Job description

About Milestone Inc

Milestone Inc. is a premier Digital Experience Software and Services provider that empowers enterprise brands to accelerate growth using AI-driven digital engagement, omnichannel marketing, and data analytics. Trusted by over 2,000 global brands across Hospitality, Financial Services, Retail, and Automotive sectors, the company merges award-winning technology with expert digital marketing to elevate brand visibility, boost direct bookings, enhance customer interaction, and maximize revenue. Its mission is to advance digital visibility through an AI-first platform enhancing discovery, personalization, and conversion at every touchpoint.

Role Overview

We are seeking a strategic and customer-oriented Director of Customer Success focused on Hospitality to lead and expand a portfolio of high-value enterprise hospitality accounts. This role involves fostering executive partnerships, driving customer outcomes, improving retention, and cultivating long-term strategic alliances. Acting as a trusted advisor, the Director will help clients utilize Milestone’s AI-powered digital experience platform fully while identifying growth and innovation opportunities. This influential individual contributor position blends strategic consulting, account management, customer success, and digital marketing expertise.

Key Challenges to Address

Maximizing ROI from AI-powered digital marketing and customer experience systems within enterprise hospitality brands.
Enhancing customer retention and promoting account growth via strategic partnerships.
Advancing omnichannel marketing techniques to increase direct bookings, engagement, and customer lifetime value.
Modernizing digital experiences through AI, SEO, CMS, and data-centric marketing.
Establishing executive collaborations aligning customer business objectives with Milestone’s product vision.

Primary Responsibilities

Manage and grow a portfolio of enterprise hospitality, entertainment, and tourism accounts.
Devise and execute long-term account strategies prioritizing success, retention, and growth.
Forge and maintain trusted relationships with executive decision-makers.
Serve as a strategic advisor throughout the entire customer lifecycle.
Guarantee customers achieve tangible business results from the platform and services.
Drive adoption, engagement, and platform utilization.
Identify and pursue expansion opportunities including upselling and cross-selling.
Collaborate with Sales to cultivate commercial growth while safeguarding customer trust.
Provide consultancy on SEO, digital marketing, CMS, AI, website optimization, and omnichannel approaches.
Lead Executive Business Reviews, delivering insights and strategic advice.
Turn customer goals into actionable digital growth plans.
Champion enterprise digital transformation projects as a trusted consultant.
Liaise across Customer Success, Product, Services, Engineering, Marketing, and Sales teams to ensure smooth customer journeys.
Advance customer priorities and influence product roadmap through insights and market intelligence.
Stay informed on hospitality technology, AI, SEO, and digital experience trends to provide forward-thinking recommendations.
Represent Milestone at industry events and in executive forums as a thought leader.

Candidate Profile

The ideal candidate is a strategic relationship builder with robust commercial understanding and deep expertise in hospitality and commercial strategy. They excel in consultative environments focusing on long-term partnerships rather than transactional account management. The candidate enjoys working with executives, solving complex challenges, and enabling clients to realize measurable results through technology and innovation.

Required Qualifications and Experience

Bachelor’s degree in Business, Marketing, or a related discipline; Master’s degree preferred.
Minimum 12 years of experience in Account Management, Customer Success, Strategic Consulting, or as an Account Director.
Proven background in Hospitality, Entertainment, Tourism, or Digital Experience fields.
Comprehensive knowledge of SEO, digital marketing, omnichannel strategies, website planning, customer experience, and AI-driven digital platforms.
Hands-on experience with enterprise CMS systems and website best practices.
Proven track record in expanding strategic enterprise accounts with demonstrable revenue growth.
Experience implementing Account-Based Marketing (ABM) strategies.
Exceptional executive communication, presentation, negotiation, and relationship building skills.

Preferred Credentials

Experience with hospitality enterprise technology.
Speaking engagements at conferences or industry forums.
Thought leadership in SEO, digital marketing, AI, or digital customer experience.
Experience collaborating with Fortune 500 or large enterprise hospitality clients.

Focus Areas and KPIs

Enterprise account growth and retention.
Executive stakeholder engagement and advocacy.
Strategic digital transformation consulting aligned with AI-driven customer success models.
Cross-team collaboration to champion customer priorities.
Key metrics include customer retention, net revenue retention, account expansion, upsell/cross-sell success, executive review outcomes, customer health, satisfaction scores, and referenceable growth.

Benefits and Work Environment

Competitive salary complemented by performance-based incentives.
Comprehensive healthcare and benefits package.
Fully remote and flexible work setup.
Opportunities to collaborate with top global hospitality brands.
Exposure to award-winning AI-powered digital experience technologies.
Career advancement in a fast-growing, innovation-centric organization.
Supportive, customer-focused, and high-performing company culture.

Why Join Milestone

Opportunity to innovate with cutting-edge AI-first digital experience solutions.
Work with leading hospitality enterprises worldwide.
Be part of an industry-recognized digital marketing platform.
Contribute to a customer-centric organization focused on measurable success.
Grow your career in a collaborative and innovative environment.

Director of Customer Success – Hospitality