Compensation: $80,000 - $95,000 base salary + bonus + commission per home closed.

Type: Full-time, Remote (Los Angeles preferred but not required)

Reports to: Co-Founder & CEO

About Fieldtrip

Fieldtrip is building the leading boutique hospitality brand in the luxury short-term rental category, currently operating over $200M in assets across Southern California. Widely recognized as the industry’s leading lifestyle brands — and a two-time Skift Award winner — our design-driven portfolio includes some of the most iconic homes in the country, from the world-famous Invisible House to a collection of architecturally significant properties featured in the Wall Street Journal, Forbes, CNN, Architectural Digest, Robb Report, Dezeen, and dozens of other publications worldwide.

Founded by professionals from law, finance, and hospitality, Fieldtrip pairs white-glove service with operational discipline.

With our high-touch service model in strong demand — and following a 60% portfolio expansion in 2025 — we’re now seeking a Revenue Operations Associate to serve as the right hand to our Co-Founder leading sales. This role ensures he can stay focused on high-value demos and proposals by owning the systems, data, and preparation that power Fieldtrip’s growth engine.

What You’ll Do

Partner Directly with the Co-Founders

Work side-by-side with the Co-Founders to prepare for homeowner pitches, demos, and proposals — ensuring they walk in with accurate data, tailored materials, and a clear strategy.
Prioritize and organize leads so leadership can focus on the highest-value opportunities.
Manage follow-ups, scheduling, and visibility across the sales pipeline.

Data Research & Lead Enrichment

Oversee and refine homeowner data enrichment performed by offshore staff.
Research new prospects using PropertyRadar, county assessor sites, Airbnb, Zillow, and Instagram.
Verify homeowner contact data (emails, phone numbers, social profiles).
Maintain segmented lead lists organized by market and property type.

Revenue & Sales Operations

Coordinate and analyze outbound mailer and email campaigns (postcards, newsletters, automated sequences).
Manage Fieldtrip’s CRM (HubSpot, Zoho or similar): data hygiene, tagging, and automation.
Build dashboards and reports visualizing campaign performance and sales metrics.
Oversee broker and referral incentive programs, including partner tracking and payout management.
Support forecasting, goal tracking, and lead conversion analytics.

Marketing & Collateral Support

Work with marketing vendors to maintain and update marketing materials (brochures, pitch decks, postcards, case studies).
Make light web page edits and add videos or new assets to collateral.
Collaborate with design and marketing vendors to ensure all assets are current and on-brand.
Compile campaign insights and communicate results to leadership.

Who You Are

Startup-minded: You’ve worked in founder-led or early-stage environments. You’re comfortable working autonomously, owning outcomes, and keeping leadership informed rather than waiting for direction. You can take a project from idea --> execution --> reporting without needing step-by-step guidance.
Builder: You love creating structure, systems, and processes from scratch.
Analytical: You’re confident with CRMs, spreadsheets, and dashboards.
Proactive: You anticipate needs and take initiative.
Organized communicator: You manage details while keeping everyone aligned.

Preferred Experience & Skills

2-5 years in revenue operations, sales operations, or marketing operations in a startup or small, high-growth company.
Strong experience with CRMs (HubSpot, Pipedrive, Salesforce) and data-enrichment tools (Apollo, RocketReach, etc.).
Proficient in Google Sheets / Excel (formulas, dashboards).
Basic comfort updating web and marketing assets (Canva, Notion, or similar).
Familiarity with property data (PropertyRadar, assessor databases) a plus.

Compensation & Benefits

Base Salary: $80,000 - $95,000 depending on experience + annual performance bonus. Performance-based growth path to Revenue Operations Manager.
Commissions: Bonus per account closed.

Benefits:

Healthcare coverage
Complimentary stays at Fieldtrip homes
Flexible remote schedule (Los Angeles preferred but not required)
Paid time off and travel opportunities
Rigorous training and the opportunity to work directly alongside Fieldtrip’s co-founders — industry leaders with backgrounds in investment banking and law — to help build one of California’s most respected boutique hospitality brands.

Fieldtrip

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