Chief of Staff (Office of the CEO) at VC-Backed Series B Startup
About Digitail
Digitail is on a mission to transform the veterinary profession with smart, customer-driven technology. We’re building the all-in-one operating system for animal hospitals – simplifying everything from client communication and patient care to scheduling and billing. Having just closed a Series B fundraise, we’re entering an exciting new chapter of growth and innovation.
About the RoleThe People Operations Analyst will partner closely with our Head of People to build and maintain smooth, compliant, and employee-friendly HR processes for our multi-country team.
You’ll own key workflows across payroll, onboarding, employee records, and internal tooling, while also supporting strategic initiatives like performance reviews, compensation tracking, and internal events. A successful People Operations Analyst will play a key role in ensuring our people processes run reliably and efficiently, creating the foundation for a smooth and scalable employee experience. This is a great opportunity for someone early in their People Ops career looking to gain HR exposure in a fast-growing tech environment.
Key Responsibilities- Strategy & Growth: partner closely with the CEO to shape and execute business strategy, identify optimisation opportunities, and address critical challenges
- Cross-Functional Projects: oversee OKR workstreams and strategic initiatives from conception to completion, ensuring delivery, alignment, and learnings across teams
- Market & Revenue Insights: conduct industry research and work with sales/revenue teams to evaluate opportunities, partnerships, and new growth levers
- Data & Reporting: build analyses, track KPIs, and prepare reports/presentations for leadership and board-level stakeholders
- Investor & Board Relations: support fundraising, prepare materials, and coordinate communications with current and prospective investors and board members
- Internal Operations & Communication: run key workflows and communication channels on behalf of the CEO, driving alignment and visibility across the company
- Experience in high-impact roles: you’ve worked as a Founder’s Associate or Chief of Staff in a VC-backed startup, or as a top-performing management consultant, and you’re hungry to put that experience into practice in a scaling SaaS company
- Strategic execution: you’re not just good at ideas - you know how to turn strategy into results, and you care about moving the needle on real business outcomes
- Leadership & ownership: you thrive when given responsibility, enjoy influencing outcomes across teams, and don’t shy away from making tough calls
- Analytical mindset: you love digging into data, building models, and using evidence to spark healthy debate and smarter decisions
- Project management chops: you’re highly organized, keep complex initiatives moving, and make sure nothing slips through the cracks
- Tools & systems comfort: you’re fluent in Google Sheets / Slides and can pick up new tools (e.g. Notion) quickly
- Clear communicator: you can write a crisp memo, build a compelling deck, and present with confidence to leadership, investors, or teammates
- Adaptable & versatile: you enjoy variety, are comfortable with ambiguity, and are just as happy running with a solo project as you are teaming up cross-functionally
- Entrepreneurial spirit: you’re proactive, hands-on, and get energy from solving problems in scrappy, creative ways
- Continuous improvement mindset: you enjoy bringing structure to messy workflows, untangling unclear handoffs, and making things run smoother for everyone involved
- Growth: Join a fast-growing, mission-driven SaaS startup improving the lives of veterinarians and pet parents
- Impact: you’ll have the autonomy to take initiative, drive meaningful change, and grow by doing – without layers of bureaucracy slowing you down
- Compensation: competitive salary and equity package, flexible to your preferences (i.e., optimize for PTO, salary, or equity)
- Hybrid Work: we’ve transitioned from fully-remote to a hybrid model, giving team members the chance to collaborate in-person at least three days a week from one of our hubs: Toronto (CA), London (UK), or Iași (RO).
- Salary is competitive and based on level of experience
- Stock options in a high-growth, VC-backed SaaS startup!
- Learning budget of USD $1,000/yr and coaching from industry professionals in our VC network
- Equipment including a Macbook and a USD $300 workstation stipend
- Vacation of 20 days per year
- Please upload your resume and email a 2-minute “why” video (e.g., Why Digitail? Why this role? Why you?) to calvin@digitail.io
- You can read through our Candidate Pack to learn more about Digitail and the interview process.
We look forward to hearing from you!
#J-18808-Ljbffr Salary: GBP 43200 - 72000 per year Experience: 5 years required