Scaling at Gusto: Introducing our Insights & Operations Team

Enoch Shih
Gusto Insights and Operations
3 min readJul 31, 2019

Hi. I’m Enoch. I lead the Insights & Operations (I&O) team at Gusto. We work on strategy, operations, and systems across the company.

Gusto is software-as-a-service for small businesses. We help over 100,000 modern employers onboard, pay, insure, and engage their team. Think of us as a people platform for small businesses. Gusto was founded in 2012. We have grown steadily in customers, revenue, headcount, and complexity ever since.

The I&O team was created in September 2015, after our Series B fundraising round. This was when our leaders realized that we needed to up-level our capabilities around strategy, planning, data, systems, and coordination; basically anything that did not fit cleanly into classic business departments like Marketing, Sales, and Product needed some attention.

As of July 2019, Insights & Operations is six teams, spread across Gusto’s San Francisco and Denver offices. These teams are:

  • Marketing I&O: Accelerating marketing through strategic projects, growth investments, and pricing optimization. Led by Tina Pastelero.
  • Sales I&O: Scaling sales through strategy, operations, analytics, and compensation. Sometimes called Sales Strategy & Operations in other companies. Led by John Black.
  • Customer Experience I&O: Amplifying Customer Experience (CX) to deliver a differentiated customer experience. Sometimes called CX Strategy. Led by Lisa Robinson.
  • Product and Partnership I&O: Connecting product, people, process, and partners across the customer journey. Sometimes called Product Operations, Product Specialists, and Technical Product Specialists. Led by Riley Bingham.
  • Business I&O: Driving cross-functional strategic projects and operational excellence for Gusto’s business teams. A cross between a Business Operations, Chief of Staff, and Corporate Strategy. Led by Maggie Chao.
  • Business Technology: Building solutions, systems, and internal tools for Gusto. Sometimes called Business Systems or IT. Led by Aurobind Ravichandran.

We measure ourselves quarterly based on business impact. We keep impeccable commitments to Objectives and Key Results (OKRs), team effectiveness, and business partnership. Our ultimate goal is to help our customers and Gusto grow successfully.

Over the past four years, in partnership with other Gusto teams, I&O has helped create and incubate many capabilities from scratch. This includes our business systems architecture, company planning cadence, company strategy, metrics and analytics, sales compensation strategy, customer success, and more.

We learned deeply from each of these efforts. Some days it felt like everything we were trying was going wrong, but it was those days that led us to doing things right. We’ve come a long way, and now these areas that used to be new projects are humming along as successful parts of the business.

At Gusto, our mission is to create a world where work empowers a better life. In that spirit, we are starting this blog to share our learnings more broadly. This blog is built for people scaling fast-growing businesses, especially for those of you facing new challenges that require expertise that may not yet exist at your company. We hope this information empowers you and your team to reach new heights.

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