Chief of Staff at Selfbook

Toronto, Ontario, Canada

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

LegalTech, Technology, SaaSIndustries

Requirements

5+ years of experience in strategy, operations, consulting, or analytics within a fast-growing SaaS or technology company
Proven track record of managing complex, cross-functional initiatives
Strong analytical and data visualization skills (e.g. Excel, Google Sheets, Metabase, Looker, or similar)
Exceptional communication and storytelling ability—particularly in translating complex data into compelling narratives
Highly organized and comfortable working in ambiguity, with a bias toward action
Able to work in-office in Toronto 2–3 days per week

Responsibilities

Oversee high-impact, cross-functional projects—from strategic initiatives to operational improvements
Ensure coordination between teams on critical priorities (e.g. product launches, process scaling, customer insights)
Track deliverables and outcomes to ensure initiatives are completed on time and with measurable results
Build and maintain business dashboards and analytics for leadership decision-making
Partner with GTM, Product, and Finance teams to ensure KPIs (e.g. growth, retention, efficiency metrics) are measured accurately
Identify opportunities to improve operational processes, systems, and data flows
Drive the company-wide OKR process: facilitate quarterly goal-setting, alignment, and progress tracking
Partner with leaders to define success metrics and ensure accountability through regular check-ins and reporting
Maintain visibility into key business priorities, proactively surfacing risks or opportunities to the leadership team
Own investor reporting and board deck construction—synthesizing company metrics, narrative, and visuals into clear, concise materials
Partner with Finance and Department Heads to ensure data accuracy and consistent storytelling
Support fundraising and investor relations by maintaining up-to-date company KPIs, benchmarks, and narratives

Skills

Key technologies and capabilities for this role

Project ManagementCross-functional CoordinationBusiness AnalyticsDashboard BuildingKPIsOperational ExcellenceStrategic PlanningProcess ImprovementData AnalysisExecutive Communication

Questions & Answers

Common questions about this position

What experience is required for the Chief of Staff role?

Candidates need 5+ years of experience in strategy, operations, consulting, or analytics within a fast-growing SaaS or technology company, along with a proven track record of managing complex, cross-functional initiatives, strong analytical and data visualization skills, and exceptional communication skills.

Is this Chief of Staff position remote or onsite?

The position is onsite.

What is the salary or compensation for this role?

This information is not specified in the job description.

What kind of projects will the Chief of Staff handle?

The role involves overseeing high-impact, cross-functional projects like strategic initiatives and operational improvements, building dashboards and board decks, driving the OKR process, and owning investor reporting.

Who will the Chief of Staff work with in this role?

The Chief of Staff will partner directly with the CEO, COO, and executive team, while coordinating with GTM, Product, Finance teams, and department heads.

Selfbook

Streamlines hotel bookings and payments

About Selfbook

Selfbook provides a range of products aimed at improving hotel bookings and payment processes in the fintech and hospitality sectors. Its main offerings—Station, Direct, and Express—work together to automate the booking and payment experience, making it easier for hotels and their guests. These products help streamline the booking process, allowing guests to enjoy features like instant room upgrades and premium booking options. Selfbook operates in nearly 20 countries, which gives it valuable insights into booking trends and user behavior. Unlike many competitors, Selfbook focuses on a comprehensive product suite that integrates smoothly with existing hotel systems, generating revenue through subscription fees and transaction-based charges. The goal of Selfbook is to enhance the guest experience while helping hotels increase booking conversions and drive additional revenue.

New York City, New YorkHeadquarters

2018Year Founded

$38.9MTotal Funding

SERIES_ACompany Stage

Fintech, Consumer GoodsIndustries

11-50Employees

Risks

Increased competition from fintech startups could threaten Selfbook's market share.

Decline in travel startup funding may limit Selfbook's future investment opportunities.

Rapid evolution of payment technologies requires continuous adaptation from Selfbook.

Differentiation

Selfbook integrates seamlessly with existing hotel systems, enhancing booking and payment processes.

The platform supports all global credit cards, digital wallets, and alternative payment methods.

Selfbook's products, Station, Direct, and Express, automate booking and payment orchestration.

Upsides

Selfbook's global reach spans nearly 20 countries, offering insights into booking trends.

The rise of digital wallets and BNPL services boosts demand for Selfbook's platform.

Strategic investment from Amex Ventures supports Selfbook's growth and global presence.

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