O

Outset

AI-driven interview solution for candidate evaluation

Head of Workplace Operations

Full-Time
$175k - $200k/yr
Senior, Expert
San Francisco, CA, USA
In PersonFive days on-site in San Francisco.
Facilities OperationsFacilities Management

About the job

Requirements
  • At least 7 years of experience in workplace operations, facilities management, office management, or real estate administration, including at least 2 years in a leadership or management role.
  • Experience managing or supporting a growing technology company through multiple growth phases.
  • Proven experience managing teams and building scalable operations.
  • Experience managing multiple office locations or scaled workplace operations across geographies.
  • Expertise in vendor and contract management, including negotiating with landlords, service providers, and cross-functional partners.
  • Experience forecasting, tracking, and optimizing operational spending and managing capital projects.
  • Ability to coordinate multiple initiatives, including renovations, moves, and events, simultaneously.
  • Strong organizational skills and attention to detail, with comfort in strategic planning and tactical execution.
  • Ability to communicate and manage stakeholders and partner with leadership across departments and levels.
  • Background in capital project management, including office buildouts, renovations, and fit-outs.
  • Familiarity with OSHA, ADA, or building code compliance.
  • Experience with cross-functional strategic planning and organizational change management.
Responsibilities
  • Hire, onboard, and mentor future workplace operations team members.
  • Build a strong operations culture and scale processes as the team grows.
  • Oversee day-to-day office operations across San Francisco and New York, including supplies inventory, maintenance scheduling, and cleanliness standards.
  • Manage vendor relationships for janitorial services, IT support, maintenance, security, and utilities, and negotiate contracts.
  • Direct office equipment and technology management, including conference room setups, audiovisual systems, Wi-Fi, hardware procurement, and troubleshooting.
  • Ensure compliance with safety, building codes, and accessibility standards across both locations.
  • Manage lease administration, including renewals, amendments, rent escalations, landlord communications, and strategic real estate decisions.
  • Plan and execute space utilization by monitoring occupancy, identifying expansion or reduction needs, and optimizing desk and meeting room allocation.
  • Lead office renovations and improvements by gathering requirements, managing contractors, and ensuring on-time and on-budget delivery.
  • Manage real estate budgets and capital expenditures across both offices, and forecast and track spending.
  • Coordinate office events, including all-hands meetings, team celebrations, client visits, conferences, and off-sites.
  • Manage meeting room scheduling and booking systems, and oversee room setups for events and presentations.
  • Source and manage office amenities, including coffee, beverages, snacks, wellness programs, and workplace culture initiatives.
  • Own the workplace operations budget by forecasting and tracking spending, identifying cost savings opportunities, and driving efficiency.
  • Track and report operational metrics, including occupancy, square footage costs, vendor performance, incident reports, and team KPIs.
  • Develop and execute long-term workplace strategy aligned with company growth and culture.
  • Hire and lead an Office Manager based in San Francisco.

About the company

Outset.ai provides an AI-powered interview platform for HR that helps businesses assess candidates more efficiently. Its core tool is an AI interviewer that conducts interviews, asks dynamic follow-up questions, and categorizes responses to reveal deeper insights about a candidate’s fit. The system works by running interviews, generating follow-up prompts as needed, and analyzing answers to produce structured data and scoring to guide hiring decisions. What sets Outset.ai apart is its focus on an automatically conducted, adaptive interview process and organized response analysis, enabling HR teams of all sizes to streamline recruitment and rely on data-driven results rather than manual screening alone. The company aims to reduce the time and resources spent on candidate evaluation while increasing the accuracy and speed of hiring decisions.

Company Size

51-200

Company Stage

Series B

Total Funding

$52M

Headquarters

San Francisco, California

Founded

2022

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Simplify's Take

What believers are saying

  • Radical Ventures led Outset's $30 million Series B in December 2025, signaling investor conviction.
  • Outset claims 8x revenue growth in 2025 and serves Microsoft, Nestlé, Uber and HubSpot.
  • August 2026 launches added MCP integrations, visual intelligence, and prototype testing for expansion.

What critics are saying

  • OpenAI, Qualtrics, and Medallia can bundle conversational research, crushing Outset's pricing power quickly.
  • Digital Twins on August 27, 2026 raises trust, bias, and validity risks for enterprise buyers.
  • A single platform outage or model failure would halt interviews, synthesis, and customer insight delivery.

What makes Outset unique

  • Outset's AI interviewer runs adaptive, human-like interviews at survey scale across 40+ languages.
  • Digital Twins by Outset, launched August 27, 2026, turns qualitative responses into synthetic respondents.
  • Outset integrates recruitment, interviewing, synthesis, and fraud detection in one workflow.

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Benefits

  • Health Insurance
  • 401(k) Retirement Plan
  • Remote Work Options
  • Flexible Work Hours
  • Paid Vacation
  • Paid Holidays
  • Stock Options
  • Company Equity
  • Wellness Program
  • Mental Health Support
  • Gym Membership
  • Phone/Internet Stipend

Growth & Insights and Company News

Headcount

6 month growth

4%

1 year growth

8%

2 year growth

-4%
FinSMEs
Dec 11th, 2025
Outset Raises $30M in Series B Funding

Outset raises $30M in Series B funding. Outset, a San Francisco, CA-based provider of an AI-moderated research platform, raised $30M in Series B funding. The round was led by Radical Ventures, with participation from M12, Microsoft's Venture Fund, as well as previous investors Y Combinator, Adverb Ventures, and 8VC. The company intends to use the funds to expand operations and its development efforts. Led by CEO Aaron Cannon, Outset specializes in AI-moderated research, empowering research and product teams to understand people with depth, speed, and global scale. Its platform delivers AI-moderated interviews, synthesis, fraud detection, and live translation across more than 40 languages. The company says that this enables organizations to finally understand both the metric and its meaning, transforming CXM from a dashboard of scores into a continuous engine for insight, action, and improvement.

Starkville Daily News
Dec 10th, 2025
Outset raises $30M Series B to launch AI-native customer experience management platform

Outset, an AI-moderated research platform, has raised $30 million in a Series B round led by Radical Ventures, bringing total funding to $51 million. M12, Microsoft's Venture Fund, participated alongside previous investors Y Combinator, Adverb Ventures and 8VC. The San Francisco-based company is launching what it calls the world's first AI-native Customer Experience Management platform. Unlike traditional CXM platforms such as Qualtrics and Medallia that rely on multiple-choice metrics, Outset deploys AI agents that conduct human-like conversations with customers to uncover deeper insights. Founded in 2023, Outset supports over 40 languages and serves clients including Microsoft, Nestlé, Uber and HubSpot. The company achieved 8x revenue growth in 2025. The funding will accelerate global expansion and development of real-time customer insight products.

Intelligence360 News
Dec 5th, 2025
Parnassus Labs raises $18.6M in new funding round

Parnassus Labs, operating as Outset, has filed a notice with the US Securities and Exchange Commission for an exempt offering to raise $18.6 million in new funding. The filing was made under Rule 504 or 506 of Regulation D or Section 4(a)(5) of the Securities Act of 1933, which allows companies to sell securities without registration. Federal securities law requires such notices to be filed within 15 days after the first sale of securities in the offering. No additional details about the funding round, investors or the company's plans for the capital were disclosed in the filing.

MR Web
Jun 12th, 2025
Daily Research News Online

In San Francisco, AI-moderated research platform Outset has announced a $17m Series A round, which it will use to expand its team and accelerate product expansion.

Traumjob
Jun 11th, 2025
Outset raises $17M to replace human interviewers with AI agents for enterprise research

Outset raises $17M to replace human interviewers with AI agents for enterprise research.