that bring our world to life beyond our permanent doors. This person will be the connective tissue between landlords, retail partners, campuses, hotels, and our internal creative, merchandising, and operations teams, ensuring every activation is sourced, negotiated, designed, built, and executed on brand, on time, and on budget. This role also supports permanent store buildouts and renovations to existing locations as they arise, making it a strong fit for someone who enjoys moving fluidly between fast-turn temporary experiences and longer-horizon capital projects.

Description

Experiential Retail Director

Pop-Ups, Campus Tours, Activations & Store Development | Full-Time

Reports to: Chief Executive Officer | Location: NYC HQ (Hybrid - 3 days in-office / 2 days remote) | Travel: 25-50%

Salary Range: $120,000 - $150,000 base, commensurate with experience, plus performance bonus

POSITION OVERVIEW

Roller Rabbit is seeking an Experiential Retail Director to own the end-to-end lifecycle of our pop-up shops, campus tours, pop-ins, and brand activations - the perennial experiences that bring our world to life beyond our permanent doors. This person will be the connective tissue between landlords, retail partners, campuses, hotels, and our internal creative, merchandising, and operations teams, ensuring every activation is sourced, negotiated, designed, built, and executed on brand, on time, and on budget.

This role also supports permanent store buildouts and renovations to existing locations as they arise, making it a strong fit for someone who enjoys moving fluidly between fast-turn temporary experiences and longer-horizon capital projects.

WHAT YOU'LL DO

Site Sourcing & Deal Negotiation
• Identify and cultivate relationships with landlords, retail partners, campuses, hotels, and event venues for short-term and seasonal activations.
• Lead negotiations on short-term leases, licenses, and pop-in agreements - terms, rent structure, build-out allowances, and exit provisions.
• Evaluate prospective locations against foot traffic, demographics, seasonality, and brand fit; build the business case for each opportunity.
• Maintain a pipeline and calendar of activations across markets, balancing lead time, capital, and staffing capacity.

Concept, Design & Visual Merchandising
• Partner with creative, marketing, and merchandising teams to concept each activation's look, feel, and product story, tailored to the venue and audience.
• Brief and manage third-party designers, fabricators, and vendors to bring concepts to life within budget and timeline.
• Ensure every activation reflects Roller Rabbit's brand aesthetic and visual merchandising standards.

Build-Out & Field Execution
• Own physical set-up, bump-in, and bump-out logistics for every activation, including staffing, freight, fixtures, signage, and technology (POS, Wi-Fi, security).
• Serve as the on-the-ground lead or manage a field team through installation and de-installation, troubleshooting issues in real time.
• Develop and refine repeatable operational playbooks so activations can scale efficiently across multiple simultaneous sites.

Budget & Vendor Management

Build and manage budgets for each activation, from site cost through build-out, staffing, and tear-down; track actuals against plan.
• Source, negotiate, and manage relationships with general contractors, fabricators, freight/logistics providers, and other third-party vendors.
• Report on activation performance (sales, cost-per-activation, ROI) and translate learnings into sharper future site selection and design.

Permanent Stores & Renovations
• Support new permanent store buildouts, including landlord coordination, permitting, and contractor management, in partnership with the retail and construction teams.
• Assist with renovations of existing store locations as they arise, applying the same rigor around budget, timeline, and brand consistency.

CROSS-FUNCTIONAL PARTNERSHIP

This role sits at the intersection of retail, marketing, merchandising, finance, and legal, and will work closely with department leadership across Roller Rabbit and the broader Vivid Group portfolio to keep activations aligned with company priorities and brand standards.

WHAT YOU BRING
• 8+ years of experience in experiential retail, pop-up/activation management, retail operations, or a related field, with a track record of owning projects end-to-end.
• Demonstrated success negotiating short-term leases, licenses, or venue agreements with landlords and partners.
• Strong eye for visual merchandising, retail design, and brand storytelling in physical space.
• Hands-on experience managing construction, fabrication, or build-out vendors and general contractors.
• Excellent budget management skills, with comfort building, tracking, and reporting on project-level P&Ls.
• A flexible, get-it-done operating style - comfortable both in strategic partner conversations and on-site during a bump-in at 6am.
• Willingness and ability to travel frequently to activation sites, campuses, and store locations.
• Fashion, lifestyle, or specialty retail experience strongly preferred.

WHAT SUCCESS LOOKS LIKE
• A well-managed, forward-looking calendar of pop-ups, campus tours, and pop-ins that hit sales, budget, and brand-experience targets.
• Strong, repeatable landlord and partner relationships that give Roller Rabbit first look at premium short-term real estate opportunities.
• Smooth, low-drama bump-ins and bump-outs, with a playbook other team members can execute against.
• Permanent store buildouts and renovations delivered on time and on budget, in close partnership with retail leadership.

Roller Rabbit is a fashion and lifestyle retail brand under the Vivid Group portfolio. This role reports directly to the Chief Executive Officer and partners closely with marketing, merchandising, finance, and legal. Based at our NYC headquarters on a hybrid schedule (3 days in-office / 2 days remote), with 25-50% travel to activation sites, campuses, and store locations.

Salary

$120,000 - $150,000 per year

About Gusto

Gusto is a cloud-based human resources software platform that provides payroll, benefits, and HR management services to small businesses. The company was founded in 2011 and is headquartered in San Francisco, California. Gusto's platform automates many of the administrative tasks associated with HR, such as payroll processing, tax filings, and benefits administration. The company also offers a range of HR services, including compliance support, employee onboarding, and time tracking. Gusto is committed to helping small businesses succeed by providing them with the tools and resources they need to manage their HR operations more efficiently.
Learn more about Gusto
Size
1,000 employees
Industry
Founded
2012

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