Head of Customer Experience (New York)

Overview

Lead and scale post-sales CX operations, building delivery, onboarding, support & growth.

Key Responsibilities

• implementation
• technical delivery
• delivery ops
• onboarding
• support ops
• post-sales systems

Tasks

Jump into implementations when complexity demands it. Coordinate delivery across Solutions, engineering, and client stakeholders while creating clear scoping processes that set expectations before work begins. Triage ruthlessly, what needs custom work vs. what can be templated vs. what we push back on. Be the intelligent filter between "customer wants it" and "engineering builds it." Fix operational problems directly when it's faster than delegating, broken Hubspot workflow? Just fix it. Execute & Project Manage Technical Delivery Cross-functional team leadership: Managed delivery teams that include Solutions, Customer Success, Account Management, and Support Manage Solutions and AM/CS teams across US and UK, coaching them to handle complex implementations and strategic accounts independently. Your success is measured by what your team can do without you, build the leverage that lets junior team members handle work that previously required senior intervention. Create capacity planning frameworks that let us scale predictably. Build Delivery Operations at Scale Transform our bespoke implementations into repeatable frameworks that let us onboard enterprise clients every week. Create onboarding programs that drive rapid adoption, build support that scales efficiently, and design account management processes that systematically capture expansion. You'll make smart trade-offs between customer requests and engineering capacity, directing technical resources to deliver brilliantly. Step into the most complex enterprise accounts ($1M+) and demonstrate how it's done. Navigate C-suite relationships, drive expansion conversations, and build business cases that justify account growth. Handle difficult escalations that require senior presence and drive NRR >140% through delivery excellence, not just relationship management. This is a player-coach role for someone who's built technical delivery operations from scratch at early-stage startups. You'll own the full post-sales P&L: implementations, onboarding, support, renewals, expansion and the revenue growth targets that come with it. You'll transform bespoke implementations into repeatable delivery, create onboarding that drives adoption, build support that scales, and establish account management processes that capture expansion. You'll coach a cross-functional team (Solutions, Account Manager, Customer Success) to operate independently while personally demonstrating excellence on our most strategic relationships. Lead Cross-Functional Delivery Teams Post-sales systems builder: Created scalable onboarding programs, training frameworks, and support operations; you know how to move clients from purchase to active usage to expansion

Requirements

• technical fluency
• delivery ops
• scale delivery
• enterprise
• startup
• people development

What You Bring

Technical fluency: Delivered products requiring real customization; comfortable translating between technical and business audiences; can triage what work creates leverage vs. technical debt Built and scaled technical delivery operations: Proven experience taking implementation/solutions/professional services from chaotic to systematic; you've created the frameworks that made delivery repeatable You must have experience scaling delivery operations in complex technical products, be comfortable managing across US/UK time zones, and thrive in ambiguity. If you need structure and perfect information before moving, this isn't for you. Relationship builder: Built C-suite relationships by delivering brilliantly; can have strategic expansion conversations and handle difficult escalations with senior stakeholders Early-stage startup/scale-up experience: Comfortable with ambiguity, autonomy, and rapid change; has built systems while executing at speed We’re looking for a Head of CX to build and run our post-sales operation at enterprise scale. Someone who builds systems while executing flawlessly on our most complex accounts. NY-based, in office 3 days/week, willing to travel regularly in US (25%) and semi-regularly internationally Enterprise delivery excellence: Successfully delivered complex technical implementations for $1M+ enterprise accounts; can navigate complex organizations and project manage multi-stakeholder rollouts Grit and bias to action: Runs at problems; bias to action in difficult situations; doesn't wait for perfect information or permission People development: Demonstrable experience coaching teams to operate independently; builds leverage through others, not just personal execution

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Benefits

We're building something extraordinary, and we want extraordinary people. Our benefits package goes beyond the standard startup offering, from tailored support for life's challenges (IVF, gender-affirming care, ADHD diagnosis, and more) to meaningful parental leave. -Unlimited PTO -Salary: $160,000 - $200,000 annually -Company-sponsored healthcare, dental and life insurance -$1000 annual training budget -Enhanced Parental Leave -2% Company-sponsored 401(k) contributions -Meaningful equity (on a standard vesting schedule) 📈 -$100 monthly well-being budget - for whatever helps you feel your best

About Fifth Dimension

-Launched by real estate and AI veterans in 2023 to tackle document-heavy workflows. -Typical projects include automating lease data extraction, due-diligence workflows, valuation reports, planning summaries, and branded content creation. -Platform integrates with CRMs, ERPs, email, APIs, and document stores like SharePoint. -In early 2025, they rebranded their name, marking the product's evolution into a full-fledged AI coworker.

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