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Clara Lee

AMA: PayPal VP, Product, Clara Lee on SMB Product Management


October 16, 2025 @ 10:00AM PT

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  1. How do you structure your Product team? How big is it, what does everyone do? How do you measure success of each function/person?

    Clara Lee
    Clara Lee

    PayPal VP, Product | Formerly Apple, Automattic, Deloitte • 8mo

    Across companies, I’ve structured teams in two different ways: By job to be done (JTBD) or domain. For me, this structure has made sense when there is a clear ideal customer profile (ICP) or primary customer segment that the company is actively prioritizing. That ICP may (for example) be defined by their industry, what they sell/offer, the geography in which they operate, and/or their size and maturity as a company. Inherent Internal alignment on customer needs allows me to hire for functional a ...Read More

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  2. What role does automation play in your SMB product strategy?

    Clara Lee
    Clara Lee

    PayPal VP, Product | Formerly Apple, Automattic, Deloitte • 8mo

    Gartner defines SMBs as businesses with fewer than 1000 employees and less than $1B in revenue. That is broad – from microbusinesses that operate out of a solopreneur’s garage, to high growth, multi-channel retailers selling across borders. Their needs could also differ across industries, product types, and countries. When thinking about automation for SMBs, it’s important to think about who within SMB the product is aiming to serve and ask where automation can help them save time, grow sales, e ...Read More

    534 Views
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  3. What does a product team do differently when targeting SMB buyers vs enterprise buyers?

    Clara Lee
    Clara Lee

    PayPal VP, Product | Formerly Apple, Automattic, Deloitte • 8mo

    SMB product table stakes typically include self-serve onboarding, intuitive UX, pricing that fits their value proposition. Depending on the SMB's budget, growth trajectory, and maturity, they may want to try a product and see the benefits before they are willing to pay, and which makes free trials are helpful for removing that financial friction. Being able to demonstrate value quickly and in that trial period or the first 30 days is key to paid conversion. Enterprise buyers typically have more ...Read More

    507 Views
    1 request
  4. What strategies do you use for upselling and cross-selling to SMB customers?

    Clara Lee
    Clara Lee

    PayPal VP, Product | Formerly Apple, Automattic, Deloitte • 8mo

    The strategies will depend on your SMB segmentation and/or ICP needs – two things to keep in mind:  You need to earn the right to upsell / cross-sell. This is about timing. What I’ve seen some SaaS companies do is try to start upselling immediately after onboarding… Asking a customer to “add-on” or “upgrade” before they’ve seen product benefits tends to be ineffective for SMBs who expect to see the ROI before shelling out more spend. Tailored recommendations convert better than generic ones. You ...Read More

    467 Views
    1 request
  5. What do products and teams that win the SMBs do different?

    Clara Lee
    Clara Lee

    PayPal VP, Product | Formerly Apple, Automattic, Deloitte • 8mo

    In addition to deeply understanding SMB needs and pain points, the products that win: Demonstrate speed to value; onboard customers with minimal friction and leverage intuitive UX to help them integrate the product into their workflows. They may actively be comparing your product to competitors – and the faster you can help them see ROI, the more willing they will be to convert. Express pricing in accessible, clear structures / packages. This should ideally be listed on either your product's hom ...Read More

    458 Views
    1 request