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...

Job Details: 

We are seeking a 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 layer operates in 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 ensure timely execution of initiatives that advance company objectives.  

Success Profile: 

This role is anchored in our company’s leadership competencies. 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-native model, and translating company-wide AI adoption into how the leadership team itself works, with appropriate governance and 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. 

• Establish, monitor, and communicate key performance indicators that measure execution progress and business outcomes. 

• Proactively identify execution risks, develop mitigation strategies, and drive timely resolution of issues impacting organizational objectives.  

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 Vista's Value Creation Team — coordinating adoption of Vista best practices across business functions and representing the company in ongoing engagement with Vista's 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 CEO's 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 

• Bachelor's degree required; MBA strongly preferred. 

• 9–12 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 experience strongly preferred. 

• 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 success operating in 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 while maintaining attention 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)