Head of Sales & Customer Success

We are partnering with a market-leading vertical SaaS platform serving experience-led / venue-based business globally as they hire a Head of Sales & Customer Success.

The platform enables operators to grow revenue, improve operational efficiency, and enhance the end-customer experience through integrated software supporting bookings, payments, memberships, reporting, guest management, and commerce workflows.

These three pillars — grow revenue, improve efficiency, and enhance the customer experience — are central to how the business goes to market and how it creates value for its customers.

Ideal Candidate Profile

This role is for a proven commercial builder and player-coach who can step into a lean, high-accountability environment and drive results quickly. The right candidate is equally comfortable building pipeline discipline, leading renewals, driving account expansion, managing agency performance, coaching a capable team, and personally stepping into important deals to move them forward.

This is not a manager-only role. It requires someone who can lead from the front, create structure where it is needed, and operate effectively across both ends of the commercial spectrum. They must support a high-velocity, PLG-style sales motion while also engaging in more complex enterprise opportunities requiring executive involvement.

Role Summary

We are looking for a Head of Sales and Customer Success to lead net new logo bookings, renewals, account management, customer expansion, and commercial marketing oversight. Reporting to the CEO, this leader will oversee Sales and Customer Success and build a more disciplined, metrics-driven commercial engine.

Sales is accountable for net new bookings. Customer Success owns renewals, account management, cross-sell, and expansion, while improving retention through stronger engagement, planning, and follow-through.

This role also requires marketing fluency. With no internal marketing headcount, this person must manage external agencies, evaluate performance, and ensure demand generation supports key growth priorities.

The role will also support revenue growth through selected strategic partnerships.

Key Responsibilities

Sales Leadership

• Own all net new logo bookings
• Build and manage a disciplined sales motion across lead follow-up, qualification, demos, proposals, forecasting, and close
• Lead both high-velocity PLG and consultative enterprise sales motions
• Support strategic deals to improve win rates and accelerate close
• Improve pipeline quality, process rigor, and forecast accuracy

Customer Success, Renewals, and Account Growth

• Own renewals, account management, cross-sell, and expansion
• Build a commercially effective Customer Success motion
• Strengthen account planning, renewal readiness, and expansion execution
• Improve churn visibility, renewal forecasting, and customer health tracking
• Ensure proactive product adoption and commercial expansion

Player-Coach Leadership

• Lead from the front as a true player-coach
• Stay involved in strategic deals and executive relationships
• Coach and develop team performance and accountability
• Set clear expectations and standards across Sales and Customer Success

Marketing and Demand Generation

• Own commercial marketing performance with external agencies
• Manage spend across paid media, SEO, campaigns, and events
• Hold partners accountable to KPIs, lead quality, and ROI
• Align marketing with sales and customer outcomes
• Support pricing and packaging improvements

Revenue Operations and Metrics

• Build a metrics-driven operating cadence
• Use HubSpot to improve visibility across pipeline, conversion, churn risk, and expansion
• Manage KPIs including bookings, pipeline coverage, win rates, renewal rate, NRR, and campaign performance
• Improve forecasting discipline and performance tracking

AI-First Commercial Leadership

• Apply AI across prospecting, messaging, forecasting, and customer engagement
• Improve team productivity through AI-enabled workflows

Cross-Functional Leadership

• Partner with Product, Support, Finance, and Operations
• Bring customer insights into pricing, packaging, and product strategy
• Support revenue growth through partnerships and external relationships

Required Qualifications

• 10+ years in sales, customer success, or revenue leadership in B2B SaaS or vertical software
• Proven success owning net new sales and renewals/expansion
• Strong player-coach experience
• Experience across both transactional and enterprise sales cycles
• Strong commercial understanding across sales, CS, marketing, and pricing
• Data-driven mindset with KPI ownership
• Experience with CRM tools (e.g. HubSpot)
• Experience managing external marketing agencies
• Strong leadership presence
• Comfortable working onsite in Irvine, CA

Preferred Qualifications

• Experience in family entertainment, hospitality, payments, commerce, or vertical SaaS
• Experience selling into multi-location or franchised businesses
• Experience building Customer Success functions
• Familiarity with pricing, packaging, and cross-sell strategies
• Experience applying AI tools in commercial workflows

What Success Looks Like

• Improved net new bookings and forecast accuracy
• Faster lead follow-up and better funnel execution
• Stronger conversion on strategic deals
• Improved renewals, retention, and expansion
• Better marketing ROI and alignment with revenue
• More disciplined, accountable commercial team