# Bobby Jaffari

> Bobby Jaffari is the chief executive officer of Osano, a data privacy management software company. A veteran SaaS operator, he previously led revenue and customer success at Iterable and spent more than six years building Freshworks' Americas business through its 2021 public offering. His operating philosophy centers on aligning product, go-to-market, operations, and culture around customer success.

- **Role:** Chief Executive Officer at Osano
- **Organizations:** Osano, Iterable, Freshworks, Freshdesk, Satmetrix Systems, Hightail, Cisco WebEx, WebEx
- **Known for:** Helped WebEx grow before Cisco acquired it for $3.2 billion in 2007., Led midmarket and enterprise teams at Hightail to threefold revenue growth, according to Freshworks' 2016 appointment announcement., Built Freshworks' Americas business from its early North American presence through the company's 2021 public offering.

## Career timeline

- **Before 2011** — Spent more than 10 years in leadership roles at WebEx, including leading sales teams as the business grew; WebEx was acquired by Cisco for $3.2 billion in 2007.
- **Before 2016** — Held sales leadership roles at Hightail and Satmetrix Systems after WebEx.
- **2016** — Joined Freshdesk as vice president of sales for North America, with responsibility for scaling the midmarket business.
- **2019** — Served as president of North America at Freshworks.
- **2021** — Helped lead Freshworks' Americas business through the company's U.S. public offering.
- **2022** — Ended a tenure of more than six and a half years at Freshworks and joined Iterable as chief revenue officer, leading sales, customer success, and revenue operations.
- **2025** — Became chief executive officer of Osano; founder Arlo Gilbert moved from CEO to chief innovation officer.
- **2026** — Reported two consecutive record quarters and 100% year-over-year Q4 growth, and set a goal of accelerating growth while bringing new products to market.

## Achievements

- Helped WebEx grow before Cisco acquired it for $3.2 billion in 2007.
- Led midmarket and enterprise teams at Hightail to threefold revenue growth, according to Freshworks' 2016 appointment announcement.
- Built Freshworks' Americas business from its early North American presence through the company's 2021 public offering.
- Led sales, customer success, and revenue operations as Iterable's chief revenue officer.
- Was selected unanimously by Osano's board to succeed founder Arlo Gilbert as chief executive officer in 2025.
- Reported two consecutive record quarters and 100% year-over-year Q4 growth during his first six months as Osano CEO.

## Latest updates

- **2026-04** — Jaffari wrote that data privacy is becoming central to customer trust and highlighted Osano's launch of Compliance Check, a website scanner that identifies potential compliance gaps.
- **2026-01** — About six months into his first CEO role, Jaffari reported two consecutive record quarters and 100% year-over-year Q4 growth, and said Osano planned to accelerate growth and launch new products in 2026.
- **2025-07** — Jaffari became CEO of Osano, succeeding founder Arlo Gilbert, who moved into the chief innovation officer role.

## Links

- Website: https://www.osano.com
- LinkedIn: https://www.linkedin.com/in/bobbyjaffari

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Profile page: https://yespress.io/bobby-jaffari
Published by YesPress — https://yespress.io
Last updated: 2026-08-18