Showpad · 16 hours ago
Chief of Staff
Boston, MA
Full-time
Hybrid
Director/Executive
15+ years expShowpad is a company seeking a Chief of Staff to the CEO, a senior leadership role designed for an experienced operator. The Chief of Staff will help the CEO run the business with operational excellence and lead a significant cross-functional transformation initiative.
AnalyticsContentEnterprise SoftwareMarketingMeeting SoftwareSaaSSales AutomationSales EnablementSoftwareTraining
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
Qualification
Required
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
Benefits
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
Professional stretch assignments
Company
Showpad
The best thing to ever happen to your sales team
501-1000 employees
Funding
Current Stage
Late StageTotal Funding
$159.5MKey Investors
Insight PartnersDawn CapitalHummingbird Ventures
2025-08-26Acquired
2019-06-25Series D· $70M
2018-01-24Series C· $25M
Leadership Team
Matt Miller
Chief Financial Officer
Patrick Debois
Vice President of Engineering - cms and apps foundations
Recent News
2025-11-04
Crowdfund Insider
2025-11-02
2025-11-01
Company data provided by crunchbase