Senior Client Success Manager
Remote- based position
About BookingsCloud
BookingsCloud is a pioneering SaaS platform and demand-generation operating system developed for professional vacation rental managers. Backed by a major media company, we score portfolios, run the media, and own the direct-booking loop using real-time property, PMS, and market data, helping managers grow direct bookings, maximize revenue, and reduce reliance on OTAs. Our clients are operators who care deeply about their homes and guests. We succeed by helping them own their demand instead of renting it from the OTAs.
Position Overview
We are seeking an experienced, data-savvy Senior Client Success Manager who can combine strong analytics skills with client-facing strategy. In this role, you will own a portfolio of accounts end to end as the revenue strategist and technical point of contact, lead client reviews, and translate BookingsCloud attribution, PMS reservation data, and Meta and GA4 signals into clear ROI stories that drive trust and earned growth in campaign budgets.
This is a senior individual contributor position with the opportunity to help shape the future of client success and analytics at BookingsCloud. It’s ideal for someone who thrives on turning complex performance data into compelling client narratives and is eager to prove how marketing investments can fuel revenue growth. You will be the steady, credible voice that keeps clients anchored to results, even when a month is soft, tracking breaks, or the numbers are questioned.
Key Responsibilities
Client Success & Analytics
- Lead the conversation with clients through onboarding, monthly calls, and monthly business reviews.
- Reconcile BookingsCloud attribution with PMS, Meta, and GA4 data, and translate it into ROI-focused recommendations.
- Create client-facing report packs (Page engagement, booking windows, same-store velocity vs. prior year, revenue, gross and net ROAS). Flag soft months and rising cancellations plainly.
- Identify and recommend opportunities to earn budget increases through verified results, refine property prioritization, and align spend to each portfolio’s booking seasonality.
- Own the revenue strategy for each account by building annual demand plans from the client’s own PMS history, and frame budget conversations around demand the client already owns.
- Lead retention and escalation conversations, including pause requests and off-season budget reductions, in partnership with billing and leadership.
Playbook & Best Practices
- Refine and implement the 90-day client success playbook across your accounts.
- Document client success stories and share best practices with the team.
- Develop repeatable templates and reporting frameworks that scale.
Collaboration & Insights
- Partner with product and data teams to improve dashboards, attribution models, and reporting.
- Own technical triage end to end with product and engineering: tracking and GTM issues, ad feed and catalog mismatches, and PMS integration discrepancies.
- Provide actionable client feedback as we expand into new channels and products, including Google search and owner acquisition.
- Support marketing and sales with referrals, case study development, and client expansion opportunities.
Qualifications
- Bachelor's degree or an equivalent combination of education and experience
- Minimum 7 years in client success, account management, or marketing analytics
- Strong command of attribution models and cross-channel campaign reporting, with working fluency in GA4
- Technical aptitude to diagnose tracking (GTM, CAPI), ad feed, and PMS integration issues and write clear escalations to engineering
- Experience with Google Ads/PPC and familiarity with SEM and multi-channel tracking
- Proven ability to grow client budgets by earning trust with verified data, including when a month is soft
- Executive presence with excellent communication skills for business owner, GM, and ops leadership conversations
- Process-oriented with experience creating playbooks, templates, or scalable client programs
- Comfortable using AI tools to analyze data and draft client narratives, with the judgment to verify and refine the output.
- Strong presentation skills
Nice to Have
- Experience driving budget expansion or account growth through marketing analytics
- Hands-on campaign execution in paid social or paid search.
- Vacation rental or hospitality experience, including PMS platforms and OTA economics
Location & Travel
- Remote (U.S.), though role operates on CST/EST business hours
Travel- up to 20% of the time for conferences or team meetings; reliable transportation is required.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
