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Kevin Zentmeyer

AMA: Jobber Senior Director, Product Marketing, Kevin Zentmeyer on Storytelling


October 22, 2025 @ 9:00AM PT

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  1. With AI-generated content becoming mainstream, how do you preserve originality and human insight in your brand storytelling?

    Kevin Zentmeyer
    Kevin Zentmeyer

    Upwork Senior Director, Marketplace Experience Marketing • 8mo

    Specificity! AI is vague and general. At this point, AI is great for producing generic, mild product marketing content that won't look off-base and also won't resonate well with anyone. As part of your process, generative AI can be great for polishing or helping copy-edit work created by PMMs, but it can't replace good PMMs who are doing the job well. A key watchout is that AI will make your work sound more generic and toned down in the editing process if A) you aren't using a custom GPT that wo ...Read More

    11,596 Views
    2 requests
  2. What is your recommended process to craft story narratives?

    Kevin Zentmeyer
    Kevin Zentmeyer

    Upwork Senior Director, Marketplace Experience Marketing • 8mo

    Storytelling isn’t just a persuasion tool; it’s how we can keep product marketing grounded in the reality of what customers actually experience. My process blends anecdotes and data to make problems feel real, meaningful, and solvable. Start with a single, specific pain point. Apply the Pragmatic test to validate it. Is it a sharp pain that is widely felt? Find a human example. A customer, a rep’s story, or a support ticket that perfectly captures the struggle. Add the proof. Quantify the scope ...Read More

    8,265 Views
    3 requests
  3. If your product and your biggest competitor's product are very similar in features, benefits, what can you focus on to differentiate?

    Kevin Zentmeyer
    Kevin Zentmeyer

    Upwork Senior Director, Marketplace Experience Marketing • 8mo

    When features are nearly identical, I focus on the company instead of the product. Brand, customer experience, and employees who interact with customers become the real differentiators. Lead with brand trust. In my opinion, a strong brand is either large and corporate - displaying safety and trust, or takes on a challenger voice that is honest and aligns closely with its customers. Shopify is a good example here, despite being the largest player in its space at this point. Tell stories, not spec ...Read More

    1,098 Views
    3 requests
  4. How do you use storytelling to get executive buy-in?

    Kevin Zentmeyer
    Kevin Zentmeyer

    Upwork Senior Director, Marketplace Experience Marketing • 8mo

    Executives switch contexts constantly, and it’s easy to forget how much mental gear-shifting that takes. Storytelling helps in two important ways: it earns their attention and helps them quickly reorient to the problem space you’re asking them to weigh in on. Doing it already gets you halfway to "yes." Start with a story, not a slide. Open with a short, vivid example of the customer, team, or outcome that’s at stake. It immediately grounds the discussion. I mean this literally. If you're present ...Read More

    618 Views
    3 requests