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Olivia Montgomery, PMP
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Olivia Montgomery is an associate principal analyst at Capterra, covering program and project management with a focus on the strategic alignment of IT and operations to optimize digital transformation. Drawing from her experience as a former IT PMO leader and her background in humanities studies, Olivia delivers data-driven insights that empower business leaders to drive business growth through projects.

Her expertise is featured in Forbes, Bloomberg, CIO Dive, and TechRepublic, as well as in podcasts, such as The Digital Project Manager. Recently, she presented her research on emotional intelligence (EQ) and decision-making at PMI's Global Summit conference, shedding light on the crucial role of EQ in driving project success. When she's not analyzing tech trends, you can find Olivia horseback riding or re-watching Jurassic Park.

It's Time to Optimize Your Digital Experience to Meet Customer Expectations
Published November 24, 2020
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Consumers are familiar with online shopping and digital marketing, but working online with a lawyer or an accountant is still a pretty new experience. Not all consumers are comfortable with a fully digital experience, especially with professional service providers who have traditionally relied on in-person meetings.
How Digital Business Transformation is Happening in Months, Not Years
Published September 29, 2020
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In December 2019, Gartner published a report recommending that to build and expand a digital business, businesses should “prepare for a complete retooling and skills renovation in the next five years (full report available to Gartner clients)."
New Remote Work Skills Small Businesses Should Be Developing
Published August 28, 2020
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Your business operates differently than it did pre-COVID-19. The job of customer service now requires a certain level of tech-savvy. An online storefront and marketing approach requires a different skill set than a brick-and-mortar business typically needs. And online payments and remote device security are likely new concerns you weren’t considering before.
A Business Model Innovation Story With Tips & Treats From the Owner
Published August 6, 2020
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Did you know that Airbnb, Venmo, and Uber were each started during the Great Recession? Economic crashes seem like the worst time to start a small business—but not if you have an innovative business model that fills a new need in a new environment.
Digital Marketing Strategies of Small-Business Owners
Published July 28, 2020
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I’ve talked with nearly a hundred small business owners about how they’re adapting their businesses to comply with social distancing requirements. This article is part of an ongoing series where we’ll share the tips, ideas, and stories from these business owners. I hope you find inspiration and insight that will help you pivot to a more digital business model for today’s “new normal.”
Advice for Small-Business Owners From Your Peers
Published May 29, 2020
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In this article, I’m going to share the advice your small-business owner peers have for how to adapt in these unprecedented circumstances. From yoga studios to health and beauty business owners, these leaders shared what’s top of mind, what’s getting prioritized, and what advice they have for other small businesses.
The Impact of COVID-19 and How Digital Strategies Are Helping Small Businesses Survive
Published May 5, 2020
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Capterra surveyed more than 500 small-business leaders to learn about how businesses have been impacted by the unprecedented crisis posed by the novel coronavirus.
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