Chief of Staff

Showpad•Boston, MA

3d•Hybrid

About The Position

The Chief of Staff (CoS) to the CEO is a senior, high-impact leadership role designed for an experienced operator with strong business judgment, exceptional communication skills, and the ability to operate with discretion and authority. Reporting directly to the CEO, the Chief of Staff acts as a force multiplier—helping the CEO run the business with rigor, clarity, and operational excellence. This role has two primary dimensions: CEO Office & Business Rhythm (80%) – Owning the quality, preparation, and flow of executive and board-level operating cadence. Enterprise Transformation Leadership (20%) – Leading a major, cross-functional strategic initiative sponsored by the CEO. This is intentionally not a long-term role. High-potential leaders are appointed for 18–24 months, gaining a 360-degree understanding of the business and preparing for larger leadership roles within Showpad. The Chief of Staff will report to the CEO and be part of the Executive Team.

Requirements

15+ years in software or closely related technology businesses.
Proven track record in senior operating, strategy, or transformation roles, working directly with C-suite executives and boards.
Exceptional written and verbal skills; ability to synthesize complex information into crisp, executive-grade narratives.
Demonstrated ability to operate with high discretion, trust, and sound judgment.
Ability to exert respectful but firm authority on behalf of the CEO.
Comfortable working in a global, multi-time-zone environment.
Trusted advisor mindset with strong interpersonal intelligence.
High standards for quality, clarity, and follow-through.
Calm under pressure; able to manage ambiguity and competing priorities.
Naturally collaborative while able to drive decisions when needed.
Motivated by impact, learning, and leadership development.

Responsibilities

Own preparation and orchestration of Executive Leadership Team (ELT) cadence meetings, including agenda creation aligned to CEO priorities.
Prepare executive-ready pre-reads, documents, presentations, and clear capture of decisions and follow-ups.
Lead continuous improvement of Monthly KPI and Operating Review (MOR) processes to drive consistency and insight.
Prepare weekly board-level Steering Committee (SteerCo) updates, ensuring accuracy and executive-level clarity.
Own end-to-end preparation for monthly Board of Directors meetings, including decks, narrative flow, and Q&A prep for the CEO.
Act as a trusted partner to the CEO by drafting talking points and anticipating risks or follow-up needs.
Develop a deep understanding of core business processes, functional strategies, and strategic priorities.
Partner with ELT members to ensure materials meet CEO- and board-level quality standards.
Represent the authority of the CEO in cross-functional interactions, driving alignment and accountability.
Act as "connective tissue" across Product, Engineering, Sales, Marketing, Customer Success, Finance, and Operations.
Lead a significant, cross-functional transformation initiative (e.g., operating model changes, GTM productivity, or AI-driven business change).
Own initiative scope, milestones, executive updates, and outcomes.
Coordinate execution across multiple functions, managing dependencies and risks while maintaining executive alignment.

Benefits

We welcome every voice and are committed to building a truly inclusive environment where your differences are not just welcomed, they are celebrated.
We’re building a best-in-class experience for our employees and are always identifying opportunities to encourage our team to be their authentic selves.
Whether that’s paid parental leave, paid holidays (including Juneteenth and paid time off to vote), paid time off to volunteer at non-profit organizations, personal development opportunities or professional stretch assignments, you can expect Showpad to support you.

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