Your browser cookies must be enabled in order to apply for this job. Please contact if you need further instruction on how to do that.

Head of People

General | San Francisco, CA | Full Time

Job Description


Head of People roles at startups can all look the same, but this is a unique opportunity. At Directly, we believe the fundamental nature of work is changing from fixed to fluid, as AI and the gig economy transform how people and companies work in the next economy.  The head of People at Directly will shape the talent model for a company that is redefining work companies like Airbnb, Autodesk, Microsoft, LinkedIn, Microsoft, Intuit, Samsung and SAP -- helping them move to better talent models that are more productive for the company and more engaging for the talent.

Salesforce capitalized on a shift from fixed to fluid technology (software to SaaS) to become a market leader and help the business world move to fluid technology models. We believe there’s an even larger opportunity for the company that helps the business world move to fluid talent models. Directly is based in San Francisco and backed by top venture firms including Microsoft Ventures, True Ventures, Costanoa Ventures, and Northgate.


We have a great opportunity for an experienced, passionate People leader with 10+ years experience to join the leadership 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 optimize 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.

The ideal candidate is an experienced and passionate talent leader who’s built a great and high-performing culture and strong recruiting engine at early and mid-stage high growth startups.


Core Responsibilities

  • Collaborate as a member of the leadership team to map talent strategy to business strategy

  • Build a recruiting engine where Directly is the employer of choice

  • Develop a set of people programs that drive a great and high-performing culture


Other Responsibilities

  • Build and manage a team responsible for people operations, HR, recruiting, onboarding, performance management, office, and ecosystem

  • Partner with security, finance, and legal to ensure people policies and practices comply with applicable law, standards and best practices - including SOC2 and GDPR

  • Partner with the leadership team and lead the implementation of high-performance systems, including OKRs, 360 degree reviews

  • Develop the compensation, variable compensation, equity structure, and benefits for the company, aligning it with OKRs and key metrics

  • Lead the development of growth and education programs for the team to foster the continual learning and development of the team

  • Design and lead formal and informal feedback, surveying, and benchmarking systems to measure and improve team member satisfaction and engagement

  • Lead the development of an office and physical environment that supports and drives performance, collaboration and supports the company’s values



  • A successful track record building and delivering talent acquisition and people programs from the ground up in a fast-growing organization

  • 10+ years of broad recruiting and leadership in Recruiting and HR/People Operations, building and implementing operational programs, with at least 5+ years managing teams

  • 3+ years in B2B software or services

  • Experience in both early startups (venture-backed, quickly growing, <100 people) and mid or later stage startups

  • Experience building distributed teams



  • Leadership that inspires and grounds others in a shared purpose

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

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

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

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

  • Data-driven — an orientation that combines qualitative and quantitative

  • Resourcefulness, pragmatism, and roll-up the sleeves mentality

  • Mission-driven, smart & humble, results-oriented, collaborative, with a sense of humor and strong EQ


Directly is an equal opportunity employer. We believe in diversity and inclusion as a strength.