Chief of Staff

Chief of Staff

Boston, MA

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. It's an award-winning, purpose-driven environment where top talent thrives. To learn more, visit InvoiceCloud.com.

We are seeking a highly strategic and execution-focused Chief of Staff to support the Executive Leadership Team. This role serves as a trusted advisor and strategic partner to executive leadership, 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

• Lead enterprise-wide, cross-functional strategic initiatives that improve organizational performance, accelerate revenue growth, and increase operational efficiency.
• Partner with the CEO, CFO, and Executive Leadership Team to execute strategic priorities, including post-merger integration activities, executive planning, and organizational initiatives.
• Coordinate implementation of company and Vista Equity Partners best practices across business functions to strengthen operational maturity.
• Evaluate and responsibly leverage AI and automation technologies to improve strategic planning, executive decision support, program execution, and operational efficiency while maintaining appropriate governance and business oversight.

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

• Partner across executive leadership and functional organizations to coordinate strategic initiatives, align priorities, and drive enterprise execution.
• 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 for Vista Equity Partners and Vista's Value Creation Team regarding strategic initiatives.
• 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 executive point of contact for sensitive matters including strategic customer escalations, litigation coordination, and executive communications.
• Foster transparency, alignment, and accountability through effective executive communication across the organization.

Requirements

• Bachelor's degree required; MBA strongly preferred.
• 9–12 years of operations experience with multiple assignments involving mergers and acquisitions integration.
• 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 and quantitative skills.
• Demonstrated ability to solve complex business problems using data-driven decision making.
• 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)

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay. The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we'll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.

Base Compensation Range

$220,000 - $290,000 USD

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.

If you require a disability-related or religious accommodation during the application or recruitment process, and wish to discuss possible adjustments, please contact View email address on click.appcast.io.