Real Talk from the Top | Five Female Software Leaders Share Their Personal Journeys

The path to leadership is not a straight line. It's a series of twists and turns that are a result of decisions and people that influence those decisions. 

To celebrate Women's History Month, Insight hosted a candid fireside chat with five incredible female software leaders sharing their personal journeys and how they got to where they are today.

Who you'll see on screen:

Paige Thomas, CEO of Saks OFF 5TH

Paige Thomas is a highly regarded leader in the retail industry with an extensive off-price background. Paige joined Saks OFF 5TH in February 2020 after spending eight years at Nordstrom where she launched NordstromRack.com and led the integration of HauteLook. Under Paige’s leadership, Saks OFF 5TH has evolved the business operating model and strategy to focus on the digital experience. With this shift, Paige has driven aggressive growth over the past year, with the online business now valued at $1 billion. In 2021, Saks OFF 5TH’s e-commerce business was established as a separate entity with a $200 million equity investment led by Insight Partners. Paige was named President and CEO of SaksOFF5TH.com to continue to build on its momentum and growth trajectory.

Neha Sampat, CEO of Contentstack

Neha Sampat is a three-time tech founder and CEO, and currently founder and CEO at Contentstack. She has raised $89M for the company over the past two years. Neha previously founded and led digital transformation consultancy Raw Engineering and digital experience Platform Built.io, which was acquired by Software AG. Neha is a relentless advocate for achieving equity in the workplace and interviews women who pursue profit and purpose in her Dreammakers podcast.

Becky Flint, CEO of Dragonboat

Becky Flint is the founder and CEO of Dragonboat, the product portfolio platform for outcome-driven product ops and product teams. Prior to starting Dragonboat, Becky has built and scaled product operations and product portfolios for fast-growing companies like PayPal, Shutterfly, Bigcommerce, and Feedzai, when they were pre-unicorns or early unicorns. In addition to leading Dragonboat, Becky is a big champion for women in tech and outcome-driven product practice. She is the founder of ResponsivePPM.org and the Outcome-Driven Product HQ Slack community for product ops and product leaDERS.

Marcia Kilgore, Founder of Beauty Pie

Marcia Kilgore founded several global companies in the beauty and footwear industries. Her ventures include industry revolutionizing Bliss Spa, sold to LVMH after only three years from its launch; bath, body, and cosmetics brand Soap & Glory, sold to British Drugstore giant Alliance Boots/Walgreen; biomechanics meets fashion footwear brand FitFlop; and naturally-derived bath & body product brand Soaper Duper. Most recently, in October 2016, Kilgore founded Beauty Pie, her radical new luxury beauty product buyers’ club, aimed at democratizing the luxury beauty industry by disrupting the existing business model.

Katie Bullard, Managing Director of Insight Partners

Katie Bullard joined Insight Partners in 2022 as a Managing Director. Prior to joining Insight, Katie spent 15 years as a software operating executive, leading the scale-up journey from $20M to $200M+ ARR multiple times over. She was most recently President of A Cloud Guru, which merged with Pluralsight in late 2021. Prior to that, she spent 4 years as the President of DiscoverOrg/ZoomInfo ahead of its successful IPO. 

Watch for some tactical tips and practical advice that you can adopt to get one step closer to the top.

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