Howard

Role Description We are looking for a detail-oriented and proactive Sales & Occupancy Tax Analyst to join our team and support our growing Sales & Occupancy Tax function. In this role, you will take full ownership of tax compliance for our hospitality and short-term rental operations. This is a fantastic opportunity for someone with a strong background in lodging tax structures who thrives in a fast-paced environment and enjoys bridging the gap between complex financial data and client satisfaction. - Tax Filing & Compliance: Prepare, verify, and file multi-jurisdictional sales, occupancy, and lodging tax returns accurately and on time. - Data Analysis & Calculation: Perform precise tax calculations based on reservation-level data, including accommodation fares, cleaning fees, and other taxable components. - Reconciliation: Reconcile transaction data across Property Management Systems (PMS), tax software reports, and internal financial records to ensure 100% accuracy. - Calendar Management: Maintain and manage tight tax compliance calendars and ensure timely remittances to avoid penalties. - Agency & Jurisdiction Communication: Act as the primary point of contact for state and local tax authorities, handling notices, audits, and inquiries directly. - Reporting: Build, maintain, and improve structured tax reports for both internal leadership and client use. - Client Advisory: Work closely with clients to understand their operational setup, aligning their business model with specific tax requirements. Qualifications - Minimum of 3 years of hands-on experience in the hospitality, lodging, or short-term rental industry, specifically focused on sales and occupancy tax compliance. - Deep understanding of the unique nuances of short-term rental and property management tax structures. - Proven experience with Property Management Systems (PMS) like Streamline, Guesty, or similar platforms. - Hands-on experience with tax automation and ERP tools such as Avalara MyLodgeTax and NetSuite is highly valued. - Advanced Excel skills for data reconciliation and analysis. - High degree of ownership, accountability, and attention to detail. - Ability to operate effectively under tight, recurring monthly deadlines. - Strong communication skills to manage relations with both tax authorities and clients. Benefits - 100% Remote & Flexible: Work from anywhere in LATAM or Europe on a schedule that respects your delivery and autonomy. - Merit-Based Growth: We operate with a flat, pod-based structure. Promotions and opportunities here are strictly earned by impact, not scheduled by tenure. - Performance Incentives: All team members are eligible for quarterly performance-based bonuses linked to the excellence and health of their portfolio.

Role Description We're looking for a Reservations Coordinator to be the behind-the-scenes engine keeping our reservations running smoothly — from individual guest inquiries to complex group room blocks and event lodging coordination. This is a remote role built for someone who brings hospitality instincts, administrative precision, and a genuine care for the guest experience. - Own day-to-day reservation management: new bookings, modifications, cancellations, confirmations, and guest inquiries - Coordinate group room blocks from setup through cutoff — including guest lists, updates, and rooming list management - Process refund requests, billing adjustments, and reservation corrections with accuracy and professionalism - Support lodging logistics for weddings, corporate groups, retreats, and other on-property events - Serve as a reliable communication bridge between remote reservation activity and the on-property team — ensuring arrival notes, special requests, and event details don't fall through the cracks - Maintain clean, accurate records across the hotel's reservation and property management systems - Handle pre-arrival guest communications, including confirmations and logistical follow-ups - Troubleshoot reservation issues proactively, with a calm, service-first approach - Pitch in on broader reservations, events, and guest experience support as the team needs Qualifications - Hands-on hospitality experience — boutique hotel, resort, or independent property strongly preferred - Experience with Mews (our PMS) strongly preferred - Familiarity with group room blocks, event lodging, or wedding/retreat coordination is a real plus - Comfortable working independently in a remote environment while staying tightly connected to an on-property team - Strong written communication and a polished, professional guest-facing tone - Highly organized and detail-oriented — you catch the things others miss - Able to juggle multiple open requests without losing track of the details - Calm under pressure, flexible by nature, and genuinely team-oriented Requirements - This role suits someone who understands that clean reservation data and responsive communication aren't just administrative tasks — they're a direct extension of the guest experience. - You don't need someone to tell you what to prioritize. - You're comfortable navigating ambiguity, you communicate proactively, and you take pride in keeping things organized even when it's busy. Compensation & Logistics - Compensation: $1,600–$2,000/month, commensurate with experience - Location: Fully remote - Schedule: Flexible, with availability aligned to hotel, guest, and event needs - Start Date: As soon as practical

Role Description We’re looking for a detail-oriented, proactive accountant to join our crew. You’ll work alongside a talented team, delivering high-quality reporting, reconciliations, and accounting support that makes a real impact. - Manage full-cycle accounting for multiple clients, including accounts payable/receivable, bank and credit card reconciliations, and month-end close. (Real Estate industry experience Required) - Prepare, review, and analyze monthly financial statements, management reports, budgets, and cash flow forecasts with accuracy. - Ensure compliance with U.S. GAAP and relevant regulations, proactively addressing discrepancies or concerns. - Perform job costing, project accounting, and budget-to-actual analysis as needed. - Support tax compliance by preparing documentation, collaborating with external tax advisors, and assisting with audit requests. - Build and maintain strong relationships with client stakeholders and internal teams; provide insights to improve financial operations and reporting. - Continuously identify and implement improvements to accounting processes and internal controls to enhance accuracy, efficiency, and scalability. Qualifications - 3+ years of accounting experience. - (Real Estate industry experience Required) - Strong knowledge of accounting. - Skilled in SAGE, QuickBooks, Excel, and other accounting tools. - Sharp, adaptable, and detail-oriented. - Fluent English (B2+) — comfortable chatting with high-profile clients. - Able to thrive in a fast-paced environment with a growth mindset. - Availability 9 AM–5 PM EST - Monday to Friday. - Works as an independent contractor.

Role Description Howard is looking for a Senior Controller to support our Hospitality vertical. You will work alongside our Accounting Director to manage the day-to-day financial operations for a portfolio of growth-stage hospitality clients—hotels, restaurants, and multi-unit operators. Your job is to turn messy books into dependable reporting, and keep it that way. Core Responsibilities - Month-end close: Own the full close cycle for a defined client set. Reconcile accounts, review journal entries, and deliver clean financials on time, every time. - Reporting: Prepare accurate monthly P&Ls, cash flow summaries, and departmental reports tailored to hospitality operators. Identify variances and surface insights before clients ask. - Payroll & compliance: Manage complex payroll structures across tipped employees, multiple departments, and seasonal staffing. Ensure filings are complete and on time. - Client support: Act as a reliable point of contact for day-to-day client questions. Communicate clearly and set expectations before issues become problems. - Process improvement: Document your workflows. Build checklists and SOPs that others can follow. Reduce dependencies on institutional knowledge. Qualifications - 5–8 years in accounting roles, with at least 2 years focused on the hospitality industry—hotels, restaurants, or multi-unit food & beverage operations. - Solid command of GAAP, multi-entity accounting, and hospitality-specific payroll. - Familiarity with tools like M3, QuickBooks, Restaurant365, or similar platforms is a plus. - You catch the small error before it becomes a large one. Your reconciliations close clean. - You write a clear email. You don't bury the answer in footnotes. You know when to escalate and when to handle it yourself. - You're not waiting to be told what to do. You see what needs fixing and you fix it. Quietly. Requirements - Reliable: Every number holds. Every report stands. - Structured: Finance should behave like a system, not a scramble. - Composed: Our work is invisible when it's done right—and that's the point. - Fun: We genuinely love working together and being a great partner for our clients.

Role Description - 5-Star Guest Relations & Communication - Monitor and respond to all incoming guest inquiries, booking requests, and in-stay communications across Airbnb, VRBO, Booking.com, and direct channels using our client’s Guesty dashboard. - Ensure Guesty automated messages are triggering correctly, send manual check-in/check-out instructions when needed, and provide curated local recommendations. - Act as the first line of defense for in-stay guest issues (e.g., tech troubleshooting, amenity questions), resolving complaints with empathy, speed, and professionalism. - Leverage Guesty’s review tools to drive 5-star reviews and professionally respond to guest feedback on behalf of our client's brand. - Guesty & Smart Home Tech Administration - Utilize the Guesty multi-calendar daily to monitor reservations, manage custom fields, adjust guest folios, and ensure data accuracy. - Monitor connected smart locks, noise decibel monitors, and smart thermostats integrated with the Guesty dashboard to ensure property compliance and guest security. - Monitor calendar syncing within Guesty to prevent double-bookings or communication gaps across platforms. - Operations & Turnover Logistics - Coordinate with our client's local housekeeping and maintenance teams to ensure properties are 100% turn-ready before guest arrival. - Log property issues reported by guests, dispatch our client’s trusted local vendors, and follow up to ensure swift resolution before it impacts the guest experience. Qualifications - 1–3 years of experience in vacation rental management, boutique hospitality, or customer success. - Must have direct, hands-on experience using Guesty (PMS). Candidates without Guesty experience will not be considered. - Flawless written and verbal English. Ability to strike the perfect balance between warm hospitality and clear, authoritative boundary-setting. - Calm under pressure with a proven ability to de-escalate tense situations and think logistically. - Flexible schedule, including readiness to work weekends, holidays, or evening shifts to align with peak guest check-in times.

Role Description We are hiring a highly detail-oriented, process-minded Client Operations Coordinator to be the connective tissue across Howard's client teams. This role sits at the intersection of client onboarding coordination, systems access, quality assurance, and billing operations. It is the seat that makes sure nothing drops between sales, controllers, IT, and the client. The ideal candidate is systematic, uncompromising on details, comfortable chasing down missing items, and able to perform high-frequency operational work without loss of accuracy or enthusiasm. This is an execution-first role for someone who enjoys structure, accountability, and maintaining control over complex workflows across multiple systems. This role reports into Business Operations and works closely with Controllers, IT, the People Team, and the founders. Qualifications - Extreme attention to detail and accuracy; errors bother you and you enjoy fixing them - Strong organizational and time management skills; comfortable auditing and operating across multiple systems in volume - Generalist mindset; not afraid of anything that comes across the desk, picks it up, figures it out, and closes the loop - Strong communication skills with the ability to chase, follow up, and hold others accountable - Familiarity with operational systems and task management tools - Comfortable escalating when needed and being direct when chasing missing work - No fear of being the "bad cop" when required - Bias toward follow-through, ownership, and closure Requirements - Run point on new client onboarding from contract signature to fully-operational engagement - Coordinate setup across client accounting systems, expense management platforms, and payment processors for new client entities, including joining live onboarding calls with clients and vendor account teams - Maintain the onboarding checklist and timeline; chase open items across IT, controllers, and the client until each engagement is fully live - Document onboarding playbooks and keep them current as our process evolves - Provision and manage controller access to Ramp across client entities; resolve access issues independently - Coordinate QBO / ERP entity setup and access for controllers as new engagements come online - Triage low-level client facing system tickets - Conduct daily audits across Howard's core systems including the Practice Management Solution (workstreams + tasks), Notion (SOPs + onboarding documentation), and FloQast (close calendars + reconciliations) - Validate that weekly, monthly, and quarterly deliverables are completed on time and at quality for each assigned client - Identify gaps in execution, missing tasks, overdue items, bottlenecks, and SLA breaches - Chase responsible team members for missing work product or overdue tasks, documenting status until resolved - Escalate persistent non-compliance issues to the applicable Director or VP of Business Operations with supporting context and detail - Maintain an auditable record of findings, follow-ups, escalations, and resolutions - Document workflows end-to-end across onboarding, systems access, and client servicing - Surface and standardize undocumented one-off arrangements that exist across the client base - Track patterns and systemic breakdowns to inform improvements to systems, SOPs, training, and workflows - Hold the organization accountable to a culture of "done means done," consistency, and zero dropped balls - Issue recurring client invoices and monitor payment status - Flag failed payments or billing exceptions and route to the appropriate owner Benefits - Be part of a high-growth company scaling operational infrastructure in real time - Influence the quality and reliability of execution across client accounts - Work with a team that values accuracy, accountability, and ownership - Clear lane, clear expectations, clear output Pluses - Hands-on experience with Ramp (entity setup, access provisioning, onboarding) is a significant plus - Experience with QBO, Stripe, FloQast, or Notion in an operational capacity - Background in client onboarding, project coordination, or operations at a professional services firm

Role Description We are hiring a Platform Engineer on a contract basis to join the team building Howard's internal platform. You'll work alongside operators, leadership, and other engineers to ship the back-end systems, dashboards, and automations that run our business: - Practice management - Internal reporting - Team operations - The connective tissue between them We expect this role to be solutions-oriented and leverage the latest technology (Claude Code, etc.) to ship quickly. What You'll Do - Internal Platform Development - Build and maintain the back-end services that power Howard's internal applications - Develop dashboards and operational tools used by leadership, controllers, and the broader team - Ensure performance and reliability across large datasets (thousands of records, recurring jobs, scheduled syncs) - Contribute to a centralized internal platform that consolidates workflows across teams - Internal Systems Integration - Build middleware and API integrations between Howard's internal systems - Replace manual workarounds and spreadsheet bridges with automated, event-driven data flows - Maintain a clean source of truth across the systems our team uses every day - Automated Workflow Development - Engineer event-triggered automations that move data and actions across our internal stack without human intervention - Build the backend logic that ties operational events to downstream effects across other internal systems - Data Normalization & Schema Mapping - Build migration and sync logic that handles inconsistent data and maps it into a standardized internal schema - Own the data engineering layer that makes our internal platforms speak to each other cleanly - Custom Auth & Permissions - Build authentication and authorization layers for internal tools, with granular permissioning so sensitive data is cordoned off by department, role, or user level - Use HRIS data (e.g., Rippling) as a schema to drive internal permissions and team-level views Qualifications - Fluent using AI tools (Claude, Cursor, similar) as a core part of your workflow - Strong full-stack background with emphasis on backend and infrastructure - Deep experience with RESTful APIs and custom middleware development - Track record handling dirty data migrations and schema normalization - Comfortable with serverless and modern cloud architecture - Frontend competence (React/HTML/JS/CSS) sufficient to ship full features when needed Requirements - You should be able to read API docs and reason about the data model for the kinds of platforms we operate on: - Practice management and workflow tools (Notion, internal task systems) - HRIS and identity platforms (Rippling and similar) - Database and serverless platforms (Supabase, Postgres, similar) The Engineer Profile - Operational empathy: You can sit with a business process and translate it directly into automation logic - Ambiguity tolerance: Comfortable when the spec evolves based on what the business is learning - Lean middleware mindset: You build the right-sized pipe, not the cathedral Benefits - Real engineering problems with real business impact - Direct collaboration with operators and founders, no layers - A working environment where AI tooling is encouraged

Role Description We are looking for a "Senior Tax Specialist" to own and scale our Sales & Occupancy Tax function for hospitality clients, particularly in the short-term rental space. This role will be critical in transitioning from a reactive, execution-focused approach to a more structured, proactive, and controlled tax operation. - Take full ownership of the end-to-end Sales & Occupancy tax function, ensuring 100% accurate and timely filings across complex multi-jurisdictional landscapes (State, County, and City levels). - Transition the tax operation from a reactive model to a structured, proactive department by designing and implementing scalable controls and reporting workflows. - Identify and resolve gaps in tax determination, specifically addressing hospitality "edge cases" such as cleaning fees, service charges, and mixed revenue streams. - Audit existing data flows between systems to identify inconsistencies, ensuring compliance and reducing financial risk across a growing geographic footprint. - Act as the primary point of contact for state and local tax jurisdictions, managing notices, inquiries, and potential audits with professional technical expertise. - Partner closely with clients to understand their operational setups, providing a service-oriented approach to align their property management structures with rigorous tax requirements. - Work with large datasets to perform deep-dive reconciliations between PMS platforms and financial records, ensuring all tax remittances are validated and audit-ready. Qualifications - Mandatory experience within the hospitality industry, specifically in short-term rentals (STR), property management, or lodging businesses. - Proven experience in end-to-end tax compliance, including direct exposure to multi-jurisdictional sales and occupancy tax filings. - You must have hands-on experience in day-to-end tax operations rather than a purely theoretical or advisory background. - Strong ability to work with and reconcile large datasets across various financial systems. - A high degree of accountability and the ability to operate under tight, recurring deadlines while navigating and improving evolving internal processes. Requirements - Experience with PMS Platforms such as Streamline, Guesty, or similar hospitality platforms (Nice to Have). - Proficiency in tax automation or ERP tools like Avalara or NetSuite (Nice to Have). Benefits - Work on complex, real-world tax problems—not theoretical compliance. - Own outcomes end-to-end with real accountability. - Be part of a rapidly scaling platform serving sophisticated clients. - Clear expectations, clean scopes, and a culture of “done means done.” - Opportunity to grow into senior tax leadership as the tax function scales.

Our client is a fast-scaling, design-led hospitality platform redefining the intersection of boutique hotels and short-term rentals. With a growing portfolio of thoughtfully designed properties and a strong foundation in data-driven performance, the business is entering an exciting phase of expansion across multiple U.S. markets. They are now looking for a Revenue Manager who can take ownership of pricing and distribution, and play a key role in shaping the next stage of growth. If you’re someone who enjoys both rolling up your sleeves and influencing strategy, this role offers the best of both worlds. What You’ll Be Doing You’ll own revenue performance across a diverse portfolio, driving both day-to-day execution and longer-term strategy. - Lead pricing strategy across hotels and short-term rental properties - Manage rates, availability, and distribution across all major channels - Continuously analyze demand trends, competitor behavior, and market dynamics - Adjust pricing proactively based on seasonality, events, and booking pace - Optimize OTA performance (Booking.com, Expedia, Airbnb, VRBO) - Monitor and improve key metrics including ADR, RevPAR, occupancy, and pacing - Deliver clear, actionable reporting on weekly and monthly performance You’ll also play a key role in broader business decisions: - Partner with Sales, Marketing, and Operations to align on revenue strategy - Support promotions, campaigns, and high-demand periods (events, buyouts, group stays) - Contribute to forecasting, budgeting, and performance analysis - Identify opportunities to improve systems, tools, and pricing models as the platform scales What Makes This Role Different - Real ownership: You’ll fully own pricing and revenue decisions—not just support them - Hybrid complexity: Work across both hotels and short-term rentals, gaining a unique skill set - Growth potential: Clear path to build and lead a revenue function as the company expands - Strategic exposure: Direct influence on commercial decisions and company performance What We’re Looking For - 3–5+ years in revenue management within hospitality - Experience with boutique hotels and/or short-term rentals is a strong plus - Strong grasp of key metrics (ADR, RevPAR, occupancy, pacing, booking window) - Hands-on experience with OTAs and distribution channels - Analytical mindset with the ability to turn data into action - Comfortable operating both strategically and tactically - Strong communicator who can work across multiple teams Why This Role This is an opportunity to step into a role where your impact is immediate and visible. You’ll be joining at a time of rapid growth, with the chance to shape how revenue management evolves across a multi-asset, multi-market platform. If you’re looking to move beyond execution into true ownership—and want to help scale something meaningful—this is the kind of role that accelerates careers.

Role Description We are seeking an Accounts Payable Accountant to join our fast-paced Finance team. This role is a key hire designed to support our high-volume transaction environment and accelerate our month-end closing cycle. You will join a collaborative team focused on bringing efficiency and precision to our financial operations within the hospitality sector. - High-Volume Processing: Manage the end-to-end AP cycle, ensuring high-volume invoices are verified and processed with speed and accuracy. - Month-End Acceleration: Directly support the month-end close by streamlining AP tasks and meeting tight deadlines to reduce turnaround time. - Process Improvement: Identify bottlenecks and implement workflows to ensure a smooth, consistent AP process throughout the month. - Vendor Relations: Serve as the main point of contact for vendor inquiries, resolving discrepancies and managing payment schedules. Qualifications - Industry Expertise: Previous experience in the hospitality industry is strongly preferred. - Efficiency-Driven: Proven ability to manage large workloads and a desire to improve existing financial processes. - Technical Proficiency: Strong accounting software skills and a high level of comfort with Excel. - Problem Solver: A proactive approach to addressing volume challenges and a sharp eye for detail. - Goal-Oriented: Focused on meeting the top 12-month priorities: stabilizing daily volume and significantly speeding up the month-end closing process.