Chief of Staff

About InvoiceCloud:

InvoiceCloud is a fast-growing fintech leader recognized with 20 major awards in 2025 including USA TODAY and Boston Globe Top Workplaces multiple SaaS Awards wins for Best Solution for Finance and FinTech and national customer service honors from Stevie and the Business Intelligence Group. Judges also highlighted our mission to reduce digital exclusion and restore simplicity and dignity to how people pay for essential services as well as our leadership in AI maturity and responsible innovation. Its an award-winning purpose-driven environment where top talent thrives. To learn more .

Job Details:

We areseekinga highly strategic and execution-focused Chief of Staff to the CEO. This role serves as a trusted strategic partner to the CEO extending their reach across the organization and reshaping how the executive layeroperatesin an AI-first environment leading enterprise initiatives that improve organizational performance accelerate growth and strengthen operational excellence.

The successful candidate will drive complex cross-functional programs influence executive decision-making coordinate strategic priorities across the organization and ensuretimelyexecution of initiatives that advance companyobjectives.

Success Profile:

This role is anchored in our companysleadershipcompetencies. These competencies reflect the mindsets and behaviors that define success in this role. Below is how each competency translates into meaningful impact and outcomes for this position.

Strategic

• Partner with the CEO to drive strategic priorities and executive initiatives engaging the CFO and Executive Leadership Team as needed to execute business separation and integration activities executive planning and organizational initiatives.

• Own the AI-first transformation of executive operations redesigning how strategic planning decision support and program execution run in an AI-nativemodel andtranslating company-wide AI adoption into how the leadership team itself works withappropriate governanceand business oversight.

• Lead enterprise-wide cross-functional programs that improve organizational performance accelerate revenue growth and increase operational efficiency.

Results-Driven

• Lead the successful execution of multiple high-impact strategic initiatives simultaneously while balancing competing priorities and organizational demands.

• Establishmonitor and communicate key performance indicators that measure execution progress and business outcomes.

• Proactivelyidentifyexecution risks develop mitigation strategies and drivetimelyresolution of issuesimpactingorganizationalobjectives.

Collaboration

• Build trust-based relationships across the executive team and functional leaders navigating competing priorities and resolving conflicts to keep enterprise programs moving forward.

• Represent executive leadership with strategic customers external stakeholders and key business partners to resolve complex business issues and strengthen organizational relationships.

• Serve as the primary company liaison to Vista Equity Partners and Vistas Value Creation Team coordinating adoption of Vista best practices across business functions andrepresentingthe company in ongoing engagement with Vistas team.

• Partner with executive leadership to coordinate enterprise planning activities including leadership offsites Board preparation and strategic operating rhythms.

Communicates Effectively

• Communicate complex business information strategic recommendations and initiative progress clearly to executive leadership and key stakeholders.

• Elevate critical business issues to the CEO with data-driven recommendations and actionable mitigation plans.

• Serve as the CEOs central point of coordination on sensitive cross-functional matters ensuring timely executive visibility and alignment on strategic customer escalations (in partnership with the customer organization) and litigation matters (in partnership with Legal) without displacing functional ownership and owning executive communications on these topics.

• Represent the CEO in communications with the Board and investors ensuring alignment and appropriately calibrated messaging on strategic priorities financial performance and organizational change.

Requirements

• Bachelors degreerequired; MBA strongly preferred.

• 912 years of operations experience including experience leading through major organizational change (e.g. carve-outs separations mergers integrations or large-scale restructuring).

• Consulting and software industry experiencestronglypreferred.

• Demonstrated success implementing business processes and operational metrics that improve organizational performance.

• Proven project management experience delivering multiple complex initiatives on time and within budget.

• Strong business and financial acumen with exceptional analytical quantitative and data-driven decision-making skills including the ability to solve complex business problems using data-driven insights.

• Executive presence with exceptional relationship-building and influencing skills.

• Outstanding written and verbal communication skills with the ability to communicate effectively across executive and cross-functional stakeholders.

• Demonstrated successoperatingin fast-paced dynamic and ambiguous business environments.

• Ability to collaborate effectively with geographically distributed teams.

• Strong organizational agility with the ability to manage multiple priorities whilemaintainingattention to detail.

Benefits:

• Medical dental vision life & disability insurance

• 401(k) plan with company match

• Flexible Time Off (FTO) wellbeing days paid holidays and summer Fridays

• Mental health resources

• Paid parental leave & backup care

• Tuition reimbursement

• Employee Resource Groups (ERGs)

InvoiceCloud is committed to providing equal employment opportunities to all employees and applicants. We do not tolerate discrimination or harassment of any kind based on race color religion age sex nationality disability genetic information veteran or military status sexual orientation gender identity or expression or any other characteristic protected under applicable laws.

This commitment applies to all aspects of employment including recruitment hiring placement promotion termination layoff recall transfer leave compensation and training.

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