Head of Success & Support

About The Company Numeral is transforming how taxes get done. Digital businesses are currently bogged down by a painful web of regulations across 47 states and 50+ countries. We’re eliminating this burden so teams can focus on their core mission. We’re the largest and fastest growing AI-native tax solution. Started in 2023, Numeral has raised over $57M from Benchmark, Mayfield, Y-Combinator, and many others. We now serve over 2,500 paying customers and have more than tripled our revenue every year in our history.

About the role

Numeral is hiring its first Head of Customer Success & Support to build and lead the entire customer success and support organization. This leader will own the customer journey post onboarding – including retention, expansion, and support, while establishing the systems, processes, and team required to scale. This role reports to CBO. What you’ll do

Customer Support Excellence

You will lead and evolve the Support organization, creating a high-quality, responsive experience for customers. This includes improving response rate, resolution times, CSAT, and NPS.

AI & Automation

You will implement scalable processes, leveraging automation and AI. You will develop the internal knowledge base and training protocols required to handle complex tax nexus and filing inquiries with 100% accuracy.

Customer Success Foundation

You will build the Customer Success function from the ground up, defining how Numeral segments and engages customers across enterprise and mid-market. This includes establishing a clear model for adopting, growing and retaining to ensure customers realize value quickly and consistently.

Customer Outcomes & Growth

You will own retention and expansion by driving measurable Net Revenue Retention (NRR), Customer Success Qualified Leads (CSQLs), customer health, and ROI. You will manage key account relationships, partner with Sales to identify upsell opportunities, and ensure customers realize the full strategic value of the platform.

Operating System & Insights

You will implement the core infrastructure for Customer Success and Support, including health scoring, feedback loops, and performance metrics. You will ensure that insights from customers directly inform product and company decisions.

Team Building & Leadership

You will hire and develop a high-performing team across Customer Success and Support, creating a culture that is deeply customer-centric while maintaining strong operational discipline.

Cross-Functional Partnership

You will serve as the voice of the customer internally, partnering closely with Product, Engineering, and GTM teams to align on priorities and ensure a seamless customer experience. What you’ll bring

A builder at heart

You have experience building or scaling Customer Success and/or Support functions in high-growth environments and are comfortable operating in ambiguity.

Customer-obsessed and outcome-driven

You focus on delivering real value to customers, with a track record of improving retention, adoption, and satisfaction.

Strategic yet hands-on

You can define long-term vision while also diving into the details when needed to ensure execution.

Strong operator

You bring experience building processes, defining metrics, and creating scalable systems that support growth across both enterprise and mid-market customers.

Modern and AI-forward

Experience leveraging AI tools, LLMs, or automated workflows to deflect common support tickets or predict customer churn before it happens.

Strong communicator and partner

You are comfortable engaging with executives externally and collaborating cross-functionally internally.

Commercial mindset

You have experience expanding revenue within an existing book of business and the ability to build expansion programs through data drive insights.

Bonus

Experience in Fintech, SaaS, financial infrastructure, tax, compliance, or finance workflows (strong plus) Background in high-growth startup environments (Series A–C+)