Director of Operations

Overview

Since 2012, Happily has helped world-positive organizations design, launch, and produce ambitious events, experiential campaigns, and community programs through a global network of creative and production talent assembled by our proprietary software.

The Director of Operations reports to the CEO and sits at the center of Happily’s operating system. This person turns company priorities into clear plans, aligns teams around the roadmap, owns pitch and proposal operations, manages goals and dashboards, improves internal systems, and ensures the company follows through.

This is a high-context, high-accountability individual contributor leadership role to start, with the potential to manage operations, systems, or people operations support as the company scales. It is designed for someone who can bring structure to ambiguity, move work across teams, and make sure the business is not just busy, but actually progressing.

Responsibilities

Operational Management

Own the operating rhythm that keeps Happily focused, accountable and moving against company priorities.

• Translate leadership priorities into clear owners, timelines and weekly next steps.
• Maintain the company operating roadmap across sales, product, client services, growth and internal systems.
• Track progress against goals and flag what is stuck, late, blocked, or no longer relevant.
• Support the sales team by tracking pipeline performance, proposal activity, conversion rates, deal size, timing, and bottlenecks.
• Help translate qualified opportunities into clear scopes, timelines, staffing plans, and budget assumptions.
• Pressure-test whether proposed scopes are operationally realistic, properly resourced, and aligned with company priorities.
• Run weekly goal reviews, leadership check-ins, and internal operating meetings.
• Identify operational risks and create practical systems to improve accountability, follow through and decision making.
• Coordinate legal and compliance workflows related to contracts, disputes, equity administration, and business operations.

Systems & Technology

Build and improve the internal systems, dashboards, and tools that make the company easier to run and scale.

• Own company dashboards across sales, revenue, marketplace performance, delivery, product usage and team goals.
• Build and maintain KPI reporting in Happily, Hubspot, Google, and other internal systems.
• Partners with product, engineering, and growth teams to connect product priorities to revenue, customer needs and operational efficiency.
• Translate business needs into product requirements, workflows, and implementation plans.
• Support rollout plans for new features, internal tools, client-facing systems and operational improvements.
• Create and maintain SOPs, templates, planning tools, and internal handoff documents for recurring workflows.
• Leverage AI tools and no-code platforms to enhance company-wide productivity.
• Ensure key systems have clear owners, clean data, and useful reporting.
• Develop, document, and refine internal and client service delivery systems to improve consistency, scalability, and efficiency.

Strategic Planning & Reporting

Help the CEO translate company strategy into clear reporting, planning materials, and leadership-level decisions.

• Monitor company performance against key metrics and recommend adjustments as needed.
• Prepare internal leadership updates, stakeholder reports, and quarterly planning materials.
• Maintain a clear view of active initiatives, product priorities, sales priorities, and operational tradeoffs.
• Support quarterly and annual planning by identifying risks, resources gaps and decisions needed from leadership.
• Track competitor, market, and customer insights to inform planning, positioning, product priorities, and operational decisions.

People Operations & HR

Own the administrative and process side of people operations so recruiting, onboarding, offboarding, reviews, and team issues do not fall back on the CEO. This person is not expected to be a full HR executive, but they are expected to own the operational administration and follow-through of people processes.

• Manage recruiting workflows, job postings, candidate tracking, interviews and hiring logistics.
• Support offer letters, onboarding plans, contractor agreements, offboarding checklists, and employee records.
• Oversee performance review cycles, compensation updates, bonuses, and role changes.
• Escalate team issues appropriately and help managers document role clarity, performance expectations, and improvement plans.

Success Metrics

This role will be measured by whether the company becomes clearer, faster, and more accountable.

Key outcomes include:

• Company priorities are translated into a visible roadmap.
• Teams know their goals and what they are accountable for each week.
• Dashboards show the real state of the business.
• Product priorities connect directly to revenue, customer needs, and operational efficiency.
• SOPs reduce repeated questions and one-off founder explanations.
• Delivery handoffs, support workflows, and client/freelancer issue resolution are clearer, faster, and better documented.
• Hiring, onboarding, offboarding, and performance processes are organized and consistently managed.
• Leadership can see what is working, what is stuck, and what needs attention.

Required Experience

• 7+ years of experience in operations, business operations, project management, consulting, chief of staff, product operations, or a related role.
• Experience working directly with a CEO, founder, or executive team.
• Proven ability to translate strategic priorities into clear plans, owners, timelines, and measurable goals.
• Strong experience managing cross-functional projects across multiple teams.
• Experience building dashboards, KPI reports, and operating systems.
• Experience working with product, engineering, sales, growth, finance, and client delivery teams to align priorities and execute cross-functional roadmaps.
• Experience with product operations, roadmap management, SOPs, or internal knowledge systems.
• Strong technical aptitude and ability to learn new tools quickly.
• Experience with tools such as HubSpot, Google Workspace, Figma, Airtable, Notion, Slack, QuickBooks, AI tools, or no-code platforms.
• Excellent written communication and documentation skills.
• High judgment, discretion, and emotional intelligence when handling sensitive team or business issues.
• Ability to operate independently in a remote, fast-moving, globally distributed company.

Preferred Experience

• Experience in a startup, marketplace, agency, events, production, media, or creative services business.
• MBA or equivalent business/operations training
• Experience managing recruiting or people operations workflows.
• Experience supporting sales operations, proposal workflows, scope development, or client-facing business development processes.

Key Attributes

• Highly organized and allergic to loose ends.
• Personable, emotionally intelligent, and able to build trust quickly across teams.
• Clear, direct, and calm under pressure.
• Comfortable managing up, across, and down.
• Adaptable and resourceful in fast-changing environments.
• Able to quickly learn new systems, tools, and business models.
• Able to turn ambiguity into structure, clarity, and follow-through.
• Strong enough to hold people accountable without creating unnecessary drama.
• Systems-minded, but practical.
• Strong technical writer for documentation, workflows, and system design.
• Comfortable with both strategic work and unglamorous operational details.
• Curious about organizational systems, the events industry, and how great service businesses scale.
• Excited by the idea of helping a founder-led company become more scalable, measurable, and less dependent on founder intervention.

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