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    Can Five9 (FIVN) Turn a New AI-Focused CEO Into Lasting Competitive Advantage?

    Simply Wall St·12/25/2025 03:47:01
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    • In December 2025, Five9, Inc. announced that Amit Mathradas will become Chief Executive Officer and join the board on February 2, 2026, bringing extensive experience from AI-focused Nintex and tax automation provider Avalara, as well as prior leadership roles at PayPal, Web.com, and Dell.
    • His background building AI-centric, agentic platforms and scaling enterprise software businesses positions him to influence how Five9 competes in AI-powered contact center solutions and partner-led ecosystems.
    • We’ll now examine how Mathradas’s AI-centric background and upcoming leadership at Five9 could reshape the company’s existing investment narrative.

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    Five9 Investment Narrative Recap

    To own Five9 today, you need to believe that its AI-powered contact center platform can convert recent product momentum into durable, profitable growth, despite slowing revenue guidance and tough competition from larger vendors. The appointment of Amit Mathradas as CEO does not immediately change the key near term catalyst, which remains enterprise AI adoption and bookings, but it could help reduce one of the biggest current risks around leadership transition and execution over time.

    The most relevant recent development here is the planned 2026 investor day, where Five9 has said it will outline its strategy and long term financial framework. That event now takes on added importance, as investors will be looking to see how Mathradas aligns Five9’s expanding AI product set and partner ecosystem with clearer targets for revenue growth, margins, and capital allocation, especially after a period of share price underperformance and mixed guidance.

    Yet even as expectations build around new leadership and AI, investors should be aware that intensifying competition and rapid AI commoditization could still...

    Read the full narrative on Five9 (it's free!)

    Five9's narrative projects $1.4 billion revenue and $98.5 million earnings by 2028.

    Uncover how Five9's forecasts yield a $34.05 fair value, a 73% upside to its current price.

    Exploring Other Perspectives

    FIVN 1-Year Stock Price Chart
    FIVN 1-Year Stock Price Chart

    Eleven members of the Simply Wall St Community currently see fair value for Five9 between US$34.05 and US$67.14, highlighting very different expectations for upside. Set against this, the leadership transition and AI execution risk mean readers may want to explore how quickly Five9 can defend margins and product differentiation before forming their own view.

    Explore 11 other fair value estimates on Five9 - why the stock might be worth over 3x more than the current price!

    Build Your Own Five9 Narrative

    Disagree with existing narratives? Create your own in under 3 minutes - extraordinary investment returns rarely come from following the herd.

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    This article by Simply Wall St is general in nature. We provide commentary based on historical data and analyst forecasts only using an unbiased methodology and our articles are not intended to be financial advice. It does not constitute a recommendation to buy or sell any stock, and does not take account of your objectives, or your financial situation. We aim to bring you long-term focused analysis driven by fundamental data. Note that our analysis may not factor in the latest price-sensitive company announcements or qualitative material. Simply Wall St has no position in any stocks mentioned.