Head of Customer Success - DMO Vertical

Role Overview

The Head of Customer Success leads the business unit that generates the largest share of Wheel the World's ARR. The role inherits an operation that is already running and a team that is engaged, and is expected to evolve it from an account-maintenance model into a customer success function with a commercial, business development, and industry expertise mindset.

The team, the playbook, and the client portfolio exist and work. The role is to evolve them, not replace them. What the company needs is a leader who can elevate how the portfolio is managed without disrupting what is already delivering: deeper relationship building with destination partners, sharper commercial instinct in renewals and expansion, and a more proactive voice into Product, Marketing, and Media Solutions.

How Customer Success works at Wheel the World

Customer Success at Wheel the World manages two relationships at once. On one side, destination clients (DMOs, tourism boards, government entities) buy verified accessibility as their value proposition. On the other side, a network of local partners (hotels, restaurants, attractions, transport providers) is what actually makes that accessibility real. The client only renews when its partner ecosystem stays active, adopted, and delivering.

Because both relationships are needed to protect and grow ARR, Customer Success and Partner Operations live inside the same unit and report to the same leader. The Head of Customer Success leads eight people across both arms: four KAMs who own the client side, a Partner Manager (with an AV Partners Coordinator and a third hire pending) who owns the partner side, and a Customer Success Expert who bridges operational execution with the strategic conversation across Product, Marketing, and Media Solutions.

Why this role exists

Customer Success at Wheel the World is the engine that protects and grows the largest revenue stream of the company. Today, that engine runs in maintenance mode: accounts are managed, renewals happen, partners are served. That is no longer enough.

The company needs a leader who treats Customer Success as a commercial discipline, who can read the destination tourism industry, who understands what destination partners need beyond the contract, and who can turn renewals into business development conversations rather than administrative ones. The Head of Customer Success is also one of the strongest providers of feedback into Product and Technology, and is expected to bring vision, not just react to client requests.

Key Responsibilities

Commercial Retention and Expansion: Own retention as a commercial discipline. Renewals at Wheel the World are not administrative milestones. They are business development conversations grounded in deep knowledge of the client, the destination, and the industry. The Head of Customer Success ensures the team approaches every renewal with a clear value narrative, a credible expansion path, and the commercial instinct to read what each account needs next. Retention is the primary metric. Expansion is its natural consequence when the relationship is managed with depth and intent.

Customer Lifecycle and Service Execution Define and sustain the customer lifecycle the KAM team executes against, from sales handoff through onboarding, engagement, quarterly cadences, renewal, and expansion. The model already runs. The work is to evolve it: stronger relationship building, sharper listening, more disciplined follow-up, and clearer service standards. Improve the playbooks, the rituals, and the account health signals without disrupting what is already delivering.

Team Leadership: Lead both arms of the unit. On the client side, lead four KAMs directly with a focus on coaching them in relationship building, client listening, and commercial conversations. On the partner side, lead the Partner Manager who owns the partner ecosystem that delivers value to the client. Lead the Customer Success Expert as an individual contributor whose job is to connect daily operations with the cross-functional conversation across Marketing, Media Solutions, and Product. Set priorities, raise the bar on quality, and protect the culture of the team without rebuilding what already works.

Voice of Customer into Product and Technology: Be the strongest source of customer insight inside the company. The ceremonies with Product and Technology already exist, but today the input is reactive. The Head of Customer Success is expected to bring vision: pattern recognition across the portfolio, a clear read on what is structural versus anecdotal, and proposals for what should be on the roadmap. This role is a priority stakeholder in how new things get built.

Cross-Functional Leadership: Lead the conversation between Customer Success and the rest of the company. Coordinate with Sales on handoff quality and account context. Work with Mapping and Operations on verification timelines and delivery. Partner with Marketing and Media Solutions on case studies, destination storytelling, and revenue opportunities tied to client visibility. The Customer Success Expert supports this work day to day, but the Head sets the agenda.

Forecasting and Business Intelligence: Report regularly to leadership on retention, expansion, account health, forecast, and team performance. Use HubSpot, the KAM Hub, and customer data to prioritize action and to anticipate risk before it materializes. Bring a portfolio view to leadership conversations, not an account-by-account list.

Success Metrics

Retention is the highest-weighted metric, but retention here is read with a commercial lens. It is the result of relationship depth, client expertise, and expansion conversations done well. The role is evaluated against:

• Gross revenue retention and net revenue retention.

• Renewal rate and churn reduction across the portfolio.

• Expansion revenue from existing accounts (upsell, cross-sell, accessibility scope growth).

• Forecast accuracy across quarters.

• Quarterly meeting completion, cadence consistency, and checklist adoption.

• Quality and impact of customer insight delivered to Product and Technology.

Required Experience

• 7+ years of combined experience across Customer Success, Account Management, Business Development, or Project Leadership in B2B environments. The role looks for a hybrid background, not a pure CS career path.

• 3+ years leading post-sale teams (KAMs, Account Managers, or equivalent) with direct responsibility over renewal targets.

• Proven track record of running retention as a commercial discipline, not as a support function.

• Direct experience in businesses where customer retention depends on the health of an ecosystem of partners, suppliers, or providers (travel, tourism, hospitality, on-demand platforms, or similar).

• Experience evolving an established operation, building on top of what already works rather than rebuilding it. Candidates whose strongest professional examples are "I built it from scratch" or "I turned it around after a crisis" are likely a better fit for builder or turnaround roles than for this one.

• Strong product sense: ability to translate portfolio-level patterns into roadmap conversations with Product and Technology teams.

• Ability to lead complex accounts with executive-level stakeholders and multi-party dependencies.

• Strong analytical skills and comfort using CRM (HubSpot or equivalent), dashboards, and customer data to drive decisions.

• Excellent written and verbal communication skills, including with C-level and board-level stakeholders.

• Fluency with modern AI tools (Claude, ChatGPT, or Gemini) as a daily working layer.

• Fluent English required. Spanish is a plus.

Preferred Experience

• B2B SaaS, travel, tourism, destination marketing, hospitality, accessibility, or social impact background.

• Direct experience working with DMOs, tourism boards, government entities, or enterprise partners.

• Experience in two-sided service businesses where customer success on the client side depends on supplier or partner adoption on the other side.

• HubSpot experience.

• Familiarity with accessibility, inclusive travel, or disability inclusion.

• Experience integrating CS work with Marketing, PR, or media-driven revenue lines.