Chief of Staff

Chief of StaffBoston, MAInvoiceCloud 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 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 ProfileThis 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.StrategicPartner 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-DrivenLead 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.CollaborationBuild 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 EffectivelyCommunicate 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.RequirementsBachelor'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.BenefitsMedical, dental, vision, life & disability insurance401(k) plan with company matchFlexible Time Off (FTO), wellbeing days, paid holidays, and summer FridaysMental health resourcesPaid parental leave & backup careTuition reimbursementEmployee 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 USDInvoiceCloud 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.