Head of Real Estate and Workplace Experience

Decagon; San Francisco, New York (CA, NY); On-site; USD 220,000 - 280,000; Full time

Benefits offered by this job

Medical, Dental, and Vision benefits

Life Insurance and Disability Benefits

Retirement Plan (e.g., 401K)

Parental Leave

Fertility and family building benefits

Wellness stipend

Daily lunches and snacks

Flexible vacation policy

Job summary

Decagon is seeking a Head of Real Estate & Workplace to own our global real estate strategy and ensure offices scale with growth. You will lead site selection, lease negotiations, and office build-outs while guiding the Workplace team to deliver exceptional employee experiences.

You will partner with Finance, People, IT, and the executive team to shape long-term space planning, manage multi-market expansions, and align real estate with Decagon’s culture of excellence.

Qualifications

• 6-8+ years of experience in corporate real estate or a brokerage/advisory firm.
• Experience negotiating commercial leases and managing multi-site expansions.
• Proven ability to lead strategic planning with hands-on execution.
• Strong financial acumen and ability to present to executives.
• Demonstrated leadership to build and scale a team.

Responsibilities

• Own global real estate strategy and multi-year portfolio planning across markets.
• Lead site selection, lease negotiations, and office build-outs; supervise Workplace team.

Skills

Real estate leadership

Lease negotiation

Strategic planning

Multisite expansions

Financial modeling

Executive communication

People leadership

Job description

About Decagon

Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences.

Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel.

We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others.

We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team.

About the Team

At Decagon, our offices are more than workplaces - they’re the center of how we build, collaborate and move fast together. From our San Francisco headquarters to expanding spaces in New York, Europe, Australia, and beyond, we create workplaces that are functional, inspiring and deeply aligned with Decagon’s culture.
The Workplace team owns the strategy and operations behind our work environments, from real estate strategy and build-outs to the systems that keep our offices running seamlessly day to day. Our work directly shapes how Decagon operates, bringing intention and precision to the spaces where innovation happens.

About the Role

The Head of Real Estate & Workplace will own Decagon’s global real estate strategy, ensuring our physical environments scale in step with our growth. You will lead site selection, execute lease negotiations, and oversee new office buildouts. You will also lead the Workplace team that delivers an excellent employee experience in these offices day-to-day.
This role is strategic in nature and backed by hands-on execution. You will build Decagon’s long-term real estate portfolio plan by turning headcount forecasts into space needs, determining when to expand, sublease, or bridge the gap with flexible space and executing accordingly.
As a senior leader, you will partner closely with Finance, People, IT, and the executive team to make high-stakes real estate decisions and deliver world-class spaces that enable collaboration, drive productivity, and embody Decagon’s culture of excellence.

In this role, you will

• Own Decagon’s global real estate strategy, building a multi-year portfolio plan tied to headcount forecasts across San Francisco, New York, London, Australia, Toronto, and future markets.

• Negotiate leases, manage brokers/vendors, and oversee build-outs and office openings across San Francisco, New York, Australia, Canada, and Europe.

• Partner with People, Finance, IT, and Leadership to plan for growth and deliver spaces that enable collaboration and high performance

• Lead a Workplace team that delivers excellent operations and employee experience across every office

Your background looks something like this

• 6-8+ years of experience in corporate real estate or a brokerage/advisory firm, ideally including time in high-growth startups or tech.

• Proven track record negotiating commercial leases, managing vendors, and leading multi-site expansions and office build-outs from site search through move-in.

• Comfortable moving fluidly between strategic planning and tactical hands-on execution.

• Strong financial acumen and executive communication skills: Comfortable building occupancy models, evaluating deal economics, and presenting recommendations to executives.

• Strong people leadership, with the ability to build, inspire and scale a team.

• Excited by the pace and ambiguity of a fast-scaling company where the playbook is still being written.

Compensation

• $220K-$280K + equity

Benefits

We proudly offer the following benefits for our full-time employees:

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• Retirement Plan (e.g., 401K, pension)

• Parental Leave

• Fertility and family building benefits through Carrot

• Monthly stipend to support your wellness, lifestyle, and work-life balance

• Daily lunches and snacks in the office to keep you at your best

• Take what you need vacation policy (subject to local requirements; UK employees receive 25 days of statutory leave)

These benefits are described in more detail in Decagon’s policies, may vary by location, and can change at any time according to applicable compensation and benefits plans.