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Head of Commercial Strategy & Enterprise Accounts – Hospitality

for Head of Commercial Strategy & Enterprise Accounts – Hospitality

About Milestone

Milestone is an AI-native Digital Experience Platform helping brands get discovered, understood, and chosen across Search, AI, Local, and Agentic experiences. Serving 2,000+ brands globally, we combine AI-powered CMS, GEO, Schema, Local, Content, analytics and AI Agents to help businesses accelerate visibility, customer acquisition, and growth in an AI-first world.

We serve complex, multi-location enterprises across hospitality, banking/financial services, and martech-driven organizations, operating a hybrid SaaS + Services business model at scale.

 

Role Overview

Milestone Inc. is seeking a Head of Enterprise Accounts - Travel & Hospitality with deep expertise in hospitality commercial strategy across the four core disciplines of Revenue Management, Distribution, Sales, and Marketing. This individual will serve as a trusted strategic advisor to enterprise customers, helping them maximize revenue, optimize channel performance, improve customer acquisition, and drive overall commercial success.  

This high-impact leadership role is responsible for leading strategic growth, retention, customer success, and commercial expansion across Milestone's most important hospitality and travel accounts. The individual will manage a team of Account Managers and Customer Success Managers, directly own a portfolio of key enterprise relationships, and work closely with customer executives to align digital, distribution, revenue, and marketing strategies with business outcomes. T 

You will serve as a trusted executive advisor to CMOs, Heads of Digital, Revenue Leaders, and senior hospitality operators while helping clients maximize digital discoverability, AI visibility, direct bookings, guest acquisition, and platform ROI through Milestone's AI-first platform ecosystem. 

The ideal candidate combines strong hospitality domain expertise with executive relationship management, commercial acumen, and a consultative mindset. They are comfortable engaging with Revenue, Distribution, Marketing, Sales, and Operations leaders, translating industry trends into actionable strategies that drive measurable business results for customers.  

 

What You Will Own (Outcome Ownership)

This role is responsible for the commercial success, retention, growth, and strategic value realization of Milestone's enterprise hospitality and travel portfolio. You will serve as a trusted advisor to customer executives across Revenue Management, Distribution, Sales, Marketing, Digital, and Operations functions while leading a team responsible for customer outcomes, adoption, retention, and expansion.  

Success in this role is measured through customer business outcomes, Net Revenue Retention (NRR), Gross Revenue Retention (GRR), expansion revenue, customer advocacy, platform adoption, and long-term strategic partnerships. 

 

1. Commercial Strategy & Enterprise Portfolio Leadership

  • Own the overall health, growth, retention, and commercial performance of Milestone's enterprise hospitality and travel portfolio.  

  • Serve as a strategic advisor to executive stakeholders, helping customers align digital investments with revenue, distribution, guest acquisition, and business growth objectives.  

  • Lead commercial planning and strategic account development across key enterprise customers.  

  • Directly manage a portfolio of high-value strategic accounts and serve as the executive relationship owner.  

  • Drive measurable customer outcomes tied to direct bookings, revenue growth, AI visibility, guest acquisition, and digital performance.  

  • Lead executive business reviews, strategic planning sessions, renewal discussions, and expansion opportunities.  

  • Navigate complex commercial negotiations involving renewals, cross-sell, upsell, and long-term partnership growth. 

 

2. Hospitality Commercial Advisory

  •  Advise customers on commercial strategies spanning Revenue Management, Distribution, Sales, Marketing, Digital Experience, and Direct Booking optimization.  

  • Help customers identify opportunities to improve channel performance, market share, guest acquisition, profitability, and digital competitiveness.  

  • Stay current on industry trends including revenue management, distribution, metasearch, OTAs, AI-driven discovery, and evolving guest behavior.  

  • Translate industry insights into actionable strategies that improve customer business performance.  

  • Position Milestone as a strategic growth partner rather than a technology vendor. 

 

3. Customer Success & Product Value Realization

  • Lead a high-performing Customer Success and Enterprise Account Management organization focused on customer outcomes, adoption, retention, and growth.  

  • Ensure customers maximize value across Milestone's platform ecosystem, including CMS, GEO, AI Search, Local Listings, Schema, Content Studio, Analytics, and AI-powered solutions.  

  • Develop scalable playbooks for onboarding, adoption, executive engagement, expansion, and risk mitigation.  

  • Establish proactive customer health monitoring and success forecasting processes.  

  • Partner with Product and Engineering teams to ensure customer needs influence product strategy and roadmap priorities.Partner directly with strategic customers to understand business context, implementation complexity, adoption barriers, and growth opportunities. 

  • Guide the team to operate with greater depth in discovery, diagnosis, solutioning, and cross-functional orchestration. 

  • Reduce hero-driven execution by creating repeatable playbooks, escalation paths, and solution frameworks that scale globally. 

  • Work closely with Product, Engineering, Services, and Delivery teams to resolve structural customer challenges and improve time-to-value 

 

4. Strategic Growth, AI Visibility & Digital Advisory

  • Act as a senior advisor on AI visibility, GEO, SEO, Local, Entity Optimization, Structured Data, and AI-powered customer acquisition.  

  • Design and execute account growth strategies that expand customer engagement and platform adoption.  

  • Identify opportunities to increase customer share of wallet and accelerate business outcomes.  

  • Collaborate with Marketing to develop thought leadership, customer success stories, executive content, and industry initiatives.  

  • Represent Milestone in executive briefings, customer workshops, webinars, conferences, and strategic industry engagements. 

 

5. Team Leadership & Cross-Functional Execution

  • Lead, coach, and develop a world-class organization of Enterprise Account Managers and Customer Success leaders.  

  • Foster a culture of ownership, accountability, customer obsession, operational excellence, and commercial thinking.  

  • Create scalable operating frameworks for forecasting, account planning, risk management, executive communication, and growth execution.  

  • Align Sales, Product, Engineering, Marketing, Professional Services, and Support around customer outcomes.  

  • Serve as the executive voice of the customer across the organization. 

 

Ideal Background & Experience

  • 12-18+ years of experience in enterprise account management, customer success, strategic sales, or commercial leadership roles 

  • Strong experience within hospitality, travel, tourism, or enterprise martech/SaaS environments 

  • Proven success leading enterprise account management and/or customer success teams including revenue management and channel distribution. 

  • Demonstrated ownership of enterprise portfolio revenue, renewals, retention, and expansion ARR 

  • Strong executive presence with experience engaging CMOs, CDOs, Revenue Leaders, and senior hospitality executives 

  • Deep expertise in digital marketing including SEO, GEO, AI search, omnichannel strategy, ABM, and content strategy 

  • Strong understanding of SaaS platforms, CMS, analytics, structured data, AI search, and digital experience ecosystems 

  • Experience managing strategic enterprise accounts directly while also leading teams 

  • Commercial mindset with strong negotiation and forecasting capabilities 

  • Strong cross-functional leadership and operational execution skills 

  • Hospitality technology ecosystem experience is a strong plus: PMS, CRS, OTAs, metasearch, loyalty systems, and revenue management platforms 

  • Experience in speaking at industry events or contributing to hospitality thought leadership is a plus 

  • Bachelor's degree in Business, Marketing, Hospitality, or related field; MBA preferred 

 

What Success Looks Like (First 12-18 Months)

  • Measurable improvement in NRR, GRR, customer adoption, and expansion ARR across the enterprise portfolio 

  • Strong executive relationships established with strategic hospitality and travel customers 

  • High-performing Account Management and Customer Success organization operating with clear accountability and forecasting rigor 

  • Increased customer adoption and measurable ROI across Milestone's AI-first platform ecosystem 

  • Scalable customer success and commercial growth playbooks operationalized across the organization 

  • Strong expansion pipeline and predictable renewal forecasting cadence established 

  • Active contribution to Milestone's hospitality thought leadership and industry visibility 

  • Tight customer feedback loops influencing product roadmap and platform innovation 

 

Key Success Measures

  • Revenue
     

    • Net Revenue Retention (NRR)

    • Gross Revenue Retention (GRR) 

    • Expansion ARR 

    • Renewal Rate 

    • Customer Growth Plans 

 
  • Executive Relationship Coverage
     

    • Advocacy & References  

    • Executive Engagement 

    • Strategic Influence 

    • Executive Satisfaction 

 
  • Customer Satisfaction
     

    • Customer Sentiment & Retention 

    • Strategic Initiative Adoption 

    • Product Adoption  

    • Customer Health Scores  

    • Platform Utilization 

    • Customer Maturity Growth  

 
  • Team Performance
     

    • Forecast Accuracy  

    • Employee Engagement  

    • Operational Efficiency  

    • Cross-Functional Alignment 

 

Why Milestone

  • Founder-led, award-winning, AI-first platform 

  • Deep focus on GEO, AI visibility, and customer outcomes 

  • Opportunity to shape Customer Success as a true growth engine 

  • Collaborative, high-bar leadership culture 

  • Certified Great Place to Work 

 

How to Apply 

We'd love to hear from you. Please submit your resume and a brief note on why this role resonates with you to:

Talent Acquisition: Kishankumar P. 

Email: kishankumar.p@milestoneinternet.com

LinkedIn: https://www.linkedin.com/in/kkpatil/

Website: www.milestoneinternet.com