# Andrew Robinson

> Andrew S. Robinson is the Houston-based chairman and CEO of Skyward Group, the holding company brand for Skyward Specialty and Apollo. He joined as CEO in May 2020, led the company through its January 2023 Nasdaq debut, became chairman in December 2023 and now leads the group following the Apollo acquisition. His earlier career spans Diamond Consulting, Hanover, Crawford, Oak HC/FT and insurance analytics businesses.

- **Role:** Chairman and Chief Executive Officer at Skyward Group
- **Organizations:** Skyward Group, Skyward Specialty Insurance, Apollo Group Holdings, The Hanover Insurance Group, Crawford & Company, Diamond Consulting, Oak HC/FT, Groundspeed Analytics, Clara Analytics
- **Education:** Bachelor of Science, Clarkson University
- **Known for:** Led the implementation of the Rule Our Niche specialty insurance strategy., Led Skyward Specialty through its January 2023 Nasdaq listing., Announced equity awards for every employee in connection with the IPO.

## Career timeline

- **Before Hanover** — Managing partner of Global Insurance at Diamond Consulting.
- **Before 2017** — Spent more than ten years at Hanover, rising to president of Specialty Insurance, executive vice president of Corporate Development and chief risk officer.
- **2017** — Global chief operating officer and executive vice president at Crawford & Company from January through July.
- **Before May 2020** — Executive in residence and then senior adviser at Oak HC/FT; leadership roles at Groundspeed Analytics and Clara Analytics.
- **2020-05** — Appointed CEO of Houston International Insurance Group, later renamed Skyward Specialty.
- **2020-07** — Joined the company board.
- **2023-01** — Led Skyward Specialty through its Nasdaq IPO.
- **2023-12** — Became chairman of the board.
- **2026-01** — Became chairman and CEO under the Skyward Group holding company brand following the Apollo acquisition.

## Achievements

- Led the implementation of the Rule Our Niche specialty insurance strategy.
- Led Skyward Specialty through its January 2023 Nasdaq listing.
- Announced equity awards for every employee in connection with the IPO.
- Oversaw the transformation during which the insurer moved from an AM Best A- rating with a negative outlook to A with a stable outlook by 2024.
- Led the group following the acquisition of Apollo, completed January 1, 2026.

## Latest updates

- **2026-10** — Apollo, a Skyward Group company, announced its Generali partnership for Red Bridge Syndicate 2031, with in-principle Lloyd’s approval and an expected January 2027 start.
- **2026-09** — Skyward Group announced the expansion of ibott autonomous vehicle capabilities into the U.S. primary insurance market.
- **2026-08** — Skyward Group announced CFO Mark Haushill’s planned March 2027 retirement and Taryn McHarg as successor.
- **2026-08** — Second-quarter results reported a combined ratio of 89.5% and diluted operating earnings per share of $1.30.
- **2026-04** — Skyward Group became USA Rugby’s exclusive insurance partner and front-of-jersey sponsor.

## Links

- Website: https://skywardgroup.com/
- LinkedIn: https://www.linkedin.com/in/andrewsrobinson

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Profile page: https://yespress.io/andrew-robinson
Published by YesPress — https://yespress.io
Last updated: 2026-10-23