We help companies find their growth markets for talent. We’re looking for thinkers, creators and growth-minded people to help drive our success and grow along with us.

Chief of Staff

San Francisco, CA

About Terrain

Terrain is a Talent + Location Intelligence Platform creating applied analytics for Investors, Advisors, and Enterprises. Our software platform unifies disparate, siloed data and uses machine learning & data science to deliver proprietary insights on investment, site selection and workforce planning decisions.

Based on our experience as entrepreneurs and investors, we founded Terrain in 2017 on the core belief that big data would significantly impact industries that had been slow to embrace technology - Real Estate and Recruiting. Systems and Technology, combined with Human Intelligence, would create more transparency faster and significantly outperform outdated structures that were reliant solely upon limited personal networks and social proof. After a few years in R&D mode, incubating early concepts with strategic partners and investors, we have created purpose-built products for real estate investors and enterprise business leaders that address uncertainty around market volatility and create actionable insights on how to build successful investment and workforce strategies.  

About the Role

Reporting to the CEO, the Chief of Staff will play a critical role working directly with Terrain’s co-founders to drive value-creation with key customers as well as excellence in internal business operations. 

We are seeking a Chief of Staff who can autonomously execute and operate in a dynamic, fast paced environment. Ideally you have a strong interest in Data, Real Estate and People and intrinsically you have a mission-driven, entrepreneurial orientation.  

No single day is like another so your role will be a never-boring mix of a variety of functions. On any given day, you will be asked to contribute to growth, operations, customer success, and finance. You’ll be asked to breathe internal programs and systems that enable, build and scale our early stage company.

What You Will Be Doing

One of your primary responsibilities will be to open up our founders’ bandwidth for scale by professionalizing business operations. Initially you will be tasked with:

  • Driving alignment around goal setting and strategy
  • Forming plans with clear objectives and asks
  • Providing visibility and performance tracking to the business by helping to build, maintain, and improve our data and reporting foundation.

Facilitate team meetings & planning

  • Weekly team meetings - prepare agendas, take notes and assign action items
  • Quarterly company-wide presentation
  • Year-in-Review company-wide presentation
  • Yearly company-wide kickoff meeting

Investor Communication & Reporting

  • Weekly update(s) to company
  • Monthly update to company & board/investors
  • Prepare for quarterly & annual board packages & meetings

Additional operating responsibilities:

  • Build and manage OKRs + KPIs, drive & maintain reporting
  • Review & synthesize metrics & initiatives to support company priority setting
  • Lead efforts to office expansion & recruiting
  • Lead critical projects based on emergent business needs and work collaboratively across the business and functions to deliver results.


What We Are Looking For

The successful Chief of Staff understands the importance of balancing business objectives and operational excellence. You will also have a passion for data and turning those data into actionable insights. The ideal candidate will be a highly organized, self-starter with executive presence and the stamina to deal with the rapid pace, ambiguity, and amount of change occurring within a growing early stage company. 

Ideal candidates will have 2-5 years of experience working in Investment Banking, Private Equity and/or Management Consulting, with 2+ years of experience working with and presenting to C-level executives.  Specifically  we are looking for people who are excited to step into a dynamic role where you will be asked to wear multiple hats within an organization.

Additionally, we’re seeking candidates with demonstrated track records of:

  • Building scalable systems & processes that improve productivity, provide increased visibility into progress made against KPIs, and building clear policies & processes to guide customer interactions
  • Financial modeling using advanced skills in Excel and PowerPoint (must have familiarity with things like print formatting, index-match-match) and a demonstrated aptitude with measurement and analytics to make decisions
  • Natural propensity to trace progress and report status following quantitative means 
  • Forming, implementing and refining strategies on how project objectives can be met efficiently, in the right sequence, by cross-functional teams within project constraints (time, budget, etc)
  • Monitoring and communicating overall project progress throughout lifecycle, as well as the ability to creatively respond to and resolve discrepancies, stalled workflows, internal/external roadblocks or setbacks
  • Proficiency with commonly used tools (Asana, Notion, etc) 
  • Extreme detail-orientation as operator with strong bias towards planning, clarity and simplicity 
  • Superior communication skills - clear verbal and written communicator, summarizing information succinctly, and the ability to adapt communication style to different audiences.
  • Track record of setting, achieving and/or surpassing goals with a proven ability to work independently, needing minimal direction in ambiguous contexts to understand and adapt quickly

Your Mindset

  • You are a builder at heart, so this may be the step you take before starting your own company
  • You’re a systems thinker who sees the full picture and thinks holistically about solving problems. 
  • You operate with a product mindset. You listen and effectively frame problems, collecting insightful data and making clear + concise recommendations
  • You relentlessly following through (and up) on tasks, actions, and deliverables
  • You are a creative problem solver and hard worker who displays humility, low ego and high EQ

Diversity, Equity and Inclusion at Terrain

Terrain is for everyone and we are committed to ensuring equal employment opportunity and to providing employees with a safe and welcoming work environment free of discrimination and harassment.


Employment decisions at Terrain are based on business needs, job requirements and individual qualifications, without regard to race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. Terrain encourages applicants from all backgrounds.

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