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Head of People

General | San Francisco, CA | Full Time

Job Description


At Directly, we believe the fundamental nature of work is changing from fixed to fluid, as AI and collaborative technology transform how people and companies work in the next economy.  We’re leading this shift with an enterprise platform that changes the way companies think about customer support. Our Crowd-Powered AI platform combines machine learning and gig work to transform and scale customer service for world-class companies like Autodesk, LinkedIn, Microsoft, Pinterest, Samsung and SAP. We’re based in San Francisco and backed by top venture firms and angels from Silicon Valley.


We have a great opportunity for an experienced, passionate People leader with 10+ years experience to join the executive team in a strategic leadership role. Reporting to the CEO, the Head of People is a critical position that will have a direct hand in driving the next phase of growth at Directly. This is an exceptional opportunity to help how we identify, recruit, develop and retain top talent for an emerging and transformative category, and be a driving force at the forefront of AI and customer experience innovation. 


  • As the Head of People, you will collaborate with our Leadership team to create and revamp existing processes to facilitate employee recruiting, growth and happiness and drive People initiatives that align with business objectives and key results. We are looking for a “DOER” who pushes boundaries of excellence to help break down barriers, drive consensus and execute decisions with a sense of urgency.

  • Responsible for driving performance and results with ethics and integrity.  Manage company-wide People programs and initiatives (e.g., compensation & benefit reviews, equity programs, workforce planning, training & development, retention and engagement strategies and organizational change).

  • Establish trusted relationships with leadership team to provide thought leadership regarding organization and people-related strategy and execution.

  • Employer branding: communicate the value proposition of the Company to the potential recruiters and recruiters, including creating content, assets, and tools such as ROI tools, pitch decks, demos, competitive briefs and other materials.

  • Manage all employees of the People department including talent and facilities and responsible for the performance management and hiring of the employees within that department.

  • Recruiter Management: drive engagement with key recruiters and ensure our story is understood and represented in their reports.

  • Execute compensation and benefits programs to include annual salary planning processes, salary surveys and analysis, benefit programs and employee services (perks).

  • Compliance: Partner with Security, Finance, and Legal to ensure People policies and practices comply with applicable law, standards and best practices. Develop a scalable approach to People Operations in line with business needs, culture and values, including relevant programs addressing global programs, compliance and processes. Ensure we scale not only in a compliant way, but in a manner consistent with and in furtherance of our culture and values.

  • Work with team and company leadership in creating and implementing contemporary, data-driven systems that ground People decision-making and strategy in empirical, predictive reality.

  • Continuously thinking about our employees, customers, stakeholders and the business and accepting personal accountability for driving results. Relentless in creating value, identifying and realizing opportunities to achieve superior results for shareholders and stakeholders.



  • Minimum of 10+ years in HR/People Operations, building and implementing operational programs. Minimum 5 years experience in Management.  Track record building and delivering People programs from the ground up in a fast-growing organization.

  • Resourcefulness, pragmatism and roll-up the sleeves mentality. Experience in fast-growth startup environments preferred.

  • Strategic vision— ability to see where the business is headed and develop programs proactively.

  • Strong project management skills— ability to translate vision into action.

  • Leadership that inspires and grounds others in a shared purpose.

  • Strong communication skills— ability to break down complex concepts and clearly explain them internally and externally.

  • Excellent oral and written communication.

  • Great organizational skills with exceptional follow through and attention to detail.

Directly is an equal opportunity employer. We believe in diversity and inclusion as a strength. This is an exempt, full-time salaried position with comprehensive benefits.