Vice President, Billing & Renewals - Operations & Transformation at FreshBooks

San Mateo, California, United States

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

SaaS, Technology, SoftwareIndustries

Requirements

Executive-level experience leading Billing and Renewals transformations in a SaaS environment, particularly with complex subscription, usage-based, and outcome-driven billing models
Proven ability to architect end-to-end Billing systems and processes for seamless, real-time experiences supporting New and Expansion customers
Expertise in deploying AI-powered automation, real-time validation, and integrated quote-to-cash workflows
Strong collaboration skills with cross-functional teams including Sales, Product, Deal Desk, IT, Pricing & Packaging, Customer Success, and Product Marketing
Experience scaling Renewals programs focused on ARR retention, pricing discipline, proactive engagement, customer segmentation, and value delivery
Capability to build predictive analytics, early warning systems for churn risk, and upsell strategies
Leadership experience building and leading high-performing teams in Billing and Renewal Operations with a focus on customer-centric and employee-centric culture
Proficiency in establishing KPIs, performance dashboards, robust controls, reporting, compliance frameworks, and global financial integrity/auditability

Responsibilities

Architect and lead the end-to-end transformation of Billing systems and processes for flawless, real-time billing across subscription, usage-based, and outcome-driven models for New and Expansion customers
Deploy AI-powered automation and real-time validation to eliminate friction in onboarding and billing processes, ensuring scalability
Collaborate with Sales, Product, Deal Desk, and IT to create integrated quote-to-cash workflows supporting rapid sales velocity and customer-first experiences
Work with Pricing & Packaging to operationalize complex pricing and support new product launches and market expansion
Establish robust controls, reporting, compliance frameworks, and global readiness for financial integrity and auditability
Lead the transformation of Renewals into a data-driven engine for proactive engagement, ARR retention, and pricing discipline
Scale dynamic Renewal programs leveraging customer segmentation, usage data, and value delivery to increase renewal value
Partner with Customer Success, Sales, and Product Marketing to develop renewal narratives, retention plays, and long-term contracts
Build predictive analytics and early warning systems to monitor churn risk, surface upsell paths, and prioritize high-impact renewals
Build and lead high-performing teams in Billing and Renewal Operations, fostering accountability and strategic urgency
Define KPIs and performance dashboards to track and provide transparency on New, Expansion, and Renewal billing motions for executive leadership

Skills

SaaS Billing

Usage-Based Billing

Renewals Management

Revenue Operations

Pricing Strategy

Customer Retention

GTM

Operations Transformation

Predictive Engagement

FreshBooks

Cloud-based accounting software for businesses

About FreshBooks

FreshBooks provides cloud-based accounting software aimed at simplifying financial management for small to medium-sized businesses and self-employed professionals. The software allows users to efficiently track expenses, time, and invoices, making it accessible even for those without accounting experience. Users subscribe to the service with various pricing tiers, and they can take advantage of a 30-day money-back guarantee and an 80% discount for the first four months. FreshBooks stands out from competitors by offering a user-friendly interface and mobile accessibility, enabling users to manage their finances on the go. The company's goal is to help business owners and accountants streamline their financial processes, improve organization, and enhance client relationships.

Toronto, CanadaHeadquarters

2003Year Founded

$149.6MTotal Funding

DEBTCompany Stage

Consumer Software, FintechIndustries

201-500Employees

Benefits

Health Insurance

Dental Insurance

401(k) Company Match

Stock Options

Unlimited Paid Time Off

Parental Leave

Home Office Stipend

Professional Development Budget

Risks

Increased competition from market leaders may impact FreshBooks' market share.

Dependency on Stripe's technology could pose risks if Stripe faces issues.

Economic downturns may threaten FreshBooks' subscription-based revenue model.

Differentiation

FreshBooks offers a user-friendly platform for non-accountants, simplifying financial management.

The company provides mobile-friendly solutions, catering to the rise of remote work.

FreshBooks' integration with Shopify enhances e-commerce capabilities for online businesses.

Upsides

FreshBooks' subscription model aligns with industry trends, boosting customer acquisition and retention.

The expansion of Stripe Connect features enhances FreshBooks Payments, improving payment processing.

AI-driven financial analytics tools can provide predictive insights, enhancing decision-making.

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